nucleophilic additions to carbonyl

strong anion nucleophile (-OH)

nucleophilic attach, proton transfer

weak neutral nucleophile (water and HA)

proton transfer, nucleophilic attack, proton transfer

carbonyl and 2 equivalent alcohols

gives acetal, proton transfer, nucleophilic attack, proton transfer, water leaves, nucleophilic attack, proton transfer

acetal back to C=O

add water or dilute acid (excess ROH)

ketone/ester with 1. LAH 2. HA

reduces both to alcohol

aldehyde/ketone with primary amine/ammonia and HA

gives imine, proton transfer, nucleophilic attack, proton transfer, proton transfer, water leaves, proton transfer

imine back to carbonyl

water, HA