CH 320M - Synthetic Transformations

H2 / Pt or Pd

complete reduction of alkyne

H2 / Ni2B

partial reduction of alkyne to syn alkene

H2 / Lindlar’s catalyst

partial reduction of alkyne to syn alkene

Na0 / NH3

partial reduction of alkyne to anti alkene

NaNH2

deprotonation of alkyne

H2SO4, H2O

nitrile hydrolysis

HgSO4, H2SO4, H2O

Markov. addition of H2O to alkyne

BH3, THF / H2O2, NaOH, H2O

Anti-Markov. addition of H2O to alkene

Hg(OAc)2, H2O, THF / NaBH4

Markov. addition of H2O

BH3, THF / H2O2, NaOH

Anti-Markov. addition of H2O

HBr, peroxides (ROOR)

Anti-Markov. addition of H and Br

HX

Markov. addition of H and X

Br2, HOR

Markov. addition of Br and OR (trans only)

MCPBA (or other ROOH)

oxidization of alkene to epoxide

CHCl3 / KOH or CH2I2 / Zn(Cu)

Alkene to cyclopropane

RO- / dilute acid

Anti-Markov. epoxide ring opening (basic conditions)

H+, HOR

Markov. epoxide ring opening (acidic conditions)

PCC

oxidize primary alcohol to aldehyde, secondary alcohol to ketone

KmNO4 or Na2Cr2O7 / acid / water, CrO3 / acid / water

oxidize primary alcohol/aldehyde to carboxylic acid, secondary alcohol to ketone

O3 / Zn, acetic acid

ozonolysis (oxidative cleavage of C double bond)

KMnO4 (hot) / H3O+/ H2O

Permanganate (strong oxidative cleavage of C double bond)