OChem 2 Reactions

Add H and X across alkene, Markovnikov, Racemic, Carbocation Rearrangment

HX

Add H and OH across alkene, Markovnikov, CC rearrangement, Racemic

H2O + Non Nucleophilic Acid Catalyst (H3O+, H+, HNO3, H2SO4)

Add H and OH across alkene, Markovnikov, NO CC rearrangement, Racemic

1) Hg(OAc)2, H2O

2) NaBH4

Add H and OH across alkene, ANTI-Markovnikov, syn-addition, racemic

1) BH3·THF

2) H2O2, NaOH

Add H2 across alkene, syn addition, racemic

H2, Metal Catalyst (Ni, Pt, Pol/C)

Add H and Br across alkene, ANTI-Markovnikov, Racemic

HBr, ROOR (t-butyl peroxide or benzoyl peroxide)

Add X2 across alkene, anti-addition, racemic

X2

Add X2 → Replace more substituted with OH, anti-addition, racemic

X2, H2O/ROH

Add 2OH across alkene, anti-addition, racemic, intermediate epoxide (before acid)

1) RCO3H (Peroxy acetic acid, mCPBA) → epoxide

2) Acid Catalyst

Add 2OH across alkene, syn-addition, racemic

1)OsO4/KMnO4

2)H2O2

Cleave alkene to generate two new C=O bonds, reducing conditions, generate aldehydes

1)O3

2)DMS, H3C-S-CH3

Cleave alkene to generate two new C=O bonds, reducing conditions, generate carboxylic acids

1)O3

2)H2O2

Elimination → Generate alkene/alkyne

EtO-, t-butoxide-, heat

Substitution

Charged, no heat

Deprotonate Alkyne

NR2-, H-, alkyl lithium

Form Internal Alkyne

XS KOH 200C

Form External Alkyne (Zipper Rxn)

1) 3eq NaNH2, 150C

2) H2O

Reduce Alkyne to Alkane, syn addition of H2

2eq H2, Pd/C

Reduce Alkyne to Alkene

2eq H2, Poisoned Catalyst

Reduce Alkyne to CIS Alkene

2eq H2, Lindlar’s Catalyst

Reduce alkyne to TRANS alkene

Na*, NH3(l), -78C

Add H and X across alkyne

Alkene: 1eq HX

Alkane: XS HX

Acid Catalyzed Hydration of alkyne, Markovnikov, mix of products if internal

HgSO4, H2SO4, H2O

Acidic Tautomerize Enol to Ketone

Add H3O+

Base-Catalyzed Hydration of Alkyne → Aldehyde, Antimarkovnikov

1) Sia2BH

2)H2O2, NaOH

Add X2 Across Alkyne

1eq → major trans alkyne

XS → alkane

Cleave Alkyne → carboxylic acids, terminal → CO2

1)O3

2)H2O

Alkylation of terminal alkyne

1) NaNH2

2) Primary alkyl halide W/O acidic proton, aldehydes/ketones, or epoxides

Alkane to Alkene

1)Br2 hV

2)E2