Organic Chemistry Exam 2

25 terms by KMarwitz 

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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

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