Por: Karinel Nieves Merced

Orgnica 2004-05

Br2 h
Br OTs

H2 Pt
Br
CN

NaCN DMSO CH3OH

Br

OCH3

Br2 CCl4
Br Br

NaI
NaOH H2O (Saytzeff)
Br

Br

Br2 H2O mCPBA CH2Cl2 MMPP CH3OH

OH

+ONa +OH (Hofmann)

Br

O Br

Br

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

Br

Br

H2 O
Br

OH

NaOH H2O
OH OCH3

HBr
OH

H CH3OH
OH OH

CH3OH
Br

NaOCH3 HOCH3
OCH3

H2SO4
OH

OH

HBr (Markovnikov)
Br

OsO4 H2O2
OH OH
Br

HBr H2O2 (anti-Markovnikov) H, H2O

KMnO4, frio H2O, NaOH

OH

1. O3 2. Me2S
OH

+ O
O OH

1. Hg(OAc)2, CH3CH2OH 2. NaBH4, CH3OH

OH

OCH2CH3

KMnO4, H2O, NaOH

+
O

HO

1. BH4:THF 2. H2O2, NaOH

H2SO4

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NaNH2 / NH3
Br
O

Orgnica 2004-05
Mg0, Et2O (Grignard)
MgBr

1.

/ HMPA 2. H2O, H

OH

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

C-H *

1.

/ HMPA 2. H2O, H

MgBr
OH

D2O
D OH

Br

NaOH

1. CH3CH2MgBr, Et2O 2. H3O+

Br Br

Br

Br2, xs CCl4
Br Br

OH

1. CH3CH2MgBr, Et2O 2. H3O+

HBr
O
Br Br

OH

1. CH3CH2MgBr, Et2O
Cl
O

H2, Pd, BaSO4 quinolina, CH3OH (Lindlar) Na / NH3

0

2. H3O+

OH

1. CH3CH2MgBr, Et2O
O
O

2. H3O+
O

HgSO4, H2SO4 H2O

O

CO2

1. CH3CH2MgBr, Et2O 2. H3O+

CN OH O C

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

1. CH3CH2MgBr, Et2O 2. H3O

+

H Br

HBr H2O2
O

O O

OH

OH O

1. CH3CH2MgBr, Et2O 2. H3O+

KMnO4, H2O warm

O OH

OCH3

1. CH3CH2MgBr, Et2O 2. CH3Br, DMSO 1. NaOH

1. O3 2. Me2S

O O HO O O HO OH

OH O

2. CH3Br, DMSO
O

1. KMnO4, KOH, H2O, 2. H, H2O

Br

1. CH3CH2Li
OH

2. H3O+
Cl

KOH,
Br Br

1. NaNH2, 2. H, H2O
Br

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

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O H O O O OH O O

Orgnica 2004-05

NaBH4 CH3OH, H2O NaBD4 CH3OH, H2O

H OH D

HBr -780C
Br

HBr
OD H

Br

NaBH4 CH3OD, D2O

O H O O O

+
OH OH H OH

(Diels-Alder)

1. LiAlH4, Et2O 2. H3O+ H2 Raney Ni (TODO)

2 electrones

HOMO

LUMO

OH OH

OH

H2 OH

PCC CH2Cl2
O

4 electrones
H

HOMO

LUMO

H2 OH

PDC CH2Cl2
O

6 electrones

HOMO

LUMO

PCC
OH

CH2Cl2
O

NBS
Br

CrO3P4
OH O

Grupos Activantes

(orto, para)

Na2Cr2O7
H2 OH

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

OH O

H2SO4 Na2Cr2O7

Grupos Desactivantes

(orto, para)

-F, -Br, -Cl, -I

O

OH

H2SO4 DMSO, (CoCl)2

H2

Grupos Desactivantes
H

(meta)

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

0

Et3N, CH2Cl2, -60 C (Swern)

TsCl, piridina

Br

Br2
OTs

OH OH

PBr3, CH2Cl2 (10, 20) SOCl2, Et2O (10, 20) ZnCl2, HCl

FeBr3
Cl

Br

OH

Cl

Cl2 AlCl3
I

OH OH

Cl

I2
H2SO4 (Pinacol)
OH O O O

HNO3
NO2

OH

HNO3 H2SO4

HIO4

OH

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SO3H

Orgnica 2004-05

Cl NO2

SO3 H2SO4, fum.

SO3H

OH NO2

1. 2NaOH, 2. H3O+

H2SO4, H2O
NO2 NO2

CH3CH2CH2Cl AlCl3 (solo con activantes)

O Cl O

Br

NH2 NH2

NaNH2/NH3 frio

AlCl3 (Fiedel-Crafts) (solo con activantes)

OH OH2

CH3

CH3 Cl

CH3

HNO3 H2SO4

3Cl2,

Cl

Cl

NO2

Cl

Cl Cl

NH2

O Cl

H N

AlCl3

3H2,

HOCH2CH2CH3 BF3
NO2 NO2

OH

H2SO4, H2O

Na, NH3 CH3CH2OH (Birch)

OCH3

OCH3

HF

Li(CH3)3COH NH3/THF
H

HCl, Co, HCOCl AlCl3,CuCl (gatterman-koch)

Cl NO2 NH2 NO2

1. KMnO4, NaOH 2. H3O+

COOH COOH

2NH3

NO2

NO2

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O O O O

Orgnica 2004-05

O HS H H SH

BF3

AlCl3
O HN NH2

1. n-BuLi
S S

2. CH3CH2I/HMPA

S O

H3 O +
NO2 NH2

HgCl2, H2SO4, H2O

S S H

HCl, Sn0
NH2 NO2

Ph3P

benceno
O

(Witting) H2O

OH OH

H2SO4
NH2 NO2

OH

H2 O2
NO2 N2

HCN, NaOH

CN

O OH OH CN H

NaNO2, HCl

H3O+

C OH H NH

N2

NH3, H3O+
HBF4
I

NH2CH3, H3O+

KI
CN

2 CH3OH PTSA
OCH3 OCH3

OCH3 OCH3

CuCN CuCl or CuBr (Sandmeyer) H3O+

OH

H3O+

O
OH OCH3

O H

OH OH (1 eq.)

O H

H+

1. NaOH 2. CH3I, HMPA (Williamson)

NO2 NO2

HCl, Zn(Hg), H2O

O
O

H2NNH2 KOH,, glima (Wolff-kishner)

NO2 NH2

O O

O H

H2Cr2O4 H2O
O

O OH

HCl, Sn0
O NO2 O

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

OH HO O H

O O O

NH2

HCl, Zn(Hg) (Clemensen)

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NH2

Orgnica 2004-05
N

3CH3I, Ag2O H2O2

1. LiAlH4 2. H3O+
N

N(CH3)2

H2 / Ni
OH

H N

H2O2
N

OH

H2O2
N O O N

NaBH3CN CH3COOH
O

I2 / NaOH

CH3NH2
Cl O

O
N H N

Br2 / NaOH
OH

NH2

H2NOH H+
N OH
(oxima)

(oxima)

NH2

CH3I
H2 Ni
NPh NH2

NH2

I H+
NH2 O OH NH3

H2NPh H
NPh
+

NHPh

1. LiAlH4 2. H3O
O N 1. H
+

HN

Ag2O H2O

HN

OH

HN

, H+
Br

OH
O Br
O

2.
O

3.H3O

Br

Br

(Stork)
1. NaOH, H2O, EtOH 2. O
O

NaOH, H2O, EtOH Br2

O

3. H3O+,
O

NaOH, EtOH, H2O2 I2

O O

1. CH3Li, Et2O 2. H3O+,

O OH

1. LDA, -780C, THF 2. CH3I

1. CH3Li, Et2O 2. H3O+

NH2

1.
H N N O

, H+

NH

HNO2 HCl

2. MCPBA 3.
N

NaN3
Br N3

1. LiAlH4, Et2O 2. H3O+

1. LiAlBH4
N3

2. H3O+ H2 / Ni

O
NH2

LiAlH(o-t-Bu)3
CN

Cl
CH2NH2

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O OTs NK
N2

Orgnica 2004-05

O N O
O O O O

DMF, 1000C
OH

H2NNH2 KOH,

NH2

+
O

NH NH

(Gabriel)

H2SO4 H2 O
H2O, H+

OH O

+ CH3COOH

NH2

OH

NO2

H2SO4
O O

+ CH3COOH

H2O2
NH2 (2eq.)

O
N OH

O
NH2

N H

+ CH3COOH

H2O, H+
O O OH OH

1. LiAlH4, Et2O 2. H3O+

+ CH3OH

H2SO4
N H NaNO2 HCl
NO

+ CH3OH + CH3OH

N
NH2 (2eq.)

N H

OH

SOCl2/piridina o PCl3/CH2Cl2
O

Cl

1. LiAlH4 2. H3O+
O

OH + CH3OH

P2O5 /
O OH O

H2O, H+
N H OH

+ H2NCH2CH3

H2SO4
O

1. LiAlH4 2. H3O+ Br2 NaOH

NH

CH2N2
O NH2 (2eq.)
O O

N H

+ CO2

P2O5
N H
O Cl O O O O O O

H2O, H+
Cl O OH O OH O
NH2

OH O O

H2SO4
O

O
O O

CH2N2
O O NH2 (2eq.)

LiOH
O OH OLi

HCl
OH

BH3:THF
N H O
O OH (xs) O OH OH O

(CH3CH2CH2)2 CuLi

H+ or -OR

O O

1. LiAlH4 2. H3O+

OH

H 1. KCN, CH OH, 30h, 650C 3

2. H3O+
Z

OH

AlCl3

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Orgnica 2004-05

O
C C

Reactivo H2, Pd, BaSO4, quinolina, CH3OH Na / NH3

0

R
NH2

OH

Cl

OR

OH

NaBH4, CH3OH, H2O 1.LiAlH4, Et2O 2. H3O

+

OH

OH

Nada
OH OH
OH

NH2

OH

OH

R-CH2-NH2

H2, Ranney Ni
OH

OH

R-CH2-NH2
OH

NH2

H2NNH2, , KOH, diglima HCl/ Zn(Hg) (BH3)2 :THF Li(tBuO)3AlH

OH

H O O O

DIBAlH
H H H

Remocin: H2O, H+ H2O, H+

H2O2
NO2 OH N

OH
O

OH

Zn(Hg)/HCl
H N

NH2

Zn(Hg)/HCl

H2O2

H2O2

HgCl2, H2SO4, H2O

S S

N O

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O O H

Orgnica 2004-05

Br2 HOAc
Br

O OH

H2O

OH O

Br2
P (trazas)

OH Br O O

OH

NH3
NH2

OH

+
H O H

NaOH
H2O, EtOH

OH

O H O

O H

O H

NaOH
H2O, EtOH

(Claisen - Schmidt)
O O O O O OEt

NaOH
O H2O, EtOH

(Dieckmann)
O O O O O O O O

1. NaOC2H5 2.
O Br

H3O ,
+

HO

(ester malonico)

Por: Karinel Nieves Merced

IUPAC:

Orgnica 2004-05

10

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

8 1 4 7

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

1 9 6 8

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

8 1 10 14 16

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

18
OH

NH(CH2CH3)

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

1
H

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

2 1

6-(1-metiletil)-2-ciclohexenocarbaldedo

1
N

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

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O O

Orgnica 2004-05

11

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

7
HO

1
O

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

1 1
O

2-metilpropanoato de 3-metilbutilo

lactona de cido 4-hidroxi-2-metilpentanoico

N-etil-N,2-dimetilpropanamida

NH

lactona de cido 4-aminobutanoico

Br CN

5-bromohexanonitrilo

N C

ciclohexanocarbonitrilo

anhidro 4-metilhexanoico

anhidro(benzoico)(butanoico)

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O O

Orgnica 2004-05

12

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

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