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Haloalkanes and Haloarenes question

2007 · Shift 0 · Q19
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Haloalkanes and Haloarenes question

2007 · Shift 0 · Q19

JEE MainChemistryHaloalkanes and HaloarenesMCQ+4 / −1
Which of the following is the correct order of decreasing SN2 reactivity?
  1. A
    RCH2XRCH_2XRCH2​X > R3CXR_3CXR3​CX > R2CHXR_2CHXR2​CHX
  2. B
    RCH2XRCH_2XRCH2​X > R2CHXR_2CHXR2​CHX > R3CXR_3CXR3​CX
  3. C
    R3CXR_3CXR3​CX > R2CHXR_2CHXR2​CHX > RCH2XRCH_2XRCH2​X
  4. D
    R2CHXR_2CHXR2​CHX > R3CXR_3CXR3​CX > RCH2XRCH_2XRCH2​X
View written solutionFree

Correct answer: B

  1. Recall the trend for SN2S_N2SN​2 reactions

    In an SN2S_N2SN​2 reaction, the nucleophile attacks the carbon atom from the backside in a single step.

    Therefore, the reaction is highly sensitive to steric hindrance around the carbon attached to the leaving group.

  2. Compare the substrates

    • RCH2XRCH_2XRCH2​X = primary alkyl halide
    • R2CHXR_2CHXR2​CHX = secondary alkyl halide
    • R3CXR_3CXR3​CX = tertiary alkyl halide
  3. Effect of steric hindrance on SN2S_N2SN​2 reactivity

    Since backside attack becomes more difficult as substitution increases:

    Primary>Secondary>Tertiary\text{Primary} > \text{Secondary} > \text{Tertiary}Primary>Secondary>Tertiary

    Hence,

    RCH2X>R2CHX>R3CXRCH_2X > R_2CHX > R_3CXRCH2​X>R2​CHX>R3​CX

  4. Match with the given options

    • A: RCH2X>R3CX>R2CHXRCH_2X > R_3CX > R_2CHXRCH2​X>R3​CX>R2​CHX ❌
    • B: RCH2X>R2CHX>R3CXRCH_2X > R_2CHX > R_3CXRCH2​X>R2​CHX>R3​CX ✅
    • C: R3CX>R2CHX>RCH2XR_3CX > R_2CHX > RCH_2XR3​CX>R2​CHX>RCH2​X ❌
    • D: R2CHX>R3CX>RCH2XR_2CHX > R_3CX > RCH_2XR2​CHX>R3​CX>RCH2​X ❌
  5. Final answer

    The correct order of decreasing SN2S_N2SN​2 reactivity is:

    RCH2X>R2CHX>R3CXRCH_2X > R_2CHX > R_3CXRCH2​X>R2​CHX>R3​CX

    So, Option B is correct.

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