PracticeQuestionsChap11&14-key

PracticeQuestionsChap11&14-key - 1(4 pts ea Provide...

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1 1. (4 pts ea) Provide an explanation for the following trends. a) S N 1 reactivity Br > > Br > > Br Br > > highest reactivity in S N 1 reactions lowest reactivity in S N 1 reactions Answer: > > > > > > + ++ + delocalized aromatic delocalized nonaromatic delocalized antiaromatic not delocalized S N 1 reactivity reflects carbocation stability: b) Acidity H > H > H > > pK a = 15 H pK a = 39 most acidic least acidic pK a . 31 pK a = 35 Answer: acidity reflects conjugate base stability: > > > > –– delocalized aromatic delocalized antiaromatic delocalized nonaromatic less delocalized nonaromatic 2. (2 pts ea) Assuming planar structures, characterize the following compounds as aromatic, antiaromatic, or nonaromatic. a) b) c) d) e) HB HN B H NH BH H N g) f) N O h) B i) B j) O + k) + l) aromatic antiaromatic aromatic nonaromatic nonaromatic aromatic aromatic antiaromatic antiaromatic aromatic aromatic aromatic antiaromatic 6e 4e 6e 6e sp 3 sp 3 6e 6e 8e 4e 6e 6e 6e 8e 3. ( 6 pts
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This note was uploaded on 09/22/2008 for the course CHEM 2261 taught by Professor Crowe during the Fall '08 term at LSU.

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PracticeQuestionsChap11&14-key - 1(4 pts ea Provide...

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