Por: Karinel Nieves Merced

Orgnica 2004-05

Br2
h

H2
Pt
Br

Br
OTs

NaCN
DMSO

CN

Br

CH3OH

OCH3

Br2
CCl4
Br
Br

NaI
NaOH
H2O
(Saytzeff)

Br

Br

+ONa
+OH
(Hofmann)

1. LDA/THF/-78C
2. H2O, H
(Hofmann)
Br

O Br

mCPBA
CH2Cl2

Br

Br

OH

Br2
H2O

Br

NaOH
H2O

OH

H2 O

MMPP
CH3OH

OH

OCH3

Br

HBr

H
CH3OH

OH

OH

OH

CH3OH

Br

NaOCH3
HOCH3

H2SO4

OCH3

OH

OH

HBr
(Markovnikov)

OsO4
H2O2
OH

Br

HBr
H2O2
(anti-Markovnikov)

OH

KMnO4, frio
H2O, NaOH

Br

OH

H, H2O

1. O3
2. Me2S

+ O
O

OH

2. NaBH4, CH3OH

OH

OCH2CH3

1. Hg(OAc)2, CH3CH2OH

KMnO4,
H2O, NaOH

OH

O
HO

1. BH4:THF
2. H2O2, NaOH

H2SO4

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Orgnica 2004-05

NaNH2 / NH3

Mg0, Et2O
Br

/ HMPA
2. H2O, H

OH

MgBr

(Grignard)

1.

* Se protona con -OH, -NH, -SH o -C

C-H *

1.

/ HMPA
2. H2O, H

D2O

MgBr

OH

OH

Br

1. CH3CH2MgBr, Et2O

NaOH

2. H3O+

Br

Br

Br

Br2, xs
CCl4

OH

1. CH3CH2MgBr, Et2O
Br

2. H3O+

Br

HBr
O
Br

OH

Br

1. CH3CH2MgBr, Et2O
2. H3O+

Cl

H2, Pd, BaSO4

quinolina, CH3OH
(Lindlar)

OH

1. CH3CH2MgBr, Et2O

Na / NH3

2. H3O+

O
O
H

HgSO4, H2SO4
H2O

1. CH3CH2MgBr, Et2O

CO2

2. H3O+

O
H

1. (Sia)2BH : THF
2. H2O2, NaOH

CN

2. H3O

OH

OCH3

1. CH3CH2MgBr, Et2O
2. CH3Br, DMSO

OH

O O

1. NaOH
HO

1. KMnO4, KOH, H2O,

2. H, H2O

OH

2. CH3Br, DMSO

OH
O O

O
O

1. CH3CH2Li

HO

Br

2. H3O+

OH

KOH,

Br

2. H3O+

Cl

1. NaNH2,
2. H, H2O

OH

1. CH3CH2MgBr, Et2O

KMnO4, H2O
warm

Br

O
C

Br

Br

1. CH3CH2MgBr, Et2O

HBr
H2O2

1. O3
2. Me2S

OH

1. (CH3CH2CH2)2CuLi
2. H3O+
(Gilman)

Por: Karinel Nieves Merced

O

OH

NaBH4
CH3OH, H2O

HBr
-780C

Orgnica 2004-05

OH

NaBD4
CH3OH, H2O

Br

HBr

Br

OD

NaBH4
CH3OD, D2O

+
O

OH
O

1. LiAlH4, Et2O
2. H3O+

OH
H

(Diels-Alder)

OH

2 electrones

HOMO

LUMO

4 electrones

HOMO

LUMO

6 electrones

HOMO

LUMO

H2
Raney Ni
(TODO)
OH OH

H2
OH

OH

PCC
CH2Cl2

H
O

H2

PDC
CH2Cl2

OH

PCC
CH2Cl2

OH

NBS

Br

CrO3P4
OH

Grupos Activantes

-OH, -NH2, -OR, -NHCOCH3, -R, -Ph

Na2Cr2O7
H2
OH

H2SO4

OH

Grupos Desactivantes

H2SO4

Grupos Desactivantes

(meta)

-COCH3, -SO3H, -CN, -NO2, -N+R3

DMSO, (CoCl)2
H2

(orto, para)

-F, -Br, -Cl, -I

Na2Cr2O7
OH

(orto, para)

Et3N, CH2Cl2, -60 C

(Swern)

Br

Br2

TsCl, piridina
OTs

OH
OH

OH

PBr3, CH2Cl2
(10, 20)

FeBr3

Br

Cl

SOCl2, Et2O
(10, 20)

Cl2
AlCl3

Cl

ZnCl2, HCl

Cl

OH
OH

I2
H2SO4
(Pinacol)

HNO3
O

OH
OH

NO2

HIO4

OH

HNO3
H2SO4

Por: Karinel Nieves Merced

SO3H

Orgnica 2004-05

Cl

OH

SO3
NO2

H2SO4, fum.

NO2

1. 2NaOH,

SO3H

2. H3O+
H2SO4, H2O
NO2

CH3CH2CH2Cl

NO2

Br

AlCl3
(solo con activantes)

NH2

NH2

NaNH2/NH3 frio

Cl

AlCl3
(Fiedel-Crafts)
(solo con activantes)

CH3

OH

HNO3

Cl

H2SO4

3Cl2,

NO2

NH2

CH3

CH3

OH2

Cl

Cl

Cl

Cl

H
N

Cl

Cl

AlCl3

3H2,

HOCH2CH2CH3
BF3
NO2

NO2

Na, NH3
CH3CH2OH
(Birch)

OH

H2SO4, H2O

OCH3

HF

Li(CH3)3COH
NH3/THF
H

HCl, Co, HCOCl

AlCl3,CuCl
(gatterman-koch)
Cl

OCH3

NH2
NO2

NO2

1. KMnO4, NaOH
2. H3O+

2NH3
COOH
COOH

NO2

NO2

Por: Karinel Nieves Merced

O

Orgnica 2004-05

O
HS

SH

BF3

AlCl3

1. n-BuLi

O
HN

NH2

2. CH3CH2I/HMPA

H3 O +

HgCl2, H2SO4, H2O

S

NH2

NO2

HCl, Sn0

Ph3P

benceno
NO2

NH2

(Witting)

OH

H2O

H2SO4

OH

NO2

NH2

OH

HCN, NaOH

H2 O2
NO2

CN

N2

O
OH

OH
CN

NaNO2, HCl

H3O+

OH

H
F

N2

NH

NH3, H3O+
HBF4
O

NH2CH3, H3O+

KI
O

CN

2 CH3OH

OCH3
OCH3

PTSA

CuCN
CuCl or CuBr
(Sandmeyer)

OCH3
OCH3

OH

H3O+

H3O+
O
OH

OH OH (1 eq.)

OCH3

1. NaOH
2. CH3I, HMPA
(Williamson)

NO2

H2NNH2
KOH,, glima
(Wolff-kishner)

O
H

HCl, Zn(Hg), H2O

O
H

NH2

O
OH

Ag(NH3)2,NaOH
H2O
H
(Tollens)

HCl, Sn0

H2Cr2O4
H2O

NO2

OH
NO2

NO2

O
O

H+

HCl, Zn(Hg)
(Clemensen)

NH2

HO
O

O
H

Por: Karinel Nieves Merced

NH2

N(CH3)2

3CH3I, Ag2O

Orgnica 2004-05

1. LiAlH4
2. H3O+

H2O2

H2 / Ni
OH

H
N

H2O2
N

H2O2
N

NaBH3CN
CH3COOH

OH
N

O
O

I2 / NaOH

CH3NH2
O

Cl

N
H

Br2 / NaOH
OH

H2NOH
H+

NH2

(oxima)

CH3I

N
OH

NH2

NH2

H2
Ni

(oxima)

I
H+

NPh

NH2

H2NPh

NH3
OH

H
NPh

NHPh

2. H3O
O

2.

, H+

OH

HN

HN

H2O

N
1. H

Ag2O

HN

1. LiAlH4

OH
O

Br
+

3.H3O

NH2

Br

Br

Br

NaOH, H2O, EtOH

Br2

(Stork)
O

1. NaOH, H2O, EtOH

2. O

O
O

NaOH, EtOH, H2O2

I2

3. H3O+,
O

1. CH3Li, Et2O
2. H3O+,

1. LDA, -780C, THF

2. CH3I

OH

1. CH3Li, Et2O
2. H3O+
NH2

HNO2
HCl

1.

1. LiAlH4, Et2O

N3

1. LiAlBH4
N3

2. H3O+

2. H3O+
O

NH2

LiAlH(o-t-Bu)3
H2 / Ni
CN

NH

NaN3
Br

, H+

2. MCPBA
3.

H
N

Cl
CH2NH2

Por: Karinel Nieves Merced

O

Orgnica 2004-05

OTs
NK
N2

DMF, 1000C
OH

NH2

H2NNH2
KOH,

NH

NH

(Gabriel)

H2SO4
H2 O

H2O, H+

+ CH3COOH

OH
O
OH

NH2

NO2

H2SO4

+ CH3COOH

O
O

H2O2
NH2 (2eq.)

O
N

OH

H2O, H+

NH2

OH

O
OH

H2SO4
NaNO2

+ CH3OH

N
H

+ CH3OH

HCl

NH2 (2eq.)

NO

OH

+ CH3OH

1. LiAlH4, Et2O
2. H3O+

N
H

+ CH3COOH

N
H

SOCl2/piridina
o PCl3/CH2Cl2

Cl

1. LiAlH4
2. H3O+
O

OH + CH3OH

P2O5 /

H2O, H+
O

N
H

1. LiAlH4
2. H3O+

OH

H2SO4

+ H2NCH2CH3
OH

NH

Br2
NaOH

CH2N2
O

P2O5

NH2 (2eq.)

N
H

+ CO2

N
H

H2O, H+
Cl

OH

Cl
O

OH
O

NH2

OH

H2SO4

O
O
O

CH2N2

LiOH

HCl

O
O

OH

NH2 (2eq.)

OLi

N
H

OH

OH
O

(CH3CH2CH2)2 CuLi

OH (xs)
O

H+ or -OR

1. LiAlH4
2. H3O+

OH

H 1. KCN, CH OH, 30h, 650C

3

2. H3O+
Z

AlCl3

OH

BH3:THF

OH

Por: Karinel Nieves Merced

O
C

Reactivo

Orgnica 2004-05

OH

NH2

OR

Cl

H2, Pd, BaSO4,

quinolina, CH3OH

Na / NH3
OH

NaBH4, CH3OH, H2O

OH

1.LiAlH4, Et2O
2. H3O

OH

Nada

OH

OH

OH

NH2

OH

OH

R-CH2-NH2

OH

H2, Ranney Ni

R-CH2-NH2
OH

H2NNH2, , KOH,
diglima

HCl/ Zn(Hg)

NH2

OH

(BH3)2 :THF

OH

Li(tBuO)3AlH
H
O

DIBAlH
H

Remocin:

OH
O

OH

H2O, H+

Zn(Hg)/HCl

H2O, H+

Zn(Hg)/HCl

HgCl2, H2SO4, H2O

S

NH2

H2O2
NO2

H
N

H2O2

OH
N

H2O2

N
O

Por: Karinel Nieves Merced

Orgnica 2004-05

O
O

Br2
HOAc

H
Br

OH
O

H2O

OH
O

Br2
P (trazas)

OH

OH

NH3

OH

Br
O

NH2
OH

NaOH

H2O, EtOH

H
O

O
O

NaOH

H2O, EtOH

(Claisen - Schmidt)
O
O

NaOH

OEt

H2O, EtOH

(Dieckmann)
O
O
O

H3O ,
+

1. NaOC2H5
O

(ester malonico)

2.

O
Br

HO

Por: Karinel Nieves Merced

Orgnica 2004-05

IUPAC:

7,8-dietil-3,5,10-trimetil-4-(1-metiletil)dodecano
1

8
1
4

4-etil-1,7,7-trimetilbiciclo[4.1.1]octano

1
9

8-etil-3,3-dimetil-9-(1-metiletil)espiro[5.6]dodecano

6
8

8
1

(6E, 10S, 13Z)-8-(2,2-dimetilbutil)-7-etil-10-(2-metilpropil)-6,13octadien-1,16-diino

10
14
16

18
OH

NH(CH2CH3)

4-bromo-2-(N-etilamino)fenol
4
Br
O

(5S, 8E)-5-metoxi-10-oxo-8-undecenal
H3CO

2
1

6-(1-metiletil)-2-ciclohexenocarbaldedo

1
N

(3E)-1-(N-metil-N-propilamino)-3-hexeno

10

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Orgnica 2004-05

4-hidroxi-5-oxo-1-hexanal
H

1
OH

7
HO

cido (5E)-8-oxo-5-nonen-3-inoico

1
O

1
1

2-metilpropanoato de 3-metilbutilo

lactona de cido 4-hidroxi-2-metilpentanoico

N-etil-N,2-dimetilpropanamida

lactona de cido 4-aminobutanoico

NH

Br
CN

5-bromohexanonitrilo

N
C

ciclohexanocarbonitrilo

anhidro 4-metilhexanoico

anhidro(benzoico)(butanoico)

11

Por: Karinel Nieves Merced

O

Orgnica 2004-05

cloruro de (3E)-7-oxo-3-octenoilo
Cl

Prioridades:
cido > ester > amida > nitrilo > aldehido > cetona > alcohol > amina > alqueno > alquino

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