Biblia organica

Por: Karinel Nieves Merced

Orgánica 2004-05

1

Br2 h!
OTs

H2 Pt
Br

Br
CN

NaCN DMSO CH3OH

Br

OCH3

Br

Br2 CCl4
Br

NaI
NaOH H2O (Saytzeff) +ONa +OH (Hofmann) 1. LDA/THF/-78C 2. H2O, H (Hofmann)
Br

Br

Br

Br2 H2O mCPBA CH2Cl2 MMPP CH3OH NaOH H2O
OH OCH3

OH

O Br

Br

O

Br

Br

O

H2 O
Br

OH

HBr
OH

O

H CH3OH
OH OH

CH3OH"
Br

O

NaOCH3 HOCH3
OCH3

H2SO4 "
OH

OH

HBr (Markovnikov)
Br

OsO4 H2O2
OH
Br

HBr H2O2 (anti-Markovnikov) H, H2O

OH

KMnO4, frio H2O, NaOH
OH

1. O3 2. Me2S
OH

O OH

+ O

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

OCH2CH3

KMnO4, " H2O, NaOH

+
O

O

HO

1. BH4:THF 2. H2O2, NaOH

2

H2SO4

Por: Karinel Nieves Merced
NaNH2 / NH3
Br
OHOrgánica 2004-05
Mg0, Et2O (Grignard)

2

H O

MgBr

1.
O

/ HMPA 2. H2O, H 1. / HMPA 2. H2O, H

* Se protona con -OH, -NH, -SH o -C D2O

C-H *

MgBr
OH

D OH

Br

O

NaOH

1. CH3CH2MgBr, Et2O 2. H3O+
Br Br

Br

Br2, xs CCl4
Br Br

O

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

H

HgSO4, H2SO4 H2O
O

CO2

1. CH3CH2MgBr, Et2O 2. H3O+
CN OH O C

H

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

1. CH3CH2MgBr, Et2O 2. H3O
+

H Br

H

HBr H2O2
O

O

O O

OH

OH O

1. CH3CH2MgBr, Et2O 2. H3O+
OCH3

KMnO4, H2O warm
O OH

O

1. CH3CH2MgBr, Et2O 2. CH3Br, DMSO 1. NaOHOH O

1. O3 2. Me2S

O O HO O O HO OH

2. CH3Br, DMSO
O

O

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

1. CH3CH2Li
OH

2. H3O+
Cl

KOH,#"
Br Br

O

1. NaNH2, " 2. H, H2O
Br

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

O

Por: Karinel Nieves Merced
O H O O O OH O O D

Orgánica 2004-05

3

NaBH4 CH3OH, H2O NaBD4 CH3OH, H2O

H OH

HBr -780C
Br

O

OD

HBr "
HBr

NaBH4 CH3OD, D2O
O H O O O

+
OH OH H OH

" (Diels-Alder)

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

H

2 electrones

HOMO

LUMO

OH OH

O

OH

OH

H2

PCC CH2Cl2 PDC CH2Cl2

4 electrones
H O

HOMO

LUMO

H2 OH

H O

6 electrones

HOMO

LUMO

PCC
OH

CH2Cl2
O

NBS

Br

CrO3P4
OH O

Grupos Activantes
OH

(orto, para)

Na2Cr2O7OH H2

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

H2SO4 Na2Cr2O7

Grupos Desactivantes

(orto, para)

-F, -Br, -Cl, -I
O

OH

H2SO4 DMSO, (CoCl)2
H2

Grupos Desactivantes
H

(meta)

Et3N, CH2Cl2, -60 C (Swern)
TsCl, piridina

0

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

OH OH

OTs

Br2 FeBr3
Cl

PBr3, CH2Cl2 (10, 20) SOCl2, Et2O (10, 20) ZnCl2, HCl H2SO4 (Pinacol)Br

OH

Cl

Cl2 AlCl3
I

OH

OH

Cl

I2 HNO3
O O O

OH OH

NO2

HIO4
OH

HNO3 H2SO4

+

Por: Karinel Nieves Merced
SO3H

Orgánica 2004-05

4

Cl NO2

SO3 H2SO4, fum.
SO3H

OH NO2

1. 2NaOH, " 2. H3O+
NO2

H2SO4, H2O

NO2 NH2 NH2

CH3CH2CH2Cl AlCl3 (solo con activantes)
O Cl O

Br

NaNH2/NH3 frio

+

AlCl3 (Fiedel-Crafts) (solo conactivantes)
OH OH2

CH3

CH3 Cl

CH3

HNO3 H2SO4

3Cl2, "

Cl

Cl

NH2

NO2

Cl

Cl Cl

O Cl

H N

AlCl3

O

3H2, "

HOCH2CH2CH3 BF3
NO2 NO2

OH

H2SO4, H2O

Na, NH3 CH3CH2OH (Birch)

OCH3

HF

OCH3

O

Li(CH3)3COH NH3/THF
H

HCl, Co, HCOCl AlCl3,CuCl (gatterman-koch)
Cl NO2 NH2 NO2

2NH3

1. KMnO4, NaOH 2. H3O+
COOH COOH

NO2

NO2

Por:Karinel Nieves Merced
O O O O

Orgánica 2004-05

5

O HS H H SH

BF3 1. n-BuLi

S

S

AlCl3
O HN NH2

S

S

2. CH3CH2I/HMPA

S O

S

H3 O + "
NO2 NH2

HgCl2, H2SO4, H2O
S O S H

HCl, Sn0
NH2 NO2

Ph3P

benceno
O

(Witting) H2O

OH OH

H2SO4
NH2 NO2

O

OH

H2 O2
NO2 N2

HCN, NaOH

CN

OH CN H

O OH

NaNO2, HCl
F

H3O+

C OH H...