synthesis reagants ochem

reagants for addition of water to alkene/alkyne

1. H2SO4

2. H2O

oxymercuration-reduction reagants (adding OH to alkene)

1. HgCl2, H2O

2. NaBH4

hydroboration-oxidation reagants (adding OH to alkene)

1. BH3

2. H2O2, HO-

oxidizing reagents

1. OsO4, KMnO4, H2CrO4, O3

2. HSO3- or (CH3)2S (alkynes)

reducing agents (alkene and alkyne to alkane)

1. H2

2. Pd or Pt

ozonolysis reagants

1. O3

2. CH3SCH3

alkyne-alkyne synthesis reagants

1. LDA

2. CH3X

alkene to alkyne synthesis reagants

1. X2

2. 3 LDA

borane reduction agents (alkyne to alkene)

1. BH3

2. CH3COOH

borane reduction agents when an C-H/not two R groups  (stops double addition of borane by adding steric hindrance)

1. (Sia)2BH

2. CH3COOH

weak Nu-s (mechanisms)

X-, H2O, ROH, CH3CO2-

mild Nu-s (mechanisms)

HO-, NH3, CO32-

strong Nu-s (mechanisms)

RO-, alkyne with e- pair on one C so -, H-, H2N-, R-

polar protic solvents (mechanisms)

H2O, CH3OH, CH3CH2OH, ROH

polar aprotic solvents (mechanisms)

DMSO, DMF, acetone

apolar solvents (mechanisms)

CHCl3, CH2Cl2, hexane, benzene

other/general reducing agents (not H2/Pt)

NaBH4, LiAlH4, H2

alkyne reduction to make cis alkene

1. H2

2. Lindlar’s cat

alkyne reduction to make trans alkene

1. Na/Li excess

2. NH3

ROH —> RX for tertiary and secondary alcohols

HX

ROH —> RX for primary, methyl, and secondary alcohols (for RBr and RCl)

RBr: PBr3

RCl: SOCl2

1,2 diol oxidation reagants

1. HIO4

2. H2O

oxidation of primary and methyl alcohols (nonstop/2 oxidations)

1. chromium salt (CrO3, K2CrO7, etc.)

2. H3O+

oxidation of primary and methyl alcohols (stop, 1 oxidation)

PCC

oxidation of secondary alcohols

1. PCC or chromium salt

2. H3O+