SN2 and SN1 displacement of a leaving group
8 real reactions from the literature, on primary alkyl bromides, benzylic alkyl chlorides, α-halo esters and α-halo ketones. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.
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Leaving group displacement: 1-bromododecane (a primary alkyl bromide) with KCN gives tridecanenitrile (the substitution product).
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Leaving group displacement: benzyl chloride (a benzylic alkyl chloride) with aq. NaCN; CH3CH2OH, Δ gives phenylacetonitrile (the substitution product).
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Leaving group displacement: sodium chloroacetate (an α-halo ester) with NaCN gives sodium cyanoacetate (the substitution product).
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Leaving group displacement: 1-chloropinacolone (an α-halo ketone) with 1) NaN3, aq. acetone, Δ; 2) H2, Pd/C, CH3OH gives 1-amino-3,3-dimethylbutan-2-one (the substitution product).
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Leaving group displacement: 1,3-dibromopropane (a primary alkyl bromide) with NaCN; aq. CH3CH2OH, Δ gives glutaronitrile (the substitution product).
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Leaving group displacement: methylamine (a primary amine) and chloroacetic acid (an α-halo acid) with NaOH; H2O; (2 equiv.) gives N-methyliminodiacetic acid (the substitution product).
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Leaving group displacement: 2-bromoethyl ethyl ether (a primary alkyl bromide) with NaCN, H2O; CH3CH2OH, Δ gives 3-ethoxypropanenitrile (the substitution product).
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Leaving group displacement: 1-bromo-3-chloropropane (a primary alkyl chloride) with KCN, Δ; aq. CH3CH2OH gives 4-chlorobutyronitrile (the substitution product).