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Show how you would synthesize each tertiary alcohol by

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

Solution for problem 15P Chapter 10

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 15P

Show how you would synthesize each tertiary alcohol by adding an appropriate Grignard reagent to a ketone.

(a) 3-phenylhexan-3-ol (3 ways)

(b) Ph 3 COH

(c) 1-ethylcyclopentanol

(d) 2-cyclopentylpentan-2-ol

Step-by-Step Solution:

Solution 15P

Step 1 </p>

(a)

1 st Way: Treatment of hexan-3-one with phenylmagnesium bromide in the presence of ether followed by the hydrolysis gives 3-phenylhexan-3-ol.

Step 2 </p>

2 nd Way: Treatment of propiophenone with propylmagnesium bromide in the presence of ether followed by the hydrolysis gives 3-phenylhexan-3-ol.

Step 3 </p>

3 rd Way: Treatment of 1-phenylbutan-1-one with ethylmagnesium bromide in the presence of ether followed by the hydrolysis gives 3-phenylhexan-3-ol.

Step 4 of 6

Chapter 10, Problem 15P is Solved
Step 5 of 6

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

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