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Haloalkanes and Haloarenes question

2025 · 24 Jan · Shift 1 · Q5
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  5. /2025 · 24 Jan · Shift 1 · Q5

Haloalkanes and Haloarenes question

2025 · 24 Jan · Shift 1 · Q5

JEE MainChemistryHaloalkanes and HaloarenesMCQ+4 / −1
Given below are two statements: Statement I: The conversion proceeds well in the less polar medium. CH3−CH2−CH2−CH2−Cl→HO−CH3−CH2−CH2−CH2−OH+Cl(−)\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{CH}_2-\mathrm{CH}_2-\mathrm{Cl} \xrightarrow{\mathrm{HO}^{-}} \mathrm{CH}_3-\mathrm{CH}_2-\mathrm{CH}_2-\mathrm{CH}_2-\mathrm{OH}+\mathrm{Cl}^{(-)}CH3​−CH2​−CH2​−CH2​−ClHO−​CH3​−CH2​−CH2​−CH2​−OH+Cl(−) Statement II: The conversion proceeds well in the more polar medium. JEE Main 2025 (Online) 24th January Morning Shift Chemistry - Haloalkanes and Haloarenes Question 11 English In the light of the above statements, choose the correct answer from the options given below
  1. A
    Statement I is false but Statement II is true
  2. B
    Statement I is true but Statement II is false
  3. C
    Both Statement I and Statement II are false
  4. D
    Both Statement I and Statement II are true
View written solutionFree

Correct answer: B

  1. Identify the reaction type

The reaction is:

CH3CH2CH2CH2Cl+HO−→CH3CH2CH2CH2OH+Cl−\mathrm{CH_3CH_2CH_2CH_2Cl} + \mathrm{HO^-} \rightarrow \mathrm{CH_3CH_2CH_2CH_2OH} + \mathrm{Cl^-}CH3​CH2​CH2​CH2​Cl+HO−→CH3​CH2​CH2​CH2​OH+Cl−

This is the conversion of a primary alkyl halide (1-chlorobutane) to an alcohol by nucleophilic substitution.

For a primary haloalkane, the reaction with HO−\mathrm{HO^-}HO− generally proceeds by the SN2S_N2SN​2 mechanism.


  1. Effect of solvent polarity on SN2S_N2SN​2 reaction

In an SN2S_N2SN​2 reaction, the nucleophile must attack the carbon directly. The reactivity depends strongly on the solvent.

  • In polar protic solvents (more polar medium like water/alcohol), HO−\mathrm{HO^-}HO− is heavily solvated by hydrogen bonding.
  • Heavy solvation reduces the nucleophilicity of HO−\mathrm{HO^-}HO−.
  • Therefore, SN2S_N2SN​2 reactions are generally slower in such more polar protic media.

Hence, the conversion proceeds better in a less polar medium (more precisely, less strongly solvating medium).

So, Statement I is true.


  1. Check Statement II

Statement II says the conversion proceeds well in the more polar medium.

For this particular reaction involving HO−\mathrm{HO^-}HO− and a primary haloalkane, a more polar protic medium strongly solvates the nucleophile and lowers its nucleophilicity, so the substitution does not proceed better there.

Thus, Statement II is false.


  1. Choose the correct option
  • Statement I: True
  • Statement II: False

Therefore, the correct option is:

B\boxed{\text{B}}B​


  1. Comparison with stored correct answer

The stored correct answer is D.

My derived answer is B. These do not match.

The likely issue is that the stored answer treats “more polar medium” too generally, but for an SN2S_N2SN​2 reaction with HO−\mathrm{HO^-}HO−, increased protic polarity usually decreases nucleophilic strength due to solvation. Hence Statement II should not be true in the standard JEE context.

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