Solution Found!
A formate ester, such as ethyl formate, reacts with an
Chapter 2, Problem 18P(choose chapter or problem)
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 allyl- magnesium bromide gives, after protonation, hepta-1,6-dien-4-ol.
(b) Show how you would use reactions of Grignard reagents with ethyl formate to synthe-
size the following secondary alcohols.
(i) pentan-3-ol (ii) diphenylmethanol (iii) trans,trans-nona-2,7-dien-5-ol
Questions & Answers
QUESTION:
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 allyl- magnesium bromide gives, after protonation, hepta-1,6-dien-4-ol.
(b) Show how you would use reactions of Grignard reagents with ethyl formate to synthe-
size the following secondary alcohols.
(i) pentan-3-ol (ii) diphenylmethanol (iii) trans,trans-nona-2,7-dien-5-ol
ANSWER:
Solution 18P
The mechanism for reacting of ethyl formate with excess allyl magnesium bromide is givan as
(a).
