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Chemistry · Ch 11 — Hydroxy Compounds and Ethers

Preparation of Alcohols from Alkyl Halides

11.3.1

Preparation of Alcohols from Alkyl Halides

Alkyl halides, on heating with dilute aqueous NaOH, undergo nucleophilic substitution to give alcohols: R-X + NaOH(aq), heat, gives R-OH + NaX. Primary alkyl halides react by the bimolecular SN2 mechanism (backside attack of hydroxide with inversion at carbon), while secondary and tertiary alkyl halides usually react by the unimolecular SN1 mechanism, via a carbocation intermediate -- for example, tert-butyl halide first …