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Ch 15 Answers - Ch 15 Extra problem Answers 1...

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Ch. 15 Extra problem Answers 1. After “reactivity:” under the structure write whether the compound is more or less reactive towards Br + than benzene. Write 3 resonance structures for the MOST STABLE arenium ion given by reaction with Br + . Show the electron-pushing arrows that convert your first structure to the second, and second to the third. Briefly, why is the orientation shown observed? It allows methyl to stabilize one of the ring carbons bearing positive charge. Briefly, why is the orientation shown observed? It keeps one of the ring carbons bearing positive charge from having the acetyl group. 2. Give an arrow-pushing mechanism for the following reaction: Cl + HCl AlCl 3 _ Cl + Al Cl Cl Cl + + (C-C rotations) + Cl 1,2 hydride AlCl 3 shift _ + H H _ + H _ Al Cl Cl Cl Cl H H AlCl 3 Cl HCl Cl this is an intramolecular Friedel-Crafts alkylation H Br H 3 C + H 3 C H Br H 3 C + Br H H 3 C + more (reactive) H 3 C O + H 3 C O H Br + H 3 C O H Br + H 3 C O H Br less (reactive)
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2 3. Give the major organic products for the following reactions a. OMe is o,p directing and activating; an activating group dominates (but Ac is meta directing anyway). b. c. d. e. f. HNO 3 ,H 2 SO 4 OCH 3 O CH 3 OCH 3 O CH 3 NO 2 Na, NH 3 CH 2 CH 3 C(CH 3 ) 3 CH 3 CH 2 OH (Birch reduction) CH 2 CH 3 C(CH 3 ) 3
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