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JEE Advanced 2022 Paper 1 · Chemistry · General Organic Chemistry and Isomerism · hard

(s) regarding nucleophilic substitution and elimination reactions.

One or more options correct

Choose the correct statement(s) regarding nucleophilic substitution and elimination reactions.
  1. A. (R)(R)-2-Bromobutane reacts with NaI in dry acetone by an SN2S_N2 pathway to give (S)(S)-2-iodobutane
  2. B. The rate of hydrolysis of tert-butyl chloride in aqueous ethanol doubles when the concentration of OH−\mathrm{OH^-} is doubled at a fixed concentration of the halide
  3. C. mesomeso-2,3-Dibromobutane on treatment with NaI in acetone (anti-elimination of two bromine atoms) gives (E)(E)-but-2-ene
  4. D. transtrans-1-Bromo-2-methylcyclohexane on E2 reaction with a strong base gives mainly the more substituted alkene 1-methylcyclohexene
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Answer: A, C

A is correct: SN2S_N2 proceeds with inversion. In the substrate the priority order is Br>C2H5>CH3>H\mathrm{Br}>\mathrm{C_2H_5}>\mathrm{CH_3}>\mathrm{H} and in the product I>C2H5>CH3>H\mathrm{I}>\mathrm{C_2H_5}>\mathrm{CH_3}>\mathrm{H}, so the same ranking pattern holds and inversion changes RR to SS. B is incorrect: the rate-determining step of an SN1S_N1 reaction involves only the halide, so doubling [OH−][\mathrm{OH^-}] leaves the rate unchanged. C is correct: in the anti-periplanar conformation of the meso isomer the two methyl groups are also anti, giving the trans alkene; the dldl pair gives ciscis-but-2-ene. D is incorrect: E2 requires an axial leaving group and an axial anti H. In the trans isomer the diaxial conformer places the methyl axial, so the hydrogen on that carbon is equatorial; the elimination goes towards the other side, giving 3-methylcyclohexene. Hence A and C.
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