Alkenes and Alkynes Final (copy)

H20, H+, H3O

1) Hg2, H2O / 2) NaBH4

1) BH3 / 2) H2O2, NaOH

Br2, H2O

NH2

Br2

O3

H2, Lindlar (Pd, Ni)

OsO4

H-X (X = Br, Cl)

H2, Lindlar (Pd, Ni)

1) (sia)2 BH / 2) NaOH, H2O2

• (sia)2 BH used for terminal alkynes. BH3 for internal alkynes.

1) Br2 / 2) 3 (-)NH2 / 3) H2O

(-)NH2 or NaH or LDA

R - CH2 Br

(on an alkyne) H20, H2SO4 or H30

H+, hv

PBr3

TsCl OR MsCl

SOCl2

Trimethylsilyl chloride

TBAF (N+ 4butane, F-)

mCPBA

LiAlH4

2° Jones

1° Jones

PCC

HIO4

Br2, hv

Br2, hv

HBr, peroxide (R-O-O-R)

EtMgBr

H+, EtOH

HBr

NaCN, H2O

LiAlH4, H2O

H+, MeSH

H+, MeOH

H2, Lindlar

2 H2, Pt(also Pd or Ni)

Polar Aprotic (SN2)

DMSO, DMF, acetone, acetalnitrile

Polar Protic (SN1)

H2O, CH3OH, COOH (carboxylic), ethanol

Strong Base (E2)

-OH, CH3O-, tBuO-, LDA

Protic Nucleophilicity

I- > Br- > Cl- > F-

Aprotic Nucleophilicity

I- < Br- < Cl- < F-