CHAPTER 8    Hydroxy Functional Group: Alcohols: Properties, Preparation, and Straategy of Synthesis


8-1   Naming the Alcohols

8-2         Structural and Physical Properties of Alcohols

The boiling points of alcohols are strongly influenced by hydrogen bonding. Steric hinderance decreases hydrogen bonding and results in lower boiling points.

8-3         Alcohols as Acids and Bases

Alcohols are acids, with pka values in the range of 15.5 to 18. Alcohols are also bases because of the presence of lone pairs of electrons.

8-4   Industrial Sources of Alcohols: Carbon Monoxide and Ethene

8-4         Synthesis of Alcohols by Nucleophilic Substitution

Primary and secondary alcohols can be prepared from alkyl halides by SN2 substitution. Tertiary alcohols can be prepared by SN1 substitution of tertiary alkyl halides.

8-5         Synthesis of Alcohols: Oxidation-Reduction Relation between Alcohols and Carbonyl Compounds

Oxidation levels can be determined by a mental process of breaking bonds to an atom, giving both electrons the the more electronegative partner. The result charge is the oxidation level.

Alcohols can be formed from ketones and aldehydes by reduction with either NaBH4 or LiAlH4.

8-7   Organometallic Reagents: Sources of Nucleophilc Carbon for Alcohol Synthesis

           Reaction of Alkyl Halides with either Li or Mg produces ogranometallic reagents.


8-8   Organometallic Reagents Reagents in the Synthesis of Alcohols

              Because of the polarization of the C–M bond in organometalic reagents, these reagents have a nucleophilic carbon that will react with aldehydes and ketones, resulting in the formation of alcohols.

8-9         Complex Alcohols: An Introduction to Synthetic Strategy

By combining the oxidation of alcohols to ketones and aldehydes with the reaction of these functional groups with organometallic reagents, large molecules can be formed from smaller ones by the formation of carbon–carbon bonds.