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Q8.7(vi):
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. (vi) 1-Phenylpropanone

Solution :

Step 1: Structural Analysis of 1-Phenylpropanone

The chemical structure of 1-phenylpropanone (also known as propiophenone) is $C_6H_5-CO-CH_2CH_3$. The molecule consists of a carbonyl group attached to a phenyl ring and an ethyl group. To determine the reactivity, we examine the $\alpha$-carbons adjacent to the carbonyl group ($>C=O$).

  • Carbonyl Carbon: $C_1$ of the propanone chain.
  • $\alpha$-Carbon: The carbon at the $C_2$ position ($CH_2$ group) is directly attached to the carbonyl carbon.
  • $\alpha$-Hydrogen Availability: The $CH_2$ group contains two hydrogen atoms. Therefore, 1-phenylpropanone possesses $\alpha$-hydrogens.

Step 2: Evaluating Reaction Pathways

Reactivity is determined by the presence of $\alpha$-hydrogens:

Reaction Type Condition Applicability to 1-Phenylpropanone
Aldol Condensation Requires $\alpha$-hydrogens Applicable (Due to the presence of two $\alpha$-hydrogens).
Cannizzaro Reaction Requires absence of $\alpha$-hydrogens Not Applicable.

Step 3: Derivation of the Aldol Condensation Product

Under basic conditions, the $\alpha$-hydrogen is abstracted to form an enolate, which attacks another molecule of 1-phenylpropanone. The condensation reaction proceeds as follows:

$2 C_6H_5COCH_2CH_3 \xrightarrow{OH^-} C_6H_5-C(OH)(CH_2CH_3)-CH(CH_3)-CO-C_6H_5 \xrightarrow{\Delta, -H_2O} C_6H_5-C(=C(CH_3)-CO-C_6H_5)-CH_2CH_3$

Visual Representation of the Molecular Framework

C6H5 - CO - CH2 - CH3 Alpha-Carbon Contains 2 H-atoms

Step 4: Conclusion of Reactivity

Since 1-phenylpropanone contains $\alpha$-hydrogens, it undergoes Aldol Condensation. It does not undergo the Cannizzaro reaction because the latter is restricted to aldehydes lacking $\alpha$-hydrogens (or hindered ketones in specific non-standard scenarios, which do not apply here).

Final Solution: 1-Phenylpropanone undergoes Aldol Condensation. The product is 2-methyl-1,3-diphenylpent-2-en-1-one (formed via self-aldol condensation followed by dehydration). It does not undergo the Cannizzaro reaction.


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