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Haloalkanes and Haloarenes question

2020 · 2 Sep · Shift 1 · Q11
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Haloalkanes and Haloarenes question

2020 · 2 Sep · Shift 1 · Q11

JEE MainChemistryHaloalkanes and HaloarenesMCQ+4 / −1
Which of the following compunds will show retention in configuration on nucleophilic substitution by OH– ion?
  1. A
    JEE Main 2020 (Online) 2nd September Morning Slot Chemistry - Haloalkanes and Haloarenes Question 118 English Option 1
  2. B
    JEE Main 2020 (Online) 2nd September Morning Slot Chemistry - Haloalkanes and Haloarenes Question 118 English Option 2
  3. C
    JEE Main 2020 (Online) 2nd September Morning Slot Chemistry - Haloalkanes and Haloarenes Question 118 English Option 3
  4. D
    JEE Main 2020 (Online) 2nd September Morning Slot Chemistry - Haloalkanes and Haloarenes Question 118 English Option 4
View written solutionFree

Correct answer: C

The question asks which compound shows retention of configuration when undergoing nucleophilic substitution by \ceOH−\ce{OH^-}\ceOH−.

However, the actual structures/options A, B, C, D are missing from the prompt. Since retention/inversion/racemization depends completely on the substrate structure and mechanism, the answer cannot be derived rigorously without seeing the compounds.

1. Key idea

For nucleophilic substitution:

  1. SN2\mathrm{S_N2}SN​2 reaction gives inversion of configuration (Walden inversion).
  2. SN1\mathrm{S_N1}SN​1 reaction usually gives racemization (often partial racemization).
  3. Neighbouring group participation / double inversion can lead to overall retention of configuration.

So, the correct compound must be one whose structure allows retention, usually through:

  • neighbouring group participation,
  • cyclic intermediate formation,
  • or a sequence equivalent to double inversion.

2. Limitation in this problem

The options are shown as:

  • A:
  • B:
  • C:
  • D:

but the chemical structures are not provided. Therefore, a step-by-step structural comparison is not possible from the given data alone.

3. Comparison with stored answer

The stored correct answer is C. Since the actual options are missing, I cannot independently verify it from first principles here. But if the exam source marks C, then likely option C is the substrate that undergoes substitution with overall retention of configuration, probably via neighbouring group participation / double inversion.

Thus, based only on the provided stored answer, I will report C, while noting that the question statement is incomplete without structures.

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