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Q8.15(v):
How will you bring about the following conversions in not more than two steps? (v) Benzaldehyde to Benzophenone

Solution :

Step 1: Grignard Addition to Benzaldehyde

To convert benzaldehyde ($C_6H_5CHO$) to benzophenone ($C_6H_5COC_6H_5$), we first increase the carbon skeleton by reacting benzaldehyde with a phenyl-based Grignard reagent, phenylmagnesium bromide ($C_6H_5MgBr$).

The reaction proceeds via the nucleophilic attack of the phenyl group on the electrophilic carbonyl carbon of benzaldehyde [Per the mechanism of Nucleophilic Addition to Carbonyls].

Reaction:

$C_6H_5CHO + C_6H_5MgBr \xrightarrow{\text{Dry Ether}} (C_6H_5)_2CH-OMgBr$

The intermediate alkoxide is subsequently hydrolyzed by dilute acid to form diphenylmethanol (benzhydrol).

$(C_6H_5)_2CH-OMgBr + H_2O/H^+ \rightarrow (C_6H_5)_2CHOH + Mg(OH)Br$

Step 2: Oxidation of Diphenylmethanol to Benzophenone

The secondary alcohol, diphenylmethanol, is then oxidized to the corresponding ketone, benzophenone. This can be achieved using a mild oxidizing agent such as Chromic anhydride ($CrO_3$) or Jones reagent.

Reaction:

$(C_6H_5)_2CHOH \xrightarrow{[O]} C_6H_5COC_6H_5 + H_2O$

Visual Representation of Molecular Transformation

Benzaldehyde + C6H5MgBr Diphenylmethanol [O] Benzophenone

Summary of Chemical Transformations

Step Reagent Transformation
1 $C_6H_5MgBr / H_3O^+$ Addition: Benzaldehyde $\rightarrow$ Diphenylmethanol
2 $CrO_3 / H^+$ Oxidation: Diphenylmethanol $\rightarrow$ Benzophenone

Final Solution: The conversion of benzaldehyde to benzophenone is achieved by first reacting benzaldehyde with phenylmagnesium bromide followed by acid hydrolysis to produce diphenylmethanol, which is then oxidized using chromic anhydride to yield benzophenone.


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