CHM 221 Organic Chemistry I Name: __| March 25, 2011 Box: J Multiple Choice (36 pts): Write the letter of the correct answer on the answer sheet provided (page 6) You may tear off these first 5 pages if you'd like. 1. Enantiomers are: ‘molecules that have a mirror image. molecules that have at least one stereogenic center. non-superposable molecules. non-superposable constitutional isomers. non-superposable molecules that are mirror images of each other. Foose 2. Pairs of enantiomers are: CH; 7% CHs 7 HC PmaCl Cima, HCC CH,CH.CHy / CHACHCHy CH,CH.CHy 1 i i gui a CH,CH,CHy Iv ¥ A. i.lland il, V B. LI Cc. ULV Dz. WV,V E. None of the structures 3. (R)-2-Chlorobutane is represented by: CH CH u Hcmpacl cimpacH, Cm PSC! (OHCHs —_/CHACHs CHyCHy I n mM " Mm v ikeh> <4. Which structure represents (S)-2-bromobutane? Che Hs ae Hebe Brea HoChepaaBr e CH,CHs CH,CHs CHCHs L I mm (M1 B) a c) Th Dd) More than one of the above E) None of the above 5. Which of the following is NOT true of enantiomers? They have the same: A) boiling point. B) melting point. ©) specific rotation. D) density, E) chemical reactivity toward achiral reagents. 6, Which of the following is true about any (R)-enantiomer? A) Itisdextrorotatory. B) It islevorotatory. ©) tisan equal mixture of + and -. D) It is the mirror image of the (S)-enantiomer. E) —(R) indicates a racemic mixture. 7. Land Mare; OH woe Br Br 1 it A) constitutional isomers. B) enantiomers. ©) identical. D) diastereomers. B) _notisomeric.8. Land Tare: HO NH, 1 " A) constitutional isomers. B) enantiomers. ©) identical. D) diastereomers. ) notisomeric. 9. Hexane and 3-methylpentane are examples of: A) enantiomers. B) stereoisomers. C) diastereomers. D) constitutional isomers. E) None of these 10. The two compounds shown below are: Br FE A) enantiomers. B) diastereomers. ©) constitutional isomers. D) identical. E) different but not isomeric. 11. The hybridization state of the charged carbon in a carbocation is spt sp? sp? sp s geen12, What product(s) would you expect to obtain from the following Sy2 reaction? H CHjONa —_—— hs pr CH3OH OCH, CHO co OCH; CH, 1 0 m Al Bw C Anequimolar mixture of land It. D. E, None of these 13, Which of the following reactions proceeds with inversion of configuration at the carbon bearing the leaving group? Swe Sul 2 EI Allofthese FUN SP 14, Identify the nucleophile in the following reaction: 2H20 + RX > ROH + HsO° + X AL xX B. H,0+ C. ROH D. HO ERX 15, Which alkyl halide would you expect to react most slowly when heated in aqueous solution? A. (CHDsCF B. (Cii)3C-C1 C. (CHa)sC-Br D. (CHa) E, They would all react at the same rate.Nomenclature (8) 19, Draw the structure for one of the enantiomers of each of the following compounds. Structure a. 2-chlorobutane ew cA,cH CHCA, b. 3-methylhexane Ons \ CHC H,CH CHC HoH, Structure and Theory (12) 20. (4) Using a 3-dimensional formula, draw (R)}2-butanol. re) \ CH, CH -CH 3 3 21, (2) Circle the most stable carbocation of those shown below. i Ne a6 \CHM 221 Organic Chemistry 1 March 25, 2011 1, wy 2. ct oA 5. Co . © 7 ; 1B A nu “ort. 2 142 1A {6a a “YEG B (also accept, P) zara?22. (6) Some of the compounds listed below have a stereogenic center; some do not. Label the stereogenic centers with an *. Reactions (28) OCH; 23.(20) Predict the mechanism (Sw, Sy2, E1, E2) by which the major product would be formed for the reactions below and select the appropriate response to the questions below, a. CHaCH2CH2CH2CHal + (CHa)3CO ‘The likely reaction would be The alkyl halide in this reaction is ‘The nucleophile in this reaction is ‘The leaving group in this reaction is 25% cN b. (CHs)2CHF ‘The likely reaction would be ‘The alkyl halide in this reaction is ‘The nucleophile in this reaction is ‘The leaving group in this reaction is ‘The temperature of this reaction is rived (CHs)sCOH Syl Sy2 BL (2) (circleone) + S = w) 2 30 (circle one) ve i small strong (uty strong (circle one) ( we) page cee cele one) svt (sua) E12 (circle one) 10 (2) ) 30 (circle one) (weak ) strong (circle one) good poor ) ) (circle one) (moderate high (circleone) |or 30°C mretnatol e + CH20H ‘The likely reaction would be (circle one) ‘The alkyl halide in this reaction is (circle one) ‘The nucleophile in this reaction is, (circle one) ‘The leaving group in this reaction is poor (circle one) ~ ‘The temperature of this reaction is (moderate 2) high (circle one); 24, (8) For each pair, circle the faster Sw2 reaction. If both reactions would have the same rate, write the word “same”. &_CHsCHaCHeal +NaCN ——> CHsCHaCH2CN + Nal) CHsCH2CH2F +NaCN = + CHsCH2CH2CN + NaF b. CHsCH2CH2Cl + CHsCH20- (2.0 M)_———»CHsCH2CH20CHzCHs + NaCl CCHsCH2CHACI + CHsCH20: (4.0 M) > CHsCH2CHzOCH2CHs + NaCl) “CHsCHaCHeCl + NacNn Aprotic,polar CHsCHACHLCN + NaCl > «e 2M solvent” CHsCHeCH2Cl + NaCN piled ied CHsCH2CH2CN + NaCl @. (CHs)2CHI +NaCN > CHaCH2CH2CN + Nal (CHsCHACHaI+ NaCN +» CHsCH2CH2CN + Nal ‘ ¢ >Mechanisms (12) 25. (8) Using Curved Arrows, draw the mechanism for the Sv2 reaction shown below. + CHO" — VN SO ‘OCH, 26. (4) Draw the carbocation that is formed in the first step of the reaction shown below. ot, cH moderate temp A; CHy- 1 ———> Chs ‘OH CH2— ca chy HOH 5S os om acy Synthesis and Spectroscopy (8) “4 27.Your task is to prepare styrene by one of the following reactions. The IR for styrene shows a peak at 1620-1680 cm7. Draw the structure of styrene. Circle the reaction you would choose to give the better yield of styrene? Explain. a want Eliminchon— Styrene Pa a strong ,srnail kon Kon — — ~/ A BOK Kea g. 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