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Organic Chemistry | 7th Edition | ISBN: 9781269406772 | Authors: Paula Yurkanis Bruice
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Solved: The Swern oxidation oxidizes primary alcohols to

Chapter 11, Problem 71P

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QUESTION:

The Swern oxidation oxidizes primary alcohols to aldehydes and secondary alcohols to ketones using dimethyl sulfoxide and oxalyl chloride, followed by reaction with triethylamine. The actual oxidizing agent is the dimethylchlorosulfonium ion, (\(\mathrm{CH}_3)_2\mathrm{SCl}\). (To see how this compound is formed from the reactants, see \(\text{Problem} \ 77\) in \(\text{Chapter} \ 17\).) Propose a mechanism for the oxidation. (Hint: the first step is an \(\mathrm{S}_\mathrm{N}2\) reaction, the last step is an \(\mathrm{E}2\) reaction.)

Equation Transcription:

(CH3)2SCI

Problem 77

Chapter 17

SN2

E2

Text Transcription:

(CH_3)_2 SCI

Problem 77

Chapter 17

S_N 2

E2

Questions & Answers

QUESTION:

The Swern oxidation oxidizes primary alcohols to aldehydes and secondary alcohols to ketones using dimethyl sulfoxide and oxalyl chloride, followed by reaction with triethylamine. The actual oxidizing agent is the dimethylchlorosulfonium ion, (\(\mathrm{CH}_3)_2\mathrm{SCl}\). (To see how this compound is formed from the reactants, see \(\text{Problem} \ 77\) in \(\text{Chapter} \ 17\).) Propose a mechanism for the oxidation. (Hint: the first step is an \(\mathrm{S}_\mathrm{N}2\) reaction, the last step is an \(\mathrm{E}2\) reaction.)

Equation Transcription:

(CH3)2SCI

Problem 77

Chapter 17

SN2

E2

Text Transcription:

(CH_3)_2 SCI

Problem 77

Chapter 17

S_N 2

E2

ANSWER:

Solution 71P

The mechanism of the reaction is as follows:

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