Karinel-1
12
1 Por: Karinel Nieves Merced Orgánica 2004-05 Br 2 hν Br OTs NaCN DMSO CN Br CH 3 OH OCH 3 Br H 2 O NaOH Br +OH +ONa Br 1. LDA/THF/-78C 2. H 2 O, H (Saytzeff) (Hofmann) (Hofmann) Br H 2 O OH Br CH 3 OH ∆ OH H 2 SO 4 ∆ HBr H 2 O 2 Br H, H 2 O OH OCH 2 CH 3 1. Hg(OAc) 2 , CH 3 CH 2 OH 2. NaBH 4 , CH 3 OH 1. BH 4 :THF 2. H 2 O 2 , NaOH OH OH HBr Br HBr Br (Markovnikov) (anti-Markovnikov) H 2 Pt Br 2 CCl 4 Br Br Br 2 H 2 O Br mCPBA CH 2 Cl 2 O MMPP CH 3 OH O H 2 O O Br OH NaOH Br Br NaI OH H O OH O NaOCH 3 CH 3 OH OCH 3 HOCH 3 OH OCH 3 OsO 4 H 2 O 2 OH OH KMnO 4, frio H 2 O, NaOH OH OH 2. Me 2 S KMnO 4, ∆ H 2 O, NaOH 1. O 3 O O + O O + HO OH 2 H 2 SO 4
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Transcript of Karinel-1
1 Por: Karinel Nieves Merced Orgánica 2004-05
Br2hν
BrOTs NaCN
DMSOCN
Br CH3OH OCH3
Br
H2ONaOH
Br
+OH+ONa
Br
1. LDA/THF/-78C2. H2O, H
(Saytzeff)
(Hofmann)
(Hofmann)
BrH2O OH
Br
CH3OH∆
OH
H2SO4∆
HBrH2O2 Br
H, H2O
OH
OCH2CH31. Hg(OAc)2, CH3CH2OH
2. NaBH4, CH3OH
1. BH4:THF2. H2O2, NaOH
OH
OH
HBrBr
HBr
Br
(Markovnikov)
(anti-Markovnikov)
H2Pt
Br2
CCl4
Br
Br
Br2H2O
BrmCPBACH2Cl2
O
MMPPCH3OH
O
H2O
O
Br
OH
NaOH
Br
Br
NaI
OH
HO
OH
O NaOCH3
CH3OH
OCH3
HOCH3
OH
OCH3
OsO4H2O2
OH
OHKMnO4, frioH2O, NaOH
OH
OH
2. Me2S
KMnO4, ∆H2O, NaOH
1. O3 OO
+
O
O
+
HO
OH
2 H2SO4
2 Por: Karinel Nieves Merced Orgánica 2004-05
HNaNH2 / NH3
O1. / HMPA
2. H2O, HOH
O
1. / HMPA2. H2O, H
OH
Br
Br
NaOH
Br2, xsCCl4
HBr
Br
Br
Br
Br
BrBr
H2, Pd, BaSO4quinolina, CH3OH
(Lindlar)
Na0 / NH3
HHgSO4, H2SO4
H
HBr
H2O
O
H
O
1. (Sia)2BH : THF2. H2O2, NaOH
HBrH2O2
KMnO4, H2Owarm
O
O
1. O32. Me2S
OO
1. KMnO4, KOH, H2O, ∆2. H, H2O
HO
OH
OO
HO
OH
Br
Br
Br
Br
KOH, ∆
1. NaNH2, ∆2. H, H2O
O1. CH3CH2MgBr, Et2O
2. H3O+
OH
1. CH3CH2MgBr, Et2O2. H3O+
O
(Grignard)
OH
1. CH3CH2MgBr, Et2O2. H3O+
Cl
O OH
BrMg0, Et2O
MgBr
* Se protona con -OH, -NH, -SH o -C C-H *
MgBr DD2O
O
1. CH3CH2MgBr, Et2O2. CH3Br, DMSO
OCH3
OH
1. NaOH2. CH3Br, DMSO O
1. CH3CH2MgBr, Et2O2. H3O+
OH
1. CH3CH2MgBr, Et2O2. H3O+
O
O
CO2
OH
O
CN1. CH3CH2MgBr, Et2O
2. H3O+ CO
O O1. CH3CH2MgBr, Et2O
2. H3O+O
OH OH
O
OH
O
1. CH3CH2Li2. H3O+
O
Cl
O
1. (CH3CH2CH2)2CuLi2. H3O+
O(Gilman)
3 Por: Karinel Nieves Merced Orgánica 2004-05
Grupos Activantes (orto, para)
-OH, -NH2, -OR, -NHCOCH3, -R, -Ph
Grupos Desactivantes (orto, para)
-F, -Br, -Cl, -I
Grupos Desactivantes (meta)
-COCH3, -SO3H, -CN, -NO2, -N+R3
H
O
O
O
CH3OH, H2ONaBH4
H
OH
O
O
H
O
O
O
2. H3O+1. LiAlH4, Et2O
H
OH
H
OH
O
O
CH3OH, H2ONaBD4
CH3OD, D2ONaBH4
OHD
ODH
O
OH
Raney NiH2
(TODO)
OH
OH
H2
OH
CH2Cl2 H
O
OH
PCCCH2Cl2
O
H2
OH
Na2Cr2O7
H2SO4 OH
O
OH
Na2Cr2O7
H2SO4
O
H2
OH
Et3N, CH2Cl2, -600C H
O
PCC
H2
OH
CH2Cl2 H
O
PDC
OH
CrO3P4
O
DMSO, (CoCl)2
(Swern)
OHTsCl, piridina
OTs
OHPBr3, CH2Cl2
Br
OH Cl
OH Cl
SOCl2, Et2O
ZnCl2, HCl
(10, 20)
(10, 20)
OH
OH
OH
OH
HIO4
H2SO4(Pinacol)
O
O O
+
HBr-780C
BrHBr∆
Br
+ ∆
(Diels-Alder)
2 electrones LUMOHOMO
4 electrones LUMOHOMO
6 electrones LUMOHOMO
NBSBr
Br2
FeBr3
Br
AlCl3
Cl
I2
HNO3
I
HNO3
H2SO4
NO2
Cl2
4 Por: Karinel Nieves Merced Orgánica 2004-05
SO3
H2SO4, fum.
SO3H
H2SO4, H2O
CH3CH2CH2ClAlCl3
AlCl3
SO3H
Cl
O
O
(Fiedel-Crafts)(solo con activantes)
(solo con activantes)
H2SO4
OH2
HNO3
OH
NO2
1. KMnO4, NaOH2. H3O+
COOH
COOH
AlCl3
HN
Cl
ONH2
O
BF3
H2SO4, H2O
HF
AlCl3,CuCl
NO2
HOCH2CH2CH3
OH
HCl, Co, HCOCl H
O
(gatterman-koch)
NO2
Cl
2NH3
NO2
NO2
NH2
NO2
NO2
Cl
1. 2NaOH, ∆2. H3O+
NO2
NO2
OH
CH3
Br
NaNH2/NH3 frio
CH3
NH2
CH3
NH2
+
3Cl2, ∆
Cl
Cl
Cl
Cl
Cl
Cl
3H2, ∆
Na, NH3
NO2 NO2
OCH3 OCH3
CH3CH2OH
Li(CH3)3COHNH3/THF
(Birch)
5 Por: Karinel Nieves Merced Orgánica 2004-05
AlCl3
O
O
O
O
OHN
∆
NH2
H3O+
NO2 NH2
HCl, Sn0
NO2
N2
NH2
H2SO4
NO2
NaNO2, HCl
NO2NH2
H2O2
N2
HBF4
F
KI
I
CuCN
CN
H3O+
OH
CuCl or CuBr(Sandmeyer)
OH
1. NaOH
OCH3
2. CH3I, HMPA(Williamson)
NO2
NO2
O
O
NO2
O
NO2
NH2
O
NH2
H2NNH2KOH,∆, glima
(Wolff-kishner)
HCl, Sn0
HCl, Zn(Hg)(Clemensen)
H H
O
HS SH
BF3 S S
S S2. CH3CH2I/HMPA
1. n-BuLi
S S
S S
HgCl2, H2SO4, H2O
H
O
O
bencenoPh3P
(Witting)O
H2OOH
OH
OHCN, NaOH
OHCN
ONH3, H3O+
NH
ONH2CH3, H3O+ N
H
OHCN H3O+
H
OHC
O
OH
O2 CH3OH
PTSA
OCH3
OCH3
OOCH3
OCH3 H3O+
O
H
OOH OH
H+
(1 eq.)OOO
H
H
OAg(NH3)2,NaOH
H2O(Tollens) O
O
OHO
H
HOO O
OO HCl, Zn(Hg), H2O
OOO
H
H2Cr2O4H2O
O
OH
O
6 Por: Karinel Nieves Merced Orgánica 2004-05
NH2 3CH3I, Ag2O∆
N(CH3)2
∆
H2O2
HN H2O2
N
OH
NH2O2
N
OH
Cl
O
NH
OCH3NH2
O
H2NOHN
H+OH
(oxima)
NOH
(oxima)H2
NH2
Ni
OH2NPh
H+
NPh
NPh
2. H3O+
NHPh1. LiAlH4
O
2.1. , H+
O
3.H3O+
NH
Br
(Stork)O
O1. NaOH, H2O, EtOH2.
3. H3O+, ∆
O
O
1. CH3Li, Et2O2. H3O+, ∆
O
1. CH3Li, Et2O2. H3O+
OH
NH2 HNO2
HCl
HN
N
O
Br
NaN3
N3
N3
1. LiAlBH4
NH22. H3O+
H2 / Ni
CH2NH2CN
N1. LiAlH4
2. H3O+
H2 / Ni
N
N
NNaBH3CNCH3COOH
OI2 / NaOH
O
O
NH2
OBr2 / NaOH
NH2
NH2
CH3IN
NH2
H+
NH3
OH
O
HN Ag2OH2O
I
IHN
OH
HN
OH
∆
O OBr
BrBr
NaOH, H2O, EtOHBr2
O
NaOH, EtOH, H2O2I2
O
O
O O
1. LDA, -780C, THF2. CH3I
O1. , H+
2. MCPBA3. ∆
N NH
N1. LiAlH4, Et2O
2. H3O+
Cl
O
LiAlH(o-t-Bu)3
O
7 Por: Karinel Nieves Merced Orgánica 2004-05
NK
O
O
OTs
DMF, 1000C N
O
OKOH, ∆H2NNH2
NHNH
O
O
NH2+
(Gabriel)N2
H2SO4
H2O
OH
NH2
H2O2
NO2
N OH
1. LiAlH4, Et2O2. H3O+
NH2
NH
NaNO2
HClN
NO
OH
O
Cl
O
O
O
O
O
O
O
O
NH
O
SOCl2/piridinao PCl3/CH2Cl2
P2O5 / ∆
OH
H2SO4
CH2N2
NH2 (2eq.)∆
Cl
O
OH
O
O
O
O
O
O
O
O
NH
O
H2O, H+
OH
H2SO4
CH2N2
NH2 (2eq.)∆
OH
O
(CH3CH2CH2)2 CuLiO
1. LiAlH42. H3O+ OH
ZZAlCl3 O
O
O
O
OH
O
H2O, H+
O
OOH
H2SO4
NH
O
NH2 (2eq.)∆
+ CH3COOH
+ CH3COOH
+ CH3COOH
O
O
OH
H2SO4
O
O
OH
O
H2O, H+
NH
O
NH2 (2eq.)∆
+ CH3OH
1. LiAlH42. H3O+ OH
+ CH3OH
+ CH3OH
+ CH3OH
NH
O
OH
O
H2O, H+
1. LiAlH42. H3O+ NH
+ H2NCH2CH3
Br2NaOH
P2O5∆
NH
+ CO2
N
Cl
O
O
O
O
O
O
NH2
O
C N
OH
O
LiOH
OLi
O
HCl
OH
O
OH
O
BH3:THF
OH
O
O
O
O
OH (xs)
H+ or -OR
H
O
2. H3O+
1. KCN, CH3OH, 30h, 650CO
OH
8 Por: Karinel Nieves Merced Orgánica 2004-05
Reactivo
H2, Pd, BaSO4, quinolina, CH3OH
Na0/ NH3
NaBH4, CH3OH, H2O
1.LiAlH4, Et2O
2. H3O+
Nada
R-CH2-NH2
H2, Ranney Ni
R-CH2-NH2
H2NNH2, ∆, KOH, diglima
HCl/ Zn(Hg)
(BH3)2 :THF
Li(tBuO)3AlH
DIBAlH
Remoción: H2O, H+ ó Zn(Hg)/HCl H2O, H+ ó Zn(Hg)/HCl HgCl2, H2SO4, H2O
H
O O
OH
OO
NH2
O
Cl
O
OR
O
C NRC C
H
H
OH
OH
OH
OH
OH
OH
OH OH
OH
OH
OH
NH2
NH2
OH
H
O
H
O
H
O
H
O
H
O
OH OH
OO
SS
H2O2
H2O2
H2O2
NO2NH2
HN
OHN
N NO
9 Por: Karinel Nieves Merced Orgánica 2004-05
OH
OBr2
P (trazas)OH
O
BrOH
O
NH2
OH
O
OH
NH3
H2O
H
OBr2
HOAcH
O
Br
H
O
H
O
+NaOH
H2O, EtOH∆
OH
H
O
H
O
H
O
+
ONaOH
H2O, EtOH
O
(Claisen - Schmidt)
O
O
+O
O
NaOHH2O, EtOH
O
OEt
O
(Dieckmann)
O
O
O
O
O
O
O
O
HO
O
1. NaOC2H5
2. Br
H3O+, ∆
(ester malonico)
10 Por: Karinel Nieves Merced Orgánica 2004-05
IUPAC: 7,8-dietil-3,5,10-trimetil-4-(1-metiletil)dodecano 4-etil-1,7,7-trimetilbiciclo[4.1.1]octano 8-etil-3,3-dimetil-9-(1-metiletil)espiro[5.6]dodecano (6E, 10S, 13Z)-8-(2,2-dimetilbutil)-7-etil-10-(2-metilpropil)-6,13- octadien-1,16-diino 4-bromo-2-(N-etilamino)fenol (5S, 8E)-5-metoxi-10-oxo-8-undecenal 6-(1-metiletil)-2-ciclohexenocarbaldeído (3E)-1-(N-metil-N-propilamino)-3-hexeno
1
1
8
4 7
1
68
9
18
10
1416
18
OH
NH(CH2CH3)
Br
1
4
O
O
H15
HH3CO
H
O
1
2
6
N
51
11 Por: Karinel Nieves Merced Orgánica 2004-05
4-hidroxi-5-oxo-1-hexanal ácido (5E)-8-oxo-5-nonen-3-inoico 2-metilpropanoato de 3-metilbutilo lactona de ácido 4-hidroxi-2-metilpentanoico N-etil-N,2-dimetilpropanamida lactona de ácido 4-aminobutanoico 5-bromohexanonitrilo ciclohexanocarbonitrilo anhidro 4-metilhexanoico anhidro(benzoico)(butanoico)
O
H
O
OH
1
HO
O
O
17
O
O1
1
O
O
N
O
NH
O
CN
Br
C
N
O
O
O
O
O
O
12 Por: Karinel Nieves Merced Orgánica 2004-05
cloruro de (3E)-7-oxo-3-octenoilo Prioridades: ácido > ester > amida > nitrilo > aldehido > cetona > alcohol > amina > alqueno > alquino
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