One or more options correct
Choose the correct statement(s) regarding nucleophilic substitution and elimination reactions.
- A. -2-Bromobutane reacts with NaI in dry acetone by an pathway to give -2-iodobutane
- B. The rate of hydrolysis of tert-butyl chloride in aqueous ethanol doubles when the concentration of is doubled at a fixed concentration of the halide
- C. -2,3-Dibromobutane on treatment with NaI in acetone (anti-elimination of two bromine atoms) gives -but-2-ene
- D. -1-Bromo-2-methylcyclohexane on E2 reaction with a strong base gives mainly the more substituted alkene 1-methylcyclohexene
Show answer and solution
Answer: A, C
A is correct: proceeds with inversion. In the substrate the priority order is and in the product , so the same ranking pattern holds and inversion changes to . B is incorrect: the rate-determining step of an reaction involves only the halide, so doubling 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 pair gives -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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