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Q.(a) Which halogen compound in the following pair will react faster in SN2S_N2 reactions and why ? CH3−CH2−ICH_3-CH_2-I

(OR)
CH3−CH2−BrCH_3-CH_2-Br
(b) Why is chloroform stored in closed dark coloured bottles ?
CBSECBSE Class XII Board 2024Subjective· 2mImportance★★★★★
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  1. CH3CH2ICH_3CH_2I reacts faster in SN2S_N2 because I−I^- is a better leaving group than Br−Br^-.
  2. Chloroform is stored in closed dark bottles because light and air slowly oxidise it to poisonous phosgene, COCl2COCl_2.

Part (a) — Which reacts faster in SN2S_N2?

An SN2S_N2 reaction is a single-step, back-side attack in which the nucleophile bonds as the leaving group departs. Its rate is strongly influenced by how good the leaving group is — i.e. how weak the C–X bond is and how stable the departing halide ion is.

Comparing the two ethyl halides (same alkyl group, so sterics are identical):

  • Bond strength: C–I (~240 kJ mol⁻¹) is weaker than C–Br (~285 kJ mol⁻¹), so C–I breaks more easily.
  • Leaving-group stability: I−I^- is the larger, more polarisable ion; its charge is spread over a bigger volume, making it more stable and a better leaving group.

Leaving-group ability: I−>Br−>Cl−>F−\text{Leaving-group ability: } I^- > Br^- > Cl^- > F^-

Therefore ethyl iodide, CH3CH2ICH_3CH_2I, reacts faster than ethyl bromide. …

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