Reactions from Loudon Chapters 1 - 14 - Page 1 of 2

1) BH3

OH

OH

[O] =

PCC
PDC
CrO3 Pyr
Jones reagent

2) H2O2

1) H2O (or ROH) / Hg2+

R'

2) NaBH4

H2O

R'

H2SO4

(O-R)
R OH
Me
R'

OH
R

R OH
Me
R'

OH

Me3N-O

PCC
PDC
CrO3 Pyr

Jones reagent
R

(CrO3 + H2SO4)

OH

R'

NaIO4

OH
OH

MCPBA
R'

O
R

OH

OH

OsO4 / H2O
R'

[O]
[O] =

[O]

O3

R'

DMS

OOH

Cl

O
O

OH

Me

H2SO4 (1%)

Me

OH
Me HCl

Cl
(Br, I)

(HBr, HI)

OH
(OR)

H2O (ROH)

Na

R'

NH3

H2
Pd/C

SR

RS(-)
R

R'

2 OK

R'

R'

Me

Lindlar 's
Catalyst
Pd / BaSO4 / Pb
+ quinoline

Reactions from Loudon Chapters 1 - 14 - Page 2 of 2

X
R

N3

NaN3
R'

Wiliamson ether synthesis:

R'

OH

2 OK

HCl

R'

(or HBr)

2) R
Must be primary

R Cl
Me
R'

HBr

OH
R

Br

Peroxides
(cat.)
R
Br

Br2

Br

Me

Br2
H2O

OTs

R'

R'

R'

R'

Br

HBr

R''

or PBr3

OH

OH
Me

TsCl

OH

R'

R''

Cl

SOCl2

R''

Br

1) NaH

R'

R''

Mg
Br

MgBr

1) MeLi
H
R'

2) R'

2 Li

Br

Li

(Br, OTs)

Must be primary

CuBr

1) MeLi
R

2)

R'

Li(+)

R'

(Br, OTs)

OH

R'

R'

CHBr3

tert-Butoxide

(-)
Cu

Li

Br Br
C
R'

R2CuLi

R'

Both must be primary

R'

CH2I2 / Zn / Cu
R

CH2
R'

OH
R2CuLi

R2