cyanide-cyanohydrines

alkyl lithium or alkyl magnesium (Grignard)

• aldehydes go to secondary alcohols
• ketones go to tertiary alcohols
• carbon dioxide goes to carboxylic acids

Wittig-alkenes

intermediate of making imine derivatives is called a hemiaminal, geminal amino alcohol or carbinol amine

ammonia-imines or Shiff base
primary amines-imines
secondary amines-iminiums, enamines
hydroxylamine-oximes
hydrazine-hydrazones

water

• aldehydes favor hydrate, geminal diol
• ketones favor keto form

one equivalent of a primary alcohols

• aldehydes go to hemiacetals
• ketones go to hemiketals

two equivalents of a primary alcohol with acid catalysis

• aldehydes go to acetals
• ketones go to ketals

proton

• oxonium ion
• enol

base

• enolate

alcohol and acid or base catalysis

• enol ether

hydride

• aldehydes go to primary alcohols with NaBH₄ or LiAlH₄
• ketones go to secondary alcohols with NaBH₄ or LiAlH₄
• imines go to amines with NaB(CN)H₃ and H⁺

two equivalents of a primary thiol with acid catalysis

• aldehydes go to thiol acetals
• ketones go to thiol ketals