Sciencemadness Discussion Board

Acylation of alcohol with acyl chloride - effect on chirality?

RareEarth - 15-1-2016 at 17:17

I was having a little difficulty finding information on this. If an acyl chloride is reacted with a chiral alcohol, is the chirality inverted, or retained? I couldn't find any information whether this would be an SN1 or an SN2, but maybe I didn't look in the right place yet.

Etaoin Shrdlu - 15-1-2016 at 17:49

It's neither SN1 nor SN2.

Look at the reaction closely. On which atom are you worrying about chirality?

blogfast25 - 15-1-2016 at 17:57

http://www.chemguide.co.uk/mechanisms/addelim/alcohol.html#t...

Can't see how chirality can be affected here.

RareEarth - 15-1-2016 at 18:04

Ah, you guys are right. I had a brain fart moment there. My brain seemed to be mixing up information about alkyl halide/alcohol reactions and acyl chlorides.