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Chapter 6: Q57P (page 331)

Propose mechanisms to account for the observed products in the following reactions.

Short Answer

Expert verified

(a)

(b)

Step by step solution

01

Allylic substitution

In allylic bromination, the Br atom appears on the carbon next to the double bond which proceeds via a radical mechanism. The allylic radicals are very stable because of resonance-stabilization.

02

Proposing the mechanism

Here, NBS will create a radical on the allylic position of the double bond and one more isomer will be formed by the rearrangement of the radical formed. The Br will be attached to

the radical position and will lead to the final product formation. Below are the mechanisms proposed for the given two parts:

(a)

Mechanism for reaction (a)

(b)

Mechanism for reaction (b)

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Most popular questions from this chapter

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

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.

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

e)

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

Predict the major product of the following substitutions.
See all solutions

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