JEE Main 2022 · 25 Jul · Shift 1 · Chemistry Q75

ChemistrySingle correct+4 / -1Question 75 of 90

Which one of the following reactions does not represent correct combination of substrate and product under the given conditions ?

4-Methylbenzoyl chloride with

\mathrm{H_2}

, Pd-BaSO

_4

gives 4-methylbenzaldehyde

4-Methylbenzonitrile with (i) DIBAL-H, (ii) H₂O gives 4-methylbenzaldehyde

Ethyl 4-methylbenzoate with (i) AlH(iso-Bu)

_2

, (ii) H

_2

O gives 4-methylbenzaldehyde

4-Methylbenzyl alcohol with (i)

\mathrm{Na_2Cr_2O_7}

, (ii)

\mathrm{H_2SO_4}

, H

_2

O gives 4-methylbenzaldehyde

Answer and worked solution

Official answer: D

Acidified dichromate oxidises the primary alcohol on to 4-methylbenzoic acid, not the aldehyde.

(D)

Topics:Oxidation and reduction

JEE Main 2022 · 25 Jul · Shift 1, Chemistry question 75