JEE Main 2022 · 28 Jun · Shift 1 · Chemistry Q75

← JEE Main 2022 · 28 Jun · Shift 1

ChemistrySingle correct+4 / -1Question 75 of 90

Which one of the following compounds is inactive towards S $_N$ 1 reaction ?

tert-Butyl chloride,

\mathrm{(CH_3)_3C{-}Cl}

Allyl chloride,

\mathrm{CH_2{=}CH{-}CH_2Cl}

1-Chlorobicyclo[2.2.1]heptane (Cl at the bridgehead)

Norbornane skeleton with Cl on a bridgehead carbon.

1-Chloro-1-phenylethane,

\mathrm{C_6H_5CH(CH_3)Cl}

Benzene ring attached to a carbon bearing CH3, H and Cl.

Answer and worked solution

Official answer: C

Bridgehead halide. The carbocation at a bridgehead of norbornane cannot become planar, so 1-chlorobicyclo[2.2.1]heptane does not react by $\mathrm{S_N1}$ .

(C)

Topics:SN1 and SN2 Reactive intermediates

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JEE Main 2022 · 28 Jun · Shift 1, Chemistry question 75