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Summary of Reactions

Summary of Reactions

19 • Summary of Reactions

19 • Summary of Reactions

  1. Preparation of aldehydes (Section 19.2)
    1. Oxidation of primary alcohols (Section 17.7)
      A primary alcohol, R C H 2 O H reacts with Dess-Martin periodinane and methylene chloride to form an aldehyde, R C H O.
    2. Partial reduction of esters (Section 19.2)
      An ester, R C O O R reacts with diisobutylaluminum hydride in toluene, then hydronium ion to form aldehyde, R C H O and an alcohol, R dash O H.
  2. Preparation of ketones
    1. Oxidation of secondary alcohols (Section 17.7)
      A secondary alcohol reacts with periodinane or chromium trioxide to form a ketone.
    2. Diorganocopper reaction with acid chlorides (Section 19.2)
      An acyl chloride with substituent R reacts with R prime C u L i in the presence of ether to form an R, R prime ketone.
  3. Oxidation of aldehydes (Section 19.3)
    An aldehyde, R C H O reacts with chromium trioxide and hydronium ion to form a carboxylic acid, R C O O H.
  4. Nucleophilic addition reactions of aldehydes and ketones
    1. Addition of hydride to give alcohols: reduction (Section 19.7)
      An R, R prime carbonyl reacts with sodium borohydride, ethanol, then hydronium ion to form an alcohol.
    2. Addition of Grignard reagents to give alcohols (Section 19.7)
      An R, R prime carbonyl reacts with R double prime Mg Br and ether, then hydronium ion to form an alcohol.
    3. Addition of HCN to give cyanohydrins (Section 19.6)
      An R, R prime carbonyl reacts with H C N to form a compound with C bonded to R, R prime, O H, and C N.
    4. Addition of primary amines to give imines (Section 19.8)
      An R, R prime carbonyl reacts with N H 2 R double prime to form imine: C bonded to R, R prime, and double bonded to N R double prime.
    5. Addition of secondary amines to give enamines (Section 19.8)
      A carbonyl with one R group and one substituent with an alpha hydrogen reacts with H N R prime 2 to give an enamine.
    6. Wolff–Kishner reaction to give alkanes (Section 19.9)
      An R, R prime carbonyl reacts with H 2 N N H 2 to form alkane with R and R prime groups and two hydrogens on former carbonyl carbon.
    7. Addition of alcohols to give acetals (Section 19.10)
      An R, R prime carbonyl reacts with 2 equivalents of R double prime alcohol in acid to give acetal with substituents R, R prime, and two O R double prime.
    8. Addition of phosphorus ylides to give alkenes: Wittig reaction (Section 19.11)
      A carbonyl compound reacts with phosphorus ylide in the presence of tetrahydro furan to form an alkene and a phosphoryl group linked to three phenyl groups.
  5. Conjugate additions to α,β-unsaturated aldehydes and ketones (Section 19.13)
    1. Conjugate addition of amines
      An alpha beta-unsaturated compound reacts with an amine to form a compound with carbonyl and beta amine group.
    2. Conjugate addition of water
      An alpha beta-unsaturated compound reacts with water to form a compound with carbonyl and beta hydroxyl group.
    3. Conjugate addition of alkyl groups by diorganocopper reaction
      An alpha beta-unsaturated compound reacts with R dash 2 C u L i, ether and hydronium ion to form a compound with carbonyl and beta R prime group.