w_acid_2 - Exam Name_ MULTIPLE CHOICE. Choose the one...

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Exam Name___________________________________ MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question 1) Which of the following is the most reactive carboxylic acid derivative? A) amide B) nitrile C) anhydride D) acid chloride E) ester 1) 2) N - Methylacetamide is an example of: A) a secondary amide B) a primary amide C) a tertiary amide D) an imine E) an N, N - disubstituted amide 2) 3) Which of the following are strongly hydrogen bonded in the liquid phase? A) secondary amides B) acid chlorides C) esters D) nitriles E) tertiary amides 3) 4) While the carbonyl stretching frequency for simple aldeydes, ketones, and carboxylic acids is about 1710 cm - 1 , the carbonyl stretching frequency for esters is about: A) 1800 cm - 1 B) 2200 cm - 1 C) 1660 cm - 1 D) 1735 cm - 1 E) 1700 cm - 1 4) 5) While the carbonyl stretching frequency for simple aldehydes, ketones, and carboxylic acids is about 1710 cm - 1 , the carbonyl stretching frequency for acid chlorides is about: A) 1800 cm - 1 B) 1660 cm - 1 C) 2200 cm - 1 D) 1735 cm - 1 E) 1700 cm - 1 5) 6) While the carbonyl stretching frequency for simple aldehydes, ketones, and carboxylic acids is about 1710 cm - 1 , the carbonyl stretching frequency for amides is about? A) 1700 cm - 1 B) 2200 cm - 1 C) 1660 cm - 1 D) 1735 cm - 1 E) 1800 cm - 1 6) 7) The chemical shifts for protons α to a carbonyl group: A) are similar for all acid derivatives. B) are farthest downfield for carboxylic acids. C) fall between δ 3.1 and δ 4.2 (ppm). D) fall between δ 1.3 and δ 1.8 (ppm). E) are farther downfield than those α to a nitrile. 7) 1
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8) In the proton NMR spectrum of a secondary amide, the amide proton's signal is: A) sharp, around δ 10.0 (ppm). B) broad, around δ 9.0 (ppm). C) broad, around δ 7.0 (ppm). D) usually not observed. E) sharp, around δ 5.0 (ppm). 8) 9) In nucleophilic acyl substitution, : A) protonation of the carbonyl is followed immediately by loss of the leaving group. B) an S N 2 reaction occurs. C) ester hydrolysis is followed by deprotonation. D) loss of the leaving group is followed by rearrangement of the carbocation. E) addition to the carbonyl by a nucleophile is followed by loss of the leaving group. 9) 10) A correct order of reactivity of acid derivatives towards nucleophilic attack is: A) anhydrides > amides > carboxylates. B) anhydrides > amides > esters. C) anhydrides > acids > acid chlorides. D) esters > acid anhydrides > amides. E) carboxylates > esters > amides. 10) SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question. 11) Using the two key resonance structures for an ester, show how resonance stabilization is lost when an ester is attacked by a nucleophile. 11)
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This note was uploaded on 12/17/2010 for the course CHEM 101 taught by Professor Silva during the Spring '08 term at Binghamton University.

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w_acid_2 - Exam Name_ MULTIPLE CHOICE. Choose the one...

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