Given the following information, why don't chemists just use butyllithium itself to deprotonate the aldehyde or ketone and form the enolate?

Question

Given the following information, why don't chemists just use butyllithium itself to deprotonate the aldehyde or ketone and form the enolate?

Enolates are frequently formed by treating an aldehyde or ketone with LDA. However, the LDA must first be generated by reacting diisopropylamine with butyllithium.

1 Answer

Impact of this question

3685 views around the world

You can reuse this answer
Creative Commons License

Answer 1 · 2016-03-06T20:06:05

#Bu^(n)Li# is a powerful base, but also a powerful nucleophile.

Explanation:

#Bu^(n)Li# and #MeLi# might add to the carbonyl carbon, rather than deprotonating the #alpha# hydrogen. On the other hand, #LDA# is a powerful base, but an indifferent nucleophile. The action of #LDA# on the #alpha#-hydrogen will generate the enolate.

Science

Math

Humanities

... and beyond

Given the following information, why don't chemists just use butyllithium itself to deprotonate the aldehyde or ketone and form the enolate?

Enolates are frequently formed by treating an aldehyde or ketone with LDA. However, the LDA must first be generated by reacting diisopropylamine with butyllithium.

1 Answer

Explanation:

Related questions

Impact of this question