Chem109B Midterm 2 Key W'12 - l 14 minutes 10 points Give...

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Unformatted text preview: l. 14 minutes, 10 points) Give the major product of each of the following reactions, or if no reaction will occur, so state. ((3% HCl Q Jr 1 1L0 a_ CH/ \w + CH3CH2CH20H —> /0\ CA 3 ' EXCCSS % 1.7) o O OH C|H3 l+ H3C—N+—CH3 7“ c FeCl C‘ + C12 —>3 ( / CQ 0 o (l ('i a 2: C C + CH CH OH ——> / \ + / \ — d- CH3/ ‘0’ \CH3 3 2 0‘5 Oaiufi 0‘13 O O o C C 2. 14 minutes, 8 points! What product would be formed when each of the tetrahedral intermediates collapses? o 9% I R—HH WWW» NH2 0 o’ l‘ | / \ R—Cl—OH K, DH}. NH2 0 (I OH I C/\ R —-C|—OCH3 (C/ 60% +OH H o 0‘ l I R—C—Cl @’ \OCAB I OCH3 3. (6 minutes, 6 points! Give the mechanism for the following reaction. Show all curved arrows. 'o : 0 CH3/ ‘NHCH3 + CH30H —-> CH3/ ‘OCH3 l .. ob’cf’UWB ’5 ab’i‘mwb ff 29% out} 4. 15 minutes, 12 points! Give the major product of each of the following reactions, or if no reaction will occur, so state. 1. HO" 3. ‘ _P ———> 3. HCl,H20,A O o 9 || o—lr/‘ab . ‘ AlCl3 a 4. l / + CH3Cl —-> C415 as ‘3 C .(2 c CH3CH2/ ‘NHCH3 + CH30H _’ U 00W? / + _ \ OCH3 N_=_N Cl d A) + ll ——> N Br Br colic/(E e. _ A + ——> N02 (I). ‘fi ‘3 C /C C, 6. [4 minutes, 12 points) Answer the following: a. Which of the following is NOT a true statement? An acyl halide is more reactive than an acid anhydride. An acid anhydride is more reactive than a carboxylic acid. A nitrile is more reactive than an amide. An acid anhydride is more reactive than an ester. An ester is more reactive than an amide. b. Which of the following is NOT a true statement? A methyl substituent is an ort 0 para director. An acyl substituent is a meta director. A nitro substituent is a meta director. + c. When aniline is attacked by a nitrosonium electrophile ( N=O), to what atom does the electrophile become attached? the nitrogen the ortho-carbon and the para-carbon the para-carbon the ortho-carbon the meta-carbon (1. Which of the following reagents can be used to produce ethyl benzoate by a transesterification reaction? methyl benzoate and ethano propyl benzoate and methanol benzoyl chloride and ethanol methyl benzoate and methanol phenyl ethanoate and ethanol e. Which of the following compounds cannot be prepared from benzenediazonium chloride? bromobenzene phenol benzonitrile fluorobenzene 1'. Which of the following represents the correct order of relative reactivity in a nucleophilic acyl substitution reaction? acyl halides > esters > acid anhydrides > amides amides > carboxylic acids > acid anhydrides > acyl halides esters > acid anhydrides > acyl halides > amides acyl halides > acid anhydrides > esters > amies acid anhydrides > acyl halides > esters > amides 7. 14 minutes, 10 points) Give the major product of each of the following reactions, or if no reaction will occur, so state. 0 ll H SO a. + 2—4. C3 / \ CA 03c .— ‘3’ i“ + N G CuBr b- ———> OCH3 0645 CA ‘1' AlCl3 / “a ‘3 + CH3CH2CI —‘> \ ' Cl Q 0 o .1 szQ C ~ 3 e. @ \CHZCH3 + Clz FeCl3 (IE 9. 14 minutes, 12 points) Answer the following: a. Which of the following pairs of reagents will undergo a nucleophilic addition-elimination reaction? an amide + water an acid anhydride and a chloride ion a carboxylic acid and a chloride ion an amide + an ester an acyl chloride and a carboxylate ion b. Which of the following statements best explains why protonation increases the rate of ester hydrolysis? The carbonyl carbon in the protonated ester is less positive than the carbonyl carbon in the unprotonated ester and therefore more susceptible to electrophilic addition, and the protonated leaving group is a stronger base. The carbonyl carbon in the protonated ester is more positive than the carbonyl carbon in the unprotonated ester and therefore more susceptible to nucleophilic addition, and the protonated leaving group is a stronger base. The carbonyl carbon in the protonated ester is less positive than the carbonyl carbon in the unprotonated ester and therefore more susceptible to nucleophilic addition, and the protonated leaving group is a weaker base. The carbonyl carbon in the protonated ester is more positive than the carbonyl carbon in the unprotonated ester and therefore more susceptible to nucleophilic addition, and the protonated leaving group is a weaker base. c. A carboxylic acid derivative will undergo a nucleophilic acyl substitution reaction provided that: the incoming nucleophile and the substituent attached to the acyl group in the reactant have similar basicities. the incoming nucleophile is not a much larger base than the substituent attached to the acyl group in the reactant. the incoming nucleophile is not a much weaker base than the substituent attached to the acyl group in the reactant. the incoming nucleophile is not a much stronger base than the substituent attached to the acyl group in the reactant. the substituent attached to the acyl group in the reactant is a very strong base. d. Which of the following pairs of reagents will not react to form a new carbonyl compound? propanoyl chloride and phenol + ethyl butanoate + methanol + H butanoic acid + water + HC acetic anhydride and methanol propanoyl chloride and two equiv of methylamine e. Which ofthe following is the best leaving group? CH3O- f. Which of the following dicarboxylic acids contains four carbon atoms? glutaric acid oxalic acid adipic acid malonic acid COOH COOH a © b. 1' Br CH3 1]. 5minutes 10 oints 3. Give one name for each of the following compounds: 0 ll OH C IU— ‘ 224. 1. CH3CH2CH2CH2CHZ/ ‘NCHs ’U’ bz M | CH3 "V —O 2. CH3CH2CH2CH2/ ‘OCIIHCH3 CH3 01/ M43477? age/«dz, ‘3. 3. C\c1 W G WW m b. Give two names for the following compound: 0 . . CH3C|HCH2/ ‘OH ‘6,qu M Br E. 3 l E 9 ...
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