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Question

Which one of the following compounds most readily undergoes substitution by SN2 mechanism?


A
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B
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C
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D
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Solution

The correct option is B

The explanation for the correct option

(B)

SN2 reaction

  • SN2 stands for Substitution nucleophilic bimolecular reaction.
  • In this reaction, the rate of reaction depends upon the concentration of both reactants.
  • It follows second-order kinetics.
  • This reaction occurs in one step.
  • In this reaction, the formation of the bond and cleavage of the bond occurs simultaneously.

Order of SN2 reaction

  • The increasing order of the nucleophilic substitution by SN2:

tertiary alkyl halide < secondary alkyl halide < primary alkyl halide < methyl

  • Structure compound B:
  • Compound B is the primary alkyl halide.
  • IUPAC name of Compound B is 1-chloroethane and molecular formula is C2H5Cl.

The explanation for incorrect options

(A)

  • Structure of compound A:
  • Compound A is also a primary alkyl halide but the carbon atom attached to it is more hindered.
  • IUPAC name of Compound A is 1-chloro-2-methylpropane and molecular formula is C4H9Cl.

(C)

  • Structure of compound C:
  • Compound C is also a secondary alkyl halide.
  • IUPAC name of Compound C is 2-chloropentane and molecular formula is C5H11Cl.

(D)

  • Structure of compound D:
  • Compound D is also a tertiary alkyl halide.
  • IUPAC name of Compound D is 2-chloro-2-methylpropane and molecular formula is C4H9Cl.

Therefore, the correct option is (B).


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