Organic Chemistry

HX addition
ether, KI/H3PO4, markovnikov
X2 addition
CH2Cl2 or CCl4, halonium
X-OH addition
NBS/DMSO or X2/H2O, halohydrin
H2O addition (acid catalyzed)
acid, markovnikov
oxymercuration
Hg(OAc)2, THF, NaBH4, halonium, markovnikov
hydroboration
BH3-THF, H2O2/OH, antimarkovnikov
alkene/alkyne hydrogenation
Pd/C/Pt, lindlar (cis), Li/NH3 (trans)
ozonolysis
Zn/AcOH, no CH to OH
oxidation of diols
HIO4, THF, same as ozonolysis
oxidation with permanganate
KMnO4/H, CH to OH
for alkynes same as O3
alkylation of acetylide
KNH2, NaNH2/NH3, LDA/THF, Sn2
radical chain halogenation
NBS/CCl4
alcohol conversion to halide
HX in ether (3rd/Sn1), PX3 in ether or CH2Cl2 (1st/2nd/Sn2), SOCl2 in pyridine (1st/2nd/Sn2), TosCl/pyridine followed by X− (1st/2nd/Sn2)
elimination
strong base for E2, allylic/benzylic tertiary and secondary for E1
aromatic bromination
Br2 and FeBr3 (or AlBr3) for bromination
aromatic nitration
HNO3/H2SO4 for nitration
aromatic sulfonation
SO3/H2SO4 for sulfonation
aromatic alkylation
RX and AlCl3 for alkylation
aromatic acylation
RCOX and AlCl3 for acylation
aromatic side chain oxidation
KMnO4 or Na2Cr2O7, benzylic hydrogen, converts to COOH
aromatic hydrogenation
300 atm H2/Pd, Rh/H2
aromatic side chain hydrogenation
(NO2, C=O) with Pd/C into H-C-H
aromatic phenol
sulfonate then use NaOH
aldehyde/ketone to alcohol
NaBH4/LiAlH4
carboxylic acid/ester to alcohol
BH3/THF for COOH, LiAlH4 for both, replaces OH and OR with H (OR becomes ROH)
carbonyl and grignard to alcohol
RMgX, RLi, THF, ether
replaces the OR on the ketone and saturates it
grignard/RLi preparation
any alkyl, aryl, alkene halide but no acidic H allowed
alcohol dehydration
(1st/2nd/E2) use POCl2 to convert OH into leaving group OPOCl2, (3rd) use acid, pyridine is base
oxidation of alcohol to form carbonyl
PCC for making aldehyde 1st, Jones/KMnO4/Na2Cr2O7 for making COOH 1st, any of above for 2nd to make ketone, no 3rd
williamson ether synthesis
alkoxides are nucleophiles, Sn2
x

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