Chapter 10

Na°
Chapter 6 2 H2 / Pd OH O Na
Br H3C C C CH3
HBr HCl
H2 OH Cl
H3C C C CH3
Lindlar's PBr3
OH or -OR Catalyst OH Br
H2O or ROH Na°
H3C C C CH3 SOCl2
NH3 OH Cl
H2SO4 NR3
OH
1) (sia)2BH H
Br H3C C CH H2SO4
Br2 Racemic
2) H2O2, NaOH
* Br O RSO2Cl
H2SO4 O OH OSO2R
OH H3C C CH HgSO4 Nuc.
Br2 Racemic H2O OSO2R Nuc.
* Br OH OH O
H2O 2 Br2
H3C C CH H3C CBr2 CHBr2 H2SO4
OH
1) Hg(OAc)2, H2O 2 HCl O
H3C C CH H3C CCl2 CH3
2) NaBH4
Chapter 8 H2CrO4
Br OH OH
Br2 H2O O
1) BH3 OH
h! or heat
2) H2O2, NaOH PCC
OH
NBS Br H
OH Chapter 11
1) OsO4 Racemic h!
* OH R CH2 X + NaOR' R CH2 O R'
2) NaHSO3 HBr Br
O O ROOR
C-C Bond RCO3H O
1) O3 Broken! h! or heat
H H
2) (CH3)2S Chapter 9
H H H H3C CH3
Nuc. H NaOH
R CH2 X SN2 HO
H2 / Pd CH3
Nuc. / Base
R CH X SN2 or E2
H
or SN1/E1 Cl
H3C H
Chapter 7 R R O H
OH
Nuc. / Base
R C X E2 or SN1 / E1 H H NaOR
2 NaNH2 H
H3C CHBr CHBr CH3 H3C C C CH3 HOR
R H CH3 RO CH3
1) 3 NaNH2 X
H3C CHBr CH2Br H3C C CH tBuO R = H, alkyl group
2) H2O O HO H
C C
C-C Bond Made! E2 H H ROH CH3
1) NaNH2
H3C C CH H3C C C CH2R H H
H CH3 H OR
2) RCH2X H