Nitrogen and Phosphorus Containing Compounds

amide

RCONH2

imine

RCNRR

enamine

RRCCNRRR

azide

RNNN

nitrile

RCN

isocyanate

RNCO

Strecker Synthesis reagents

aldehyde, ammonium chloride (NH4Cl), and potassium cyanide (KCN)

strecker synthesis step 1

carbonyl oxygen protonated, ammonia attacks to form imine, CN- attacks imine to form aminonitrile

strecker synthesis step 2

nitrile nitrogen protonated, water attacks to form imine and hydroxyl, imine attacked by more water, carbonyl forms and kicks off ammonia, creates carboxylic acid

strecker synthesis

makes amino acids in presence of acid and heat, forms racemic mixture of L and D AA

Gabriel Malonic-Ester reagents

potassium phthalimide and diethyl bromomalonate

gabriel synthesis reaction types

two SN2, hydrolysis, and decarboxylation

gabrial synthesis

results in racemic mixture of L and D amino acids

phosphoric acid

phosphate group or inorganic phosphate Pi

phosphoric acid at physiological pH

HPO4 2- and H2PO4 1-

pyrophosphate

PPi, P2O7 4-, released during formation of phosphodiester bonds, unstable in aqueous solutions, hydrolyzed to form two molecules of inorganic phosphate

organic phosphates

nucleotides with phosphate groups, ATP, GTP, and in DNA