Organic Chemistry 1 Reagents

hydrogenation

H2, Pt

alkyne/alkene reduction

H2(g),Ni/Pd/Pe

hydrohalogenation (Markovnikov)

HX, CCl4

hydrohalogenation (anti-Markovnikov)

HX, ROOR

halogenation

X2, CCl4

anti-addition

halohydrin formation

X2, H2O

anti-addition of OH and X

halohydrin formation (ether)

X2, ROH

acid-catalyzed hydration

H2SO4, H2O

2Hs and Markovnikov OH

Oxymercuration-Demercuration

1) Hg(OAc)2, H2O

2) NaBH4

Alkoxymercuration-Demercuration

1) Hg(OAc)2, ROH

2) NaBH4

Hydroboration-Oxidation

1. BH3, THF

2. H2O2, NaOH

epoxidation

mCPBA

Oxidative Cleavage

KMnO4, heat

or O3

Ozonolysis

1) O3, CH2CL2, -78C

2) DMS

CH3ONa, heat

E2

Alkene formed with X removal

SOCl2

replaces OH with Cl

HBr, ROOR, light

adds H to most substituted C

adds Br to most accessible C

HBr (only)

adds H to less substituted C

adds Br to most substituted C

X2 (only)

X added to each side of broken alkene

NBS

N-bromosuccinimide

adds Br to C ADJACENT to alkene=

KMnO4 (cold, dilute)

dihydroxylation

syn- addition

OsO4, NaHSO3, H2O

syn dihydroxylation

CH2I2, Zn(Cu)

alkene to cyclopropane

PBr3

molecule that replaces OH with Br in an Sn2 reaction

SOCl2, base

replaces OH with Cl

HA, heat

primary alcohol ---> ether

OTs, OMs, OTf

Williamson ether synthesis

R-O-R'

asymmetrical

HBr/ROOR (peroxide)

radical reaction

Br added to terminal end of alkene =

Br2, light

Radical Mechanism

Forms most stable intermediate

reducing agents

NaBH4 (mild)

LiAlH4 (strong)

NaBH4, H20

aldehyde--->primary OH

ketone---> secondary OH

LiAlH4, H3O+

Carboxylic acid---> primary alcohol (directly)

DIBAL-H

-Reduces esters to aldehydes

-aldehyde--->alcohol

-ketone---> alcohol

MgBr, H3O+

Grignard

*adds as many Cs attached to MgBr

Mg, EtO2

attaches Mg to Br

PCC

oxidation of primary alcohol--->aldehyde

or secondary alcohol--->ketone

NaOH

strong base

CrO3, H3O+

primary alcohol---> carboxylic acid

NaH, CH3I

OH---> OCH3

Grignard + epoxide

primary alcohol