Table of Contents 1, Molecular Structure.......... Structural Formula... Bonding... Stereochemist 2. Alkanes, Alcohols, and Substitutions... Alkanes.. . Alcohols and Substitutio 3. Carbonyls and Amines. Aldehydes and Ketones... Carboxylic Acids and Derivatives. 4, Biochemistry and Lab Techniques. Fatty Acids and Amino Aci Carbohydrates. Lab Technique: Answers and Explanations...PHYSICAL SCIENCES DIRECTIONS. Most questions in the Physical Sciences test ‘are organized into groups, each preceded by a desorintve passage. After studying the passage, select the one best fanswer to each question in the group. Some questions are ‘hot based on a descriptive passage and are’also independent fof each other, Yau must also select the one best answer to these questions I you are not certain of an answer, eliminate the alternatives that you know to be Incorrect and then select fan answer from the remaining alternatives. Indicate your Selection by blackening the corresponding oval on your fanewer document. A periodic table is provided for your use. ‘You may consul it whenever you wish. PERIODIC TABLE OF THE ELEMENTS 40 108 | 12.0 | 140 | 160 | 190 | 202 wy ul wl te] 7 | 3 230 | 243 270 | 28.1 | 31.0 | 22.1 | 36.5 | 99.9 72) 20) a] 2] ao) @] | 2] 7] we] | ol af a] sf [as | s6 K |Ca| se| Ti | V | Cr} Mn| Fe | Co| Ni | Cu] Zn | Ga| Ge | As | Se | Br | Kr 30.1 | 40.1 | 45.0 | 47.9 | 60.9 | 520 | 549 | 55.8 | sa | 50.7 | 635 | 65.4| 69.7 | 72.6 | 749 | 700 | 799 | 63.8 a7} 3a} se} 40] 41 | 42] a3] a4 | 45 | a6] a7 | 48] a0] 0] ot | 52] 53 | 54 Rb | sr| ¥ | Zr | Nb|Mo| Te | Ru| Rh| Pd| Ag] Cd/ In | Sn| Sb | Te] I | Xe 855 | 97.6 | 98.9 | 91.2 | 92.9 | 05.9 | (08) | 101.1] 102.9| 16.4] 107.9] 112.4] 114.8] 118.7] 121.8) 127.6| 126.9| 131.3 5} 66] 57 | 72] 73| 74] 75 | 76] 77 | 7 79 | a0 | a | e2| 3 | a4] os | a6 cs | Ba|La*| Hf | Ta} W| Re | Os| ir | Pt | Au} Hg| TI | Pb | Bi | Po| At | Rn 132.9| 197.31 138.9| 178.5| 180.9 | 183.9] 186.2) 190.2|192.2| 186.1 | 197.0] 200.6 204.4 207.2] 209.0 | 200) | 210) | (222), 7 | 86 | 89 | 104] 105] 106 107 | 108 | 109 Fr | Ra | Ac’ |Unq|Unp|Unh] Uns | Uno| Une (223) |226.0|227.0| 261) | 262) | 263) | (262) | i206) | (2671, we] 89] 00] 61] e2] 63] 6 | & | | 7] 8] G9] 7] 7 40.1 | 140.9 [144.2] (146) |180.4|182.0| 167:3| 158.0 | 162.5 | 164.9 | 167.3 168.9 | 173.0| 175.0} 0 | a1 | oz} sa] om | a5 | 06 | o7 | a8 | 09 | t00] tor | 102 | 103 '222.0| 231) |238.0| 2370 | c2aa) | 24a) | (247) | 247) | 281) | (262) | (267) | (268) | (259)| 260) Copyright © 2006 Examkrackers, Inc.Structural Formula 1. What is the comect Lewis dot structure for CH,CH,CHO? 3. A Lewis base donates a pair of electrons, Which of the following molecules could be a Lewis base? A. CH, B. NH; c. AICI, D. BH, 4. Which of the following molecules could NOT be @ ‘Lewis base? A. NH(CHh), B. NH, c. HO D. oF Refer to the Newman projection below to answer questions 57. on H. H H H CH 3. In the Newman projection, what does the circle represent? ‘The largest carbon in the structure, ‘The second carbon along the axis of the bond, ‘The first carbon along the axis of the bond, ‘The radius ofthe bond. PORP Molecular Structure 6. In the Newman projection, what does the intersection ofthe three lines represent?” ‘A. The largest carbon in the structure, 1B. The second carbon along the axis of the bond. C. The first carbon along the axis of the bond, D. The radius of the bond. 7. In the Newman projection, the hydroxide group and the ‘methyl group are: ‘A. attached to the same carbon. B. attached to different carbons. > CC. attached to carbons with no hydrogens attached. D. attached directly to each other, Refer tothe Fischer projection below to answer questions 8-10. CH; HO--on HO4 Ho- CH 8, Inthe Fischer projection, the hydroxide groups are: ‘A. coming out ofthe page on the right side and into the page on the left. B. coming out ofthe page on the left side and into the ‘page on the right. C. coming out ofthe page. D. going into the page. 9. In the Fischer projection, the methyl groups are: ‘A. coming out ofthe page on the top and into the page ‘on the bottom. 'B. coming out of the page on the top and into the page ‘on the bottom. CC. coming out ofthe page. D. going into the page. 10. In the Fischer projection, what do the intersections of the vertical and horizontal lines represent? A. rotation of the bond B. carbon atoms C. double bonds D. nothing Copyright © 2006 EXAMKRACKERS, Inc,1001 Questions in MCAT Organic Chemistry Refer to the dash-line-wedge formula below to answer questions 11-13. H HAC, a 1. In the dash-line wedge formula what-atom(s) is (are) coming out of the page? La Br ul H A. Lonly B. Ionly C. Mand iL D. Land 12. In the dash-line wedge formula what atom(s) is (are) going back into the page? 13. In the dash-line wedge formula what atom(s) is (ere) in the plane of the page? L cH I. Br mL A. Lonly B. only C. Mand I D. Tand Ill 14, Which of the following structures is an amide? HAN HO. 15. Which of the following structures is a ketone? A c oH ° HN. 16. What is the name of the functional group contained is, the structure shown below? ee AL ther B. ester C. carboxylic acid D. alcohol 117. What is the name of the functional group contained it the structure shown below? /_ AL other B. ester C. carboxylic acid D. alcohol 18, Isoamylacetate is a honeybee pheromone that i released on the skin when a bee stings its victim. Thi pheromone has a sweet smell and attracts other bees t join the fight. ‘The structure of isoamylacetate is show below, What functional group does it contain? > CH; Oo we oan AL other ester carboxylic acid alcohol yor Copyright © 2006 EXAMKRACKERS, Inc.19. Tetrahydrofuran (THF) is a common solvent for synthetic reactions because it is an ether. Ethers are relatively inert so they do not participate in the reaction, Which of the following structures is THF? A “Se l 0 B, D. CH,CH,OH 20. Aspirin is the common name for acetylsalicylic acid. The structure is shown below, what three functional ‘groups are present in this molecule? A. ether, aromatic ring, carboxylic acid B. ester, phenyl, carboxylic acid C. alkene, aromatic ring, carboxylic acid D. alcohol, ether, carboxylic acid 24, Luminol is a compound used by the potice to detect the presence of dried blood. Upon oxidation, luminol emits a green light in the presence of a metal ion such as the Fe ion found in blood, The structure of luminol is shown below. How many amine groups are present in this molecule? NE; O ve NY : Y Molecular Structure 22, How many amide groups are present in luminol? See question 21 forthe structure? * a0) Bo C2 D3 23, Menthol is one of the molecules responsible for the mint odor. What functional groups are present in menthol? HO A. cycloalkane and alkene B. cycloalkene and alcohol . eycloalkane and ether D. cycloalkane and alcohol 24, Similar in structure to menthol is limonene which is responsible for the Iemon odor found in natural products, What is the difference in functional groups between these two structures? ><) A. Menthol has an aleohol and limonene has an 'B. Menthol hes an alcohol and limonene has an alkene. C. Menthol has an ether and limonene has an alkyne. D. Menthol has an ether and limonene has an alkene, 25, Eugenol is a dental anesthetic that is isolated from oil of cloves, ‘The structure is shown below. What fanctional groups are present in this toothache remedy? nei ‘A. aromatic ring alkene, aleohol, and ether B. cycloalkyl ring, alkene, alcohol, and ester CC. aromatic ring, alkyne, ether, and ester D. aromatic ring, alkene, alcohol, and ester Copyright © 2006 EXAMKRACKERS, Inc.1001 Questions in MCAT Organic Chemistry 26. When eugenol (shown in question 25) is isolated from the clove flower buds, acetyleugenol (shown below) is also isolated and must be separated from the eugenol. ‘What isthe difference between these two compounds? 9° Hio=g-¢- ok cH A. The ether of eugenol i converted to an ester in acetyleugenol B, The aleohol of eugenol is converted to an ether in acetyleugenol C. ‘The ester of eugenol is converted to an ether in acetyleugenol. D. The alecho! of eugenolis converted to an ester in acetyleugenol 27. What is the index of hydrogen deficiency for the ‘molecular formula CE? AO Bod 2 D.3 28, What is the index of hydrogen deficiency for the molecular formula CyO:H1;? Ao Bd C2 D3 29, What is the index of hydrogen deficiency for the ‘molecular formula C;O3H,Br? Ao Bat C2 D.3 30. What is the index of hydrogen deficiency for the structure shown below? CD PORP ‘3A. What is the index of hydrogen deficiency for structure shown below? AL > yon 32. What is the index of hydrogen deficiency for 1 structure shown below? ee Br SORP 33. A brightener that is used for white shirts is Caleoflu White MR. The structure of this whitener is shov below. How many amine functionalities are present this molecule? i sone . < rd POs or mas f < : Re GQ 12 34, How many degrees of unsaturation (index of hydroge deficiency) are in each phenyl ring on the end of th ceateofluor shown in question 337 AL BO? C3 D4 Copyright © 2006 EXAMKRACKERS, Inc.35. Another brightener that is used on wool and nylon fabrics is 7-dimehtylamino-4-methyleoumarin, What functional groups are present inthis brightener? CH emg ‘A. aromatic ring, alkene, ketone, ether and amide B. aromatic ring, cycloalkene, ketone, and ether C. aromatic ring, cycloalkene, ester, and amine D. aromatic ring, cycloalkene, ester, and amide 36. What is the IUPAC name for the structure shown of A. 2,2-dimethyl-3-n-butylpentane B. 4,4-dimethyl-3-n-butylpentane C. S-tert-butytheptane D. 3-tert-butylheptane 37. What is the IUPAC name for the structure shown DE A. Aisopropyl-6-octanol B. 5-isopropyl-3-octanol . S-isopropyl-3-hexanol D. 42-butanol-S-methylhexane 38 Which structure below is the correct structure of 1- efhy1-3-(,1,3-trimethylbutyeyclooctans? OF OF Sone Molecular Structure 39, Ethanol reacts with sulfuric acid at 140°C to form an ether. The ether formed would bé: A. diethylether B. Lethyne . L-propene D. ethanal ‘Alcohols are converted to esters using carboxylic acids. Using anhydrides is a better way to achieve this ‘conversion, Which reagent would best convert octanol to octyl acetate an ester that has a fruity odor? c : Nh 40, ‘The structure of bilirubin is shown below. How many amide functional groups are present in this pigment? H H,c=C. HAC’ ‘CH)CH,COOH meee 42, How many amine groups are found in bilirubin (tructure shown in question 41)? A B. rom D. 43, How many carboxylic acid groups are found in bilirubin (structure shown in question 41)? Sone 5 Copyright © 2006 EXAMKRACKERS, Inc.1001 Questions in MCAT Organic Chemistry 44, 2Adinitobydrazine reacts with Ketones and aldehydes to form a 2,4dinitrohyrazone, The 24-DNP test is ‘used to determine if an unknown compound is an aldehyde or ketone. Which reagent would produce a positive 2,4-DNP test? Des Daa Ny 45. Given the information in question 44, which of the following compounds would be the best solvent forthe 2,A-DNP test? I. acetone IL cthanol TOL heptanal A. Tonly B. Tonly © Mand I only D. Tand Il only 46, If L-methyleyclopentene undergoes hydration to form ‘an alcohol, what would be the product? yk O~ "Os, 17. When 1-chloro-3-methylpentane is reacted with excess ammonia the halogen is replaced by an amine group. ‘What is the structure of the product of this reaction? A © NN “YY a B » i NE aa b “™ 6 48. In the reaction shown below, what is the functional ‘group conversion that takes place? Oo OO Gat ‘A. alkane to aldehyde B. cycloalkane to cycloketone C. alkane to cycloalkane D. cycloalkane to eycloether 9. The following Newman projection looks déwn which bond of I-choropentane, according to IUPAC carbon numbers? r H, H © P H CHCHCL ‘A. the bond between Cl and C2 B. the bond between C2 and C3 C. the bond between C3 and C4 D. the bond between C4 and C5 50, Which structure is the Fischer projection for the structure shown below? e ‘CH HO A cHo cHo uton H CH Cy B. D. Copyright © 2006 EXAMKRACKERS, Inc,51. Which structure is the dash-line-wedge formula for the structure shown below? HO-}-H HOH CH A c K Son CH one yg onc”, ‘on HOH u D. : HO HOPE H Eh W on b H Bonding '52, What force i responsible for the bonds between atoms? A. Dipote-dipote B. Hydrogen bonding C. Gravitational D. Electrostatic Refer to the Lewis Dot structure shown below to answer questions 53-57. HcHN 53. How many electrons are involved in the sigma bond between the carbon atom and the nitrogen atom? AO Bl G2 D6 54, What types of bonds exist between the C atom and the Natom in HCN? ‘A. 1 pi bond and two sigma bonds B. 2>i bonds and one sigma bond C._ 3 pi bonds and zero sigma bonds D. 3 sigma bonds and zero pi bonds 55. How many electrons does the N atom contribute to the pi bonds? ao 2 C3 5 Molecular Structure '36. What is the hybridization of the sigma bond between the carbon atom and the nitrogen atom in HCN? AL B. sp? Cs D. spd 57. What is the formal charge on the nitrogen atom in HCN? AO 1 » 2 5 3 458. Which bond is the mos stable bond? ‘A. sigma bond B._pibond in an alkene . pibond in an alkyne D. pibond in a carbonyl 59, What types of bonds are found in an allyne functional group? ‘A. one sigma bond and one pi bond B. two sigma bond and one pi bond (C. one sigma bond and two pi bonds that are perpendicular to each other . one sigma bond and two pi bonds that are parallel to each other ‘Average bond energies are shown in the table below. Use the table to answer questions 60-61. Bond “Average Bond Energy eal mol" C= #3 C=C 146 C=C 200 60, Based on the values inv the table, what is the ‘approximate average bond energy for each sigma bond? A. 60 kcal mot" B. 80 kcal mot” C. 150keal mot D. 200 kcal mot" 61, Based on the values in the table, what is the ‘approximate average bond energy for each pi bond? A. 60 keal mot” B. 80 kcal mot" C. 150 kcal mot? D. 200 keal mot Copyright © 2006 EXAMKRACKERS, Inc.1001 Questions in MCAT Organic Chemistry 62. The energy of 2sp° hybridized orbital for a carbon 68. Tho bond angle formed by Hi, C2, and H3 in atom is aspartame is: ‘A. higher in energy than the 2s atomic orbital and AL 180° Jower in energy than the 2p atomic orbital. BR 120° 1B, higher in energy than the 2p atomic orbital and fea ae lower in energy than the 2s atomic orbital ae CC. higher in energy than both the 2s and the 2p atomic orbitals i D. lower in energy than both the 2s and the 2p atomic ie) and ae ee aspartame is | orbitals. AL 180° 3. The overlap of what two orbitals form the pi bond B 120° » between carbon atoms in an alkene? ee : | ‘A. two p otbitals D. 90° B. two sp” orbitals C. two sp’ orbtials 70. The bond angle formed by C7, N8, and HO in D. two s orbitals aspartame is: 64, How much s character does an sp* hybridized orbital a ee have? B. 120 ‘A. nos character Ce eon D. 90° oe ae Cocaine is a stimulant that is isolated from coca leaves. 7 Refer to the structure of cocaine shown below to answer Rofer to the structure of aspartame, an artificial sweetener, eee to answer questions 65-70. Seu 8Nn goou 4 oct Fee P ees H s\ 3 12 unt ot ul a Eee Ea y f 0 “Aspartame H3 ell ‘The hybridization of the C2 carbon in aspartame is: ‘71. The hybridization of the C9 carbon in cocaine is: AL sp AL sp Bt a2 c c D. spd D. spd (66. ‘The hybridization ofthe CS carbon in aspartame is: 172. Tae hybridization of the NB nitrogen in cocaine is: Ap, AL sp aa B. sp 8p c = D. spd D. spd 61. ‘The hybridization of the N8 nitrogen in aspartame is: 73, The hybridization ofthe O3 oxygen in cocaine f be 8, A 9p, i sp a I c. C. sp? D. sp'd D. spd i y | Copyright © 2006 EXAMKRACKERS, Inc.74. ‘The hybridization of the C11 oxygen in cocaine is: AL sp, B, Cc. D. spd 75, The bond angle formed by C10, Cl1, and C12 in cocaine is: AL 180° B. 120° c. 109" D. 90° 76. ‘The bond angle formed by C2, 03, and C4 in cocaine is: A. 180° B. 120° c. 109° D. 90° ‘77. The bond angle with C9 in the cocaine structure at the center of the angle is AL 180° B. 120° C. 109° D. 90° 78. How much s character is in the hybridized orbital on the C2 carbon in the cocaine structure? AL no s character B. 25% C. 33.3%. D. 50% 79, How much p character is in the hybridized orbital on the N8 nitrogen in the cocaine structure? AL 33.3%. B. 50% C. 66.6% D. 75% 80. What type of bond is formed between the C2 carbon ‘atom and the O1 oxygen atom in cocaine? A. ionic bond B. pure covalent bond C. polar covalent bond D. coordinate covalent bond 9 : Molecular Structure ‘81. How much p character is in the hybridized orbital on the center carbon in acetone (CH;COCH,)? A. 33.3% B. 50% C. 66.6% D. 75% 82, Which of the following structures have delocalized electrons? L nc-gg-om A. Lonly B. Tonly C, Land IH only D. Mand If only 83. Which of the following structures have delocalized clectrons? 1 WC-¢=¢-cHy ff © Mm. HC -C-C=CH fi HO A. Lonly B. Tonly C. Land Ill only D. None of the structures. 84. What is the length of the bond between CI and C2 in the structure shown below? Geel 5 473 ‘A. the length ofa carbon-carbon bond in an alkane 'B. the length ofa carbon-carbon double bond in an. alkene C. shorter than the length of a carbon-carbon double bond in an alkene D, between the length of a carbon-carbon bond in an alkane and the length of a carbon-carbon double bond in an alkene Copyright © 2006 EXAMKRACKERS, Inc.1001 Questions in MCAT Organic Chemistry 85, What is the length of the bond between C2 and C3 in the structure shown below? 6 O 403 the length ofa carbon-carbon bond in an alkane the length of a carbon-carbon double bond in an alkene shorter than the length of a carbon-carbon double bond in an alkene D. between the length of a carbon-carbon bond in an alkane and the length of carbon-carbon double ‘bond in an alkene eer 86, Which of the structures is NOT @ resonance structure of benzene? "OO ‘oO 87, Which structure has the correct bond dipole found in ethanol? A c H Be _ poe on wR 6 HOH HOH B H % La oH OH wo sv HE HOH 10 88. Which of the three molecules pictured below contait polar bond? L L u i i ‘ _ cat ime oa Ro on ¥ of ac A. Tonly B. Wonly ©. tan litonly D. 1,0, and I 89. Which of the three molecules pictured below contait net dipole moment? L 0. 1. H a HNC eulle 4 a of A. Tonly B. only C. Land I only D. Mand only 90. What is the correct net dipole moment for the structt shown below? 91. Given the information about the dipoles of given bon shown below, which atom has the largest difference electronegativity compared to carbon? Dipole Moment inDebye _| 03D 0.22D 0.86. 156D. PORE aozm Copyright © 2006 EXAMKRACKERS, Inc.‘92, The dipole moment for the C-Br bond is 1.5 D. What is the dipole moment for carbon tetrabromide? AO in C6 D. Cannot be determined, 93, What determines the polarity of a covalent bond? A. difference in atomic size B. difference in clectronegativity C. difference in total number of protons D. difference in total number of valence electrons 94. The primary interzction between molecules of cyclohexane in the liquid phase is: ‘A. London dispersion forces. B._ hydrogen bonding. C. covalent bonding. D. dipole-dipole. 95. Thie primary interaction between molecules of acetone inthe liquid phase is ‘A. London dispersion forces. B. hydrogen bonding. . covalent bonding. D. dipole-dipole. 96, The primary interaction between molecules of dopa D. (R)-dopa 22 1196. What direction will ()-dopa rotate light? A. clockwise B. counterclockwise C. cannot be determined without measurement D. The molecule will not rotate light. 197, How many chiral centers does dopamine have? AO Beil C2 D3 198. What direction will dopamine rotate light? A. clockwise B. counterclockwise C. Itcannot be determined without measurement, D. The molecule will not rotate light. 199, The enantiomer of ()-dopa is toxic. Which of the following structure is the enantiomer of ()-dopa? A H bd a HN, 7 ‘NH 200, If a scientist needed to separate (1)-dopa from (d)-dopa, what processes would work to accomplish this resolution? 1. Distilation Ul. Recrystallization Formation of diastereomers with an enantiomerically pure compound. A. Tonly B. Ionly C. 1,1, and i D. Tand Mf only Copyright © 2006 EXAMKRACKERS, Inc.vpulegols result as a side product from the oxidation of conellol. Refer to the structure below to answer questions 1-204, HO’ Isopulegols |. How many chiral centers are present in isopulegols? AO Bd C2 D3 + What is the maximum number of optically active stereoisomers for the isopulegols? AL 2 B. 3 G4 D8 Pulegone can be synthesized from isopulegone. The structure of pulegone is shown below. How many chiral centers does pulogone have? > HO’ AO Bod ee D3 Which ofthe following structures is nota stereoisomer of the isomer of isopulegol shown below? en Pp oP op 2B Molecular Structure 205. A neat solution of I-phenylethanol is optically active, while 2-phenylethanol is not, The best explanation for this observation is A. 2-phenylethanol has a higher molecular weight than I-phenylethanol B. 2-phenylethanol as a higher boiling point than 1- phenylethanol . phenylethanol ischial, while 2-phenylethanol iss not. D. 2-phenylethanol is chiral, while I-phenylethanol is not » 206. The structures of (+)-I-phenylethanol and (1+ phenylethnaol are shown below. What is the absolute configuration of the (+) and (-) isomer, respectively? wd OT on H (+I-phenylethanol (- AL RR BSS CSR DRS 207, Given that a neat sample of (+)-L-phenylethanol rotates the sodium D line +42°, what can be determined from ‘the observation that a pure neat sample of 1- phenylethanol rotates the sodium D line +12°? A. The sample contains a mixture of R and $ isomers, with more R isomer present. B. The sample contains a mixture of R and $ isomers, with more S isomer present. C. The sample contains pure R isomer. D. The sample contains pure $ isomer, Copyright © 2006 EXAMKRACKERS, Inc.1001 Questions in MCAT Organic Chemistry 208. 209. ‘Yeast selectively reduces the ketone carbonyl in ethyl acetoacetate to §(+)-ethyl-3-hydroxybutanoate. Which of the following is the product of the reaction shown below? teat HyC—C-G-C-OCHLCHs Se b A c CH "H,OOCHs 1, Hy HY rcooaie, — MYNocuscis B D. Hy 1H,COCH, HA, Hf 7 cH,COOCHLHs yd OCHCH In what direction would the ethylacetoacetate and the S(+)-cthyl-3-hydroxybutanoate (discussed in question 208) rotate plane polarized light respectively? A. clockwise then counterclockwise B. counterclockwise then clockwise C. no rotation then clockwise D. no rotation then counter clockwise 24 Copyright © 2006 EXAMKRACKERS, Inc.Alkanes 210. Which of the following structures is an alkane? A c VArLE ~RW B. D. VAHL son 211. Which of the following is not an alkane? A c Yer La B, Oo D. sk 212. Which of the following could not be an alkane? A. Gillie B. GH C. Cyl D. CioH2O 213. Which of the following is a haloalkane? A © 6 po yc T BON a HO Poe ™ Aan, A c , AW nerfs HO cl 25 Alkanes, Alcohols, and Substitutions Refer to the structure of 4-methytheptane shown below to answer questions 215-217. 3 aed 215. The carbon labeled C1 in 4-methylheptane is a A. methyl carbon B. primary carbon CC. secondary carbon D. tertiary carbon » 246. The carbon labeled C4 in 4-methylheptane is a A. methyl carbon B. primary carbon C. secondary carbon D. tertiary carbon 217. ‘The carbon labeled C3 in 4-methylheptane is a A. methyl carbon B. primary carbon C. secondary carbon D. tertiary carbon Refer to the structure of 3B-cholestanol to answer questions 218-219. HO 3B-cholestanol 248, How many tertiary carbons are in 3B-cholestanol? A 3 BS G7 Do 219, How many primary carbons are in 38-cholestanol? Copyright © 2006 EXAMKRACKERS, Inc.1001 Questions in MCAT Organic Chemistry 220, Which of the following isa radical? A : HC Hs t© : of Be ae HyC HC » Hy lo be not’ nod He HC 221. Which of the following radicals is the most stable? A c gts CH we-6 we CH Ht » og, HsC-O # 222. Which of the following radicals is the least stable? 223. In the structure shown below which carbon would be ‘most reactive in a radical reaction? ‘A. carbon 1 B. carbon 2 C. carbon 3 D. carbon 4 224, The IUPAC name forthe structure shown below is A. 4-butyl-2-methytheptane B. 2-methyl-4-butylheptane C. 6-methyl-4-propytheptane D. 2-methyl-4-propylheptane 225, ‘The IUPAC name for the structure shown below is: ‘A. 1-G-methylpenty!)-3-methyleyclohexane B. 1-(-ethylbutyl)-3-methyleyclohexane CC, 2-ethyl-7-methyldodecane D. 7-othyl-2-methyldodecane 226. Which of the following alkanes has the highest boiling point? A c point? A © B. . D. on A 228. Which of the following alkanes has the lowest density? A c Copyright © 2006 EXAMKRACKERS, Inc,‘9. Which of the following alkanes has the lowest melting point? A nonane B. octane C. butane D. dodecane 0. Combustion is what type of reaction? A. exothermic B. endothermic C. kinetically favored D. nonspontaneous 1. Which of the following are steps in radical halogenation? initiation propagation ‘termination only Tonly Tand Il only 1,0, and I sore Bay Which of the following compounds is least reactive? A. diethyl ether B. heptanal C. butane D. acetic anhydride = Heptane has a boiling point of 98°C. Which alkane ‘would have a higher boiling point? A. pentane B. octane C. butane D. methane ‘Nonane has a boiling point of 151°C, Which alkane ‘would have a higher boiling point? A. dodecane B. octane C. 3-methyloctane D. 2,2-dimethytheptane When an alkane is reacted with oxygen at high temperatures, what are the products? A. CO; B. HO C. CO; and H,0 D. CO; and Hy Alkanes, Alcohols, and Substitutions 236. In order to achieve combustion of an alkane, what is required? 7 AL Os B. Oz and high temperatures C. Hyand high pressure D. CO; and H,0 237. A series of alkanes is separated by distillation. Which alkane would be the first to boil? A. pentane B. octane » C. hexane D. heptane 238. Given that the boiling point of pentane is 36°C, what state is octane in at room temperature? AL gas B. liquid C. solid D. The state cannot be determined. 5 239, Given that the density of pentane is 0.56 and the density of octane is 0.70, what is the density of hexane? AL 044 B. 056 C. 066 D. 0.70 240. Given that the boiling point of butane is 0°C, what state is propane in at room temperature? AL gas B. C. solid D. The state cannot be determined. 241. How many moles of Hz are produced when methane is ‘completely combusted? Ao yor 242, How many moles of H;0 are produced when butane is completely combusted? AO B.2 C4 DS Copyright © 2006 EXAMKRACKERS, Inc.1001 Questions in MCAT Organic Chemistry 243. How many moles of H,O are produced when cyclooctane is completely combusted? AO B4 C8 D. 16 244, How many moles of CO, ate produced when heptane is, ‘completely combusted? AO il C7 D. 14 245. How many moles of CO, are produced when cyclopropane is completely combusted? AO Bd C2 D.3 246, How many moles of O2 are consumed when nonane is ‘completely combusted? A 4s B7 cu D. 28 247, How many moles of O, are consumed when cyclohexane is completely combusted? A. 6 BO Cc 12 D. 15 248. Which of the following alkanes would have the largest heat of combustion? ‘A. methane B. butane C. octane D. cyclohexane 249, Given that decane has @ melting point of -30°C and hexane has a melting point of -95°C, what is the ‘melting point of octane?” AL 25°C B. 57°C C.95°C D. -100°C 28 250. Given that butane has a boiling point of 0°C and pentane has a boiling point of 36°C, what is the boiling point of isopentane? A. -10°C B. 30°C c. 36°C D. 45°C 251, Given that cyclopentane has a boiling point of 49°C. and eyclooctane has a boiling point of 148°C, what is the boiling point of cyclohexane? A. 36°C B. 49°C c. arc D. 150°C. 252. Which of the following places the densities for the alkanes from lowest to highest? ‘A. ethane 2c B, Cl +CH;CH; —> HCI+CH3CHY C. CHCH3 + CHyCH? > CH;CHs + CH,CHY D, CHjCH," +Cl*—> CH,CH,CL 267. Which ofthe following steps is a termination step? A. Ch+hv—> 2c B. Cl- +CH3CH) —> HCI+CHACHy . CH3CH3 + CH;CHy —> CH3CHs + CHACHY D. CH;CHy* +Cl*—® CHCH,Cl 268. Which of the following steps requires a homolytic cleavage? L. initiation IL. propagation IL termination A. Ionly B. Tonly C. Land If only D. 1,1, and I Which of the following steps is not a propagation step ina radical reaction? 269, A, Ch+CHsCHY —> CH;CH,Cl+ cl- B. Cle +CH,CH; —> HCI + CHyCH C. CH;CH + CHjCH} — CH3CH3 + CHaCHy D, CH;CHy* +Cl"—> CH;CH,CL 270. Which of the following steps always generates a radical IL. propagation ‘termination A. only B. Lonly . Land I only D. 1,1, and 271, Why is ultraviolet light requiréd for radical reactions? |. Ultraviolet light provides energy to break all the bonds in the reaction. B. Ultraviolet light is required to form the product bond in the termination step. C. Ultraviolet light is required to break the carbon- ‘hydrogen bond in the alkane. D. Ultraviolet light provides energy to break a bond and initiate the reaction. 30 272. Which of the bonds labeled in the structure below ‘would require the least amount of energy to break? q te 2 edi N CS G- 273. What is the order from most to least reactive for the halogen radicals? A. F>CI>Br>T B. Cl>BeF>1 ©. Br>Cl> FoI D. I>Br>Cl>F 274, When Cl; is reacted with iso-butane, the chlorine radical reacts 5.5 times faster with the tertiary hhydrogen. What is the best explanation for the distribution of products shown below? f+ 2% 38% ‘A. The distribution of products is unrelated to relative reactivities. B. There are nine primary hydrogens compared fo one tertiary hydrogen, C. Primary halogens are more stable than tertiary halogens. D. The selectivity of chlorine radicals is greater than ‘bromine radical. 275. Based the bond dissociation energies inthe table below, which reagent would be best to use for the initiation step of a radical reaction? Bond —__| Bond Dissociation Energy [__HO- 119 keal/mot HO- OH 51 keal/mol CH-F 109 kcal/mol (CH) C-H1 91 kcal/mol - CHy- Chis — 88 keal/mol— A. HO; B. H,0 C. CHE D. GH Copyright © 2006 EXAMKRACKERS, Inc.176. The bond energies shown below indicate that the allyl radical is more stable than the butyl radical. What is the best explanation for this observation? CHs 87 kano oC, V4; I= 91 keal/mole ‘The butyl radical is an unstable radical. ‘The allyl radical is an unstable radical. Steric hindrance on the t-butyl group destabilizes the bond. ‘The allyl radical is resonance stabilized, ee ‘77. The hydrogen shown on the cyclohexane ring below is a(n): H LZ axial hydrogen equatorial hydrogen cis hydrogen ‘rans hydrogen SoRP 78, The hydrogen shown on the cyclohexane ring below is a(n): Ld axial hydrogen equatorial hydrogen cis hydrogen ‘rans hydrogen Sopp "9, The geometric relationship between the two methyl ‘groups shown on the cyclohexane ring below is: Lau axial equatorial cis ‘rans SoRP au Alkanes, Alcohols, and Substitutions 280. What is the most stable confirmation of eis-1-t-butyl-3- methyleyclohexane? A Ch oo CH H H h A a cH H 7 H H 281. What is the most stable conformation of the cyclohexane ring shown below? op ae of Lf 282. What is the most stable confirmation of the cyclohexane ring shown below? aK@ a cH H H i ‘CH if H H B. ons H 1H cH H H Copyright © 2006 EXAMKRACKERS, Inc.1001 Questions in MCAT Organic Chemistry 283, What isthe best explanation for the trend observed in the table? Radical Reactod | Relative Rave (@™"™= 10) ] with CH, at 27°C F 140,000 ai 7300, Br 9x10" T 2x 10™ ‘A. As the atomic mass of the halogen increases, the rate of reaction increases. B. As the atomic radius of the halogen increases, the rate of reaction increases. C. As the reactivity of the halogen radical decreases, the rate of reaction increases. D. As the reactivity ofthe halogen radical increases, the rate of reaction increases, 284, How many monochlorinated products are possible when Cl, is treated with UV light and reacted with 3- methylpentane? AO por 1 4 8 285. How many monobrominated products result when Bry is treated with UV light and reacted with 3- methylpentane? AO BL C4 D. 8 286, NBS produces a low concentration of bromine radicals, What is the monobrominated product when NBS is reacted with 2,3-dimethylbutane? A G 32 287, Which of the following are possible monochlorinated products, when Ck is reacted with 3,5- dimethylheptane? 1 oh» i. , Ef A. Honly B. Tonly C. Land only D. 1M, and I 288, Radical helogenation has limited use in industry to produce haloalkanes. The best explanation for this fact is that ‘A. radicals ate too expensive to produce. B. radical reactions are difficult to control. C. radicals are difficult to produce on a large scale. D. the only source of radicals requires large amounts, of heat. 289. What will be the major monofluorinated product when 2amethylbutane undergoes @ free-radical reaction with EP Looky ty ‘The best explanation for the stability of the chair ‘confirmation for cyclohexane is: L. the bond angles are 109.5° IL, the hydrogens are all in staggered conformations IIL. the bonds have nonlinear overlap A. Tonly _—-B.Ilonly — C. Land If only D. 1,1,and I 290. Copyright © 2006 EXAMKRACKERS, Inc.191. What is the best explanation for the trend observed in the table below? Cyctoakane | Menofconbasn ‘eyelopropane_ 166.6 clbulne isk cyelpenine 1587 cyclohexane sr xelohepiane 1583 ‘cyclone 158s ‘The heat of combustion per CH, decreases as the ‘number of CH, groups increases. ‘The heat of combustion per CH; increases as the number of CH, groups increases. ‘The heat of combustion per CH; increases as ring strain increases, ‘The heat of combustion per CH. inereases as ring. strain decreases. Po Fw Pe 2. Combustion reactions are difficult to control. One method of control is to regulate the fuel/air ratio. What does regulation of this ratio control? ‘AL the types of reactants B. the types of product C. the ratio of reactants to products D. the ratio of reactants kenes |. Which of the following structures is an alkene? A c B D. NWN MAY Which of the following structures is an alkyne? A c Alkanes, Alcohols, and Substitutions 298. Which of the following alkenes is the most stable? a 296. Which of the following alkenes is the least stable? A c A aN D. AL aa 297. What isthe correct TUPAC name for the alkene shown below? B. B. 2-metylbutyl: C. 3-cthyl-S-methyl-2-heptene D. 3-cthyl-5-methyl-3-heptene 298, What is the correct IUPAC name for the alkyne shown below? A. 44dimethyl-2-noxyne | B, 2,2-dimethyl-4-hexyne ih C. 22-dimethyithexene D. d.ethylt-methyl-2-pentyne 299. What is the correct name for the structure shown below? H, on A. ortho-nitrotoluene B. meta-nitrotoluene C._para-nitrotoluene D. para-toluene 33 Copyright © 2006 EXAMKRACKERS, Inc.1001 Questions in MCAT Organic Chemistry 300, What is another name for 4-methoxybenzoate? , A. p-anisate B. meanisate CC. o-anisate D. metoluate 301, For the structure below, give the geometric assignment for the bond between C2 and C3 and the bond between C4 and C5, respectively. A BE B. ZZ EZ D.ZE 302, For the structure below, give the geometric assignment for the bond between Cl and C2 and the bond between CS and C6, respectively. clan 2 Ne 3 a A. neither, E B. neither, Z CBZ D. Z,E 303. Alkenes are more acidic than alkanes. What is the best explanation for this trend? ‘A. The sigma bond present in alkenes helps to stabilize the negative charge generated when a proton is removed, 1B. The sigma bond present in alkenes helps to destabilize the negative charge generated when a ‘proton is removed, . The pi bond present in alkenes helps to stabilize the negative charge generated when a proton is removed. D. The pi bond present in alkenes helps to destabilize the negative charge generated when a proton is removed. 304, Given that L-butene has a boiling point of -6°C and 1- hexene has a boiling point of 64°C, what isthe boiling point of I-pentene? A. 10°C B. -6C . c. 30°C Db. 74°C 34 305, Given that benzene molecules with symmetry pack better in a crystalline structure raising the melting point, which of the following would have the greatest melting point? A. o-dichlorobenzene B. p-dichlorobenzene C. m-dichlorobenzene D. All tree would have similar melting point. 306. What is the best explanation for the fact that I-butene has a boiling point of -6.3°C and I-butyne has a boiling, point of 81°C? ‘A. L-Butene has a higher molecular weight than 1- butyne. B. 1-Botyne has a higher molecular weight than 1- butene. CC. L-Butyne is more polar than I-butene. D. {-Butene is more polar than I-butene. 307. Given that I-butyne has a boiling point of 8.1°C, what is the phase of propyne at room temperature and 1 atm pressure? AL gas B. liquid ©. solid D. supereritial fluid 308. Which of the following carbocations is the most stable? = c Hs CH uc-GO 6 CHS H B. 1H, be nofd “ufo i i 309. Which of the following is the least stable cation? Copyright © 2006 EXAMKRACKERS, Inc.310, Which of the following is an electron withdrawing group when attached to benzene? A. CH; BC c. O8 D. OCH; 311. Which of the following is an electron donating group when attached to benzene? A. NO: B. CO:H ca D. OCH; 312, What would be the resulting product if one mole of 3- hhexyne were hydrogenated with 1 mole of H;? A. hexane B. cis-3-hexene C. trans-3-hexene D. L-hexene 313, What would be the resulting product if one mole of 3- hhexyne were hydrogenated with an excess of H:? Ay hexane B. cis-3-hexene C. trans-3-hexene D. L-hexene 314, What conditions are required for hydrogenation of an alkene? ‘A. metal catalyst 1B. metal catalyst and high temperatures CC. metal catalyst and low temperatures D._ low temperatures and high pressures M15. Which of the following can be used to catalyze hydrogenation? LN i Pt m. A. Lonly B. Tonly C. Land I D. Iand I 16. How many moles of hydrogen are required to convert a ‘mole of pentyne to pentane? A. B. c D. Copyright © 2006 EXAMKRACKERS, Inc. Alkanes, Alcohols, and Substitutions ‘A lower heat of hydrogenation indicates a more stable alkene. Refer to the table below to answer questions 317- 322, ‘Molar heat Alkene ‘of hydrogenation ethylene 137k propene 126 KI —_1-butene 127k is-2-butene 120k ‘rans-2-butene GK cis-2-pentene 120kF ‘2-methyl-2-butene 113k 2,3-dimethyl-2-butene wig | 317. Which of the following alkenes is the most stable? ‘A. ethylene B. cis-2-butene C. 2-mothyl-2-butene D. 2,3-dimethyl-2-butene 318. Which of the following alkenes is the least stable? A. ethylene B. cis-2-butene C trans-2-butene D. 2,3-dimethyl-2-butene 319, What would be the predicted molar heat of hydrogenation for trans-2-pentene? AL Lid B. 1161 c. 12010 D. 124K 320, The data in the table supports which of the following statements, A. Stability of an alkene increases with molecular weight. B. Stability of an alkene decreases with molecular . Stability of an alkene increases with substitution on the alkene carbons. D. Stability of an alkene decreases with substitution on the alkene carbons. 381001 Questions in MCAT Organic Chemistry 321. Why does cis-2-butene have a molar heat of hydrogenation of 120 ki, while érans-2-butene has one of 16 KI? A. The cis isomer is more stable than the trans due to steric interactions. B. The trans isomer is more stable than the cis due to steric interactions. C. The double bond in the trans isomer has more potential energy. D. Trans-2-butene has a higher molecular weight. 322, Why does cis-44-dimethyl-2-pentene have a heat of hydrogenation that is 4 keals greater than trans-4,4- dimethyl-2-pentene, while the heat of hydrogenation of cis-2-pentene is only 1 kcal greater than that of trans-2- ppentene? A. Cis and trans isomers always differ by 1 keal of energy. B. Cis isomers always have greater heats of hydrogenation than trans isomers. C. Because 4,4-dimethyl2-pentene has bulkier groups, the steric effect is greater leading to a smaller difference in energy between the isomers. D. Because 4,4-dimethyl-2-pentene has bulkier groups, the steric effect is greater leading to a greater difference in energy between the isomers. 323. To completely hydrogenate benzene to cyclohexane requires H:, an Rh catalyst, and 1000 psi pressure at 100°C. Why are these conditions required? ‘A. The double bonds in benzene are more reactive than a typical alkene B. The double bonds in benzene are less reactive than atypical alkene. C. The double bonds in benzene have the same reactivity as atypical alkene. D. Hydrogenation produces an aromatic compound. 324, An alkene that has the formula CigFhis is hydrogenated ‘with an excess of H>, and the resulting alkane has the formula CioHm. How many double bonds were present in the original alkene? AO Bd C2 D3 325. An alkene that has the formula C,H: requires 3 moles of Hy per mole of alkene to form a saturated alkane, “What is the formula of the alkane? A Cis B. Cie C. His D. Cie 326, 32. 328, 329, 330. 331. 332, Oil of celery is an alkene with the molecular formula CisHlas. After hydrogenation with an excess of Hp the ‘molecular formula is CysH.. What can be concluded about the structure of oil of celery? ‘A. Oil of celery has two double bonds and two rings, B. Oil of celery has four double bonds and no rings. C. Oil of celery has no double bonds and four rings. D. Nothing can be determined about the structure. ‘What does the letter E represent in the E1 notation? A. elimination B. excess of reagent C. energy D. the "eno" in alkene ‘What does the number 1 represent in the E1 notation? A. number of mechanistic steps B. order of the rate law CC. number of bonds formed D. number of bonds broken In an El reaction, what are the bond conversions in the major product?” A. 2 sigma bonds are converted to 1 pi bond, B. 1 sigma bond is converted into 2 pi bonds. C. 1 pi bond is converted into 2 sigma bonds. D. 2pi bonds are converted into 1 sigma bond. In electrophilic addition to an alkene, what are the bond ‘conversions in the major product? ‘A. 2 sigma bonds are converted to 1 pi bond, B. 1 sigma bond is converted into 2 pi bonds. C. 1 pibond is converted into 2 sigma bonds. D. 2pibonds are converted into 1 sigma bond. ‘Which of the following is an electrophile? A. OF B. NES cH D. CH, ‘Why does benzene undergo substitution reactions rather than addition reactions? ‘A. Benzene does not have a double bond. B. Ifbenzene underwent an addition reaction, the aromaticity of the ring would be disrupted. C. When benzene undergoes a substitution reaction, the aromaticty is disrupted. D._ Benzene is an alkene. Copyright © 2006 EXAMKRACKERS, Inc.333. If 2-methyl-2-butanol is heated with sulfuric acid, what are the resulting products? 1. 2-methyl-1-butene TI, 2-methyl-2-butene IH, 3-methy!-I-butene A. Tonly B. Monly . Tand Il only D. 1,1, and I 334. What is the purpose of the sulfuric acid in the reaction discussed in question 3337 A. source of sulfate ion BL catalyst ©. control pH D. source of hydroxide ions 135. What is the product when 2-methyl-2-pentene is reacted with HBr? A. 2-bromo-2-methylpentane B. 3-bromo-2-methylpentane CC. 2-bromo-pentane D. 2-bromo-2-methylpentene 36. If 2-butanol is heated with sulfuric acid, what are the resulting products? L 1-butene U. cis-2-butene TIL trans-2-butene A. Tonly B. Monly . and Il only D. 1,0, and I 37. Which of the following will oxidize an alkene? A. concentrated H” and heat B. H, with Ni C. Osand (CHS D. O;and heat '8. Which of the following will reduce an alkyne? A. concentrated Hand heat B. Hi, with Ni C. Os and (CH,).S D. Opand heat 9. Which of the following will promote hydration of an alkene to an alcohol? AL concentrated H” and heat B. Hy with Ni C. Os and (CH,),S D. dilute acid and cold conditions 37 Alkanes, Alcohols, and Substitutions 340. Which of the following alkenes would react the fastest with HBr? ‘A. ethene B. L-butene C. 2-butene D. 2-methyl-2-butene 341. Which of the following compounds would be most reactive when Cl, and AICI, are added? © “Om wo On" 342, Which of the following compounds would be least reactive when Br, and FeBr, are added? A GQ © “O-= wn On 343, Which of the following is not a possible product of an ozonolysis? I. aldehyde ketone aleohol only only Tand Il only 1,1, and It CHy HC pe Br ee Copyright © 2006 EXAMKRACKERS, Inc.1001 Questions in MCAT Organic Chemistry ‘344, What isthe produet ofthe following reaction? tute HT and cold . i) aM. Om Se . : 346, What is the product of the following reaction? wet) : a f Quon So C-con (eon "Cpe d . 38 ‘347, What is the product of the following reaction? He oC) FB Br ‘OH Br 348, What is the product of the following reaction? a 349, What is the purpose of FeBr; in the aromatic substitution of Br? A. to provide an activated electrophile B. to provide an activated nucleophile C. tobea base D. to terminate the reaction Myrcene, a terpene found in bayberry is shown below. Use this structure to answer questions 350 - 353. ~~ syroene 350, Which of the double bonds in myrcene is the most stable? The bond labeled 1. ‘The bond labeled 2. ". The bond labeled 3. 1. All the bonds have the same stability. Copyright © 2006 EXAMKRACKERS, Inc.351. How many moles of H, would be required to hydrogenate myrcene to a saturated alkane? Sore 352. How many geometric isomers of myrcene exist? 383, Which of the following is not a product of the complete ozonolysis of mycrene? Ao @ 7 AL a avK yn oe myo ° Oe 354. Which of the following alcohols would undergo dehydration by an E1 mechanism the fastest? A on yoo Ke Nan Refer to the structure of cholesterol to answer questions 355, Alkanes, Alcohols, and Substitutions 355. What reagents could be used to covert cholesterol to the following structure? A. concentrated Ht and heat B. H, with Ni C. 0; and (CH4),S D. dilute acid and cold conditions 356. What reagents could be used to covert cholesterol to the following structure? HO" On ‘A. concentrated H* and heat 1B, Hp with Ni C. Os and (CHs),S dilute acid and cold conditions P 357. What reagents could be used to covert cholesterol to the following structure? HC concentrated H’ and heat 2H, with Ni 0, and (CH3),S dilute acid and cold conditions pOEP 39 Copyright © 2006 EXAMKRACKERS, Inc.1001 Questions in MCAT Organic Chemistry 358, What would be the product when cholesterol is reacted with Br; in the presence of CHj,COOH? ‘A terpene that is contained in the oil of citronella is o- famesene. Refer to the structure of a-famesene to answer questions 359-365 2 IS 1 4 ocfarnesene 359, How many moles of Hy would be required to produce a saturated alkane from o-famesene? Tou B.4 : - C8 D. 16 40 ‘360. What reaction conditions could be used to produce acetone from o-famesene? ‘A. H,SO, and heat B. HBr C, sand (CH)2S D. dilute acid and cold conditions 361. If c-farnesene was oxidized via ozonolysis such that all ‘the double bonds reacted, how many products would result? 7 A. 2 products B. 3 products C. 4 products D. 5 products 362. If o-famesene is reacted with an excess of HBr, what ‘would be the product? A « 1 Br Br Br Br Bi ‘Br Br B. 7 D. A Br B Br ‘br Br Br 363, In the reaction of a-farnesene with excess HBr, which double bond would be the slowest to react?” |A; The bond labeled 1. B. The bond labeled 2. C. The bond labeled 3. D. The bond labeled 4. Copyright © 2006 EXAMKRACKERS, Inc.364. What would be the product if o-famesene was completely hydrated? A c ou pr OH Hi He ‘oH on B D. Ht ou OH HO ‘oH on 365. The hydration of c-famesene is an example of a(n) ‘A. radical reaction B. combustion reaction CC. electrophilic addition D. aromatic substitution 66. Why is the following reaction impractical to use on an industrial scale to produce the given product? 804 ON eee eee ee Done CC. Alkenes cannot be formed from an alcohol. D. The alcohol is not available in large quantities. 67. Which of the following structures is a possible product, of the hydrogenation of the alkene shown below using @ i catalyst? H; (HCH o VCH c B. D. HG, PHC HG. CFCs “cH; CH; A “Alkanes, Alcohols, and Substitutions 368. How many possible alkane products are there for the hydrogenation of the alkene shown in the questions 369, Dehydrohalogenation undergoes an E1_mechanism similar to dehydration, What are the possible products if 3-bromohexane undergoes dehydrobalogenation to form an alkene? ‘ I. cis-3-hexnene Il, trans-3-hexene IIL. cis-2-hexene A. Tonly B. Ilonly C. Tand Monly D. J,H,and 370, When HBr is reacted with an alkene in the presence of peroxide, the anti-Markovnikov product results, What would be the product if 2-isopropyl-2-butene is reacted with HBr in the presence of hydrogen peroxide? A. 2-bromo-3-isopropylbulane B. 2-bromo-2-isopropylbutane C. 2-bromo-2-isopropylbutene D. 2isopropylbutane 371. Given that hydrogen peroxide is required to initiate the reaction and that the product is anit-Markovnikov, the reaction in question 370 is a(n): ‘A. radical reaction B. combustion reaction C. electrophilic addition D. aromatic subsitituion 372. Hydroboration and oxidation of an alkene result in an anti-Markovnikov addition of a hydroxyl group. What is the product of the hydroboration and oxidation of 3,4-dimethyl-3pentene? A. 3,4-dimethyl-2-pentanol B. 3-isopropyi-2-butanol CC. 2,3-dimethy1-4-pentanol D. 2isopropylbutane Copyright © 2006 EXAMKRACKERS, Inc1001 Questions in MCAT Organic Chemistry 313. The reaction of vinyl chloride to form poly (vinyl chloride), PVC, is show below. What type of reaction is this polymerization? ‘A. radical reaction B. combustion reaction C. electrophilic addition D. aromatic substitution 374, What is the product when Ck, reacts with cyclopentene? A c Al %, , B. Dv. Ch fel B 375, What is the product when Br, reacts with cyclohexene? a Cho H f f Ct, : Br, Br t 376. Which product would not form when 4-methyl-2- pentene is reacted with HBr? a2 2 377. Which of the following is (are) possible products when 2-butene is reacted with HCI? 1. 2R-chlorobutane II, 28-chlorobutane 2R, 28-dichlorobutane A. Tonly B. Ionly C. Land If only D. 1,01,and 0 ‘The results of the reaction of 2-pentene with potassium ethoxide and ethanol are shown below. Refer to the reaction to answer question 378-380. nos IN tt Am 378. Why is 55% of the product 2-pentene compared to 25% of the product being 1-pentene? ‘A. 2-pentene is more reactive than I-pentene. B. L-pentene is more reactive than 2-pentene. C. 2-pentene is more thermodynamically stable than |-pentene. | -pentene is more thermodynamically stable than 2-pentene. D. 379. Why is there approximately 3 times more trans-2- pentene than cis-2-pentene? |A. There is more steric hindrance in the trans isomer, 'B. There is more steric hindrance in the cis isomer. C. The eis isomer is the more thermodynamically stable isomer. D. The reaction goes by a E2 mechanism. 380, The formation of pentenes from 2-bromopentane is a(n) A. hydration B. dehydration CC. debydrohalogenation D. hydrogenation Copyright © 2006 EXAMKRACKERS, Inc.‘The reaction of 1,3-butadiene with HBr is shown below. At 40°C the major product is the 1,4-addition product; however, sat -80°C the major product is the 1,2-addition product. Use this information and the reaction below to answer questions 381-386, By ie +5, 1,2-addition —_1,4-addition AZ 381. Which product is more thermodynamically stable? A. 1,2-addition product B. 1,¢-addition product C. The products have the same stability. D. The relative stability cannot be determined. 382, Why are two products formed? ‘A. There are two double bonds present. B. The carbocation intermediate allows delocalization of the second double bond. C._The fact that the carbocation is planar allows attack from both sides of the plane. D. There are 2 moles of HBr. 383. Which of the two products has a lower activation energy for formation? A. 1,2-addition product B. 1/4-addition product CC. The products have the same activation energy. D. The relative activation energy cannot be determined. 184, How many products that are stereoisomers would form in the reaction of 1,3-butadiene with one mole of Br,? AO Bol C2 D4 '85, How many products that are structural isomers would. form in the acid hydration of 1,3-butadiene? AO yom 1 2 4 86. How many moles of acetone form in the ozonolysis of ‘one mole of 1,3-butadiene? AO Sor 1 2 4 “Alkanes, Alcohols, and Substitutions "Friedel-Crafts acylation is a reaction of an acid chloride with an activated aryl ring. Use the example reaction shown blow to answer questions 387-390. m g wa. 1 a‘ cnais ‘OH =o cHcH; = §=° CH;CHy 387. The Friedel-Crafts acylation is a(n) » ‘A substitution reaction B. elimination reaction C. addition reaction D. redox reaction 388. Which of the following aryl compounds would be most reactive with an acid chtoride to form an aryl ketone? Oo G Ovo Cpr: Gp ne A 389. Which of the following aryl compounds would give only one aryl ketone when reacted with an acid chloride? A. ‘OCH HCO’ 390, Wher reacted in excess acid chloride, toulene only produces one ketyl group on each aryl ring. What is the best explanation for this observation? ‘A. steric hinderance B. The ketyl group is ring activating, C. The ketyl group is ring deactivating. D. xesonance stabilization ‘Copyright © 2006 EXAMKRACKERS, Inc.1001 Questions in MCAT Organic Chemistry Methyl benzoate is converted to methyl nitrobenzoate inthe presence of HINOs and H;SO,. Use the reaction shown below to answer questions 391 = 393, OH 00H HNO = TSO, NO; 391, The acid group on the benzene ring is ‘A. meta directing and deactivating B. ortho, para directing and deactivating . ortho, para directing and activating D. meta directing and activating O Om Om 1BN@ 393. If phenol was reacted with HNO, in the place of benzoic acid, how many products would result? AO Bd G2 Di) Alcohols and Substitutions 394, Ina Syl reaction, what are the bond conversions? ‘A. 2 sigma bonds are converted to 1 pi bond, B. 1 sigma bond is converted into 2 pi bonds. C. 1 pi bond is exchanged for 1 sigma bond. D. 1 sigma bond is exchanged for I sigma bond. 395. Inn Sy2 reaction, what are the bond conversions? A. 2 sigma bonds are converted to I pi bond, [B. 1 sigma bond is converted into 2 pi bonds. C. 1 pibond is exchanged for 1 sigma bond. D. 1 sigma bond is exchanged for I sigma bond. 396, The "S" in $32 is an abbreviation for what? ‘A. single step reaction B, substitution CC. suspension D. separation 44 397. What is tre about a Sy! reaction? I. A carbocation intermediate is formed. TL. The rate determining step is bimolecular. ‘The mechanism has two steps. A. Lonly B. only . Land IIL only D. LU, and 01 398, What is true about an $2 reaction? I. A carbocation intermediate is formed. TL, The rate determing step is bimolecular. IIL. The mechanism has two steps As Lonly B. only C. Land I only D. 1,11, and I 399, The rate of a Sy? reaction depends on: ‘A. the concentration of the nucleophile only. B. the concentration of the electrophile only. C. the concentration of both the nucleophile and the clectrophile D. neither the concentration of the nucleophile nor the clectrophile. 400, The rate of a Syl reaction depends on: A. the concentration of the nucleophile only. B. the concentration of the electrophile only. C. the concentration of both the nucleophile and the electrophile. D. neither the concentration of the nucleophile nor the clectrophile. 401. How does the rate of step I in the mechanism shown below compare tothe rate of step I? R Wet R StpT RK —> R-1® + xO R R R Step ve RSG —™ RC epi RGD C-Na R R ‘A. Step Lis faster than step I 1B. Step Is faster than step L C. Step I and step I happen at the same rat. D. The relationship cannot be determined, Copyright © 2006 EXAMKRACKERS, Inc.02. Which of the following is the best nucleophile? A. COp B. HO C. CHO D. CH,OH 03, Which of the following is the best nucleophile? a B. HO. c. NH D. CHCOOH (04, Which of the following is the best leaving group? 06. A nucleophile is: ‘A. aLewis acid. B. a Lewis base C. clectron deficient . D. an oxidizing agent. 07, Which of the following alkyl halogens would react the fastest in a reaction with sodium hydroxide? A. butyl fuoride B. thutyl chloride C. t-butyl bromide D. tbutyl iodide 08, Which of the following reactions is most likely to proceed by a Sy 2 mechanism? A. L-bromopropane with sodium hydroxide B. 2-bromo-2-methyl pentane with HBr CC. 2-bromo-3-methyl pentane with methanol D. t-butyl iodide with ethanol 09, Which of the following reactions is most likely to proceed by a Sy 1 mechanism? A. L-bromopropane with sodium hydroxide B. 2-bromo-4-methyl pentane with HBr CC. 1-bromo-3-methyl pentane with HCL D. t-butyl iodide with ethanol Alkanes, Alcohols, and Substitutions 410, Which ofthe following alcohols would have the lowest boiling point? ‘A. ethanol B. L-butanol CC. 2-methyl-t-propano! D. L-pentanol 411, Which of the following alcohols would have the highest boiling point? A. ethanol B. 1-butanol , C. 2-methyl-1-propanol D. 1-pentanol 412, Given that the boiling point for 1-propanol is 97°C and the boiling point of I-pentanol is 138°C, what is the boiling point of 1-butanol? A. 100°C. B. 118°C. c. 138°C D. 150°C. 413, Given that the boiling point for 3-methyt-1-butanol is 132°C and the boiling point of I-pentanol is 138°C, ‘what isthe boiling point of I-hexanol? A. 100°C B. 132°C c. 138°C D. 156°C 414, Which of the following would have the highest boiling point? A. 1-butanol B. butane C. L-butene D. 1-butyne 415, Given that heptane has a boiling point of 98°C, what phase will heptanol be in at 98°C? AL gas B. liquid C. solid D. supercritical uid 416, Which of the following has the highest boiling point? A. dimethyl ether B. diethyl ether CC. othyl methyl ether D. diisopropyl ether 45 Copyright © 2006 EXAMKRACKERS, Inc.1001 Questions in MCAT Organic Chemistry 417, Which of the following has the highest boiling point? ‘A. ethane B. diethyl ether C. ethene D. ethanol 418, Cyclohexanol is a solid in a cool room, while cyclohexane is a liquid, what is the best explanation for the different states? ‘A. Cyclohexanol has greater London Dispersion forces than cyclohexane, B. Cyclohexanol has weaker London Dispersion forces than cyclohexane, C. Cyclohexanol has hydrogen bonding and cyclohexane does not. D. Cyclohexane has hydrogen bonding and cyclohexanol does not. 419. Dimethyl ether has a boiling point of -25°C and Propane has a boiling point of -42°C. Why does dimethyl ether have a greater boiling point? A. Dimethyl ether has hydrogen bonding and propane does not. B. Propane has a greater molecular weight than dimethyl ether. C. Dimethyl ether has a smaller dipole moment than Propane, D. Dimethyl ether has a larger dipole moment than Propane, 420. Which of the following would be more soluble in water? A. L-butanol B. butane C. L-butene D. L-butyne 421, Which of the following would be more soluble in water? AL diethyl ether B. ethene C. ethyne D. ethane 422. The word miscible means that one solvent forms homogenous solution when inixed with another solvent in any amount. Which of the following would be miscible with water? A. ethanol B. cyclohexane C. 2-butene D. hexane 3, 424, 2s. 26, 47. 428, 29, ‘Which of the following would be miscible with water? A. L-propanol B. phenol C. 4-methyl-1-octanol D. 2-methyl-2-propanol Which of the following will have the most acidic proton? A. pentane B. 3-pentene C. L-pentyne D. 1-pentanol ‘What is 2-methyl-2-butanol? A. primary alcohol B. secondary alcohol C. tertiary alcobol D. quaternary alcohol Which of the following will have the most acidic proton? ‘A. phenol B. ethanol C. t-butyl alcohol D. 2-methyl-I-hexanol Grignard reactions require a solvent that is polar but that does not contain an acidie proton. Which of the following would be the best solvent? A. hexane B. ethanol CC. acetic acid D. diethyl ether In the following reaction of ethanol with para- toluenesulfonylchloride, ethanol is a(n): g CH3CH.OH + ap) g wencof cn nucleophile electrophile radical D. reducing agent app ‘The reaction of ethanol with —_para- toluenesulfonylchloride, shown in question 428, is a: ‘A. nucleophilic substitution B. nucleophilic addition C. reductive elimination D. synaddition Copyright © 2006 EXAMKRACKERS, Inc.480. Which of the following will convert a secondary alcohol to ketone? A. LiAlH, B. PBr C. K,Cr0, D. Osand (CHS 431. Which of the following will convert a primary alcohol toan aldehyde? A. LiAlH, B. dilute cold KMn0, ©. K,cr0, D. Os and (CH).8 432, Which of the following will convert a primary alcoho! ‘to an carboxylic acid? A. LiAlH, B. dilute cold KMnO, CC. K,Cr0, D. Os and (CH),S 433. The reaction of 3-methyl-(S)3-hexanol with HBr produces an optically inactive solution. What is the Dest explanation for this result? ‘A. Tho product does not have a chiral carbon B. The product is meso. C. The reaction produces a racemic mixture of products D._ All alkyl halide solutions ae optically inactive. ‘The Lucas test is used to determine whether an alcohol is primary, secondary, or tertiary based on the rate of reaction with HCl and ZnCh. Use the table below to answer questions 434 - 442. Class of | ‘Approximate time | Mechanism alechot ‘of reaction Primary > 6 minutes 52 Secondary 1-5 minutes Sil Tertiary <1 minutes Sul 434, A. scientist wanted to increase the initial rate of reaction of t-butyl alcohol with HC1 and ZnCl. Which of the following will speed up this reaction? A. Increase the concentration of t-butyl alcohol B. Increase the concentration of HCI C. Increase the concentration of ZnCl, D. Decrease the temperature of the reaction 435, Which of the following alcohols will reacted the slowest? A. L-pentanol, B. 2-methyl C. 2-methyl D. 2-hexanol * Alkanes, Alcohols, and Substitutions 436, Why do tertiary alcohols react faster than secondary alcohols with HCI and ZnCl? A. Secondary alcohols are less hindered. B. Tertiary alcohols are less hindered C. Secondary alcohols form more stable carbocations. D. Tertiary alcohols form more stable carbocations. 437, What isthe purpose of the ZnCl, in the Lucas reagent? |A. To activate the alcohol and make it better leaving group B, To provide a source of chloride ions to complete the substitution * C. To activate the chloride ion from HCI and make it abetter nucleophile D. To activate the chloride ion from HCI and make it better electrophile 438, Which of the following would be true of a reaction of 2-ethyl-(2R)-pentanol with the Lucas reagent? |A. The product would be optically active. BB. Increasing the concentration of HCI would increase ‘the rate of reaction, C. 2-ethyl-(2R)-pentanol would react slower than pentanol, D. A carbocation is formed during the reaction. 439. What would be the product of a reaction of 1-propanol with the Lucas reagent? A. I-chloropropane B. 2-chloro-1-propanol CC. A-propene D. propane 440, An unknown alcohol is reacted with the Lucas reagent and the reaction is completed in 45 seconds. ‘The unknown alcohol is a(n): A tertiary aleohol B. secondary alcohol C. primary alcohol D. The type of alcohol cannot be determined. 441. Which of the following would be true of a reaction of the unknown alcohol in question 440 with the Lucas reagent? ‘A. The product would be optically active, [B. Increasing the concentration of HCI would increase the rate of reaction. C Increasing the concentration of the unknown alcohol would increase the rate of reaction, D. Propanol would react ata faster rate with the Lucas reagent. Copyright © 2006 EXAMKRACKERS, Inc.1001 Questions in MCAT Organic Chemistry 442, An unknown alcohol is reacted with the Lucas reagent ad the reaction is complete in ® minutes. ‘The unknown alcohol is ‘A. L-butanol B. 2-pentanol C,.3-methyl-3-hexanal D. cyclohexanol 443. Which of the following reagents will convert 1-butanol to I-bromobutane? A. PBry B Bn C. LiAIH, D. KMn0, 444, Which of the following reagents will convert diethyl ether to ethanol and chloroethane? A. HEI B Ch C. SOCh, D. AICI, 445. Which of the following reagents will convert 3- hexanone to 3-hexanol? A. NaBH, B. H,Cr0, Cc. KMn0, D. AICI, 446, Why does the presence of an acid facilitate the substitution of an alcohol? ‘A. The acid converts the OH group to a good nucleophile B. The acid converts the OH group to good clectrophile. C. The acid converts the OH group to a good leaving sroup. D. The acid neutralizes the bases in solution. 4447. What isthe product ofthe following reaction? Anja u 448, Citronellol is converted to citronellal by PCC (Pyridinium chloroctromate) according the reaction shown below. PCC is a(n): Poc ‘OH cnalumyee (He ]6 citronellol cintronellal A. oxidizing agent B. reducing agent C. acid D. base 449. Which of the following could be used to convert the cintronellal back to cintronello! (question 448)? Ay PBry B. Br, C. LAI, D. KMn0, Refer to the structure of triphenylmethanol shown below to answer questions 450 - 454, (Ole 450. Which of the following reagents would form triphenylmethy] bromide? A. HBrin dilute acetic acid B. HBrin sodium hydroxide C. By D. CHisBr in methanol Copyright © 2006 EXAMKRACKERS, Inc.{51. How would the rate of triphenylmethy! alcohol ‘compare to the rate of butyl alcohol if the same reaction conditions used in the bromination reaction described in question 450 were used? ‘A. t-Butylaleohol would have a faster rate. B. Triphenylmethyl alcohol would have a fester rate, CC. The rates would be the same. D. The relationship of the rates cannot be determined. . By what mechanism is triphenylmethyl bromide formed {n the reaction described in question 450? AL Sy2 B. Sxl Cc. EL D. E2 When triphenylmethanol is dissolved in concentrated sulfuric acid and transferred to a cold solution of ‘methanol, what isthe structure of the solid that forms? A c CH; (O}eo (Ge : : > 3 3 HCO 153, 1454, In the reaction in question 453, methanol is a(n) A. electophile B. nucleophile C. reducing agent D. ether The structure of testosterone, the male sex hormone, is thown below. Refer to the structure to answer questions $55-457. OH testosterone 49 ‘Alkanes, Alcohols, and Substitutions 455, Which of the reagents will give the product shown below when reacted with testosterone?, OH HO A. LiAlHy B. PBr, C._K,Cr0, D. Oy and (CH:)2S . 456. Which of the reagents will give the product shown below when reacted with testosterone? A. LiAIH, B. PBry C. K,Cr0, D. Os and (CH:)2S 457, Why is HBr a poor choice as a reagent to do an electrophilic addition of bromine to the double bond in testosterone? 'A. The bromine placement on the double bond would not be seletive fora specific carbon in the double bond. B, The HBr would also promote a substitution at the alcohol position C. HBr does not react with alkenes D. The reaction would be too slow. 458, Whon I-chlorobutane and I-bromobutane are reacted with sodium iodide in acetone, the appearance of a precipitate indicates the completion of the reaction. ‘What i the best explanation forthe fact that precipitate appears in the reaction of I-bromobutane first? A. Cis a better leaving group than Br B._ Br isa better leaving group than CI. C. Cisabetter mucleophile than Br. D. Br is a better mcleophile than Cr 459, By what mechanism do the reactions described in question 458 proceed? AL 8x2 B. Syl CEL D. E2 Copyright © 2006 EXAMKRACKERS, Inc.1001 Questions in MCAT Organic Chemistry 460, The rate of precipitate formation increases for the reaction of I-bromobutane with Nal as the concentration of Nal is increased. When the concentration of Nal is increased in the reaction of 2- cchloro-2-methylpropane, no rate change is observed, ‘Why is there a change in rate in the frst case and not in the second? A. Cl'is a better leaving group than Br B. Br isa better leaving group than CI. C. L-bromobutane proceeds via a $y2 mechanism, while 2-chloro-2-methylpropane proceeds via a Syl mechanism. 1-bromobutane proceeds via a Sy mechanism, while 2-chloro-2-methylpropane proceeds via a Sy2. mechanism, 461. What would be the product when NaBr is reacted (S)-1- ‘iodo-1-ethanol? A G ‘Hy BAY-OH Br H Re H“Dor CH; fe he he ae 462, Kalas frm le acd incl ead ae foluion ts eas" ees ves wheat ced een eae solution. What would be the product if cold dilute KMn0, is reacted with 3-cyclohexene-1-ol? - OH i OH wi, AL, 3 D. OH JOS mah, on 463. 465. 46. 467. Given the information in question 462, what would be the product if warm concentrated KMnO, is reacted with 3-cyclohexene--ol? ‘2 ,OH 2 ,OH Co oH «OF C Co B OH 9 He PS hen cs 0 0 1. When (2R)-bromobutane is reacted with Nal the product is optically active. What is the mechanism for ‘the reaction? AL Sy2 B. Syl CEL D. £2 Dehydration of 2-hexanol to form 2-hexene and 1- hhexene proceeds by what mechanism? AL 8x2 B. Syl © EL D. ER In @ portable breath tester, fuel cells catalyze the ‘oxidation of ethanol by oxygen, What is the product of this reaction? A. ethanol B. L-hydroxy-ethanol CC. 2-hydroxy-ethanol D. ethanal Aleohols dry human skin as they evaporate from the skin’s surface, Why does ethanol have a greater drying, effect than isopropanol? ‘A Ethanol has a higher boiling point than isopropanol. B. Ethanol has a lower boiling point than isopropanol. C. Ethanol hydrogen bonds more strongly with skin ‘han isopropanol. ._Isopropanol hydrogen bonds more strongly with skin than ethanol Copyright © 2006 EXAMKRACKERS, Inc.3, Equal amounts of ammonium chloride (0.25 moles) and ammonium bromide (0.25 moles) are dissolved in an acidic solution. After the salts have dissolved 0.20 moles of I-pentanol is added to the solution. What is, the product of this reaction? A. 1-pentanol B. L-bromopentane €. -chloropentane . equal amounts of I-bromopentane and 1- chloropentane ). Why must the solution be acidic in the reaction described in question 4687 ‘A. The acid makes the OFT group into a better leaving group. B. The acid makes the OH group into a better nucleophile. C.. The acid makes Br or Cl into better leaving groups. D. The acid makes Br or Cl into better nucleophiles. ), By what mechanism do the reactions described in question 468 proceed? AL Sy2 B. Syl c. EL D. 2 L. Methyl mereaptan (CH;SH) is similar to: A. aprimary alcohol. B. a secondary alcohol. C. atertiary alcohol D. a quatemary aleobol. 2. What would be the product of the reaction shown below? —~ KMn04 $—_— aren “yee” DAS 51 _Alkanes, Alcohols, and Substitutions ‘The reaction of (2R)-iodobutane to form 2-methoxybutane proceeds by an Sy1 mechanism in methanol. However, in the presence of the methoxide ion (CHO) the mechanism is Sy2. Use this information to answer questions 473 — 479, 473. Why does the mechanism change when methanol is, replaced by methoxide? Iodide is a poor leaving group. Todide is a good leaving group. Methanol is a weak nucleophile and methoxide is a strong nucleophile. Methanol is a strong nucleophile and methoxide is weak nucleophile . S ORP 474, Given the above information, what would be the product of the reaction of (2R)-iodobutane with methanol? I. QR)-methoxybutane Il, (28)-methoxybutane IL butane Tonly Tonly Tand Ionly 1,0, and pomp 475, Given the above information, what would be the product of the reaction of (2R)-iodobutane with the methoxide ion? 1. QR)-methoxybutane IL. (28}-methoxybutane ML. butane A. Tonly B. only C. Land only D. 1,1, and I 476, Which of the following alkanes would react faster than (@R}iodobutane with methanol to form 2- ‘methoxybutane? ‘A. I-iodobutane B. 2-bromobutane CC. 2-iodopropane D. 2-iodo-2-methyIbutane 477. Which of the following alkanes would react faster than @R)-iodobutane with the methoxide ion to form 2 methoxybutane? A. J-iodobutane B. 2-bromobutane C. Q-iodopropane D. 2-iodo-2-methylbutane Copyright © 2006 EXAMKRACKERS, Inc.1001 Questions in MCAT Organic Chemistry 478. Which of the following statements regarding the reaction of (2R)-iodobutane with methanol is NOT true? ‘A. ‘The reaction proceeds with complete inversion of the stereochemistry. B. The product solution will not be optically active, C. Increasing the concentration of (2R)-iodobutane will increase the reaction rate. . Iodide isa good leaving group, 479, Which of the following statements regarding the reaction of (2R)-iodobutane with the methoxide ion is NOT true? A. The reaction proceeds with complete inversion of the stereochemistry. 1B. The product solution will not be optically active. C. Increasing the concentration of (2R)-iodobutane will increase the reaction rat, D. Iodide is a good leaving group. 480. The reaction of 1-chlorobutane with a boiling sodium hydroxide solution is a two phase reaction. When the two phase reaction is complete, why does a homogenous solution result? A. The reaction is exothermic. B. The second solution is boiled off C. The haloalkane product is soluble in water. D. The alcohol product is soluble in water. 481, Methanol is made commercially by the hydrogenation of carbon monoxide. The reaction is a(n): A. oxidation B. reduction C. elimination D. substitution Shown below is the structure of sodium cholate which is a detergent used inthe purification of proteins. Refer tothe structure to answer questions 482 485. co? COO Nf ou cd 482. Which of the three hydroxyl carbons would be most likely to participate in a $32 reaction? ‘A. The carbon labeled 1 B. The carbon labeled 2. C. The carbon labeled 3, D. Alll three would have the same reactivity 52 483. Which of the following reagents would convert sodiur cholate to the product shown below? coP A. LiAI, B. PBr C. KC, D. Oy and (CH,),S 484. Which of the carbons in sodium cholate has the highes! oxidation state? ‘A. The carbon labeled 1 B. The carbon labeled 3 C. The carbon labeled 4 D. The carbon labeled 5 485. Which of the following statements is NOT true about sodium cholate? A. Sodium cholate is optically active, B. The hydroxy groups can be oxidized to aldehydes. C. Sodium cholate is soluble in water. D. Sodium cholate is not a planar molecule. 486. What is the product when glyceraldehyde (shown below) is reacted with an excess of K;CrO,? aH Eon x08 glyceraldehyde A “ eH who eben ou oy B ». Q_oH ous Veemeare ts ae oy oH Copyright © 2006 EXAMKRACKERS, Inc,afer to the scheme below to answer questions 487 — 496, Br H DO: ‘HBr 3 a = 2)(CHDS KaCr207 LiAlH,| c B 1. How does the oxidation state of product B compare to the oxidation state of product A? ‘A. The oxidation state of A is higher than B, 1B. The oxidation state of B is higher than A. C. The two products have the same oxidation state. D. The oxidation state of the two products cannot be compared, 3, When K;C1Oy is added to the starting material shown in the scheme, the KzCrO; ‘A. gains electrons. B. loses electrons. C. maintains the same number of electrons. D. cannot transfer electrons. }. How many carbonyl groups does product A have? PoRP '. How many hydroxyl groups does product B have? + In the reaction of HBr with the hydroxyl group of the starting material, the Br is a(n) A. clectrophile B. nucleophile. C. acid, D. reducing agent. In the reaction of HBr with the hydroxyl group of the starting material, what is the first step of the ‘mechanism? ‘A. attack of the carbon by Br B. formation of a carbocation by the loss of OH C. inversion of stereochemistry D. protonation of the OH group 53 Alkanes, Alcohols, and Substitutions 493. How many chiral centers does product 1 have? Ao BL cea D3 494, The correct structure for product C is “ ce ; ‘OH o 495, When HBr adds to the starting alkene, the addition is: ‘A. aMatkovnikov eletrophilic addition. B. an anti-Markovnikov eletrophilic addition, CC. aMarkovnikov nucleophilic addition, D. an anti-Markovnikoy nucleophilic addition. 496. What reagent could be used to convert product C to a diol? A. LiATH, B. PBr C. K,Cr0, D. Os and (CH,)28 Copyright © 2006 EXAMKRACKERS, Inc.1001 Questions in MCAT Organic Chemistry Aldehydes and Ketones 497. Which of the following structures is an aldehyde? A c 9 An oO Boo, Ao, 498. Which of the following structures is a ketal? : ; . “west * mes : weaoms nen. 501. Which of the following is NOT true of carbonyl compounds? ‘A. The carbonyl carbon has a partial positive charge. B. The carbonyl oxygen has a partial negative charge. C. The carbonyl carbon i subject to electrophilic attack. D.~The carbonyl group has planar stereochemistry, ‘502. In the structure shown below, which atoms are in th same plane? un OL H ¢ HO, HL A. Atoms HI, C4, and 03. B. Atoms H7, Hl, and C4, C. Atoms 02, C4, and C6, D. Atoms 05, 03, and HI. 303, Which of the following compounds is the most acidic? A. pentane B. L-pentene CC. 2-pentanone D. pentanal 504, In the structure shown below, which hydrogen is the most acidic? 3 H, . x 1 4H HOH, ‘A. The hydrogen atom labeled 1 B. The hydrogen atom labeled 2. C. The hydrogen atom labeled 3. D. The hydrogen atom labeled 4, 505. Which of the following hydrogen atoms is a beta hydrogen? fe 3 Hy ‘4H HOH) A. The hydrogen atom labeled 1 B. The hydrogen atom labeled 2. C. The hydrogen atom labeled 3. D. The hydrogen atom labeled 4, ‘506. Which of the following hydrogen atoms is a gamma hydrogen? 3 x 1, H Z 4H HOH, A. The hydrogen atom labeled 1 B. The hydrogen atom labeled 2. ‘The hydrogen atom labeled 3. _ D. The hydrogen atom labeled 4. Copyright © 2006 EXAMKRACKERS, Inc.In the structure shown below, which hydrogen is the ‘most acidic? HH Hy Hy HOH HH ‘A. The hydrogen atom labeled 1 B. The hydrogen atom labeled 2 C. The hydrogen atom labeled 3. D. The hydrogen atom labeled 4 In the structure shown below, which carbon is the most electrophilic? HO Bra yi 3” ocHs ‘A. The carbon atom labeled 1. B. The carbon atom labeled 2. C. The carbon atom labeled 3. D. The carbon atom labeled 4. In the structure shown below, which carbon is most nucleophilic? AAK oe 2 ee A. The carbon atom labeled 1. B. The carbon atom labeled 2. C. The carbon atom labeled 3. D. The carbon atom labeled 4. Which of the following is a resonance structure of 2- ppentanone? A c HL SS F B, D. 8 AL Ab Why are the alpha hydrogens of ketones more acidic than the hydrogens of alkanes? A. The oxygen of the ketone promotes hydrogen bonding. B. The oxygen of the ketone donates electrons to the base. C. The ketone can resonance stabilize the anions generated when the proton is removed. D. The ketone can resonance destabilize the anions generated when the proton is removed, 55. Carbonyls and Amines 512. Which of the following structures shows the correct net dipole moment for acetone? vt a "a Uk Refer tothe structures below to answer questions 513 - 515. BA ALK Structure A Structure B 513. What is the relationship between structures A and B? ‘A. geometric isomers B. stereoisomers C. tautomers D. There is no relationship. 514, Structure A is a(n): ‘A. enol form B. keto form C. enatiomer D. oxidant 515. Structure B is a(n): ‘A. enol form B. keto form C. enantiomer D. oxidant 516. Which of the following will have the highest boiling point? A. Lheptanol B. heptane C. 2hepanone D. heptanal 517. Which of the following will have the greatest water solubility? A. Lheptanol B. heptane C. 2-hepanone D. heptanal Copyright © 2006 EXAMKRACKERS, Inc.1001 Questions in MCAT Organic Chemistry 518 Which of the following will have the highest boiling point? A. 2-propanone B. 2-butanone C. 2-pentanone D. 2-hexanone 519. Which of the following will have the highest water solubility? A. 2-propanone B. 2-butanone . 2-pentanone D. 2-hexanone 520. If 2-pentanone has a water solubility of 5.5 % by ‘volume, what would be true about a solution made with ‘5S mL of 2-butanone and 95 ml. of water? A. Two layers would be observed with one layer having a significantly smaller volume, B. Two layers would be observed with both layers having the same volume. C. The solution would be homogenous. D. The activity of 2-butanone cannot be predicted based on 2-pentanone. 521. Which of the following accounts for the fact the acetone is miscible in water? Acetone has a small molecular weight. ‘Acetone can form a hydrogen bond with water. Acetone molecules hydrogen bond with other acetone molecules, A. only B. only C. Land I only D. Tand [only Bee ‘522. Given that ethanal (acetaldehyde) has a boiling point of 21°C, in what phase is formaldehyde (methanal) at room temperature? A. gas B. liquid C. solid D._ super critical Liquid 523, In thé reaction of an aldehyde with the Tollen's eagen Ag’ is reduced to Ag which produces a silver mirro Why does the silver mirror not appear when Tollen reagent is added to a ketone? A. Ketones have an acidic proton and aldchydes do not. 1B, Aldehydes have an acidic proton and ketones do not C. Ketones can be oxidized while aldehydes cannot. D. Aldehydes can be oxidized while ketones cannot. 524. Given the information about the Tollen's reagent i questions 523, which of the following will react wit the Tollen's reagent? ‘A. pentanal B. 3-hexanone C. hexanoic acid D. 2-heptene 525. Given the information about the Tollen's reagent i questions 523, what are the products when butanal i reacted with the Tollen's reagent? A. butanoie acid and Ag* B. butanoic acid and Ag C. t-butanol and Ag” D. L-butanol and Ag 526. What reagents could be used to synthesize the aceta shown below? HyCQ_ ,OCH3 H A. L-butanol with methanal B. butanal with methanol CC. 1,1-dibutanol and water D. propanal with methanol 527. Butyraldehyde has a buttery odor and is used ir margarine, What reagent could be used to synthesize butyraldehyde from I-butanol? A. K:Cr0; B. PCC (mild oxidant) CC. LiAlH, D. 05,20 Copyright © 2006 EXAMKRACKERS, Inc.‘emminal alkynes can be used to synthesize methyl Ketones ‘efer to the example of this reaction below to answer uestions 528 - 532, Aw ae =e aA 28, Step one in the formation of 2-pentanone from 1- pentyne is a(n): A. hydration B. dehydration C. hydrogenation D. nucleophilic substitution 29, Step two in the formation of 2-pentanone from 1- pentyno is a(n): A. oxidation B. reduction CC. tautomerization D. nucleophilic substitution 30. The intermediate in the synthesis is a(n): A. alcohol B. enol C. alkene D. isolated product 31. Why does the reaction shown for the synthesis of 2- pentanone only form a methyl ketone and not an aldehyde? ‘A. Only the Markovnikov aleohol product forms. B. Only the ant-Markovnikoy alcohol product forms. C. Aldehydes are more unstable than ketones. D. Aldehydes are mote acidic than ketones. 2. What would be the product if I-pentene was used instead of 1-pentyne? A. L-pentanol B. 2-pentanol C. pentanal D. 2-pentanone Carbonyls and Amines When reacted with water, formaldehyde forms formalin, used to preserve biological specimens. Use the reaction shown below to answer questions 533 ~ 539. J, = ee wn fons 533, ‘The formation of formalin from flormaldehyde is a(n) A. electrophilic elimination » B. aromatic subsitituion . C. nucleophilic addition D._ nucleophilic substitution from 534. In a base catalyzed formation of formalin formaldehyde, the nucleophile is: ‘A. the carbonyl carbon in formaldehyde. B. the carbonyl oxygen in formaldehyde, c. oF D. HO 535. In a base catalyzed formation of formalin from formaldehyde, the electrobpile is: ‘A. the carbonyl carbon in formaldehyde. BB, the carbonyl oxygen in formaldehyde. c. of D. HO 536, In an acid catalyzed formation of formalin formaldehyde, what does the acid catalyst do? ‘A. Activates the electrophile by protonating the oxygen of the carbonyl, B. Activates the nucleophile by protonating the oxygen ofthe carbonyl . Activates the electrophile by protonating the oxygen of water. D. Activates the nucleophile by protonating the oxygen of wate. from $37. In an acid catalyzed formation of formalin formaldehyde, the nucleophile is ‘A. the carbonyl carbon in formaldehyde. B. the carbonyl oxygen in formaldehyde. c. OF D. HO 37 Copyright © 2006 EXAMKRACKERS, Inc.1001 Questions in MCAT Organic Chemistry 4538, In the above reaction, the formation of the product (formalin) is favored’ over the starting compound (formaldehyde). However, when this reaction is conducted with 2 butanone as the reactant, the starting compound is favored over the hydrated product. What accounts forthe difference in reactivity? ‘A. Alkyl groups are electron donating. B. Alkyl groups are electron withdrawing, C. Formaldehyde is sterically hindered D. Ketones are weaker nucleophiles. '539, What would result if formaldehyde was dissolved in ‘methanol rather than water? ‘A. The formation of hydrated formaldehyde B. The formation of an acetal C. The formation of a ketal D. No reaction would occur 540, What reagent could form the camphor product from the ‘bomeol starting material? ‘OH, > bomeol camphor A. NaBH, B. PBr ©. NaCr0; D. 0; 541, What reagent could convert camphor to borneol (see ‘question 540)? A. NaBH, B. PBs C._NaCr,0; D. Oo; 542. What nucleophile could be used to form cyanohydrin (Shown below) when reacted with 2-hexanone? ‘cyanohydrin Cc. #0 D. oO 58 Use the generic Grignard reaction shown below to answer questions 543 - 547 Omigx HE J, orm a Ee Oe Be R R ‘543, In a Grignard reaction the Grignard reagent (R"MgX) is ‘A. strong nucleophile B. weak nucleophile C. strong electrophile D. weak electrophile 544, Which of the following solvents would be best for a Grignard reaction? A. water B. ethanol C. diethylether D. dichloromethane 545. If 2-pentanone is reacted with phenyl magnesium bromide what is true about the product? A. ‘The product has achiral center and the solution is optically active BB. "The product has achiral center and the solution is not optically ative. C. ‘The product has no chiral center and the solution is not optically active. D. ‘The product is « meso compound. ‘546. The Gringnard reaction is a(n): A. clectrophilic elimination B. aromatic subsitituion C. nucleophilic addition D. nucleophilic substitution 547, Which of the following is a Grignard reagent? CS awe , . : a NH SE” Ones Copyright © 2006 EXAMKRACKERS, Inc.8, In an aldol addition of 2-butanone and 3-pentanone the product will have: ‘A. 2carbonyl groups. B. 2hydroxyl groups C. carbonyl group, 1 hydroxyl group. D. {carbonyl group, | hydroxyl group, and one carbon earbon double bond 9, In an aldol reaction the nucleophile is a(n}: A. carbonyl carbon B. carbonyl oxygen CC. hydroxide ion D. enolate ion 10, What is the first step of a base catalyzed aldol ‘condensation? ‘A. Protonation of the carbonyl oxygen to activate the nucleophile B. Protonation of the enolate fon to activate the nucleophile C. Deprotonation of the alpha hydrogen to activate the nucleophile D. Deprotonation ofthe alpha hydrogen to activate the clectrophile 1. How does a base catalyzed aldol condensation compare ‘with an acid catalyzed aldol condesation? ‘A. An acid catalyzed aldol condensation activates the clectrophil, while the base catalyzed condensation activates the nucleophile. B. An acid catalyzed aldol condensation activates the nucleophile, while the base catalyzed condensation activates the electrophile. C. Both reactions activate the electrophil. D. Both reactions activate the nucleophile, 2, What must be done to an aldol product to obtain an 0, Brunsaturated carbonyl? A. hydration B. dehydration C. hydrogenation D. oxidation 3. A crossed aldol reaction between ethanal and propanal ‘gives how many products that are structural isomers? POR> Carbonyls and Amines 554, Which of the following is a product of the aldol condensation of 2-butanone? 7 A c on JR 555, If a scientist desired only one product from a crossed ‘aldol reaction, which of the following aldehydes should be reacted in excess with 2-propone? Use the reaction shown below to answer questions 556- 558, 1) KH in THF — 2) CH 556. Why does the methyl group add to the alpha carbon rather than the carbonyl carbon in the reaction shown above? ‘A. The alpha carbon is acidic. B. The beta carbon is acidic. C. The carbonyl is not electrophilic. D. The KH forms the enolate ion, 4557. What type of reaction is the addition of the methyl group to form 2,2,4trimethyl3-pentanone? ‘A. electrophilic addition B. nucleophilic subsitution C. conjugate addition D. elimination 59 Copyright © 2006 EXAMKRACKERS, Inc.1001 Questions in MCAT Organic Chemistry $58, In the addition of the methyl group to form 2,2,4- ‘rimethyl-3-pentanone, the methyl iodide is a(n): A. electrophile B. nucleophile C. oxidant D. reductant 559, Ifa strong nucleophile is added to the compound shown below, which carbons are possible electrophiles? © DAY A. only Cy B. Cand C; C. Cyand Cy D. C,andC 560, ‘The reaction shown below is a(n) AA TAS A. 1,2-conjugate'addition B. 14-conjugate addition C. electrophilic addition D. nucleophilic substitution 561, Aldolase is an enzyme that breaks down sugars. Fructose undergoes the reaction shown below. What type of reaction is catalyzed by aldolase? g Oo "Eo og TO Qt oe met aa SL eo H-G-OHD (ih H-0-F-0 H£-0-F-0 9-0 % fructose 1,6-diphosphate dehydration hydration aldol condesation retro aldol condensation Sopp CCis-jasmone isa perfume that can be synthesized from cis-8- undecene-2,5-dione as shown below. Use this synthesis to ‘answer questions 562 - 566, 4 be7 fost > cis-jasmone ‘562, Cis-jasmone is a(n) ‘A. enol B. ar, Bunsaturated carbonyl C. aldol product D. enamine ‘563. The formation of the intermediate in the synthesis of cis-jasmone is a(n): ‘A. base catalyzed aldol condensation, B. acid catalyzed aldol condensation. C. dehydration. D. conjugate addition. 364. ‘The formation of cis-jasmone from the intermediate is a(n): ‘A. base catalyzed aldol condensation, B. acid catalyzed aldol condensation. C. dehydration. D. conjugate addition. 565. Which hydrogen is removed in the first step of the cis- {jasmone synthesis to create the enolate ion? A. The carbon labeled 1 B. The carbon labeled 2 C. The carbon labeled 3 D. The carbon labeled 4 5366. Which carbon is the electrophile in the first step of the cis-jasmone synthesis? A. The carbon labeled 1 B. The carbon labeled 2 C. ‘Tie carbon labeled 3 D. The carbon labeled 4 Copyright © 2006 EXAMKRACKERS, Inc.Carbonyls and Amines ‘The iodoform test shown below is used to identify methyl ketones. A positive test gives the yellow crystalline CHI, Use the equation shown below to answer questions 567 ~ 569, a Ro ROC~CHy + 3h + 40> R-C-08 + CH + 3150 367. Why does the hydroxide substitute for the carbon group only after three iodine ions have added? ‘A. The presence of the iodide atoms forms a much better leaving group. B. Iodide is a good leaving group. C.Hlisa strong acid. D. Water is a good leaving group. 568. Which of the following would be a good solvent for the iodoform test? A. acetone B. hexane C. water D. dichloromethane 569. Which of the following would produce a yellow solid in the iodoform test? L Tr M. oh d, oe ee ie C. Land Il only D. 1,0, andl Dibezalacetone can be used as sunscreen because it has a tuge absorption band in the UV region. Use the synthesis, sown below to answer questions $70 - 573. HO. A+ t) +o+ oH . | or Som Gh 570. The formation of benzalacetone is a(n) A. base catalyzed aldol condensation followed by dehydration BB. acid catalyzed aldol condensation followed by dehydration, . dehydration followed by base catalyzed aldol condensation, D. dehydration followed by acid catalyzed aldol condensation 571. In the formation of benzalacetone, acetone is the: ‘A. nucleophile B. electrophile C. acid D. oxidant 572. Inthe formation of _dibenzalacetone from benzalacetone, benzaldehyde is the: A. nucleophile B. clectrophile C. base D. oxidant 573. Why does only one product form in the formation of benzalacetone? I. the symmetry of acetone Tl, the absence of an alpha proton on benzaldehyde IIL. the absence of an alpha proton on acetone A . Tonly B. Tonly C. Tand I only D. 1,01, and 574, Tautomerization can racemize optically active ketones and aldehydes. Which of the following would no longer rotate plane polarized light after reaction with acid? A. (8)-3-methyl-2-heptanone B. (R)-4-methyl-2-heptanone CC. (§)3--butylpentanal D. (R)-3.methyleyclopentanone Copyright © 2006 EXAMKRACKERS, Inc.