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25 terms

Organic Chemistry Exam 2

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OrganoLithium Preparation
Alkyl halide, 2eq Li, diethyl ether; low temperature
OrganoMagnesium Preparation
Alkyl halide, Magnesium, diethyl ether, room temperature
Grignard Reaction with CO2
forms a carboxylic acid
OrganoZinc Reaction
CH2I2, Zinc coated in copper, diethyl ether
Carbene Reaction
CHX3, bulky base
Oxymercuration Demercuration Reaction
Hg(OCOCH3)2, H20, NaBH4/KOH
What is KOH used for in Oxymercuration Demercuration reaction
neutralize the acetic acid formed.
Reduction of ketones and aldehydes
NaBH4, CH3OH/H20
Reduction of ketones, aldehydes, esters, acids, NO2, akyl halides, alkenes,
LiAlH4, diethyl ether, H30+
Leaving groups needing heat in esterification
alcohol, ester, ether, amine
Leaving group using room temperature in esterification
halide
What makes the best leaving group
Electron withdrawing group or small electron donating group.
Mild alcohol oxidizing groups
CrO3 in pyradine, PCC, NaOCl
PCC
pyridium chlorochromate
Harsh alcohol oxidizing groups
hot KMnO4, K2Cr2O7 in H2SO4, H2CrO4
Acidic dehydration of alcohol
acid and heat
Basic dehydration of alcohol
POCl3, pyrandine, heat
Alkyl halide to primary or secondary alcohol
SOCl2, PBr3
Alkyl halide to tertiary alcohol
HCl, HBr
Tosylate
p-toulenesulfonylchloride
Prepare Thiols
Alkyl halide, sodium hydrosulfide
Prepare cis Diol
cold KMnO4 or OsO4
Prepare trans Diol basic
MCPBA then OH/H20
Prepare trans Diol acidic
MCPBA then H+/H20
Protecting group for alcohol
chlorotrimethylsilane