H2O

Br
Br H
Br CH3 +
N SN1 C CH3
SN2 CH3 H3C H3 C
H 3C
CH 3 CH3 H3C
H3C
OH
E1
– E2 CH 3
Br H 3C
C N
CH3 H
H3C +
Br
C CH3
CH 3

H H
H H Br

CH 3
CH 3 –
H 3C HO H H H3C OH
CH 3
H 3C CH 3 H 3C CH 3 CH3
O
– H2 C
CH 3

CH 3
H 3C H 3C CH 3
H 2C
 H 3C Cl CH3
–
Cl Cl

CH3
H3C H
+
C H
+
CH

CH3
solo para haloácidos CH3 CH 3 eter
y da antimarkovnikov Cl + O
C CH 3

H Cl H Cl
OH
H 3C
O CH 3 H Cl
CH4 H 3C O
CH3 H 3C NH 2
H 3C OH CH 3
+ 1. Hg(OAc)2, NH3
C
hay migración H2O 2. NaBH4
amina
H Cl –
Br Br
H3 C +
Br H3C Br
Br
Br
1. Hg(OAc)2, H2O
2. NaBH4 1. BH3, THF
2. NaOH,
H2O2
H 3C OH

H2O
No hay migración H 3C
markovnikov H 3C OH
Br
HO
Alcohol H 3C O
–

markovnikov
Br
halohidrina Na H

MCPBA
H 3C
O

H 3C
O

OsO4
KMnO4 (frío y diluido)

KMnO4 H 3C OH
caliente, OH
concentrado
O3
O
H2O2
O
CH 3 Zn
H3CSCH3
OH
O

O
CH 3

H
 HO OH
Br
HBr
H 3C
H 3C CH 3
HO
RCO3H O sO 4 1)TSCl,py
H3O+
K M nO 4 HO OH CH 3 2) NaCl
f rio y

CH2
d iluid o H 3C Cl
H 3C
H3 C CH3
SOCl2/py
H2 H HS
Na2Cr2O7 H3C
lindlar's CrO3
CH 2 HO CH2Cl2

H3C 1 ) xs NaNH2
H3C CH2
O
H2/Pt
2 ) H2 O H3C
CH 3
Cl NaSH
NaOH
Cl H2O H3C
Cl
H 3C
CH 2

Cl 1) xs NaNH2 H3C
H2SO4, H2O PCC
Cl HgSO4 DMP
2) H2O PDC
SW ERN OH
CH3 HX
H3C H 1) R2BH O CH2Cl
2) NaOH, H2O2 H 3C
xs HX
H3C H
H2/Pt

CaO H2O H3C X2 1 equi

Ccoque CaC2 CCl4
2500°c Cl H
HBr
xs X2 PBr3 ZnCl2
1) NaNH2 CCl4 SOCl2
2) CH3I 1) O3 H 3C Cl py
2) H2O
Br
Cl Cl
Cl
H3C CH3 CH 3
O H3C H
O
H 3C
H 3C CH3
Cl Cl
H3C OH O

Na
NH3 (l) +
H2 H2
Pt, Pd
lindlar's
o Ni
CH 3
H 3C

CH 3
H 3C

H 3C CH3
 H

+ H2O
CH3
+
Br Br
O OH H H 3C
N OH CH3
CH 3 CH3
H 3C S H3C H H3C H S
S CH 3
1.NaH
2.CH3CH2Br
H3C H
CH 3
Xs HBr HO
calor O
OH
HCl, Zn KCN, H2O H3C
H2SO4 NaSCH3 H O2
NaOH, H2O CH3CH2OH Slow H3C O
Br2
H3C H3C H CH3 O
O H H
NaBH4 H3C
CH3 O
HS NaH
CH3
(CH3)2CH- CH3CH2Br H
P(Ph)3 H3C H
H3C H H3C H
H3C H 1.Hg(OAc),
BH3, THF CH3CH2OH

HS
+ H2O2,
NaOH

H2/Ni2B
2.NaBH4

H
H H
Br Br MCPBA
NaSH H2/Pt 1 equi HBr
CH3
O
H3C H H3C 1. Br2, H3C
H3C H H3C H H2O NaOH
2. NaH H2O
1.NaOH NaNH2 NaSH NaCN
2.CH3CH2Br 2 Li eter H2O H2O
THF
H OH
H
N
H3C Li
– H SH
C H3C O
H3C H H3C O
S H 3C
H
H
H H H3C O 1.TMS
Cl
H3C H ET3N LiAlH4,eter
O H
HBr 2.CH3 H2O
H2O LAH
H2O
MgBr,
eter
NaIO4 2 equi H3O+ H
NH2
H2O2 3.
H Br TBAF CH
3
H 3C H H
CH3 H3C O
CH3 OH H
NH
O H3C O H
S O H3C O
S H
H2/PbO2 H H3C O
O
H3C
H
H H3C H

H 3C OH

DMP
/CH2Cl2
CH 3
OH
NaOH
CH3MgBr, H2O
H 3C O CuCl
H 3C O H 3C OH

CH3MgBr NaCN
CH 3 H2O EtOH
(CH3CH2)2CuLi, N
THF
H 3C OH NH4Cl, H2O
H 3C H 3C OH
CeCl3
NaBH4

H 3C O

H 3C OH
 O
H 3C CH 3 Zn(Hg)
HCl.H2O
H 3C CH 3

H3 C
H2O, HCl NH

H 3C CH 3
NH3 + H3 C O
H 3C CH 3 OH
HO
1, H2NNH2/ ácido NH3
acetico, levemente O H2O/
ácido CH 3 HCl
H2O/dietilenglicol
1.NaOH, Br2 2. NaOH H 3C

+
O Br
2. H2SO4 HO CH 3
H 3C CH 3
Br H H3 C
O H3C OH Br CH 3

H 3C HO
H3C CH3
O OH H3 C NH
NaH CH2CH3OH H3 C NH2
H3O+ NaBH4 CH2CH3Br H+/OH- OH
CH 3 H 3C OH
H2O O CH 3
H 3C O MCPBA
O H2O CH3CH2MgBr
CF3SO3H, H3O+
O CH2Cl2
LiAlH4
H 3C CH 3 /eter
CH 3 HOCH2CH2OH
H 3C H2SO4 N
CH3 CH3

HO H3 C
NH N
S OH
NaBH4 H2NCH2CH3 CH2
H3C H3C
H3 C CH3
CH3 CH3 H3C KCN, H2O
OH H2SO4
H 3C CH 3 H3CNHCH3 H3 C CH3
N levemente ácido
H2SO4, H2O
NaSCH3 OH
KCN,H2O CH3CH2OH
H2SO4 HgSO4 CH3CH2MgBr
H 3C CH 2 H3O+
H BH3,THF,H2O2 H3 C H3 C
NaOH 1.LiAlH4/eter
O 2.NH4Cl, H2O OH
H 3C
H2O CH 3
H2SO4 NaNH2 HSCH2CH2CH PBr3
H 2N CH 3 2SH
N CH 3
CH 3 CH3OH xs CH3 H3 C
OH H2SO4
O C
–
Br
OH
H2O H 3C
S 1.ftalamina
NaOH S 2.KOH xs
HCOH
H2O
H2O H2O
H2SO4 NaOH
OH
H3 C
O H3 C
H 3C O CH3 NH2
H 2N CH 3 H PCC CH3
CH 3
HO CH 3 PBr3 CH2Cl2
O
CH 3 CH3CH2SH
S O
CH 3 – H2O
O OH H 3C
O OH Br
H
H 3C
OH
H
H 3C 1. KOH, tBUOK
2. HCl, H2O H 3C O
H H 3C CH 3
Mg/eter N H

Br H 3C O CH 3
Mg
H
O O
H 3C 1.KOH,CH2OH
2.HCl, H2O
H H 3C O
H3CNHCH3
1.CO2 Na+-OCOR H
2. NH4Cl
CH 3
OH SOCl2 Cl O
Py NaOCH3
CH3OH 1.CH3Li eter H 3C
H 3C O CH 3
H 3C O H 3C O 2. H3O+

H H 3C
H H OH
LIAlH(O-t-Bu)3 H
HCl
H
CH3CH2OH
H2SO4, H2O
H2O
H 3C O
OH
H
OH
H 3C O CH 3

H H 3C O 1.Br2 PCl3
2.H2O OH
H
H 3C O

Br

1.Br2, P(s) CCl4

2.H2O