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Question 45

Identify A in the given chemical reaction.

The reaction undergoes an intramolecular aldol condensation.

The starting compound is a dialdehyde containing acidic $$\mathrm{\alpha}$$-hydrogens adjacent to both aldehyde groups.

In the presence of sodium hydroxide:

$$\mathrm{NaOH}$$

one $$\mathrm{\alpha}$$-hydrogen is removed to form a resonance-stabilised enolate ion.

$$\mathrm{R-CH_2-CHO + OH^- \longrightarrow R-CH^- -CHO + H_2O}$$

The enolate ion acts as a nucleophile.

Since another aldehyde group is present within the same molecule, intramolecular nucleophilic attack occurs on the second carbonyl carbon.

$$\mathrm{Enolate + CHO \longrightarrow Cyclic\ \beta\text{-}Hydroxy\ Aldehyde}$$

Because the two side chains are ortho-substituted on the benzene ring, they remain close together, favouring cyclisation.

This forms a new seven-membered ring fused to the benzene ring.

On heating:

$$\mathrm{\Delta}$$

the cyclic $$\mathrm{\beta}$$-hydroxy aldehyde undergoes dehydration.

$$\mathrm{\beta\text{-}Hydroxy\ Aldehyde \longrightarrow \alpha,\beta\text{-}Unsaturated\ Aldehyde + H_2O}$$

image

Dehydration of this product gives us the required answer.

The final product contains:

1. A fused seven-membered ring

2. An $$\mathrm{\alpha,\beta}$$-unsaturated double bond

3. Conjugation with the remaining aldehyde group

Therefore, the major product $$\mathrm{A}$$ is the conjugated cyclic $$\mathrm{\alpha,\beta}$$-unsaturated aldehyde.

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