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    Sn1 Reactions

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    In contrast to SN2 reactions, SN1 reactions show little nucleophile selectivity; that is, when more than one nucleophile is present in the reaction medium, SN1 reactions show only a slight tendency to discriminate between weak and strong nucleophiles, whereas SN2 reactions show a marked tendency to discriminate.

    a. Provide an explanation for this behavior.

    b. Show how your answer to (a) accounts for the fact that CH3CH2CH2CH2Cl reacts with 0.01M NaCN in ethanol to yield primarily CH3CH2CH2CH2CN, whereas under the same conditions (CH3)3CCl reacts to yield primarily (CH3)3COCH2CH3.

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    Solution Preview

    a. SN2 reactions require the nucleophilic attack on the electrophile. The stronger the nucleophile (that is, something with a negative charge or with long pair of electrons, like CN-), the easier the reaction. Whereas in SN1 reaction, ionization of C-X bond leads to a carbocation intermediate. And ...

    Solution Summary

    The solution is comprised of an explanation for the behavior of SN1 reactions.