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9.14: Summary of Reactions

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

    1. Preparation of alkynes
      1. Dehydrohalogenation of vicinal dihalides (Section 9.2)
        The figure shows two reactions that give the same products named alkyne, water and KBr. The reactant in the first reaction is dihalide and in the second reaction is alkene.
    • Alkylation of acetylide anions (Section 9.8)
      Acetylene reacts with sodium amide to produce sodium acetylide that further reacts with an alkyl bromide to give a terminal alkyne.
    A terminal alkyne reacts with sodium amide to produce sodium acetylide that further reacts with an alkyl bromide to give an internal alkyne.
    • Reactions of alkynes
      1. Addition of HCl and HBr (Section 9.3)
        The figure shows an alkyne reacting with a hydrogen halide in ether to give a dihaloalkene. This further reacts with hydrogen halide in ether to form a tetrahaloalkane.
      2. Addition of Cl2 and Br2 (Section 9.3)
        The figure shows an alkyne reacting with a halide in dichloromethane to form an alkene. This further reacts with a halide and dichloromethane to form an alkane.
      3. Hydration (Section 9.4)

        (1) Mercuric sulfate catalyzed

        Alkyne reacts with sulfuric acid, water and mercuric sulfate to form an enol. This further forms a methyl ketone.

        (2) Hydroboration–oxidation

        Alkyne reacts with borane and hydrogen peroxide undergoing hydroboration–oxidation to form an aldehyde.
      4. Reduction (Section 9.5)

        (1) Catalytic hydrogenation

        The figure shows two catalytic hydrogenation reactions. The first reaction is an alkyne reacting to form an alkane. The second reaction is an alkyne reacting to form a cis alkene.

        (2) Lithium in liquid ammonia

        Alkyne reacts in the presence of lithium and ammonia to form a trans alkene.
      5. Conversion into acetylide anions (Section 9.7)
        Alkyne reacts with sodium amide and ammonia to form sodium acetylide ion and ammonia.

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