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General Reactivity
The aldehyde and ketone are reactive in two places:
- They are electrophilic at the carbon of the carbonyl.
- They are nucleophilic when deprotonated at the alpha-carbon.
Wize Concept
The aldehyde and ketone are more electrophilic (i.e. more reactive) than the carboxylic acid derivatives.
The aldehyde is more reactive than the ketone due to sterics.
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General Mechanism at the Carbonyl
The carbon at the base of the carbonyl is electrophilic because of a bond dipole between the carbon and the oxygen atom.
- The nucleophile attacks the carbon atom.
- The tetrahedral intermediate is formed.
- The final product is protonated upon work-up.
Wize Tip
This is called a nucleophilic addition reaction (carboxylic acid derivatives undergo substitution reactions).
Wize Tip
"Work-up" just means that the reaction is treated with something to balance charges when it is done.
- If a reaction has negative charges, acid is added in a work-up.
- If a reaction has positive charges, base is added as a work-up.
Wize Concept
Since the tetrahedral intermediate does not have a good leaving group, it "gets stuck" until the work-up step.