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Problem_Set_3_solutions - Chem 358 Spring 2007 Problem...

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Chem 358 Spring 2007 Problem Set #3 - Answers Chapter 16 : 16 .11, 15, 19, 23, 24, 29, 38(a) and (c), 40, 44, 47, 48, 49, 54, 55, 57 – See answers to Chapter 16 problems in the PS#2 folder at course web site Additional problems - solutions 1. Sometimes it is easier to work backwards. In this case we realize the new bond formed is what we have to break in a retro process. We also recognize that this is Friedel-Crafts alkylation since only alkyl groups are attached to the benzene ring. This is a tertiary carbocation which can attack the benzene ring in the manner we have seen in Freidel-Crafts alkylation reaction. Now we can write down the mechanism as follows: H + H H H — H + H Secondary carbocation. Can rearrange to a more stable one. Rearrangement gives the tertiary carbocation formed by the retro method above Loss of proton rearomatizes the ring H H 2. Begin by writing down the resonance structures for each carbocation. Br Br CH 3 O Br Br Br O Br O Br CH 3 O CH 3 CH 3 ..
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