JEE Main 2022 · 26 Jul · Shift 1 · Chemistry Q74

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ChemistrySingle correct+4 / -1Question 74 of 90

The products formed in the following reaction, A and B are

4-Oxocyclohexanecarbaldehyde treated with [Ag(NH3)2]+ OH⁻ to give A, then NaBH4 to give B.

A = 4-(hydroxymethyl)cyclohexanone, B = 4-(hydroxymethyl)cyclohexanol

A: cyclohexanone with CH2OH at C4; B: cyclohexanol with CH2OH at C4.

A = 4-hydroxycyclohexanecarbaldehyde, B = 4-(hydroxymethyl)cyclohexanol

A: cyclohexanol with CHO at C4; B: cyclohexanol with CH2OH at C4.

A = 4-oxocyclohexanecarboxylic acid, B = 4-hydroxycyclohexanecarboxylic acid

A: cyclohexanone with COOH at C4; B: cyclohexanol with COOH at C4.

A = 4-oxocyclohexanecarboxylic acid, B = 4-(hydroxymethyl)cyclohexanol

A: cyclohexanone with COOH at C4; B: cyclohexanol with CH2OH at C4.

Answer and worked solution

Official answer: C

Tollens' oxidises only the aldehyde: A is 4-oxocyclohexanecarboxylic acid. $\mathrm{NaBH_4}$ reduces only the ketone: B is 4-hydroxycyclohexanecarboxylic acid.

(C)

Topics:Oxidation and reduction

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JEE Main 2022 · 26 Jul · Shift 1, Chemistry question 74