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Reviewquestions_17 - 1 Provide the major resonance...

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1) Provide the major resonance structures of the intermediate sigma complex in the reaction of benzene with the generic electrophile E + . Answer: Diff: 1 4) Provide a detailed, stepwise mechanism for the reaction of benzene with Br 2 and FeBr 3 . Make sure to include the activating reaction between Br 2 and FeBr 3 in your mechanism. Answer: Diff: 3 1
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6) Which of the following species is attacked by benzene in the electrophilic nitration reaction? A) HNO 3 B) NO 2 + C) NO 2 D) NO + E) N 3 - Answer: B Diff: 1 11) Which of the following is the strongest activating group in electrophilic aromatic substitution reactions? 2
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12) Rank the following groups in order of increasing activating power in electrophilic aromatic substitution reactions: -OCH 3 , -OCOCH 2 CH 3 , -CH 2 CH 3 , -Br. 13) In electrophilic aromatic substitution reactions a bromine substituent: 14) Draw the four major resonance structures of the sigma complex intermediate in the reaction of anisole with HNO 3 /H 2 SO 4 to yield p -nitroanisole. Answer: Diff: 3 15) Draw the three major resonance structures of the sigma complex intermediate in the reaction of acetophenone with HNO 3 /H 2 SO 4 to yield o -nitroacetophenone. Circle the resonance form which is less stable than the other two. Answer: Diff: 3 16) Rank the following sigma complexes in order of increasing stability. Answer: A < B < C Diff: 2 3
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17) Provide a series of synthetic steps by which 2-bromo-4-nitrobenzoic acid can be prepared from toluene. Answer: 1. HNO 3 , H 2 SO 4 2. Br 2 , FeBr 3 3. KMnO 4 , OH - , Δ 4. H + Diff: 3 18) Provide a series of synthetic steps by which 3-bromoethylbenzene can be prepared from benzene. Answer: 1. CH 3 COCl, AlCl 3 2. Br 2 , FeBr 3 3. Zn(Hg), HCl Diff: 3 19) Provide a series of synthetic steps by which 4- t -butylbenzoic acid can be prepared from toluene. Answer: 1. (CH 3 ) 3 CCl, AlCl 3 2. KMnO 4 , OH - , Δ 3. H + Diff: 3 20) Provide a series of synthetic steps by which p -nitrobutylbenzene can be prepared from benzene.
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