1. Preparations of Alcohols & Phenols

2. 1. Hydration of Alkenes - addition of water
- uses H2SO4 and heat
Ex.; Hydrate propene.

3. 2. Hydrogenation of Aldehydes & Ketones –
All carbon-carbon double bonds in the molecule will be hydrogenated at the same time
Uses hydrogen, Pt, heat and pressure
Ex. A. aldehydes – form primary alcohols
Hydrogenate ethanal (acetaldehyde).

4. Ex. B. ketones – form secondary alcohols
Hydrogenate 2-butanone.
Hydrogenate 4-penten-2-one.

5. 3. Reduction of Aldehydes & Ketones –
Reagent is either lithium aluminum hydride (LiAlH4) or sodium borohydride (NaBH4)
Will form unsaturated alcohols because metal hydrides do not react with carbon-carbon double bonds
Ex. A aldehydes - form primary alcohols
Reduce ethanal (acetaldehyde).

6. Ex. B. ketones - form secondary alcohols
Reduce propanone.
Reduce 4-penten-2-one

7. 4. Reduction of Aldehydes & Ketones with Grignard Reagents
Ex. A. aldehydes - form secondary alcohols
Ex. B. ketones – form tertiary alcohols

8. 5. Hydroboration of Alkenes
Water seems to add “anti-Markovnikoff” because in the catalyst borane (BH3), the hydrogen is negative, not positive
This is used as a complement to hydration in order to add the –OH to the carbon with the most hydrogens
Ex. Hydroborate propene.

9. 6. Hydrolysis of Alkyl Halides
This is the reverse of the reaction that converts alcohols to alkyl halides
Reacts with water or hydroxide ions
Ex. Hydrolize bromoethane.

10. Catechol - an antioxidant in paint
Resorcinol – used in adhesives, dyes, antiseptics
Hydroquinone – a photographic developer

11. Thiols: Sulfur Analogs of Alcohols & Phenols
Sulfur - has similar properties to oxygen and forms similar compounds
Sulfur analogs of alcohols are called thiols
-SH group – called the sulfhydral group
Usually have very disagreeable odors
Ex. 1-butanthiol (responsible for the odor of skunks

12. Polyhydric Alcohols & Phenols
Polyhydric - compounds with several hydroxy groups attached to different carbon atoms
Ex. Ethylene glycol
IUPAC name:
Ex. Glycerine