- Athe transfer of hydride to the carbonyl group
- Bthe abstraction of proton from the carboxylic group
- Cthe attack of at the carboxyl group
- Dthe deprotonation of Ph
View written solutionFree
Correct answer: A
- Recall the mechanism of Cannizzaro reaction
For benzaldehyde (), which has no -hydrogen, Cannizzaro reaction occurs in concentrated base.
Overall reaction:
The mechanism is:
Step 1: Nucleophilic addition of hydroxide to benzaldehyde
This gives a tetrahedral alkoxide intermediate.
Step 2: Hydride transfer from this intermediate to a second molecule of benzaldehyde
This is the characteristic disproportionation step.
Step 3: Proton transfer
- Identify the rate-determining (slowest) step
In the Cannizzaro reaction, the difficult step is the transfer of hydride from the tetrahedral intermediate to another carbonyl carbon. This intermolecular hydride migration has the highest activation energy and is known to be the rate-determining step.
So the slowest step is:
- Check the options
-
A: the transfer of hydride to the carbonyl group
✅ Correct. This is the slowest step. -
B: the abstraction of proton from the carboxylic group
❌ Not the slow step; proton transfer steps are generally fast. -
C: the attack of at the carboxyl group
❌ Not relevant here; hydroxide attacks the aldehyde carbonyl, not a carboxyl group. -
D: the deprotonation of
❌ Not the rate-determining step; also the key proton-transfer processes are fast.
- Final answer
The slowest step is:
- Comparison with stored correct answer
Stored correct answer = A
Derived answer = A
So they agree.
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