Ochem - chemicals to know

man there's more stuff to memorize

H2CrO4 (made from CrO3 and H2SO4)

Very strong oxidizing agent, can do everything including aldehydes to carboxylic acid

PCC & PDC & Collin’s Reagent

Weaker oxidizing agent, can oxidize primary + secondary alcohols one level

DMSO + (COCl)2

Alternative to PCC, can oxidize stuff too.

Used in Swern Oxidation

Need a non-nucleophilic base, done at -78 C.

DMP

Dess Martin Oxidation, not as smelly as Swern Oxidation.

Does the same, can be handled in less extreme conditions (room temp, neutral pH, easy workup)

CH2Cl2

Aprotic Solvent

TEA

Triethylamine, non-nucleophilic base

DIPEA

Diisopropylethylamine, non-nucleophilic base

Pyridine

Benzene with a N in place of C, non-nucleophilic base… kind of.

Can actually perform nucleophilic attack, but drops away as a leaving group after

DBU

Another non-nucleophilic base, two rings with an N double bonded to a C that’s bonded to another N.

Protonation happens on the double bonded N, since it can pick up the electrons in its double bond.

DCC

Coupling agent

Works with alcohol and amines with c. acids to make esters and amides, respectively

DIC/DIPC

Coupling agent, same role as DCC

EDC + NHS

Another coupling agent, this time primarily for amines

SOCl2

Used to turn c. acids into acid chlorides

Can also turn -OH into Cl, with inversion

PCl5

Used to turn c. acids into acid chlorides

Oxayl chloride (COCl)2

Alone, also can turn c. acids into acid chlorides.

TsCl

Replaces -OH with TsO. (No inversion of stereochem.)

MsCl

Replaces -OH with MsO (No inversion of stereochem.)

PBr3

Replaces -OH with Br (INVERSION of stereochem)

P2O5

Dehydrates amides into nitriles.