Key Terms

  • acetal, R2C(OR′)2
  • acyl group
  • aldehyde (RCHO)
  • cyanohydrin
  • enamine (R2N–CR═CR2)
  • hemiacetal
  • imine (R2C═NR)
  • ketal
  • ketone (R2CO)
  • nucleophilic addition reaction

Summary of Reactions

  • Preparation of aldehydes (Section 10.2)
  • Oxidation of primary alcohols (Section 9.8)

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.

  • Preparation of ketones
  • Oxidation of secondary alcohols (Section 9.8)

A secondary alcohol reacts with periodinane or chromium trioxide to form a ketone.

  • Oxidation of aldehydes (Section 10.3)

An aldehyde, R C H O reacts with chromium trioxide and hydronium ion to form a carboxylic acid, R C O O H.

  • Nucleophilic addition reactions of aldehydes and ketones
  • Addition of hydride to give alcohols: reduction (Section 10.7)

An R, R prime carbonyl reacts with sodium borohydride, ethanol, then hydronium ion to form an alcohol.

  • Addition of Grignard reagents to give alcohols (Section 10.7)

An R, R prime carbonyl reacts with R double prime Mg Br and ether, then hydronium ion to form an alcohol.

  • Addition of HCN to give cyanohydrins (Section 10.6)

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.

  • Addition of primary amines to give imines (Section 10.8)

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.

  • Addition of alcohols to give acetals (Section 10.9)

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.

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Fundamentals of Organic Chemistry Copyright © by Kirsten Kramer and Cassandra Lilly is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License, except where otherwise noted.