Now we're going to talk about a way that you can make ketones from acid chlorides. Acid chlorides and esters have something in common. They both have a pretty good leaving group next to the carbonyl. If nucleophilic addition takes place on that carbonyl carbon, that leaving group is prompted to leave allowing a double bond to be reformed. This process is called nucleophilic acyl substitution and it's the subject of another set of videos that can be found in your carboxylic acid derivatives chapter. But for right now, all I'm trying to say is that acid chlorides and esters when reacted with organometallics are going to react twice instead of reacting once. Let's take a look. First of all, remember that organometallics have a negative charge on the R. The M ionizes. We don't really care about it. The negative winds up attacking the carbon. We form a tetrahedral intermediate. This makes a compound look like this. We've got R
21. Aldehydes and Ketones: Nucleophilic Addition
Acid Chloride to Ketone
21. Aldehydes and Ketones: Nucleophilic Addition
Acid Chloride to Ketone - Online Tutor, Practice Problems & Exam Prep
1
concept
Ketones from acid chlorides
Video duration:
5mPlay a video:
Video transcript
2
Problem
ProblemProvide the major product for the following reaction
A
B
C
D