Ochem synthetic transformations

HX + cold/dark (x = I, Cl, Br)

Markov. addition of X and H

(1) Hg(OAc)2 + HOR + THF (solvent)

(2) NaBH4

Alkoymercuration - demercuration

no rearrangement

Markov.

(1) BH3 + THF (solvent)

(2) NaOH + H2O2 + H2O (solvent)

Anti-Markov. addition of OH and H

(1) Hg(OAc)2 + H2O + THF (solvent)

(2) NaBH4

Oxymercuration - demercuration

Markov.

NO rearrangment

HBr2 + Peroxide (ROOR) + Heat/Light

Anti-Markov. addition of H and Br

Br2

Addition of Br2 to an alkene

Trans Only

MCPBA

oxidation of an alkene to an epoxide

(1) Srong Base (RO-)/Nucleophile

(2) Dilute acid (neutralize) (H2SO4, H+, H3O+)

Anti-Markov epoxide ring opening, Basic

H+ + HOR

Markov opening of an epoxide ring, Acidic

Br2 + HOR

Markov addition of OR and Br to an alkene

CHCl3 + KOH

or

CH2I2 +Zn(CH3)

cyclopropane ring from and alkene

PCC

oxidaton of a 1* alcohol to an aldehyde

PCC is the carboxylic acid police

PCC

or

KMnO4

or

Na2Cr2O7 + water + acid

or

CrO3 + water + acid

oxidaton of a 2* alcohol to a ketone

PCC is the carboxylic acid police

KMnO4

or

Na2Cr2O7 + water + acid

or

CrO3 + water + acid

oxidaton of a 1* alcohol to a carboxylic acid

H2 + Pd* (metal)

or

H2 + Pt* (metal)

stereoselective alkyne reduction

Na (metal) + NH3 (liquid amonia)

Trans alkyne reduction

H2 + Ni2B

or

H2 + lindar catalyst

cis alkyne reduction

(1) O3

(2) Zn + Acetic Acid (HOAc)

Ozonolysis (cut and cauterize)

(1) BH3 + THF (solvent)

(2) H2O2 + NaOH + H2O (solvent)

Hydroboration - oxidation

Anti-Markov

H and OH added cis to each other

(1) KMnO4 (hot)

(2) H3O+ + H2O

Permangenate

H2 + Pd* (metal)

or

H2 + Pt* (metal)

Catalytic Hydrogenation

H2 added cis

(1) OSO4

(2) H2O2 or NaHSO4

cis/syn addition of 2 OH groups to a pi bond

Na(+) NH2(-)

deprotonation of an alkyne

H20 + H2SO4 +HgSO4

Markov. addition of H2O to an alkyne

(1) BH3 + THF (solvent)

(2) H2O2 + NaOH + H2O

Anti-Markov addition of H2O to an alkyne

H2O + H2SO4

Nitrile hydrolysis

(1) HX + dark/cold

(2) HX + dark/cold (excess)

geminial dihalide

(1) X2

(2) X2 (excess)

x = I, Cl, Br

geminial dihalide

HX (x= Cl, Br, I)

Halogenation of an alcohol

SOCl

Halogenation of an alcohol

PBr3

Halogenation of an alcohol

Any nucleophile in the table

Sn2

NaOR

Sn2

NaOH + KOH

Sn2

1. NaNH2

2. RC(H2)LG (LG= I, Cl, Br, OTs)