Question 80 of 83
Q.(a) Write salient features of S2 mechanism.
(b) What is the action of following reagents on bromomethane:
(i) bromobenzene
(ii) mercurous fluoride
Maharashtra MsbshseMaharashtra HSC (MSBSHSE) Board 2025Subjective· 4mImportance★★★★★
96% · 80/83 Questions
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Start your 14-day free trial to unlock the full solution →: concerted, bimolecular, backside attack → inversion; rate = k[substrate][Nu⁻]. Bromomethane + bromobenzene/Na (Wurtz-Fittig) → toluene; + HgF (Swarts) → fluoromethane.
(a) Salient features of the mechanism:
- It is a bimolecular, single-step (concerted) reaction — bond breaking (C–LG) and bond forming (C–Nu) happen simultaneously, with no carbocation intermediate.
- Rate depends on the concentration of BOTH the substrate and the nucleophile: (second order overall).
- The nucleophile attacks from the side opposite to the leaving group (backside attack), passing through a trigonal bipyramidal transition state.
- This backside attack causes inversion of configuration at the reacting carbon (Walden inversion).
- 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:
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