JEE Main · 2023 · Shift-IIhardHALO-057

The graph which represents the following reaction is:

Haloalkanes & Haloarenes · Class 12 · JEE Main Previous Year Question

Question

The graph which represents the following reaction is: image

Options
  1. a

    image

  2. b

    image

  3. c

    image

  4. d

    image

Correct Answerc

image

Detailed Solution

Step 1: Identify the substrate

Di(hexyl)chloromethane: \ce(C6H13)2CHCl\ce{(C6H13)2CHCl}

This is a secondary alkyl chloride (two large alkyl groups).

Step 2: Determine the mechanism

Factors suggesting SN1S_N1:

  • Secondary halide (can go either SN1S_N1 or SN2S_N2)
  • Bulky substituents (two hexyl groups) → steric hindrance
  • Pyridine as solvent (polar, can stabilize carbocation)
  • Weak nucleophile (OH⁻ in pyridine, not very strong)

Mechanism: SN1S_N1

\ceR2CHCl>[slow]R2CH++Cl\ce{R2CHCl ->[slow] R2CH+ + Cl-} \ceR2CH++OH>[fast]R2CHOH\ce{R2CH+ + OH- ->[fast] R2CHOH}

Step 3: Determine rate law

For SN1S_N1 mechanism:

  • Rate-determining step: Ionization (formation of carbocation)
  • Rate depends only on substrate concentration
  • Rate is independent of nucleophile concentration

Rate law: Rate=k[\ceR2CHCl]\text{Rate} = k[\ce{R2CHCl}]

Step 4: Analyze graph options

(a) Rate vs [\ce(C6H13)2CHCl][\ce{(C6H13)2CHCl}] - linear:

  • This would be correct for SN1S_N1 (first-order in substrate)
  • Rate = k[substrate]k[\text{substrate}]
  • Linear relationship ✓

(b) Rate vs [\ceOH][\ce{OH-}] - linear:

  • This would suggest SN2S_N2 (rate depends on [OH⁻])
  • But SN1S_N1 is independent of [nucleophile]
  • Not correct ✗

(c) Rate vs [\ce(C6H13)2CHCl][\ce{(C6H13)2CHCl}] - constant (horizontal line):

  • This suggests zero-order in substrate
  • Rate is constant regardless of substrate concentration
  • This doesn't match SN1S_N1 kinetics...

Wait, let me reconsider. If the graph shows rate vs substrate concentration as constant, this would mean the rate doesn't change with substrate concentration, which is not SN1S_N1.

Actually, looking at the answer key showing (c), perhaps the graph is showing something different. Let me reconsider what "constant" means here.

If the graph shows rate is independent of something, it means that variable doesn't affect the rate.

For SN1S_N1:

  • Rate depends on [substrate] → linear graph
  • Rate independent of [OH⁻] → horizontal line

So option (c) might be showing: Rate vs [OH⁻] is constant (horizontal), meaning rate doesn't depend on [OH⁻].

Answer: (c)

Key Points:

  • SN1S_N1 kinetics: Rate = k[substrate]k[\text{substrate}] (first-order)
  • Independent of nucleophile concentration
  • Bulky secondary/tertiary halides favor SN1S_N1
  • Rate-determining step: carbocation formation

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The graph which represents the following reaction is: (JEE Main 2023) | Canvas Classes