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Chapter 6: 6-26P (page 320)

Propose a mechanism involving a hydride shift or alkyl shift for each solvolysis reaction. Explain howeach rearrangement forms a more stable intermediate.

(a)

(b)

(c)

(d)

Short Answer

Expert verified

(a)

(b)

(c)

(d)

Step by step solution

01

Rearrange product 1

First product is formed by simple SN1 reaction. Second product is the rearrangement product formed by more stable carbocation.

(a)

02

Rearrange product 2

(b)

03

Rearrange product 3

First product is formed by simple SN1 reaction. Second product is the rearrange product formed by more stable carbocation.

(c)

04

Rearrange product 4

First product is formed by simple SN1 reaction. Second product is the rearrange product formed by more stable carbocation.

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Most popular questions from this chapter

Propose an SN1 mechanism for the solvolysis of 3-bromo-2,3-dimethylpentane in ethanol.

Question: Using cyclohexane as one of your starting materials, show how you would synthesize the following compounds.

b)

Predict the compound in each pair that will undergo the SN2 reaction faster.

(a.)

(b.)

(c.)

(d.)

(e.)

(f.)

(a)Optically active 2-bromobutane undergoes racemization on treatment with a solution of KBr. Give a mechanism for this racemization.

(b)In contrast, optically active butan-2-ol does not racemize on treatment with a solution of KOH. Explain why a reaction like that in part (a) does not occur.

(c)Optically active butan-2-ol racemizes in dilute acid. Propose a mechanism for this racemization.

Predict the major product of the following substitutions.
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