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Some alkyl halides undergo substitution ...

Some alkyl halides undergo substitution whereas some undergo eleimination reaction on treatment with bases. Discuss the structural freature of alkyl halides with the help of examples which are responsible for the difference.

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Primary and secondary alkyl halides prefer to undergo substitution reaction by `S_(N)2` mechanism. Thus n-butyl chloride and sec-butyl chloride react with aqueous NaOH to form the corresponding alcohols as the substitution product. On the other hand, tert-alkyl halides prefer to undergo elimination reaction (mainly by E2 mechanism). Thus, tert-butyl bromide reacts with ethanolic KOH to form isobutene as the predominant product. `underset("n-butyl chlorid")(CH_(3)CH_(2)CH_(2)CH_(2))-Clunderset(S_(N)2)overset(aq.NaOH)(rarr)CH_(3)CH_(2)CH_(2)CH_(2)OH`
`underset("sec-butyl chloride")(CH_(3)CH_(2)underset(CH_3)underset(|)(C)H-Cl)underset(S_(N)2)overset("aq.NaOH)(rarr)CH_(3)CH_(2)underset(CH_3)underset(|)(C)H-OH`
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Knowledge Check

  • Which is true regarding E1 reaction of an alkyl halide?

    A
    Different halides (Fluoride, chloride,bromide and iodide) with same alkyl group have same reactivity.
    B
    A stronger base react at faster rate.
    C
    Rate =[alkyl halide][base`]^2`
    D
    It always competes with SN1 reaction.

  • A primary alkyl halide would prefer to undergo-

    A
    `S_(N)1` reaction
    B
    `S_(N)2` reaction
    C
    `alpha`-Elimination
    D
    Recemisation

  • Which alkyl halide possesses highest tendency to undergo S_(N)2 reaction-

    A
    2-bromobutane
    B
    1-bromobutane
    C
    2-bromo-2-methylpropane
    D
    1-bromo-2-methylpropane