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Q8.7(iv):
Which of the following compounds would undergo aldol condensation, which the Cannizzaro reaction and which neither? Write the structures of the expected products of aldol condensation and Cannizzaro reaction. (iv) Benzophenone

Solution :

Step 1: Structural Analysis of Benzophenone

The chemical structure of benzophenone is $C_6H_5-CO-C_6H_5$ (Diphenylmethanone). To determine its reactivity toward Aldol Condensation or Cannizzaro reaction, we must analyze its molecular architecture:

  • Alpha-Hydrogen Presence: The carbonyl carbon is attached to two phenyl groups. There are no $\alpha$-hydrogens present on the carbons adjacent to the carbonyl group. [Per definition, an $\alpha$-hydrogen is a hydrogen atom attached to a carbon atom directly bonded to the carbonyl group ($C=O$).]
  • Structure: $Ph-C(=O)-Ph$ where $Ph = C_6H_5$.

Step 2: Evaluation of Reactivity

We evaluate the criteria for the two named reactions:

Reaction Requirement Applicability to Benzophenone
Aldol Condensation Must possess at least one $\alpha$-hydrogen. No. Benzophenone lacks $\alpha$-hydrogens.
Cannizzaro Reaction Must not possess $\alpha$-hydrogens. Must contain a non-enolizable carbonyl group. No. While it lacks $\alpha$-hydrogens, the phenyl groups provide significant steric hindrance and electronic stabilization, rendering the carbonyl carbon insufficiently electrophilic for the hydride transfer mechanism characteristic of the Cannizzaro reaction.

Step 3: Visual Representation

C O Ph Ph Benzophenone (Diphenylmethanone)

Step 4: Conclusion on Reactivity

Because benzophenone lacks $\alpha$-hydrogen atoms, it is incapable of undergoing aldol condensation [Per the mechanism requiring an enolate ion intermediate]. Furthermore, despite the absence of $\alpha$-hydrogens, benzophenone is generally inert to the Cannizzaro reaction because the two bulky phenyl groups inhibit the nucleophilic attack of the $OH^-$ ion on the carbonyl carbon, which is the requisite first step for the intermolecular hydride transfer. [Per the mechanism of nucleophilic addition to diaryl ketones].

Final Solution: Benzophenone undergoes neither aldol condensation nor the Cannizzaro reaction.


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