OH

Br

OH

Br2, H2O

H2SO4
H2O
Lg

BH3, H2O2

OH

OH

SN2 or SN1
Lg = Cl, Br, I or OTs
Lg = leaving group

OH

O
OH

MeOH, H+

MeOSN2

epoxide
OH

HOE2

H2SO4
E1

OH

Some Reactions of Alcohols"

CrO3
O
pyridine/H2SO4

T
py sCl
rid
ine

OTs

These
leavin groups
can be used
f or
E2
E1
SN1
SN2

CrO3
pyridine

OH

pyridine +
PBr3 or
SOCl2 (SN2)

C
H rO
2S 3
O

OH

OH

POCl3, pyridine

Base
R-X
O
R

(E2)

X = Cl, Br or I
X
X
H-X

X
X2
X

O
, H2
2

major
products
shown

OH

H 3O

OH

BH ,
3 H

2 O2

OH
O3
H2, Pd

mCPBA
O

HX
Conjugated Dienes are special

allyl cations (resonance)

ALLY L CAT IONS are MORE stable
than trisubstituted cations

X
1,2addition
product

1,4addition
product

X
X

X2

OR

HX

X2

ROH
X

OTs
OH

PBr3
pyridine
Cl

pyridine

NaX

TsCl
X

SOCl2
HX

pyridine

Some Reactions of Halides

X

E1/E2

SN2

SN1
Nu

Nu

(mix of E/ Z)
X
X X
H2, Lindlar

Na/NH3

H-X

H-X

X X

X
alkylation
reaction
bas
e

H2, Pd

H-X

(1 equivalent)

X2

( 1 eq

Lg
X2

BH

BH

3,

X
O
ketone

X2, H2O
X

lent )
uiv a

H3O+
H2, Pd

X2

3,

2O
2

H3O+

2O
2

O aldehyde

O
X