Practice Ch 21ans PDF

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Chapter 21 Carboxylic Acid Derivatives 1) is an example of: A) a primary amide B) a secondary amide C) a tertiary amide D) an N, amide E) an imine Answer: B Diff: 1 Section: 21 2) Cyclic amides are called: A) lactones. B) lactams. C) aminals. D) animals. E) imines. Answer: B Diff: 1 Section: 21 3) A...

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Chapter 21 Carboxylic Acid Derivatives 1) N-Methylacetamide is an example of: A) a primary amide B) a secondary amide C) a tertiary amide D) an N, N-disubstituted amide E) an imine Answer: B Diff: 1 Section: 21.2 2) Cyclic amides are called: A) lactones. B) lactams. C) aminals. D) animals. E) imines. Answer: B Diff: 1 Section: 21.2 3) Amides are less basic than amines because: A) the carbonyl group donates electrons by resonance. B) the carbonyl group withdraws electrons by resonance. C) the nitrogen does not have a lone pair of electrons. D) the nitrogen has a full positive charge. E) amides do not contain nitrogen. Answer: B Diff: 1 Section: 21.2 4) Cyclic esters are called: A) lactones. B) lactams. C) lacrimals. D) imides. E) enamines. Answer: A Diff: 1 Section: 21.2

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6) Which of the following structures are carboxylic acid derivatives?

A) 3 B) 1 & 3 C) 1, 2 & 3 D) 4 E) All are carboxylic acid derivatives Answer: B Diff: 2 Section: 21.2 9) Provide the structure of cyclohexyl formate. Answer:

Diff: 2 Section: 21.2 10) Provide the structure of γ-butyrolactam. Answer:

Diff: 2 Section: 21.2 11) Provide the structure of (R)-4-ethoxypentanenitrile. Answer:

Diff: 2 Section: 21.2 2

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12) Provide the structure of o-bromobenzoyl chloride. Answer:

Diff: 2 Section: 21.2 13) Provide the structure of trifluoroacetic anhydride. Answer: (CF3CO)2O Diff: 2 Section: 21.2 14) Provide the IUPAC name of the following compound.

Answer: ethyl hexanoate Diff: 2 Section: 21.2 15) Provide the IUPAC name of the following compound.

Answer: N,N-diethylformamide Diff: 2 Section: 21.2 16) Provide the name of the compound shown below.

Answer: ethyl hexanoate Diff: 2 Section: 21.2 4

17) Provide the name of the compound shown below.

Answer: N,N-dipropylbutanamide Diff: 2 Section: 21.2 18) Provide the proper IUPAC name for the compound below.

Answer: trans-5-octenoyl chloride Diff: 1 Section: 21.2 19) Provide the structure of propanoic anhydride. Answer: (CH3CH2CO)2O Diff: 1 Section: 21.2 20) Provide the proper IUPAC name for the compound below.

Answer: isopropyl cyclohexanecarboxylate Diff: 2 Section: 21.2 21) Provide the proper IUPAC name for ClCH2CH2CONHCH3. Answer: N-methyl-3-chloropropanamide Diff: 2 Section: 21.2 22) Provide the proper IUPAC name for the compound below.

Answer: 3,3-dimethylcyclobutanecarbonitrile Diff: 2 Section: 21.2 5

23) Provide the proper IUPAC name for NCCH2CH2CH2CH2CO2CH3. Answer: methyl 5-cyanopentanoate Diff: 2 Section: 21.2 24) Provide the structure of N,N-diethylbutanamide. Answer: CH3CH2CH2CON(CH2CH3)2 Diff: 2 Section: 21.2 25) Provide the structure of 3-oxobutanenitrile. Answer: CH3COCH2CN Diff: 2 Section: 21.2 26) Provide the structure of 2-bromo-2-methylbutanoyl chloride. Answer: CH3CH2CBr(CH3)COCl Diff: 2 Section: 21.2 27) Provide the IUPAC name for HCONHCH2CH2CH3. Answer: N-propylmethanamide Diff: 2 Section: 21.2 28) Which of the following are strongly hydrogen bonded in the liquid phase? A) nitriles B) esters C) secondary amides D) tertiary amides E) acid chlorides Answer: C Diff: 2 Section: 21.3 32) 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) 1660 cm-1 B) 1700 cm-1 C) 1735 cm-1 D) 1800 cm-1 E) 2200 cm-1 Answer: C Diff: 2 Section: 21.4 6

33) 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) 1700 cm-1 B) 1735 cm-1 C) 1800 cm-1 D) 1660 cm-1 E) 2200 cm-1 Answer: C Diff: 2 Section: 21.4 34) 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) 1735 cm-1 C) 1800 cm-1 D) 1660 cm-1 E) 2200 cm-1 Answer: D Diff: 2 Section: 21.4

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35) 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) are farther downfield than those α to a nitrile. D) fall between δ 3.1 and δ 4.2 (ppm). E) fall between δ 1.3 and δ 1.8 (ppm). Answer: A Diff: 2 37) The most characteristic IR stretch of butanenitrile occurs at approximately what wavenumber? A) 3500 cm-1 B) 3100 cm-1 C) 2600 cm-1 D) 2200 cm-1 E) 1750 cm-1 Answer: D Diff: 2 Section: 21.4 38) Which compound has a carbonyl stretch in its IR spectrum at the lowest wavenumber? A) acetic anhydride B) formamide C) cyclohexanone D) propanoyl chloride E) ethyl acetate Answer: B Diff: 2 Section: 21.4

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39) Which of the following is the most reactive carboxylic acid derivative? A) ester B) anhydride C) nitrile D) acid chloride E) amide Answer: D Diff: 1 Section: 21.5 40) A correct order of reactivity of acid derivatives towards nucleophilic attack is: A) esters > acid anhydrides > amides. B) anhydrides > amides > esters. C) carboxylates > esters > amides. D) anhydrides > acids > acid chlorides. E) anhydrides > amides > carboxylates. Answer: E Diff: 1 Section: 21.5 41) In nucleophilic acyl substitution, : A) protonation of the carbonyl is followed immediately by loss of the leaving group. B) loss of the leaving group is followed by rearrangement of the carbocation. C) addition to the carbonyl by a nucleophile is followed by loss of the leaving group. D) ester hydrolysis is followed by deprotonation. E) an SN2 reaction occurs. Answer: C Diff: 2 Section: 21.5 42) Arrange the carboxylic acid derivatives below in order of increasing reactivity towards nucleophilic acyl substitution.

A) 1 < 2...