JEE Main 2022 · 27 Jun · Shift 1 · Chemistry Q75

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ChemistrySingle correct+4 / -1Question 75 of 90

The major product of the following reaction is :

Reactant: 1-(2-fluoro-4-nitrophenyl)-1-iodobutane, I on a wedge at the benzylic carbon, F ortho and NO2 para on the ring; treated with PhS⁻Na⁺ in DMF.

SPh hashed at the side-chain carbon, ring F kept (inverted)

Benzylic SPh on a hashed bond (configuration inverted), ring F and para NO2 kept.

I kept at the side chain, ring F replaced by SPh

Benzylic I on a wedge kept; ring F replaced by SPh, para NO2.

SPh wedged at the side-chain carbon, ring F kept (retained)

Benzylic SPh on a wedge (configuration retained), ring F and para NO2 kept.

SPh at the side chain (wedged) and ring F replaced by SPh

Benzylic SPh on a wedge and ring F also replaced by SPh, para NO2.

Answer and worked solution

Official answer: A

Where it reacts. The ring F is meta to $\mathrm{NO_2}$ , so it is not activated for $S_NAr$ . The secondary benzylic iodide undergoes $S_N2$ with $\mathrm{PhS^-}$ in DMF, with inversion: SPh on a hashed bond, F kept.

(A)

Topics:SN1 and SN2 Haloarenes

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JEE Main 2022 · 27 Jun · Shift 1, Chemistry question 75