Reagents/Catalysts Organic Chemistry Exam 4

Addition of HX to an alkene

HX

Addition of X2 to an alkene

X2

Addition of HO-X to Alkene

X2, H2O

Addition of H2O by Acid Catalyst to an Alkene

H3O+

Addition of H2O to Alkene via Hydroboration

1. BH3-THF

2. H2O2, OH-

Generation of Acetylide Anions

Na+NH2-

Alkylation of Acetylide Anions

CH3X

Addition of H2O through Oxymercuration-Demercuration

1. Hg(OAc)2, H2O/THF

2. NaBH4

Oxidation of an alkene through epoxidation/acid catalyst

1. epoxidation

2. H3O+

Cleavage of Alkenes with Ozone

O3, CH2Cl2, -78 Celsius or O3, H2O2

Hydration of Alkynes

HgSO4, H2O

Addition of H2 to Alkene w/ Platinum Catalyst

H2, Pt/Pd

Preparation of Alkynes by Eliminating HX

1. X2, CH2Cl2

2. 2KOH, EtOH (ethanol)

Addition of HX Alkynes

1. HX, acetic acid

2. HX, acetic acids

Addition of X2 to Alkynes

1. X2, CH2Cl2

2. X2, CH2Cl2

Reduction of Alkynes w/ H2/Lindlar’s catalyst

H2, Lindlar’s catalyst

Reduction of Alkynes w/ LiNH3

Li, NH3

Oxidative Cleavage of Alkynes

KMnO4, O3

Allylic Bromination

N-bromosuccinimide (NBS), hv, CCl4

Halogenation of alcohols, tertiary alcohols

HX (g), ether, 0 degrees Celsius

Chlorination of primary and secondary alcohols

SOCl2, pyridine

Bromination of primary and secondary alcohols

PBr, Ether, 35 degrees Celsius

Grignard Reagents

Mg, Ether, THF

Alkyl Lithium

2Li, Pentane

Gilman Reagents

ether