Strong base + Ketone

[Djdents]

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When combining a strong base and a ketone how do you know whether the base will attack the carbonyl group or deprotonate the alpha carbon

 

[PeterScroggins]

I believe it has to do with how nucleophilic the base is... if you use something like LDA, which is highly basic & not very nucleophilic then you should see the deprotonation occur... Where as a more nucleophilic species will be more prone to attack the carbonyl carbon.

Hope that helps

 

[Mr. Thirsty]

I believe it has to do with how nucleophilic the base is... if you use something like LDA, which is highly basic & not very nucleophilic then you should see the deprotonation occur... Where as a more nucleophilic species will be more prone to attack the carbonyl carbon.

Hope that helps

👍

 

[Djdents]

I believe it has to do with how nucleophilic the base is... if you use something like LDA, which is highly basic & not very nucleophilic then you should see the deprotonation occur... Where as a more nucleophilic species will be more prone to attack the carbonyl carbon.

Hope that helps

It does thanks

 

[HAWKDDS2014]

LDA, hydroxide, alcohols, (i.e. weak nucleophiles & good bases will deprotonate at the alpha carbon). Better nucleophiles like amines, etc.. will usually attack the carbonyl.