Oxygen-containing Compounds

1. Alcohols
   1. Important reactions
      1. Dehydrations (formation of carbocations)
      2. Substitution reactions (S_N1 or S_N2 depending on alcohol and derived product)
   2. General principles
      1. Hydrogen bonding
      2. Effect of chain branching on physical properties

2. Aldehydes and ketones
   1. Important reactions
      1. Nucleophilic addition reactions at C=O bond
         1. Acetal, ketal, hemiacetal, hemiketal
         2. Imine, enamine
      2. Reactions at adjacent positions
         1. Aldol condensation
         2. Keto-enol tautomerism
   2. General principles
      1. Effect of substituents on reactivity of C=O
      2. Steric hindrance
      3. Acidity of -H
      4. Carbanions
      5. , unsaturated carbonyls

3. Carboxylic acids
   1. Important carboxyl group reactions
      1. Decarboxylation
      2. Esterification
   2. General principles
      1. H bonding
      2. Inductive effect of substituents
      3. Resonance stability of carboxylate anion

4. Common acid derivatives (acid chlorides, anhydrides, amides, esters, keto acids)
   1. Important reactions
      1. Hydrolysis of fats and glycerides (saponification)
      2. Hydrolysis of amides
   2. General principles
      1. Relative reactivity of acid derivatives
      2. Steric effects

5. Ethers
   1. Cleavage by acid
   2. Weak basicity of ethers

6. Phenols
   1. Geenral principles
      1. Effects of substituents on acidity
      2. Hydrogen bonding