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Organic Chemistry
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30
Chemistry
Undergraduate 1
12/13/2008

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