Chapter 10.9D, Problem 10.18P

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.

1. 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.

1. b. Show how you would use reactions of Grignard reagents with ethyl formate to synthesize the following secondary alcohols.
   1. i. pentan-3-ol
   2. ii. diphenylmethanol
   3. iii. trans,trans-nona-2,7-dien-5-ol