Ch 20/21 Reactants

Reduction to alditol

NaBH4, H3O+

Oxidation to aldonic acids (ketoses/aldoses)

-OH, Ag+, NH3

oxidation to aldaric acid (aldehydes and primary alcohols)

HNO3/Heat

Lengthening (Kiliani-Fischer Synthesis)

-CN, HCl, H2/Lindlar’s catalyst

Shortening (Wohl Degradation)

NH2OH/trace acid, Ac2O 100C, -OH/H2O

AA synthesis - HVZ and ammonia

1. Br2/PBr3 2. H2O, excess NH3

AA synthesis - reductive amination

alpha-keto acid. 1. NH3 (excess), trace acid 2. H2, Pd/C

N-phthalimidomalonic ester synthesis

forms tetrahedral → AA

Strecker Synthesis (aldehyde → imine)

NH3/trace acid, -CN, HCl/H2O/Heat

disulfide bonds

-OH/H2O, Br2

Amino protecting group

t-Boc, remove with TFA/CH3Cl2

carboxyl activating group

DCC, remove with HF