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Chapter 6: Q57P (page 331)

Question: 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

For each of the following compounds,

  1. give the IUPAC name.
  2. give the common name (if possible).
  3. classify the compound as a methyl, primary, secondary, or tertiary halide.

Give a mechanism to explain the two products formed in the following reaction.

(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.

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.

Classify each compound as an alkyl halide, a vinyl halide, or an aryl halide.

(a) (CH3)3CF

(b) CH3CHCBrCH3

(c) CH3CF3

(d)

(e)

(f)
See all solutions

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