Carbonyl a-Substitution Reactions

For each of the reactions on the left, predict the major organic product. Pay particular attention to the regiochemistry and stereochemistry of the reaction.

Click the mouse on the reactant molecule to view the answer;

click on the reagent to briefly review the reaction.

Acetic acid will catalyze the enolization of aldehydes and ketones; when this enol reverts back to the carbonyl compound, the anion which is formed on the a-carbon can be trapped by reaction with Br2 to give the a-bromo carbonyl compound. 

























Aqueous mineral acid will catalyze the enolization of aldehydes and ketones;  when this enol reverts back to the carbonyl compound, the anion which is formed on the a-carbon can be trapped by reaction with Cl2 to give the a-chloro carbonyl compound.






























Acetic acid will catalyze the enolization of aldehydes and ketones;  when this enol reverts back to the carbonyl compound, the anion which is formed on the a-carbon can be trapped by reaction with Br2 to give the a-bromo carbonyl compound.































Aqueous mineral acid will catalyze the enolization of aldehydes and ketones;  when this enol reverts back to the carbonyl compound, the anion which is formed on the a-carbon can be trapped by reaction with Cl2 to give the a-chloro carbonyl compound.




























Acetic acid will catalyze the enolization of aldehydes and ketones;  when this enol reverts back to the carbonyl compound, the anion which is formed on the a-carbon can be trapped by reaction with Br2 to give the a-bromo carbonyl compound.




























Aqueous mineral acid will catalyze the enolization of aldehydes and ketones;  when this enol reverts back to the carbonyl compound, the anion which is formed on the a-carbon can be trapped by reaction with Cl2 to give the a-chloro carbonyl compound.





























Acetic acid will catalyze the enolization of aldehydes and ketones;  when this enol reverts back to the carbonyl compound, the anion which is formed on the a-carbon can be trapped by reaction with Br2 to give the a-bromo carbonyl compound.






























Aqueous mineral acid will catalyze the enolization of aldehydes and ketones;  when this enol reverts back to the carbonyl compound, the anion which is formed on the a-carbon can be trapped by reaction with Cl2 to give the a-chloro carbonyl compound.