Chemical Forums

Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: BeepoGirl on May 15, 2009, 06:37:27 AM

Title: Synthesis of a tertiary alcohol with 3 different substituents
Post by: BeepoGirl on May 15, 2009, 06:37:27 AM

I was given 4 alcohols to synthesise
PhCH(OH)Et, and PhC(OH)Et₂ which I used grignard reagents for, PhCH₂(OH) for which I used 'H-' -LiAlH4 with an ester. But I'm stumped on the last one: PhC(OH)(Me)Et.

I can't use grignard to add an ethyl group and then add a methyl group to an ester because I won't be able to control which groups are added and can't ensure one of each.. Any help?

Title: Re: Synthesis of a tertiary alcohol with 3 different substituents
Post by: Squirmy on May 15, 2009, 07:05:30 AM

Your PhCH(OH)Et is a secondary alcohol with 3 different substituents. What Grignard/carbonyl compound did you use for that?

Title: Re: Synthesis of a tertiary alcohol with 3 different substituents
Post by: StarvinMarvin on May 15, 2009, 07:16:41 AM

For the last one: use acetophenone (commercially available) and react it with EtMgBr.