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Allylic halides have the structure (a) Show how the

Chapter 8, Problem 52SP

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QUESTION:

Allylic halides have the structure

(a) Show how the first-order ionization of an allylic halide leads to a resonance-stabilized cation.

(b) Draw the resonance structures of the allylic cations formed by ionization of the following halides.

(c) Show the products expected from \(S_{N} 1\) solvolysis of these halides in ethanol

Equation Transcription:

Text Transcription:

C=C-C-X

S_N1

Br

CH2Br

Br

Br

Questions & Answers

QUESTION:

Allylic halides have the structure

(a) Show how the first-order ionization of an allylic halide leads to a resonance-stabilized cation.

(b) Draw the resonance structures of the allylic cations formed by ionization of the following halides.

(c) Show the products expected from \(S_{N} 1\) solvolysis of these halides in ethanol

Equation Transcription:

Text Transcription:

C=C-C-X

S_N1

Br

CH2Br

Br

Br

ANSWER:

Solution:

Step 1

The structure of allylic halide is,

(a) The  first-order ionization of an allylic halide and the resonance stabilization is given below-

In this 1st order ionization process, the halide group (X), from the allyl halide has been released as X- ion and forms a carbocation. This carbocation has two resonance structures.

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