Académique Documents
Professionnel Documents
Culture Documents
OH
CH2CH2
CH3 OH
C OH
3- alcohol 3 butil-propil-3- OH
(bromomet (bromometil (bromometil)
CH3CH2CHCHCH2CH2CH2CH3
il)-4- )-4- carbinol
octanol octanilico CH2Br
3- alcohol 3- 3-ciclopentenil OH
ciclopente ciclopenteni carbinol
n-1-ol lico
3- alcohol 3- Etil-propil-
ciclohexil- ciclohexil-3- ciclohexil
3-hexanol hexanilico carbinol
CH3CH2 C CH2CH2CH3
OH
3- alcohol 3-
SH
ciclopente ciclopenten
no tiol tiolico
1-2- disulfuro de S S
dimetilsulfu dimetilo CH3 CH3
ro
2- alcohol Propentricarbi
OH OH
propenotri propenotrioli nol
OH
ol co
a) ciclopentanol y 3-clorofenol
OH
Cl
O
C OH
OH
c) ciclohexanol y 2-clorociclohexanol
El 2-cloro ciclohexanol es mas acido por que los átomos de halógeno, que
atraen electrones, aumenta la acidez de los alcoholes.
OH
OH
Cl
d) 2,2-dimefil-1-butanol y 1 –butanol
M
g
Br H
-
B
r
a).- alcohol secpentílico
O O
H
b).- alcohol isobutílico
OH
1) BH3 THF
2) NaBH4, OH-
1) BH3, THF
OH
d).- Ciclopentanol
OH
H2SO4. H2O
e).- 1-feniletanol
OH
CH=CH2
CH-CH3
H2O
H+
1)Hg(OAc)2, H2O
CH2=CH-CH2-CH3 CH2-CH2-CH2CH3
2)NaBH4
OH
g).- isohexanol
H3C
1) Hg(OAc)2, H2O H3C
OH |
CH3 2) NaBH4
CH3
CH3 CH3
- - (BH3)2 - -
CH3 C CH2-OH
CH3 C CH=CH2
CH3 CH3
i).- 2-feniletanol
CH=CH2 CH2-CH2-OH
(BH3)2
1) BH3 THF
2) NaBH4, OH-
OH
b).-
CH3 CH3
1)(BH3)2
OH
2) HOOH,OH-
OH
1)Hg(OAc)2,H2O
2) NaBH4
d).-
OH
1)Hg(OAc)2,H2O
2) NaBH4
a) propanol
H H
4CH3CH2CH O H B H Na CH3CH2CH O Na B
H H H
H
H OH
3veces más HOH
CH3CH2CH O B H Na (CH3CH2CH O)4 B Na 4CH3CH2CH2 OH B NaOH
HCl OH
H H H OH
O CH
HBr CH2 CH3 eter
CH3CH CH2CH2CH3 CH3CHCH2CH2CH3 CH3CH CH3CH Br
Mg
OH OMgBr MgBr
c) alcohol isobutilíco
CH3CHCH2 OH H2SO4
d) 3-metil, 3-octanol
H H C9H21
CH3 CH3
B H HOH C9H21 B O OH
3 CH3CH2C CHCH2CH2CH3 (CH3CH2CCH2CH2CH2CH2CH3)3 B NaOH
C9H21
C9H21 C9H21
O O
3veces
C9H21 OH C9H21 O B OH HOH 2veces
O B
O O
C9H21 C9H21
CH3
NaOH HO B OH CH3CH2CCH2CH2CH2CH2CH3
OH OH
B H CH3 CH3
CH3 C5H11
HOOH
H (CH3CCHCH3 )3B
3CH3 C CH CH3
CH3CCH2CH3 C5H11 B O C5H11 OH
NaOH
H C5H11 B O OH
C5H11
C5H11 C5H11
O O CH3 OH
2veces 2veces
C5H11 O B OH C5H11 O B OH H2O CH3 C CH2CH3 NaOH B OH
O O O OH
CH3
C5H11 C5H11
CH3 C CH2CH3
OH
f) alcohol bencílico
Na H
CH2 O B H
CH O CH H
H H Na
H B H Na
4 BH3
H
CH2 O CH2 OH
OH
3veces HOH
B Na 4 B OH NaOH
HCl
4
OH
g) difenil metanol
H OH
3veces HOH
C O B H Na C O B Na 4 CH OH NaOH B OH
HCl
H H H OH
4
h) metilciclohexanol
i) butanol
O
Mg CH2 HBr
OH 2Br Mg
CH3CH2CH2 Br
eter
CH3CH2CH2 MgBr CH3CH2CH2CH2 OMgBr HOH CH3CH2CH2CH2
j) 3-fenilpropanol
CH2CH2CH2 OH H2SO4
k) 3-metil, 2-butanol
O
O H
O C CH3 O
H O Hg
O C CH3
HOH
CH3CH C CH3 Hg CH3CH C CH3 O C CH3
H
O O
OH CH3 H B H Na OH H H
CH3CH C CH3 HOCCH3 H CH3CHCHCH3 B Hg H2O 2Na O C CH3
NaOH H2O
Hg O C CH3 CH3 H
CH3 CH3 O
O
H
O O
OH CH2CH3 H B H Na OH CH2CH3 H H
CH3CH2C C CH2CH2CH2CH3 HOCCH3 H Hg H2O 2Na
CH3CH2C C CH2CH2CH2CH3 B O C CH3
NaOH H2O
CH3 CH Hg O C CH3
CH3 CH H
CH3 O CH3
O
CH3
CH3
CH3 Mg CH3 OMgBr HBr
HCH OH
Br eter MgBr 2Br Mg
HOH
CH2 O B H
CH O CH H
H H Na
H B H Na
4 BH3
H
CH2 O CH2 OH
OH
3veces HOH
B Na 4 B OH NaOH
HCl
4
OH
c) 1-hexeno hexanol
OH
H2SO4 H2SO4
HOH
vapor
C CH3
O
Hg H
O C CH3
H B H Na
CH3 CH3
O H
CH2 C CH3 CH2 C CH3 BH3 Hg
HOH NaOH H2O
OH
CH CHCH3 OH
H2SO4
CH CH2CH2 Mg 2Br
vapor
CH2 OH CH2 Br
NaOH
acetona
HBr CH2
HS CH2CH CHCH2CH3 BrMgS CH2CH CHCH2CH3 MgBr CH CHCH2CH3
eter
Br CH CHCH2CH3
Mg
a) 1-fenil propanol
..
CH O :
PBr3 ..
Mg º "A" CH CH OH
"C" "B" 3 2 ..
éter seco éter 0º C
H
CH O
CH3 CH2 CH OH
Mg0 PBr3
CH3 CH2 MgBr CH3 CH2 Br CH3 CH2 OH
+
H eter 0ºC
Eter seco
b) trifenil carbinol
Br2
Mg º "A"
"C" "B" .. ..
H éter seco :Cl Al Cl :
.. ..
: Cl
.. :
O
C
OH MgBr Mg0
C Br
Br2
+
H Eter seco
AlCl3
c) dimetil,etil,carbinol
..
O:
C
CH3 CH3 Mg º "A"
PBr3 ..
"C" "B" .. CH2 CH3
HO
H éter seco éter 0º C
O
CH3 C
CH3 CH3 Mg0 PBr3
CH3 CH2 C OH CH3 CH 2 Br CH3 CH2 OH
CH3 CH2 MgBr
CH3 Eter seco eter 0ºC
d) 1-fenil, 2-propanol
O
C
H CH2 Br
CH3 CH2 MgBr CH2 OH
CH2 CH OH Mg0 PBr3
CH3 H+
Eter seco eter 0ºC
e) 2-fenil, 2-propanol
:O:
C
CH3 Mg º "A"
PBr3 ..
"C" "B" .. CH3
HO
H éter seco éter 0º C
OH O
CH3 C CH3 C
CH3
Mg0 PBr3
CH3 Mg Br CH3 Br CH3 OH
H+ Eter seco eter 0ºC