Test problems for Chapter 20 with answers

Test problems for Chapter 20 with answers - 1. Rank the...

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Page 1 1. Rank the following carboxylic acid derivatives in order of decreasing reactivity toward hydrolysis (most reactive on left): H 3 C C O Cl H 3 C C O OCH 3 H 3 C C O NH 2 H 3 C C O O CH 3 C O ABC D A) D > B > A > C D) A > B > D > C B) C > A > B > D E) D > B > C > A C) B > D > A > C Ans: A 2. Which of the following is not an intermediate in the Hofmann rearrangement of ethanamide to methylamine? H 3 CC O NH 2 CH 3 NH 2 Br 2 NaOH H 2 O A) H 3 O NH - B) H 3 CN O C C) H 2 O NH 2 - D) O H OH H 3 C NC E) H 3 O NHBr Ans: C
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Page 2 3. In the reaction shown below, which product(s) would be formed? H 3 CC H 2 C O OH ? H + heat + CH 3 18 OH A) H 3 H 2 C O OCH 3 18 B) H 3 H 2 C O OCH 3 18 C) H 3 H 2 C O OCH 3 18 18 D) H 3 H 2 C O OH 16 16 E) both A and B Ans: A
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Page 3 4. Which of the following would be properly named as 2-chloroethyl benzoate? A) CH 2 CH 3 C O O Cl B) CH CH 3 C O O Cl C) CH 2 CH 3 C O O Cl D) CH 2 CH 3 C O O Cl E) CH 2 CH 2 Cl C O O Ans: E 5. Which reagent(s) would accomplish the following transformation? H 3 CC H 2 C O Cl H 3 H 2 C O CH 3 ? A) CH 3 Li B) CH 3 I, NaOH C) CH 3 MgBr D) (CH 3 ) 2 CuLi E) either A or C Ans: D
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Page 4 6. How many different CH 3 signals would you expect in the room-temperature proton NMR spectrum of the molecule below? H 3 CC O N(CH 3 ) 2 A) One B) Two C) Three D) Four E) Five Ans: C 7. What would be the name of the following cyclic ester? O O H 3 C A) γ -valerolactone D) 2-methyl- β -butyrolactone B) β -butyrolactone E) 2-methyl- γ -valerolactone C) 2-methyl- γ -butyrolactone Ans: C 8. What would account for the fact that the molecule below racemizes easily, despite having three chiral centers? O O H H HOH 2 C A) Lactones are configurationally unstable B) Molecule loses CO 2 easily C) Enolization occurs easily D) Intramolecular transesterification occurs easily E) This molecule is not chiral. Ans: D
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Page 5 9. What would be the major organic product of the following reaction? C O NH 2 ? 1. LiAlH 4 2. H 2 O A) CH 2 OH B) CH 2 NH 2 C) C O H D) C O OH E) CH 3 Ans: B 10. What type of functional group do the natural products known as waxes have? A) Ester B) Amide C) Carboxylic acid D) Alcohol E) Amine Ans: A
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Page 6 11. What would be the major organic product expected from the following reaction?
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Test problems for Chapter 20 with answers - 1. Rank the...

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