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Chemistry / Organic Chemistry 8 / Chapter 9 / Problem 31SP

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

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The application box in the margin of page 401 states, “The

Chapter 21, Problem 31SP

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QUESTION:

The application box in the margin of page 401 states, “The addition of an acetylide ion to a carbonyl group is used in the synthesis of ethchlorvynol, a drug used to cause drowsiness and induce sleep.” Show how you would accomplish this syn-thesis from acetylene and a carbonyl compound.

Equation Transcription:

$OH$

$C{H}_{3}C{H}_{2}-C-C\equiv{}CH$

$CHCl$

Text Transcription:

OH

CH_{3}CH_{2}-C-C{equiv}CH

CHCl

Questions & Answers

QUESTION:

The application box in the margin of page 401 states, “The addition of an acetylide ion to a carbonyl group is used in the synthesis of ethchlorvynol, a drug used to cause drowsiness and induce sleep.” Show how you would accomplish this syn-thesis from acetylene and a carbonyl compound.

Equation Transcription:

$OH$

$C{H}_{3}C{H}_{2}-C-C\equiv{}CH$

$CHCl$

Text Transcription:

OH

CH_{3}CH_{2}-C-C{equiv}CH

CHCl

ANSWER:

Solution:

Here we have to show the synthesis of ethchlorvynol from acetylene and a carbonyl compound

Step 1

The structure of ethchlorvynol is,

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