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Solved: Show how you would accomplish the following

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 7P Chapter 18

Organic Chemistry | 8th Edition

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

Organic Chemistry | 8th Edition

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Problem 7P

Show how you would accomplish the following synthetic conversions by adding an organolithium reagent to an acid.

(c) pentanoic acid  heptan-3-one

(d) phenylacetic acid  3,3-dimethyl-1-phenylbutan-2-one

Step-by-Step Solution:
Step 1 of 3

Solution 7P

  1. Dianion is protonated in presence of  to form hydrate and followed by removal of water to form target product.

(b)

Bromocyclopentane reacts with two equivalents of lithium to form one equivalent of cyclopentyl lithium.

Here one equivalent of cyclopentyl lithium is formed. So, in order to react with one equivalent of cyclopentyl lithium 0.5 equivalent of acetic acid is required.

One equivalent of cyclopentyl lithium reacts with 0.5 equivalent of acetic acid to form a dianion.

Dianion is protonated in presence of  to form hydrate and followed by removal of water to form target product.

(c)

Ethyl lithium is commercially available (inexpensive). So, the carboxylic acid reacts with two equivalents of ethyl lithium.

Pentanoic acid reacts with two equivalents of ethyl lithium and followed by protonation in presence of  to form heptan-3-one.

Step by step reaction is as follows:

One equivalent of ethyl lithium abstracts ion pentanoic acid to form lithium pentanoate.

Another molecule of ethyl lithium attacks the lithium pentanoate to form a dianion.

Dianion is protonated in presence of to form hydrate and followed by removal of water to form target product.

(d)

Step 2 of 3

Chapter 18, Problem 7P is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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Solved: Show how you would accomplish the following