Solution Found!

Draw the enolate that is formed when each of the following

Chapter 22, Problem 22.63

(choose chapter or problem)

Get Unlimited 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)

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”.

Add to cart


Study Tools You Might Need

Not The Solution You Need? Search for Your Answer Here:

×

Login

Login or Sign up for access to all of our study tools and educational content!

Forgot password?
Register Now

×

Register

Sign up for access to all content on our site!

Or login if you already have an account

×

Reset password

If you have an active account we’ll send you an e-mail for password recovery

Or login if you have your password back