Solution Found!
Draw the enolate that is formed when each of the following
Chapter 22, Problem 22.63(choose chapter or problem)
QUESTION:
Draw the enolate that is formed when each of the following compounds is treated with LDA: H O (a) O (b) OEt O (c) O (d)
Questions & Answers
QUESTION:
Draw the enolate that is formed when each of the following compounds is treated with LDA: H O (a) O (b) OEt O (c) O (d)
ANSWER:Step 1 of 5
Recall that LDA is a sterically-hindered base as it contains two isopropyl groups. If there is a choice of deprotonation sites (with roughly equal acidity, usually protonated carbons lying alpha to the carbonyl) the LDA will preferentially abstract the more accessible proton. This usually translates into deprotonation occurring at the less substituted site, forming the “kinetic enolate”.