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Q8.13(ii):
Give simple chemical tests to distinguish between the following pair of compounds. (ii) Acetophenone and Benzophenone

Solution :

Step 1: Theoretical Basis for Differentiation

To distinguish between Acetophenone ($C_6H_5COCH_3$) and Benzophenone ($C_6H_5COC_6H_5$), we utilize the Iodoform Test. This test is specific for compounds containing the methyl ketone group ($-COCH_3$) or alcohols that can be oxidized to methyl ketones [Per the Haloform Reaction Mechanism].

  • Acetophenone ($C_6H_5COCH_3$): Contains an acetyl group bonded to an aromatic ring. It possesses the necessary $-COCH_3$ structural moiety.
  • Benzophenone ($C_6H_5COC_6H_5$): Comprises two phenyl groups attached to a carbonyl carbon. It lacks the methyl group ($CH_3$) adjacent to the carbonyl function, rendering it Iodoform-negative.

Step 2: Chemical Reaction Mechanism (Iodoform Test)

When Acetophenone is treated with sodium hypoiodite ($NaOI$), formed in situ by the reaction of $I_2$ and $NaOH$, the methyl group is converted into iodoform ($CHI_3$), a yellow precipitate. Benzophenone does not react under these conditions.

Reaction for Acetophenone:

$C_6H_5COCH_3 + 3I_2 + 4NaOH \rightarrow C_6H_5COONa + CHI_3 \downarrow + 3NaI + 3H_2O$

Step 3: Comparative Analysis

Reagent/Test Acetophenone ($C_6H_5COCH_3$) Benzophenone ($C_6H_5COC_6H_5$)
$I_2 / NaOH$ (Iodoform Test) Yellow precipitate of $CHI_3$ formed [Presence of $-COCH_3$]. No yellow precipitate observed [Absence of $-COCH_3$].

Visual Representation of Molecular Structure

Acetophenone CO-CH₃ Benzophenone CO-Ph

Step 4: Conclusion

The Iodoform test provides a definitive distinction: the formation of a characteristic yellow precipitate of $CHI_3$ confirms the presence of the methyl ketone group in Acetophenone, whereas the absence of such a precipitate in the case of Benzophenone confirms its structure lacks the terminal acetyl group.

Final Solution: Use the Iodoform Test ($I_2/NaOH$). Acetophenone produces a yellow precipitate of Iodoform ($CHI_3$), while Benzophenone does not react.


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