Reaction cond summary

Fisher Esterification

Acid Cat (H2SO4 or ArSO3H or HCl), fully reversible

Saponification

excess base

Transesterification

either strongly acidic or strongly basic

Esters to amides

mildly basic conditions (zwitterion interm.)

Ter-butyl ester cleavage

acidic condition, with reso interm and carbocation

Acid chloride synthesis

mildly basic looking (cause of zwitterion), carbocation interm.

Acid chloride to anhydride

strongly basic conditions (salt of COOH attacks it).

Acid chloride to Esters

mildly basic conditions (zwitterion interm.) with sacrificial base (Et3N or pyr).

Acid chlorides or anhydrides to Amides

mildly basic conditions (zwitterion interm.) with sacrificial alcohol or base (Et3N or pyr).

Schotten Baumann

biphasic mildly basic cond. (base = NaOH or Na2CO3)

Anhydrides to esters

mildly basic conditions (zwitterion interm.) with sacrificial base (Et3N or pyr).

Amide hydrolysis

under strongly acidic conditions or strongly basic, and heat

Amides to nitriles

mildly basic looking (cause of zwitterion) (resembles Acid chloride synthesis). Uses base: pyr or Et3N

Carbon derivative reduction using LiAlH4

strongly basic looking, with acidic workup.

Reduction using DIBAL-H

in toluene, -78 C to stop at aldehyde, 25 C for full reduction

Gabriel Amine synthesis

1 equiv of Base for deproto, alkyl halide, and either hydrolysis or hydrazine

Enolization

base (strength depending on product pka)

Aldol addition

2 carbonyls, and catalytic OH- or OMe- (cause we using aldehydes or ketones), polar protic solvent, followed by workup.

Aldol condensation

aldol addition followed by catalytic acid or base (H3O+ or NaOH) and heat.

Knoevenagel reaction

donor with very acidic proton + mild base (e.g. Et3N).

Claisen condensation

NaOR in ROH, H3O+ w.u. (notice how the R are the same, that's so if substitution with solvent occurs, the group doesn't change). Here we do have an -OR leaving group.

Dieckman condensation

Intramolecular claisen,1,6 or 1,7 diester, NaOR and H3O+ w.u.

Malonic Ester and Acetoacetic synthesis

either malonic ester or acetoacetate ester, NaOR in ROH, RX (for SN2), followed with H3O+, heat (ester hydrolysis and decarboxylation).

Michael Addition

a-b unsaturated carbonyl (acceptor), and double stabilized enolate (donor), catalytic base (e.g. KOH) in ROH solvent.

Robinson annulation

michael addition + intramolecular aldol + dehydration to from 2-cyclohexenone.