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Haloalkanes and Haloarenes question

2024 · 9 Apr · Shift 1 · Q18
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Haloalkanes and Haloarenes question

2024 · 9 Apr · Shift 1 · Q18

JEE MainChemistryHaloalkanes and HaloarenesMCQ+4 / −1
Given below are two statements : one is labelled as Assertion (A) and the other is labelled as Reason (R). Assertion (A) : SN2\mathrm{S}_{\mathrm{N}} 2SN​2 reaction of C6H5CH2Br\mathrm{C}_6 \mathrm{H}_5 \mathrm{CH}_2 \mathrm{Br}C6​H5​CH2​Br occurs more readily than the SN2\mathrm{S}_{\mathrm{N}} 2SN​2 reaction of CH3CH2Br\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{Br}CH3​CH2​Br. Reason (R) : The partially bonded unhybridized p-orbital that develops in the trigonal bipyramidal transition state is stabilized by conjugation with the phenyl ring. In the light of the above statements, choose the most appropriate answer from the options given below :
  1. A
    Both (A) and (R) are correct but (R) is not the correct explanation of (A)
  2. B
    Both (A) and (R) are correct and (R) is the correct explanation of (A)
  3. C
    (A) is not correct but (R) is correct
  4. D
    (A) is correct but (R) is not correct
View written solutionFree

Correct answer: B

  1. Identify the two substrates

    • Benzyl bromide: C6H5CH2Br\mathrm{C_6H_5CH_2Br}C6​H5​CH2​Br
    • Ethyl bromide: CH3CH2Br\mathrm{CH_3CH_2Br}CH3​CH2​Br

    We need to compare their reactivity in the SN2\mathrm{S_N2}SN​2 reaction.

  2. Check Assertion (A)

    In an SN2\mathrm{S_N2}SN​2 reaction, the nucleophile attacks from the back side and passes through a transition state in which the carbon is approximately pentacoordinate (trigonal bipyramidal-like).

    Benzyl halides are known to undergo SN2\mathrm{S_N2}SN​2 reactions faster than normal primary alkyl halides such as ethyl bromide.

    Therefore, C6H5CH2Br\mathrm{C_6H_5CH_2Br}C6​H5​CH2​Br reacts more readily by SN2\mathrm{S_N2}SN​2 than CH3CH2Br.\mathrm{CH_3CH_2Br}.CH3​CH2​Br.

    So, Assertion (A) is correct.

  3. Check Reason (R)

    In the SN2\mathrm{S_N2}SN​2 transition state for benzyl bromide, the reacting benzylic carbon develops partial bonding to both the incoming nucleophile and the leaving group. This transition state has increased p-character / a partially developed unhybridized ppp-orbital character that can overlap with the adjacent phenyl ring.

    Because the benzylic center is directly attached to the benzene ring, this transition state is resonance stabilized by conjugation with the phenyl ring.

    This lowers the activation energy and makes the SN2\mathrm{S_N2}SN​2 reaction faster.

    Hence, Reason (R) is also correct.

  4. Does (R) explain (A)?

    Yes. The enhanced SN2\mathrm{S_N2}SN​2 reactivity of benzyl bromide compared to ethyl bromide is due to stabilization of the transition state by conjugation with the phenyl ring.

    Thus, (R) is the correct explanation of (A).

  5. Correct option

    Therefore, the correct answer is: B\boxed{\text{B}}B​

    Both (A) and (R) are correct and (R) is the correct explanation of (A).

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