Orgo Exam 1 Reactions

Synthesize the Grinard Reagent

Synthesize the Organolithium reagent:

Grignard + Expoxide (in aqueous acid)

OH replaces MgBr and adds C’s from epoxide (*markovnikov) least sub C on Epoxide adds to MgBr C

Synthesize the Gilman Reagent

Gilman +alkyl/alkenyl/aryl halide

New C-C bond (extends C chain by amount of C in chain attached to CuLi *stereospecific (trans and cis stay E —> E or Z —> Z)

(KOtBu = strong base)

Di chloro carbon

Di chloro carbon + C=C containing molecule

Simmons Smith Reaction

Alkene + Zn(Cu) —> Triangle where ene was (*show stereochem (both dash or both wedge = major product))

Grinard + Ketone or Aldehyde

—> OH where =O was AND extended C chain from Ketone/Aldehyde (*tertiary centers with ketones)

Carbonyl reactions in acidic conditions

1. protonation

2. H-Nu: attaches to C+ intermediate (*ALL Nu: are WEAK in ACIDIC conditions)

3. Base deprotonates H-Nu:

Carbonyl reactions in basic conditions

1. Nu: attaches straight to C=O

2. Racemic mixture (*ONLY if stereochem)

Cyanohydrin + H2 metal catalyst

Reduced to an amine

Cyanohydrin + Aqueous acid

COOH

Wittig reagent

Phosphonium

Aldehyde/Ketone + Witting Reagent

Alkene (in place of C=O) + Triphenyl P Oxide

Horner-Emmens-Wadsworth (Wittig variation)

Ketone —> 1. Base 2. Aldehyde or ketone → Alkene on ketone that was originally there

Carbonyl + H20

Hydrate

Aldehyde/ Ketone + OH

Acetal/Ketal

Acetal in aqueous acid