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10.12: Summary of Reactions

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    No stereochemistry is implied unless specifically indicated with wedged, solid, and dashed lines.

    1. Preparation of alkyl halides
      1. From alkenes by allylic bromination (Section 10.4)
        The bromination reaction of alkene in the presence of N-bromosuccinimide, light, and carbon tetrachloride produces an allyl bromide through replacement of an allylic hydrogen.
      2. From alcohols (Section 10.6)
        1. Reaction with HX
          The reaction of tertiary alcohol with HX in the presence of ether forms an alkyl halide. The reactivity of alcohols in decreasing order is tertiary, secondary, and primary.
        2. Reaction of 1° and 2° alcohols with SOCl2
          The reaction of secondary alcohol with thionyl chloride in the presence of pyridine forms alkyl chloride where the OH in the reactant is replaced by Cl in the product.
        3. Reaction of 1° and 2° alcohols with PBr3
          The reaction of secondary alcohol with phosphorus tribromide in the presence of ether forms an alkyl bromide where the OH in the reactant is replaced by Br in the product.
        4. Reaction of 1° and 2° alcohols with HF–pyridine
          The reaction of cyclohexanol with HF in the presence of pyridine forms fluorocyclohexane. Pyridine is shown as a six-membered aromatic ring containing five carbon atoms and one nitrogen.
    2. Reactions of alkyl halides
      1. Formation of Grignard (organomagnesium) reagents (Section 10.7)
        The reaction of RX with magnesium in the presence of ether forms a Grignard reagent having formula R-Mg-X.
      2. Formation of Gilman (diorganocopper) reagents (Section 10.8)
        The reaction of RX with 2 equivalents of lithium in the presence of pentane forms R-Li and Li-X.
        The reaction of 2 equivalents of R-Li with CuI in ether forms lithium di-R copper and Li I.
      3. Organometallic coupling (Section 10.8)

        (1) Diorganocopper reaction

        The reaction of di-R copper with R'-X in ether forms three products, R-R', R-Cu, and Li-X.

        (2) Palladium-catalyzed Suzuki–Miyaura reaction

        The reaction between phenylboronic acid and iodobenzene in the presence of Pd (P Ph 3) 4, calcium carbonate, and tetrahydrofuran forms biphenyl.

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