CHEM 221 Lecture Notes - Lecture 1: Geminal Diol, Hemiaminal, Wittig Reaction
15 Jul 2016
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Document Summary
Protic solvents are bad in organometallics because the reaction will be driven by acidity and will disrupt normal mechanism. Amount of h, reactivity stability formaldehyde aldehyde ketone carbinolamine / hemiacetal is a rxn. Lone pair comes down from nitrogen to make a double bond, and the oh leaves. Oh- grabs adjacent h and e2 mechanism happens. New double bond forms and the old double bond is kicked up, becoming nitrogen"s lone pair. 12-crown-4 ether speeds up reaction and brings things into a solution. H"s act as nucleophiles since they attack electrophilic carbonyl. Anti-addition br and oh react with naoh makes epoxide which retains the stereochem of the oxygen. Grignard reagent comes in, backside attack the less substituted carbon and inverts stereochem to anti-addition again. Hclo4 to make a geminal diol which is syn oh"s. Amides can be reduce to amines via the wittig reaction. Oh is protonated and then becomes h2o+ lg via resonance from or group in tetrahedral array.
