Which of the following reagents are not correctly matched with the reaction?

C H_{3} C H = C H C H O \to C H_{3} C H = C H C O O H : A m m o n i a c a l A g N O_{3}

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C H_{3} C H = C H C H O \to C H_{3} C H - C H C H_{2} O H : K M n O_{4}

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R - C H O \to R - C H_{2} O H : N a B H_{4}

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C H_{3} C H_{2} C O C l \to C H_{3} C H_{2} C H O : H_{2}, P d / B a S O_{4}

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Solution

The correct option is B $C H_{3} C H = C H C H O \to C H_{3} C H - C H C H_{2} O H : K M n O_{4}$
(1) Tollen's reagent refers to the chemical reagent which is used in the detection of an aldehyde functional group, an aromatic aldehyde functional group, or an alpha hydroxy ketone functional group in a given test substance.
Ketones don't give silver mirror with Tollens' reagent.
Tollen's reagent is a solution of silver nitrate $(A g N O_{3})$ and Ammonia $(N H_{3})$ .
A postive test gives precipitate of elements silver. $R C H O + 2 [A g (N H_{3})_{2}]^{+} + 3 O H^{-} \to R C O O^{-} + 2 A g ↓ + 2 H_{2} O + 4 N H_{3} Aldehyde Tollen's Reagent Carboxylate ion Silver mirror$

(2) $K M n O_{4}$ oxidises aldehyde to carboxylic acid as it is an oxidising agent.

(3) $N a B H_{4}$ reduces aldehyde to primary alcohol.

(4) $H_{2}, P d / B a S O_{4}$ reduces carbonyl chloride to aldehyde.

Hence, the correct answer is option (b).

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