ochem 2 reagents

Hg(OAc)2, H2O

THF

Oxymercuration

NaBH4, HO-

Demercuration

BH3:THF

Hydroboration

H2O2, HO-

Oxidation

POCl3

Pyridine

Dehydration

Hg(O2CCF3)2, t-BuOH

NaBH4, HO-

Alkoxymercuration

LiAlH4 in Et2O

H2O/H2SO4

Reduces carboxylic acids, esters, aldehydes, ketones, and alkyl halides

NaBH4

MeOH

Reduces aldehydes and ketones

Primary to aldehyde to carboxylic acid

Oxidation of primary alcohols

Secondary to ketone

Oxidation of secondary alcohols

Nothing happens

Oxidation of tertiary alcohols

1) DMSO, (COCL)2

2) Et2N

Swern Oxidation

H2 CrO4

Acetone

Chromic acid oxidation

Pyridium chlorochromate

Won’t overoxidize

PCC

HNO3

H2SO4

Nitration

X2, FeX3

Halogenation

SO3, H2SO4

Sulfonation

RCl, AlCl3

Friedal-Crafts Alkylation

RCOCl, AlCl3

Friedal-Crafts Acylation

KMnO4, OH-

H2O, heat

Oxidizes primary alcohol to carboxylic acid

Permanganate Oxidation

Zn(Hg)

HCl, reflux

Only works at benzylic position

Clemmensen Reduction

H2NNH2, KOH

Heat

Wolff-Kishner Reduction

NH2, NHR, NR2, OH, O, OR

Ortho-para strongly deactivating

NHCOR, OCOR

Ortho-para, moderately activating

R, C6H5

Ortho-para, Weakly activating

F, Cl, Br, I

Ortho-para, weakly deactivating

CN, SO3H, CO2H, CO2R, Aldehydes, Ketones

Meta Directing, Moderately Deactivating

NO2, CF3, NR3, CCl3

Meta Directing, strongly deactivating