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Organic Chemistry INSTRUCTION: Select the correct answer for each of the following sections. Mark only one answer for each item by shading the box corresponding to the letter of your choice on the answer sheet provided. STRICTLY NO ERASURES ALLOWED. Use pencil no. 1 only.

1. In the nucleophilic aromatic substitution reaction of nitrobenzene, which of the following does not apply?

a. It is a two step bimolecular displacement

b. Electron withdrawing groups increase the rate of reaction

c. The type of halide does not affect the reaction rate

d. A large isotopic effect is observed

2. The dehydration of alcohol involves E1 elimination with the

formation of a carbonium (or carbocation) ion. This occurs in:

a. Basic medium

b. Strongly basic medium

c. Acidic medium

d. pH is not important

3. For the chemical transformation of benzamide to aniline, the reagents(s) needed is/are:

KMnO 4 NaOH + Br 2

c. NaNO 2 + H 2 SO 4

d. None of the given answers

b.

a.

4. Why do electron withdrawing substitutents such as the halogens increase the acidity of acetic acid?

a. The halogens stabilize the carboxylate ion

b. The halogens intensify the negative charge on the carboxylate ion

c. The halogens destabilize the carboxylate ion

d. None of the given answers

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5. Which of the following compounds forms the most stable carbocation?

a. Nitrobenzene

b. Aniline

c. Toluene

d. Benzaldehyde

6. The proper sequence of events to convert benzene to mbromonitrobenze is:

a. Simultaneous bromination and nitration

b. Bromination followed by nitration

c. Nitration followed by Friedel Crafts alkylation and bromination

d. Nitration followed by bromination

7. The nitration of benzene does not exhibit a significant isotope effect because:

a. A C–H bond is broken at the rate determining step

b. K 1 > K 2

c. No C–H is broken at the rate determining step

d. None of the given answers

8. Which of the following gives a positive iodoform test?

a.

b.

c. Ethanol

d. tertbutyl alcohol

3pentanone

Methanol

9. What would be the product(s) of the reaction of ethyl bromide and sodium tertbutoxide?

a. 2methyl propane and ethanol

b. 2methyl propene and ethanol

c. Ethyl tertbutyl ether

d. None of the given answers

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10. Predict the order of reactivity towards alkaline hydrolysis of (most reactive first):

I. methyl acetate, II. methyl formate, III. methyl propionate

15. Which compound does not contain a carbonyl group?

a. Ester

b. Ketone

a. II >

I

>

III

c. Ether

b. II >

III

>

I

d. Carboxylic acid

c. I

>

II > III

d. III

>

I

>

II

16. In the Claisen condensation of CH 3 COOC 2 H 5 and O 14 C 2 H 5 ion, the C 14 label will be detected in which product?

11. The hydrolysis of ethyl benzoate labeled with 18 O (CO 18 O) yields the following:

a. Phenol labeled with 18 O

b. Ethanol labeled with 18 O

c. Acetic acid labeled with 18 O

d. Benzoic acid labeled with 18 O

12. Nylon 66 is formed from adipic acid and hexamethylenediamine by:

a. Cation chain reaction polymerization

b. Free radical chain reaction polymerization

c. Stepreaction polymerization

d. Anion chain reaction polymerization

e. None of these

13. The reactivity of the C=O group in propanal is primarily due to:

a. Ability of oxygen to acquire electrons

b. Inductive effect of neighboring groups

c. Polarity of the C=O group

d. None of these

14. Glycogen consists of monomeric units of:

a. Mannose

b. Galactose

c. Fructose

d. Sucrose

e.

Glucose

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a. Ethylacetoacetate

b. Ethyl acetate

c. Carbon dioxide

d. Ethanol

e. None of these

17. Which of the following can disrupt hydrophobic bonds in proteins?

a. Dichloroacetic acid

b. Sodium lauryl sulfate

c. Mercaptoethanol

d. Dioxane

e. No correct answer

18. A Kjeldahl nitrogen analysis of 4.27 mg of nitrobenzene required 5.35 mL of 0.0150 N HCl to neutralize the ammonia produced. Calculate the % nitrogen in the compound.

a. 26 %

b. 1.3 %

c. 13 %

d. 2.6 %

e. None of the given answers

19. 2OH butane reacts with HCl in the presence of zinc chloride and under strong heat. The final product of the reaction:

a. Has a retention of configuration

b.

Is racemic

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c. Has inversion of configuration

d. None of the choices

20. A polypeptide chain is treated with LiAlH 4 , then hydrolyzed, 2amino1propanol separates out. The C terminal amino acid of the polypeptide is:

a. Alanine

b. Lysine

c. Praline

d. None of the given answers

21. Catalytic cracking of oil directly yields:

a. Alkenes

b. Anti knock compounds

c. Gasoline

d. All of these

22. Which of the following compounds is the most reactive by SN1 mechanism?

a. Isopropyl chloride

b. n butyl chloride

c. n propyl chloride

d. tertbutyl chloride

23. Which of the following are manmade polymers?

a. Silk

b. Plastics

c.

d. Natural rubber

e. All are correct answers

Lignin

24. When CH 3 CO 18 OH was made to react with methanol, the methyl

acetate was found to contain only ordinary O. Which bonds were broken?

a. C–OH of acid and C–OH of alcohol

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b. CO–H of acid and CO–H of alcohol

c. C–OH of acid and CO–H of alcohol

d. None of these

25. What carboxylic acid is prepared from p bromotoluene by free radical halogenation followed by nitrile synthesis?

a. p bromophthalic acid

b. p bromobenzoic acid

c. p bromophenylacetic acid

d. None of these

26. In the conversion of acetyl chloride to acetamide, what would be the effect of electron withdrawing substitutents on the tetrahedral intermediate?

a. They stabilize the partial charge on oxygen

b. The acyl compound undergoes nucleophilic addition

c. They destabilize the partial charge on oxygen

d. None of the given answers

27. What is the substrate of trypsin?

a. Coconut oil

b. Starch

c. None of the given answers

d. Protein

28. How many isomeric disubstitution products are theoretically possible upon the bromination of benzene?

2

b. 4

c. 3

d. 6

e. None of the choices

a.

29. Cleavage of isopropylphenylether by HBr yields:

a. Benzene and isopropylBr

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b. isopropylBr and phenol

c. bromobenzene and isopropanol

d. none of these choices

30. The major product of dehydrohalogenation of 5Cl 2heptene is:

a. 2,4heptadiene

b. Propanoic acid and butenoic acid

c. 2,5heptadiene

d. None of the given choices

31. Consider the chlorination of methane in the presence of light. Oxygen acts as an inhibitor because it breaks the chain reaction by:

a. Reacting with methane

b. Reacting with chlorine atom

c. Reacting with Cl 2

d. None of the given answers

32. Oxidation of hexanol by acidic dichromate yields:

a. Hexanal

b. 2hexanone

c. Hexanoic acid

d. None of the given answers

33. Predict the major product of dehydration of 3OH 3,4dimethylhexane:

a. 3,4dimethyl 2hexene

b. 2,4dimethyl 1hexene

c. 3,4dimethyl 1hexene

3,4dimethyl 3hexene

d.

34. The IR spectrum of the chair form of cyclohexane differs from that of the boat form in the following aspect(s):

a. C–H stretching bands are on same wavenumber

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b. C–H stretching band for the boat form is at higher wavenumber

c. C–H stretching band for chair form is at higher wavenumber

d. None of the given answers

35. Enantiomers of methylethylbutylamine are difficult to isolate because of:

a. Conformation

b. Rotation

c. Inversion

d. None of these

36. A solution of bromine in carbon tetrachloride becomes colorless in the presence of ethene. The product formed is:

a. Bromoethane

b. 1,2dibromoethane

c. 1,1,2,2tetrabromoethane

d. None of these

37. 2OH butane reacts with HCl in the presence of zinc chloride and under strong heat. What is the reaction mechanism involved in this reaction?

a. E2

b. SN2

c. E1

d. SN1

38. Ozonolysis of 2methyl1,3butadiene yields:

a. Aldehyde and acids

b. Acids

c. Aldehydes

d. None of the choices

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39. Give the product of esterification between benzoic acid and ethanol.

a. Ethyl benzoate

b. Ethyl benzaldehyde

c. Benzyl acetate

d. None of the given answers

40. The Bataan Nuclear Power Plant is being proposed for conversion

to a combined cycle power plant using natural gas as fuel. Natural gas consists of:

a. Butane

b. Methane

c. Ethane

d. None of these

41. The IR spectrum of a dilute solution of ethanol shows an O–H stretching band at 3640 cm 1 . This band becomes broader and

shifts to 3350 cm 1 as the ethanol concentration is increase. Explain this shift.

a. H bonding to the second oxygen strengthens the OH bond

b. The energy of vibration is increased as the ethanol concentration is increased

c. H bonding to the second oxygen weakens the OH bond

d. None of the given answers

42. Tertiary alcohols react with HX via SN2 mechanism. The feature(s) of this reaction is(are):

a. It is acid catalyzed

b. Rearrangement is possible

c. A carbonium ion is formed

d. All of the given answers

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43. In the halogenation of alkanes at ordinary temperature, the rate of abstraction of H follows the sequence 3 o > 2 o > 1 o . An explanation for this trend is:

a. Free radical from 1 o H is most stable

b. Energy of activation is lowest in 3 o H

c. The probability of collision is greatest between halogen atom and 3 o H

d. The collision frequency is greatest between the halogen atom and alkane with 3 o H

44. Cite reason(s) why quarternary ammonium salts (A) with four different groups attached to nitrogen have been found to exist as configurational enantiomers while enantiomers of simple amines (B), also with four different groups attached to the nitrogen, have not been isolated.

a. A has sp 3 orbitals

b. Positive charge on quarternary N

c. Unshared pair of electrons on N

d. Rapid inversion about N in B

e. None of the given answers

45. Which of the following compounds is the most acidic?

a. Methyl amine

b. Methane

c. Methyl fluoride

d. Methyl alcohol

46. Arrange the following in order of basicity (most basic first):

I, methyl fluoride; II, methyl chloride; III, methyl bromide; IV, methyl iodide.

a. I

b. IV >

c. I

d. None of the given answers

>

>

II > III

III > II

III >

II

> IV

>

I

> IV

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47. The carbon atoms of acetylene contain the following hybrid orbitals:

a. sp

b. sp

c. s

d. sp

3

2

48. In dehalogenation of alky halides, the order of reactivity is 3 o > 2 o > 1 o . This may be due to:

a. Greater number of H available for attack by base

b. Lower energy of activation

c. More stable transition state

d. All of these

49. Which of the following exists as a pair of conformational diastereomers?

a. trans1,3cyclohexanediol

b. cis1,2cyclohexanediol

c. trans1,2cyclohexanediol

d. cis1,3cyclohexanediol

50. Arrange the following aliphatic acids in order of increasing acidity:

I, formic acid; II, acetic acid; III, propionic acid; IV, chloroacetic acid:

a. III, II, I, IV

b. I, II, III, IV

c. IV, III, II, I

d. IV, I, II, III

e. No correct answer

51. Give the reaction product of tertpentyl alcohol with alkaline KMnO 4 .

a. 3methyl2butanone

b. 3methyl1butanal

c. 3mehyl 1butanoic acid

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d. No reaction

5 2. Which of the following halides is the most reactive by SN1 mechanism?

a. Benzyl chloride

b. tertbutyl chloride

c. Chloroethane

d. 2chloro2 propane

53. Which of the following compounds is the most reactive towards I 2 by the SN2 reaction?

a. Ethyl bromide

b. Isobutyl bromide

c. tertbutyl bromide

d. Methyl bromide

e. Isopropyl bromide

54. Give the product of the reaction of propanal with NaCN followed by hydrolysis with acid.

a. 2OH 2methylpropanoic acid

b. Propanoic acid

c. 2OH butanoic acid

d. None of these

55. Arrange the following in order of increasing reactivity towards a hydroxyl group via SN2 mechanism: I, 1bromopentane; II, 1 bromo2methylpentane; III, 1bromo2,2dimethylpentane; IV, 1bromo3methylpentane; V, 2bromopentane

a. III, II, IV, V, I

b. I, II, V, III, IV

c. I, V, IV, II, III

d. III, II, V, IV, I

e. None of these

56. Addition of HBr to propylene in the presence of peroxides yields:

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a. Equal amounts of isopropyl bromide and n propyl bromide

b. n propyl bromide

c. Isopropyl bromide

d. None of the given answers

57. What chemical tests will distinguish 3chloropropene from n propyl chloride? I, Br 2 in CCl 4 ; II, KMnO 4 ; III, CrO 3 ; IV, H 2 SO 4

a. I, II, IV

b. I, II, III

c. I, II, III, IV

d. I, III

e. None of the given answers

58. In the reaction of 1naphthol with phenyldiazochloride, the phenyldiazonium ion will bind to which carbon atom of the naphthalene moiety?

61. The aldol condensation reaction of two moles of acetaldehyde with a base catalyst yields:

a. 2OH butanone

b. 3OH butanal

c. 3OH butanone

d. 2OH butanal

62. The isoelectric point of serum albumin is 4.9. At pH = 7.0, which of the following statements would be true? I, the protein moves to the cathode II, the protein moves to the anode III, majority of its ionizing groups are basic IV, majority of its ionizing groups are acidic

a. I, IV

b. II, III

c. I, III

d. II, IV

a. C

7

e. None of the given answers

b. C

2

c. C

5

63. Acid catalyzed hydrolysis of ethylene oxide yields:

d. C

4

a. Ethylene glycol

e. C

8

b. Ethanol

59. What is the shape of a methyl radical?

a. Trigonal

b. Orthogonal

c. Pyramidal

d. None of the given choices

60. What is the shape of an ethylene molecule?

a. Linear

b. Trigonal

c. Tetrahedral

d. Pyramidal

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c. Carbon dioxide

d. None of these

64. What would be the products of mild alkaline hydrolysis of 1oleyl2palmitoyl 3laurylglycerol?

a. Glycerol, sodium linoleate, sodium palmitate, sodium laurate

b. Glycerol, sodium oleate, sodium palmitate, sodium laurate

c. Glycerol, oleic acid, palmitic acid, lauric acid

d. Glycerol, linoleic acid, palmitic acid, lauric acid

e. None of the given answers

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65. Compound Z forms a clear solution with benzenesulfonylchloride,

from which an insoluble material separates out upon acidification. Compound Z is:

a. Ethyl amine

b. Methyl ethyl amine

c. Trimethyl amine

d. None of the given answers

66. Bromination of isobutene under UV light at 127 o C yields:

a. Equal amounts of tertbutyl Br and isobutyl Br

b. Isobutyl bromide as the primary product

c. Tertbutyl bromide as the primary product

d.

No reaction

67. Hydrolysis of αlauroβpalmitin yields:

a. Lauric acid, palmitic acid and glycerol

b. One molecule each of lauric acid, palmitic acid, and glycerol

c. Lauric acid and palmitic acid

d. None of the given answers

68. Arrange the following alcohols in order of reactivity in the esterification of acetic acid (most reactive first):

a. Methanol > n propyl = sec butyl > tertpentyl alcohol

b. Methanol > n propyl > sec butyl > tertpentyl alcohol

c. Tertpentyl alcohol > sec butyl > n propyl > methyl alcohol

d. Methanol = n propyl > sec butyl > tertpentyl alcohol

e. None of the given answers

69. The basicity of aniline is increased by:

a. COOH, halide groups

b. Amino, methoxy, halide groups

c. Amino, methyl, halide groups

d. None of these

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70. Arrange the following in increasing order of delocalization of electrons by hyperconjugation (compounds with greatest delocalization of electrons first):

a. t butyl > isopropyl > ethyl > methyl

b. t butyl > isopropyl > ethyl = methyl

c. methyl > ethyl > isopropyl > tbutyl

d. t butyl = isopropyl > ethyl > methyl

e. None of the given answers

71. Which of the indicated bonds has the lowest bond dissociation energy (D)?

a.

b.

c.

d.

e. All have equal D

C

C

C

C

6 H 5 6 H 5 6 H 5 6 H 5

–H CH 2 –CH 3 –CH 3 CH 2 –H

72. A product development manager wants a low molecular weight polystyrene product. Given the chain transfer constants of

several chain transfer agents, which of these would be the most effective to use?

a. Benzene; 0.02

b. Ethylbenzene; 0.70

c. Toluene; 0.20

d. Isopropyl benzene; 1.00

73. The following compounds are used as Lewis acid catalysts in organic reactions except:

a. BF 3

b.

c. CH 3 MgBr

d. SnCl 4

AlCl 3

74. The total number of possible structures corresponding to the formula C 4 H 9 I is:

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a. 7

b. 5

c. 4

d. 6

e. None of these

75. By end group analysis, the hydrolysis of one molecule of completely methylated amylase gives rise to:

a. Equal number of tetra OmethylD glucose and tri OmethylD glucose

b. One molecule of tetra OmethylD glucose

c. One molecule of tri Omethyl D glucose

d. None of the given answers

76. Arrange the following in order of increasing boiling point (lowest boiling point first):

I, butanal; II, butyl alcohol; III, butanoic acid; IV, ethyl ether

a. I, IV, II, III

b. IV, II, I, III

c. IV, I, II, III

d. None of the given answers

77. The ease of abstraction of hydrogen atoms from alkyl halides

follows the trend: tertiary H > secondary H > primary H. This maybe due to:

a. Change in the R substituents

b. Length of the R substituents

c. Differences in activation energies

d. None of the given answers

78. Examine the structure of the following polymer and identify the monomeric unit: –(CH 2 CCl 2 CH 2 CCl 2 ) n

a. 1,1dichloroethene

b.

Styrene

c. Vinyl chloride

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d. None of the given answers

79. What is the monomer comprising the plexiglass?

a. Ethylene glycol

b. Acrylonitrile

c. Methyl methacrylate

d. Adipic acid

e. Vinyl acetate

80. In the dehydrogenation of 1pentene, platinum:

a. Lowers the energy of activation

b. Changes the net energy change of reaction

c. Shifts the position of equilibrium

d. All of these

81. Alcohols can be produced by reacting alkenes with hydroxymercurial compounds by oxymercurationdemercuration reaction. 2 methyl1butene yields:

a. 2methyl2butanol

b. 2methyl1butanol

c. A mixture of 2methyl2butanol and 2methyl1butanol

d. None of the given answers

82. A substituent R which withdraws electrons from the carbocation has the following effect:

a. It destabilizes the cation

b. It stabilizes the cation

c. It makes the cation structure tetrahedral

d. None of the given answers

83. This test will show whether an amine is primary, secondary, or tertiary:

a.

b. Sanger’s test

Periodic test

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c. Lucas’ test

d. Benedict’s test

e. Hinsberg’s test

84. Which amino acid provides kinks in the structure of proteins?

a. Cysteine

b. Cystine

c.

d. Proline

Histidine

e. No correct answers

89. Which of the following converts acetaldehyde to acetic acid?

a. Sodium borohydride

b. Hydrogen/Ni

c. Potassium permanganate

d. Lithium borohydride

e.

Na metal

90. What is the major product(s) of dehydration of

85. The hydrolysis of one mole of mannose gives:

(CH 3 ) 2 C(OH)CH

2 CH 3 ?

a. 2 moles glucose

a. 3

CH 2

=CHCH

b. 1 mole glucose + 1 mole galactose

b. )CH

CH 2

=C(CH 3

2 CH 3

c. 2 moles Galactose

d. 1 mole fructose + 1 mole glucose

e. None of these

86. HCl has a higher bond dissociation energy than:

a. HBr

b. H 2

c. H F

d. HOH

87. The carboxylate anion contains sigma bonds that utilize:

a. sp 3 orbitals

b. p orbitals

c. sp orbitals

d. sp 2 orbitals

e. d orbitals

88. C 6 H 12 belongs to a series of hydrocarbons known as:

a. Arenas

b. Alkanes

c. Alkenes

d. Alkynes

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c.

CHCH=CH 2

e. None of the given answers

d.

(CH 3 ) 2 (CH 3 ) 2

C=CHCH 3