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1) Br2 a) Li
----- ------
calor b) CuI
................................................................................................................................................................................................
1-Metil-3-(1-metil-1-propenil)-ciclopentano
2) a) Mg/E.S. O2 (exceso)
------------- --------------
b) Agua calor
................................................................................................................................................................................................
3-Bromo-2-metilbutano
3) i-Bu-Br a) 2 Br2/luz
---------- --------------
b) Zn/NaI
................................................................................................................................................................................................
Cupro-diciclohexil-litio
4) Br2 Cuprodietil-
----- --------------
calor. Litio
................................................................................................................................................................................................
3-Ciclohexil-ciclohexeno
5) a) 2 Br2/calor a) Mg/E.S.
------------------- ------------------
b) H2/Ni b) PhCH2Br
................................................................................................................................................................................................
4-Metil-2-penteno
6) Sodio a) 2 Br2/luz
----------- -------------------
b) 2 Mg/ES
................................................................................................................................................................................................
Cloruro de p-metoxibencilo
7) a) Br2/calor a )H2/Ni
-------------------- -----------------
b) Mg/E.S. b) Br2/luz
................................................................................................................................................................................................
4-Cloro-3-metil-ciclopenteno
8) Br2/calor LiAlH4
--------------- -------------
................................................................................................................................................................................................
1-Bromo-2-metil-pent-3-eno
1
9) Bromuro de Br2 (1 mol)
------------------ ------------------
bencilo luz
................................................................................................................................................................................................
Cloruro de isopentil-magnesio
10) a) Li 1-Cloro-2-
------------ --------------------
b) CuI feniletano
................................................................................................................................................................................................
Cloruro de alilo Compuesto A
11) 2 Br2 Mg
----------- ------------
calor E.S.
................................................................................................................................................................................................
Compuesto A
12) Mg H2
------------ -----------
E.S Ni
................................................................................................................................................................................................
2-Cloro-3-bromo-1-etil-biciclo[2.2.2]octano
13 Mg Br2 (1 mol)
----- ----------------
E.S. calor
................................................................................................................................................................................................
3-Bromo-4-cloro-2-metil-hexano
14) Bencilgrignard Mg
----------------- ------
. THF
................................................................................................................................................................................................
Cloruro de m-clorobencilo
15) Mg 1-Bromo-2,3-
---------- ----------------------
E.S. dimetilbutano
................................................................................................................................................................................................
1,4-Diclorociclohexano
................................................................................................................................................................................................
1,4,5- Trimetilbiciclo-[2.2.1]-hept-2-eno
2
17) H2 (exceso) Br2/luz
------------------ -------------
Pd
................................................................................................................................................................................................
3-Vinil-hex-4-en-1-ino
................................................................................................................................................................................................
Isopentano
19)
Mg a) H2SO4
---------- ------------------
E.S. b) H3O+
................................................................................................................................................................................................
2-Bromo-4-cloro-hexano
20) Mg Br2
-------- ---------
E.S. calor
................................................................................................................................................................................................
2,3-Dicloro-metilciclohexano
21) Alilgrignard Mg
------------------ ---------
. THF
................................................................................................................................................................................................
1-Bromo-2-(m-bromofenil)-propano
22) Mg 1-Bromo-2,3-
--------- ---------------------
E.S. dimetilbutano
................................................................................................................................................................................................
1,4-Dicloro-2-metil-cicloheptano
................................................................................................................................................................................................
1,4,5- Trimetilbiciclo-[2.2.1]-hept-2-eno
24) Br2 a) Li
--------- --------------
calor b) CuI
................................................................................................................................................................................................
1-Metil-3-(1-metil-1-propenil)-ciclopentano
3
25) a) Mg/E.S. O2 (exceso)
----------------- ------------------
b) Agua calor
................................................................................................................................................................................................
3-Cloro-2-metilpentano
26) H2 Bromuro
--------- -------------------
Ni. de sec-butilo
................................................................................................................................................................................................
2-Metil-biciclo [4.3.0]-non-3-eno
................................................................................................................................................................................................
Cupro-diciclopentil-litio
................................................................................................................................................................................................
3-Ciclopentil-ciclohexeno
................................................................................................................................................................................................
3-Metil-ciclohexeno
................................................................................................................................................................................................
3-Cloro-1-fenil-2-metil-pentano
................................................................................................................................................................................................
Cloruro de isobutilo
4
ASIGNACION INICIAL 2
................................................................................................................................................................................................
1-Bromo-5-cloro-2-metilpentano
2) LiAlH4 a) H2/Ni
------------ ---------------
b) Br2/luz
................................................................................................................................................................................................
1-Cloro-2-metil-but-2-eno
3) a) Br2/CCl4 H2O/H2SO4
------------------- ------------------
b) KNH2 HgSO4
................................................................................................................................................................................................
1-Fenil-3-metil-pent-1-eno
4) a) H2/Pt Li
--------------- ---------
b) NaNH2 NH3
................................................................................................................................................................................................
2,3-Dicloro-pent-2-eno
5) a) NaNH2 H3PO4
-------------------- ------------
b) H2O/H3PO4 calor
................................................................................................................................................................................................
2-Cloro-3,4-difenil-3-metilpentano
6) a) HBr/AcOH a) H2O/HgSO2
--------------------- ----------------------
b) Vinil-MgBr b) NaBH4
................................................................................................................................................................................................
3-Fenil-propeno
................................................................................................................................................................................................
4-Bromo-3-metil-but-2-eno
5
8) HBr (mol) KMnO4 dil.
---------------- ----------------
AcOH base – T.A.
................................................................................................................................................................................................
2-(Ciclopent-1-enil)-propeno
9) Br2 a) KNH2
---------- ------------------
calor b) HBr/AcOH
................................................................................................................................................................................................
3-Metil-hexa-1,3-dieno
10)
H2SO4/ HBr/R2O2
-------------- ----------------
................................................................................................................................................................................................
3-Fenil-2-metil-ciclohexanol
................................................................................................................................................................................................
2-Metil-pentano-2,4-diol
................................................................................................................................................................................................
5-Fenil-2,4-dimetil-pent-2-eno
................................................................................................................................................................................................
1,3-Dimetilciclopentano
................................................................................................................................................................................................
1,1-Dicloro-3-metilpentano
................................................................................................................................................................................................
1-Bromo-3-fenil-but-1-eno
6
16)
Cl2 a) 2 Vinil-MgBr
---------- ---------------------
FeCl3 b) Ozonólisis
................................................................................................................................................................................................
Ciclopropano
................................................................................................................................................................................................
4-Fenil-ciclopentanol
................................................................................................................................................................................................
1-Bromo-1-(4-fenilciclohexil)propano
19)
Br2 (1 mol) a) KNH2
----------------- ---------------------------
calor b) HBr ( mol)/AcOH
.......................................................................................................................................................................................
1-Metil-3-fenilciclohexeno
.......................................................................................................................................................................................
1-Bromo-1-(4-fenilciclohexil)propano
21)
H2SO4 a) Ozono
-------------- ---------------
calor b) H2O/Zn
.......................................................................................................................................................................................
1-(2-Metilciclohexil)-1-propanol
22)
KOH a) H2O/Hg(OAc)2
-------------- -------------------------
metanol b) NaBH4
.......................................................................................................................................................................................
1-Bromo-2-metil-3-fenil-vinilciclohexano
23)
Br2 Mg/THF
-------------- -----------
CCl4
.......................................................................................................................................................................................
Metilciclopenteno
7
24) Br2 (1 mol)
---- -----------------
CCl4
................................................................................................................................................................................................
3-Cloro--propino + Cupro-dialil-litio
................................................................................................................................................................................................
2-(p-Metoxifenil)-but-2-eno
................................................................................................................................................................................................
1,2-dimetilen-cilopentano
................................................................................................................................................................................................
1-(2-Naftil)-pent-2-eno
................................................................................................................................................................................................
Bromo-2-Cloro-3-fenil-butano
................................................................................................................................................................................................
1-Fenil-ciclopenta-1,3-dieno
................................................................................................................................................................................................
1,2-Dicloro-3-fenil-penta-1,4-dieno
8
ASIGNACION INICIAL 3
1) Mg (1 mol) BnBr
--------------------- -----------
Et2O exceso
................................................................................................................................................................................................
1-Bromo-3-bromometil-ciclopentano
2) a) Br2/calor c) CuLi
----------------- ---------------
b) Li d) i-Bu-Br
................................................................................................................................................................................................
Biciclo-[4.2.1]-non-3-eno
................................................................................................................................................................................................
2-Cloro-1-fenil-4-metil-ciclohexano
................................................................................................................................................................................................
6-Etil-3-vinil-ciclohexeno
5) Bn-Br Br2/luz
----------- -----------
................................................................................................................................................................................................
Cupro-di-terc-butil-litio
6) a) Mg/E.S. H2
----------------- ---------
b) H3O+ Pd
................................................................................................................................................................................................
1-Cloro-biciclo-[2.2.1]-hept-2-eno
7) Mg a) H2SO4
------------ ----------------
b) H2O
................................................................................................................................................................................................
1-Bromo-3-cloro-butano
9
8) a) Br2/calor Bn-Br
----------------- ---------
b) Mg
................................................................................................................................................................................................
3-Metil-biciclo [4.3.0]-non-3-eno
9) a) n H2/Ni
------- ---------------
b) 2 Br2/
................................................................................................................................................................................................
Cupro-dialil-litio + 1,4-Dibromociclohexeno
40) Mg Br2
---------- ------------
E.S. calor
................................................................................................................................................................................................
3,4-Dicloro-2-metil-hexano
................................................................................................................................................................................................
Bromuro de (p-bromobencil)-bencilo
12) Mg i-C5H11-Br
--------- ---------------------
E.S.
................................................................................................................................................................................................
1,4-Dibromo-biciclo-[4.3.0]-nonano
................................................................................................................................................................................................
1,4,5- Trimetilbiciclo-[2.2.1]-hept-2-eno
14) Mg H2/Ni
---------- ------------
E.S.
................................................................................................................................................................................................
1-Bromo-2-bromometil-ciclohexano
................................................................................................................................................................................................
3-Bromo-3-bencil-ciclopenteno
10
16) Zn Vinil2CuLi
--------------- ---------------
b) Br2/
................................................................................................................................................................................................
1-Bromo-3-vinilciclohexano
................................................................................................................................................................................................
Bromuro de isopentilo
................................................................................................................................................................................................
1-Etil-3-etinil-ciclohexeno
................................................................................................................................................................................................
2-(3-Bromo-fenil)-propeno
20) KNH2 Na
------------ ----------
. NH3
................................................................................................................................................................................................
2-Cloro-1-fenil-pent-1-eno
................................................................................................................................................................................................
1-fenil-propeno
................................................................................................................................................................................................
m-Cloro-estireno
................................................................................................................................................................................................
1-(Prop-1-enil)-ciclopenteno
11
24) a) Br2/ a) KNH2 (exceso)
------------------ -----------------------------
b) Br2/CCl4 b) HBr (1 mol)//AcOH
................................................................................................................................................................................................
p-Vinil-cumeno
................................................................................................................................................................................................
4-Fenil-3-metil-pent-2-eno
................................................................................................................................................................................................
4-Bromo-3-cloro-1-etil-ciclopenteno
................................................................................................................................................................................................
3-Metil-pent-1,4-dieno
................................................................................................................................................................................................
3-Metil-penta-1,3-dieno
................................................................................................................................................................................................
4-(3-bromo-prop-2-enil)-ciclopenteno
................................................................................................................................................................................................
2-Bromo-1-metil-4-ciclopentiliden-ciclohexano
12
ASIGNACION INICIAL 4
……………………………………………….……………………………………………………………………………………………
Cumeno
a) NaOH 1-Bromopropano
2) ---------------- -------------------------
b) i-Bu-Br AlCl3
……………………………………………….……………………………………………………………………………………………
p-Cresol
H3PO4 AlCl3
3) ------------- -----------
……………………………………………….……………………………………………………………………………………………
p-Metilanisol + 5-Bromo-1-penteno
4) AlCl3 a) Clemmensen
---------- -----------------------
b) Ozonólisis
……………………………………………….……………………………………………………………………………………………
Anhidrido 2,3-Dimetilmaleico + p-Bromoanisol
……………………………………………….……………………………………………………………………………………………
1-(p-Clorofenil)-1-propino
a) Br2/luz a) Ozonólisis
6) --------------- --------------------
b) KNH2 b) Cl2/Fe
……………………………………………….……………………………………………………………………………………………
m-Isobutilanisol
……………………………………………….……………………………………………………………………………………………
4-Bromo-ciclopenteno + o-Etoxitolueno
13
8) AlCl3 a) Wolf-Kishner
---------- -------------------------
b) Ozonólisis
……………………………………………….……………………………………………………………………………………………
Anhidrido succínico + Bromobenceno
……………………………………………….……………………………………………………………………………………………
1-(3-Bromofenil)-1-propino
……………………………………………….……………………………………………………………………………………………
Isobutil-benceno
……………………………………………….……………………………………………………………………………………………
p-Etoxi-estireno
12) Cloruro de H2
------------------- ------------
isobutilo Pd (S)
……………………………………………….……………………………………………………………………………………………
3-Fenil-1-butinuro de sodio
……………………………………………….……………………………………………………………………………………………
m-(m-Bromobencil)-tolueno
14
16) KNH2 a) Base
------------ ----------------
b) i-Pr-Br
……………………………………………….……………………………………………………………………………………………
2-Bromo-but-1-eno
……………………………………………….……………………………………………………………………………………………
1-Fenil-ciclohexeno
18)
a) H2O/Hg(OAc)2 Et-MgBr
-------------------------- ----------------
b) NaBH4
……………………………………………….……………………………………………………………………………………………
2-Fenil-propiliden-ciclohexeno
……………………………………………….……………………………………………………………………………………………
p-Cloro-benzoato de etilo
……………………………………………….……………………………………………………………………………………………
Cuprodiisopropil-litio
21) HBr Mg
---------------- ----------
Peróxido THF
……………………………………………….……………………………………………………………………………………………
1-Bromo-2-metil-1-buteno
……………………………………………….……………………………………………………………………………………………
1-Bromo-3-fenil-2-bencil-cicloheptano
……………………………………………….……………………………………………………………………………………………
1,2-Dibromo-1-fenil-eteno
15
24) HCl (1 mol) a) Mg/E.S.
---------------
------------------------
AcOH b) Bromuro de
2-clorobencilo
……………………………………………….……………………………………………………………………………………………
1-Vinil-ciclopenteno
25)
HBr AlCl3
------------ -----------
R2O2
……………………………………………….……………………………………………………………………………………………
1-Fenil-3-metil-1,3-butadieno
……………………………………………….……………………………………………………………………………………………
p-Metoxifenol
……………………………………………….……………………………………………………………………………………………
2,4-Dibromohexano
……………………………………………….……………………………………………………………………………………………
3-Metil-5-fenil-1,3-pentadieno
……………………………………………….……………………………………………………………………………………………
p-Etoxi-tolueno
30) a) Potasio H2
----------------- ----------
b) i-Bu-Br Pd(S)
……………………………………………….……………………………………………………………………………………………
Bencilacetileno
16
ASIGNACION INICIAL 5
……………………………………………….……………………………………………………………………………………………
1-Metil-4-(2-propinil)-ciclohexeno
3)
HBr Cupro-di-sec-
----------------- ----------------------
Peróxidos butil-litio
……………………………………………….……………………………………………………………………………………………
p-Metoxi-estireno
……………………………………………….……………………………………………………………………………………………
2--Metil-3-etinil-ciclohexeno
4) H2 - Ni Br2 (1 mol)
------------- -------------------
Fe
……………………………………………….……………………………………………………………………………………………
1-(p-metoxifenil)-2-(m-clorofenil)-acetileno
……………………………………………….……………………………………………………………………………………………
1-Fenil-ciclohexeno
6) Mg/THF a) H2SO4
-------------------- --------------------
luego H3O+ b) Agua/calor
……………………………………………….……………………………………………………………………………………………
1,2-Dibromo-2-metil-3-fenilciclohexano
7) a) Sulfonación Bromuro
-------------------------- ---------------
b) Fusión alcalina de alilo
……………………………………………….……………………………………………………………………………………………
p-Etil-anisol
17
8) a) Potasio H2
--------------- -----------
b) i-Pr-CH2-Br Pd(S)
……………………………………………….……………………………………………………………………………………………
Bencilacetileno
……………………………………………….……………………………………………………………………………………………
1-Etil-3-metil-ciclopenteno
……………………………………………….……………………………………………………………………………………………
Bromuro o-bromo-bencilo
……………………………………………….……………………………………………………………………………………………
Tolueno + 4-Bromo-1-penteno Producto A
13)
HBr (1mol) LiAlH4
------------------- -----------
Peróxidos
……………………………………………….……………………………………………………………………………………………
Producto A
……………………………………………….……………………………………………………………………………………………
3-Metil-5-(3-clorofenil)-1,3-pentadieno
……………………………………………….……………………………………………………………………………………………
1-Bromo-but-2-eno
18
16) HBr HBr
---------------- -----------
Peróxidos calor
……………………………………………….……………………………………………………………………………………………
p-Metoxi-estireno
17)
a) KMnO4 a) NaOH
------------------ ---------------
b) HI - calor b) BnBr
……………………………………………….……………………………………………………………………………………………
p-(n-propil)-anisol
……………………………………………….……………………………………………………………………………………………
Cloruro de -fenilbutirilo
……………………………………………….……………………………………………………………………………………………
1,3-Ciclopentadieno + Anhidrido maleico
……………………………………………….……………………………………………………………………………………………
p-vinil-anisol
……………………………………………….……………………………………………………………………………………………
3,5-bis-(1-propinil)-acetanilida
……………………………………………….……………………………………………………………………………………………
1-Fenil-3-etiliden-ciclopenteno
……………………………………………….……………………………………………………………………………………………
Isobutil-benceno
19
24) a) HBr – R2O2 a) Ozonólisis
------------------------ ------------------------
b) Mg b) Wolf-Kishner
……………………………………………….……………………………………………………………………………………………
3-Bromo-1-fenil-2-metil-but-1-eno
2 NBS KOH
25) -------------- -----------
MeOH
……………………………………………….……………………………………………………………………………………………
3,6-Dimetilciclohexeno
……………………………………………….……………………………………………………………………………………………
Cloruro de o-bromo-bencilo
……………………………………………….……………………………………………………………………………………………
2,4-Dibromo-hexano
……………………………………………….……………………………………………………………………………………………
3-Metil-5-fenil-1,3-pentadieno
……………………………………………….……………………………………………………………………………………………
3-Cloro-pent-1-eno
……………………………………………….……………………………………………………………………………………………
Cuprodibencil-litio + 1,4-Dibromobutano
20