If you react an ester with an organometalic would you just get a tertiary alcohol?

Question

If you react an ester with an organometalic would you just get a tertiary alcohol?

Answer 1

That depends on the organometallic compound you're dealing with. Grignard reagents and lithium organics will give you a tertiary alcohol via a consequent double addition. However, Gilman reagents (lithium cuprates) won't react with an ester. So, you can do a Michael-type addition to an a,b-unsaturated ketone with lithium cuprates in the presence of an ester group safely, while LiR or RMgBr will react with carbonyl and an ester.

Answer 2

Yes.  Carboxylic esters react with 2 equivalents of a Grignard reagent (organo-metal) to produce tertiary alcohols.