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two-step method involving an SN2 attack of an alkoxide on an unhindered primary halide or tosylate
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- LDA (or NAH... H2 product) can convert a carbonyl compound completely to its enolate, avoiding an equilibrium mixture of carbonyl compound and enolate
- carbonyl carbon has a partial positive charge and will react as an electrophile; the oxygen atom has a partial negative charge and is nucleophilic
- when attack takes place at chirality center, inversion of configuration takes place SN2