JEE Main 2022 · 26 Jul · Shift 1 · Chemistry Q76

ChemistrySingle correct+4 / -1Question 76 of 90

The major product of the following reaction is

1-Methoxy-6-nitrocyclohexa-1,4-diene (H and NO₂ on the sp³ carbon next to C-OCH₃)

1-Methoxy-6-aminocyclohexa-1,4-diene

2-Nitrocyclohexa-1,4-dien-1-ol

1-Methoxy-2-nitrocyclohexa-2,5-diene (H and OCH₃ on the sp³ carbon)

Answer and worked solution

Official answer: A

Birch reduction. The electron-withdrawing $\mathrm{NO_2}$ carbon becomes sp³ while the OMe-bearing carbon stays on a double bond (option A).

(A)

Topics:Aromatic hydrocarbons and electrophilic substitution

JEE Main 2022 · 26 Jul · Shift 1, Chemistry question 76