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Hydrocarbons question

2024 · 8 Apr · Shift 2 · Q15
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Hydrocarbons question

2024 · 8 Apr · Shift 2 · Q15

JEE MainChemistryHydrocarbonsMCQ+4 / −1
Given below are two statements : Statement (I) : SN2\mathrm{S}_{\mathrm{N}} 2SN​2 reactions are 'stereospecific', indicating that they result in the formation of only one stereo-isomer as the product. Statement (II) : SN1\mathrm{S}_{\mathrm{N}} 1SN​1 reactions generally result in formation of product as racemic mixtures. In the light of the above statements, choose the correct answer from the options given below :
  1. A
    Both Statement I and Statement II are false
  2. B
    Statement I is false but Statement II is true
  3. C
    Statement I is true but Statement II is false
  4. D
    Both Statement I and Statement II are true
View written solutionFree

Correct answer: D

  1. Analyze Statement (I): SN2\mathrm{S_N2}SN​2 reactions are stereospecific

    In an SN2\mathrm{S_N2}SN​2 reaction, the nucleophile attacks the carbon atom from the backside of the leaving group.

    This causes Walden inversion at the chiral center.

    So, if the substrate is optically active and has a chiral center, the configuration changes in a definite way: R→SorS→RR \to S \quad \text{or} \quad S \to RR→SorS→R (depending on priority order after substitution).

    Thus, the reaction is stereospecific because a given stereoisomeric reactant gives a specific stereoisomeric product.

    Therefore, Statement (I) is true.

  2. Analyze Statement (II): SN1\mathrm{S_N1}SN​1 reactions generally give racemic mixtures

    In an SN1\mathrm{S_N1}SN​1 reaction, the leaving group first departs to form a planar carbocation intermediate.

    Since the carbocation is planar, the nucleophile can attack from either side:

    • front side attack
    • back side attack

    Hence, both enantiomers are formed, and the product is generally a racemic mixture (though often not perfectly 50:50 due to ion-pair effects, but generally racemization is observed).

    Therefore, Statement (II) is true.

  3. Choose the correct option

    Since both statements are true, the correct option is: D\boxed{D}D​

  4. Comparison with stored answer

    Stored correct answer: DDD

    My derived answer also is DDD, so they agree.

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