Chapter 6: Q14P (page 300)
Predict the major product of the following substitutions.

Short Answer
Answer

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Chapter 6: Q14P (page 300)
Predict the major product of the following substitutions.

Answer

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For each pair of compounds, predict which one has the higher molecular dipole moment, and explain your reasoning.
(a) ethyl chloride or ethyl iodide
(b) 1-bromopropane or cyclopropane
(c) cis-2,3-dibromobut-2-ene or trans-2,3-dibromobut-2-ene
(d) cis-1,2-dichlorocyclobutane or trans-1,3-dichlorocyclobutane.
(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.
Question: For each of the following compounds,
a)

b)

c)

d)

e)

f)

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

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