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Q8.7(vii):
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. (vii) Phenylacetaldehyde

Solution :

1. Structural Analysis of Phenylacetaldehyde

The chemical structure of Phenylacetaldehyde is $C_6H_5CH_2CHO$. Upon structural analysis:

  • The molecule contains an aldehyde functional group ($-CHO$).
  • The carbon atom adjacent to the carbonyl group (the $\alpha$-carbon) is bonded to two hydrogen atoms. These are known as $\alpha$-hydrogens.

2. Reactivity Determination

Aldol Condensation: Since the molecule possesses $\alpha$-hydrogens, it is capable of forming an enolate ion in the presence of a dilute base. Therefore, it undergoes Aldol Condensation. [Per the mechanism of Aldol Condensation, compounds with at least one $\alpha$-hydrogen are reactive.]

Cannizzaro Reaction: This reaction is specific to aldehydes lacking $\alpha$-hydrogens. Since Phenylacetaldehyde contains $\alpha$-hydrogens, it does not undergo the Cannizzaro reaction. [Per the defining criteria of the Cannizzaro reaction, the absence of $\alpha$-hydrogens is a strict prerequisite.]

3. Product of Aldol Condensation

In the presence of dilute $NaOH$, two molecules of Phenylacetaldehyde condense to form a $\beta$-hydroxy aldehyde, which subsequently undergoes dehydration to form an $\alpha,\beta$-unsaturated aldehyde.

Reaction: $2 C_6H_5CH_2CHO \xrightarrow{dil. NaOH} C_6H_5CH_2CH(OH)CH(C_6H_5)CHO \xrightarrow{\Delta, -H_2O} C_6H_5CH_2CH=C(C_6H_5)CHO$

The final product is 2,4-diphenylbut-2-enal.

4. Visual Representation of the Reactant

CH₂ CHO C₆H₅

5. Summary Table

Reaction Type Result
Aldol Condensation Yes
Cannizzaro Reaction No

Final Solution: Phenylacetaldehyde undergoes Aldol Condensation to yield 2,4-diphenylbut-2-enal ($C_6H_5CH_2CH=C(C_6H_5)CHO$) and does not undergo the Cannizzaro reaction because it possesses $\alpha$-hydrogens.


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