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17.15: Summary of Reactions

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    1. Synthesis of alcohols
      1. Reduction of carbonyl compounds (Section 17.4)

        (1) Aldehydes

        An aldehyde reacts with sodium borohydride or lithium aluminum hydride, then hydronium ion to form a primary alcohol.

    (2) Ketones

    A ketone reacts with sodium borohydride or lithium aluminum hydride, then hydronium ion to form a secondary alcohol.

    (3) Esters

    An R C O O R prime ester reacts with lithium aluminum hydride, then hydronium ion to form R O H (primary) and R prime O H.

    (4) Carboxylic acids

    A carboxylic acid reacts with lithium aluminum hydride, then hydronium ion to form a primary alcohol.
    • Grignard addition to carbonyl compounds (Section 17.5)

      (1) Formaldehyde

      Formaldehyde reacts with R M g B r, ether, then hydronium ion to form primary alcohol.

      (2) Aldehydes

      Aldehyde R C H O reacts with R prime M g B r and ether, then hydronium to form secondary alcohol with both R and R prime groups.

      (3) Ketones

      Ketone R C O R double prime reacts with R prime M g B r, ether, then hydronium to form tertiary alcohol with R, R prime, and R double prime.

      (4) Esters

      Ester R C O O R double prime reacts with R prime M g B r, ether, then hydronium to form tertiary alcohol with R and two R prime.
    • Reactions of alcohols
      1. Dehydration (Section 17.6)

        (1) Tertiary alcohols

        A tertiary alcohol reacts with hydronium ion to form an alkene.

        (2) Secondary and tertiary alcohols

        An alcohol reacts with phosphoryl chloride to form an alkene.
      2. Oxidation (Section 17.7)

        (1) Primary alcohols

        A primary alcohol reacts with Dess-Martin periodinane and methylene chloride to form an aldehyde.
        A primary alcohol reacts with chromium trioxide, hydronium ion and acetone to form a carboxylic acid.

        (2) Secondary alcohols

        A secondary alcohol reacts with Dess-Martin periodinane and methylene chloride to form a ketone.
    • Oxidation of phenols to quinones (Section 17.10)
      Phenol reacts with sodium dichromate and water to form benzoquinone.

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