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Question 62

Given below are two statements:
Statement I: Cross aldol condensation between two different aldehydes will always produce four different products.
Statement II: When semicarbazide reacts with a mixture of benzaldehyde and acetophenone under optimum pH, it fonns a condensation product with acetophenone only.
In the light of the above statements, choose the correct answer from the options given below

We need to evaluate two statements about aldol condensation and semicarbazide reactions.

Considering Statement I: "Cross aldol condensation between two different aldehydes will always produce four different products."

In a cross aldol condensation between two different aldehydes (say A and B), the possible products arise from four combinations:

- A acts as both nucleophile (enolate) and electrophile (carbonyl)

- B acts as both nucleophile (enolate) and electrophile (carbonyl)

- A (enolate) attacks B (carbonyl)

- B (enolate) attacks A (carbonyl)

However, this produces four products ONLY when both aldehydes have alpha-hydrogens (needed to form the enolate). If one aldehyde lacks alpha-hydrogens (e.g., formaldehyde HCHO or benzaldehyde $$C_6H_5CHO$$), it cannot form an enolate and can only act as the electrophile. In such cases, fewer than four products are formed.

Since the statement says "always," it is FALSE because there are common cases (involving aldehydes without alpha-H) where fewer than four products form.

Considering Statement II: "When semicarbazide reacts with a mixture of benzaldehyde and acetophenone under optimum pH, it forms a condensation product with acetophenone only."

Semicarbazide ($$H_2N\text{-}NH\text{-}CO\text{-}NH_2$$) is a nucleophile that reacts with carbonyl compounds to form semicarbazones (C=N-NH-CO-NH$$_2$$). The reaction involves nucleophilic addition to the carbonyl group followed by elimination of water.

Between benzaldehyde (an aldehyde) and acetophenone (a ketone), benzaldehyde is more reactive toward nucleophilic addition because:

- Aldehydes are generally more reactive than ketones due to less steric hindrance at the carbonyl carbon

- Aldehydes have only one electron-donating group attached to C=O (vs. two in ketones), making the carbonyl carbon more electrophilic

Therefore, semicarbazide would preferentially react with benzaldehyde, not acetophenone. The statement claims the opposite, so it is FALSE.

Since both statements are false, the correct answer is Option (2): Both Statement I and Statement II are false.

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