Organic Chemistry Reactions

H-X

X adds Markovnikov

H-Br and ROOR

X adds anti-Markovnikov

H+ and H2O

OH adds Markovnikov

H3O+

OH adds Markovnikov

H2SO4 (dilute)

OH adds Markovnikov

1. Hg(OAc)2, H2O

2. NaBH4

OH adds Markovnikov

1. BH3

2. H2O2, NaOH

OH adds Anti-Markovnikov, groups add syn

H2, Pt

H’s add syn

X2

X’s add anti

X2, H2O

OH adds Markovnikov, add anti

1. RCO3H

2. H3O+

OH’s add anti

1. OsO4

2. NaHSO3, H2O

OH’s add syn

1. MCPBA

2. H3O+

OH’s add anti

1. O3

2. DMS

cleavage

NaNH2

alkyne

NaNH2

alkyne

HX

X adds Markovnikov

2HX

2X adds Markovnikov

2X2

add 2 to each side of pi bonds

X2

Xs add anti

HgSO4, H2SO4, H2O

OH adds Markovnikov to make enol then tautomerization to ketone

1. R2BH

2. H2O2, NaOH

OH adds anti Markovnikov to make enol then tautomerization to aldehyde

H2, Pt

cannot stop at alkene, goes all the way to alkane

H2, Lindlar

H’s add syn

Na, NH3

H’s add anti

H2, Lindlar

only cis product is made

Na, NH3

only trans product is made

1. O3

2. H2O

ozonolysis

1. O3

2. H2O

ozonolysis

1. NaNH2

2. low substituted alpha carbon

coupling reaction

Br2 and light (hv)

Br adds most substituted

NBS and light (hv)

Br adds more substituted allylic

H2O

only works on tertiary alpha C

NaOH

only works on primary alpha C

NaBH4 and ROH

mild reduction

1. LAH

2. H2O

strong reduction

1. RMgBr

2. H2O

reduction and coupling

1. RMgBr

2. H2O

reduction and coupling

HX

only works on primary or tertiary alpha carbons

SOCl2

Cl adds 180 opposite

PBr3

Br adds 180 opposite

PCC

mild oxidation

CrO3

strong oxidation