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Question 80 of 83

Q.(a) Write salient features of SN_N2 mechanism.

(b) What is the action of following reagents on bromomethane:
(i) bromobenzene
(ii) mercurous fluoride
Maharashtra MsbshseMaharashtra HSC (MSBSHSE) Board 2025Subjective· 4mImportance★★★★★
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SN2S_N2: concerted, bimolecular, backside attack → inversion; rate = k[substrate][Nu⁻]. Bromomethane + bromobenzene/Na (Wurtz-Fittig) → toluene; + Hg2_2F2_2 (Swarts) → fluoromethane.

(a) Salient features of the SN2S_N2 mechanism:

  1. It is a bimolecular, single-step (concerted) reaction — bond breaking (C–LG) and bond forming (C–Nu) happen simultaneously, with no carbocation intermediate.
  2. Rate depends on the concentration of BOTH the substrate and the nucleophile: Rate=k[substrate][Nu−]\text{Rate} = k[\text{substrate}][Nu^-] (second order overall).
  3. The nucleophile attacks from the side opposite to the leaving group (backside attack), passing through a trigonal bipyramidal transition state.
  4. This backside attack causes inversion of configuration at the reacting carbon (Walden inversion).
  5. Favoured by primary alkyl halides, strong nucleophiles, and polar aprotic solvents; hindered by bulky substrate groups.

(b)(i) Bromomethane + bromobenzene: this is a Wurtz–Fittig reaction — an aryl halide and an alkyl halide are coupled using sodium metal in dry ether, joining the alkyl and aryl groups:

CH3Br+C6H5Br+2Na→dry etherC6H5−CH3 (toluene)+2NaBrCH_3Br + C_6H_5Br + 2Na \xrightarrow{dry\ ether} C_6H_5-CH_3\ (\text{toluene}) + 2NaBr

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