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A formate ester, such as ethyl formate, reacts with an

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

Solution for problem 18P 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 18P

A formate ester, such as ethyl formate, reacts with an excess of a Grignard reagent to give (after protonation) secondary alcohols with two identical alkyl groups.

(a) Propose a mechanism to show how the reaction of ethyl formate with an excess of allylmagnesium bromide gives, after protonation, hepta-1,6-dien-4-ol.

(b) Show how you would use reactions of Grignard reagents with ethyl formate to synthesize the following secondary alcohols.

(i) pentan-3-ol (ii) diphenylmethanol (iii) trans,trans-nona-2,7-dien-5-ol

Step-by-Step Solution:
Step 1 of 3

Solution 18P

The mechanism for reacting of ethyl formate with excess allyl magnesium bromide is givan as

(a).

(b) The reaction of Grignard reagent with ethyl formate is given below - -

Step 2 of 3

Chapter 10, Problem 18P is Solved
Step 3 of 3

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

Since the solution to 18P from 10 chapter was answered, more than 634 students have viewed the full step-by-step answer. This full solution covers the following key subjects: formate, ethyl, diphenylmethanol, Secondary, dien. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. The answer to “A formate ester, such as ethyl formate, reacts with an excess of a Grignard reagent to give (after protonation) secondary alcohols with two identical alkyl groups. (a) Propose a mechanism to show how the reaction of ethyl formate with an excess of allylmagnesium bromide gives, after protonation, hepta-1,6-dien-4-ol. (b) Show how you would use reactions of Grignard reagents with ethyl formate to synthesize the following secondary alcohols.(i) pentan-3-ol (ii) diphenylmethanol (iii) trans,trans-nona-2,7-dien-5-ol” is broken down into a number of easy to follow steps, and 72 words. Organic Chemistry was written by and is associated to the ISBN: 9780321768414. The full step-by-step solution to problem: 18P from chapter: 10 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8.

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