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Question 31 of 48

Q.(i) What will happen when bromomethane reacts with an aqueous solution of sodium hydroxide? Write the mechanism of the reaction.

(ii) What will happen when chlorobenzene reacts with a mixture of conc. HNO3 and conc. H2SO4?
West Bengal WbchseWest Bengal HS (WBCHSE) Board 2016Subjective· 3mImportance★★★★★
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Figure — The stem explicitly asks to write the mechanism of bromomethane with aqueous NaOH, a textbook SN2; the catalog
Figure — The stem explicitly asks to write the mechanism of bromomethane with aqueous NaOH, a textbook SN2; the catalog

Bromomethane undergoes SN2 substitution with aqueous NaOH to give methanol; chlorobenzene undergoes electrophilic nitration (Cl directs o,p) to give mainly p-chloronitrobenzene.

(i) Bromomethane + aqueous NaOH: Since bromomethane is a primary (methyl) halide, the hydroxide ion, a strong nucleophile, attacks the carbon bearing bromine from the side opposite to the leaving group (backside attack) in a single, concerted step — a bimolecular nucleophilic substitution (SN2S_N2).

Mechanism: OH⁻ approaches carbon from the face opposite to Br⁻; a pentacoordinate transition state forms (OH⁻...C...Br⁻ partial bonds); as the C–OH bond forms, the C–Br bond breaks, and the configuration at carbon inverts (Walden inversion, though not stereochemically visible here since CH₃Br has no stereocentre).

CH3Br+OH−→CH3OH+Br−CH_3Br + OH^- \rightarrow CH_3OH + Br^-

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