CH3-CH3

producto y cuando el esqueleto es

CH3-CH2

Luz u.v o
calor

Insercin de Metileno (-CH2-): Reacciona C 1 y pone un CH2

cuando es etano solo tienes un

largo tienes dos productos

CH2N2

CH3-CH3

CH3-CH2-CH3

Luz u.v

+ Halgena con todos y tienes contaminantes

CH3-CH2-Cl

CH2CO

CH3-CH2-CH3

Sin contaminantes

Br2

Luz u.v

Br especifico halgena 1ro C terciarios,sino

CH3-CH2-Br hay C secuandario o sino hay a C primarios

Luz u.v o
calor

Doble Enlace: solamente rxn con el doble enlace

Ejemplo:

2R-X

Cl
Na
R-R+2Nax CH3-CH2 ter,

2Na
ter,

CH2N2

CH2-CH2

Rxn de Wrtz, (duplica)

CH2-CH2 +N2
CH2

Luz u.v

CH3-CH2-CH2-CH3

CH2CO
Luz u.v

CH2-CH2+CO2

CH3-CH2-CH2-Cl

H-O-O-H
R-O-O-R

CH3 -C

CH3-CH2-CH2-CH3

C- CH3

CH3 CH3
CH3

CH3
CH3-CH-CH3

Br2

ter,

CH3
Isobutano

CH3 CH3
CH3-C
C-CH3

Na

CH3-C-Br

CH3 CH3

CH3

(H2O2)

Biciclo [1.1.o]butano
CH2

CH2CO

H-C-C-H

Luz u.v

H-C - C-H

H-C - C-H

Ciclacin: unin de los C.

X
Zn, NaI(ac.)

(CH2) n

(CH2) n

EtOH,

Na

Ciclo

n=3,4,5 o 6

ter,

CH3
CH3
CH3-CH-CH2-CH2-CH-CH3

+ ZnX2

Ejemplo:

ciclopropano

propano

CH3-CH2-CH3

Rxn de Corey-Hause (dialquilcuprato de litio)

R-X

Li

(1,2,3)

ter

R-Li

2SO2Cl2

CuI

Ejemplo: Propano

CuLi

R-X

Cl-CH2-CH2-CH2-Cl

Perxido

R-R

Isohexano
CH3
CH3-CH-CH2-CH2-CH2-CH3

CH3-CH2-CH3

Zn, NaI(a.c),
EtOH,

Rxn de Grignurd: formacin de enlaces de C-C.

CH3-CH2-CH2-Cl

Mg
ter

CH3-CH2-CH2-Mg-Cl
OH-+H+

Li
ter

CH3-CH2-CH2-Cl

CH3-CH-Li
CuI

CH3

CH3-CH2-CH2-Cl

CH3-CH-CH2-CH2-CH2-CH3

CuLi
CH3-CH
CH3

Cl: cloro

Br: bromo

Li: litio

CuLi: dialquilcuprato de litio

CH2CO: cetona

Na: sodio

SO2Cl2: Dicloruro de sulfurilo

CH2N2: diazometano

Cloruro de sulfonilo
Cloruro de xido de azufre

CH2N2
u.v

H2O

OH

CH3-CH2-CH2-H-Mg
Cl

Hidrogenacin cataltica: rompe el 2 enlace

H H
H
C=C

CH3-CH

CH3

CH3-CH2-CH2-CH3

H2

Ni o Pd o Pt

CH3-CH2-CH3

CH3

Cl2

Cl
CH3-CH-CH3
+

C: + CO
H

CH2

CH3

CH3
CH3
SO2Cl2
CH3-CH-CH3 H-O-O-H CH3-CH-CH2-Cl

H
C:: C-O

Triple enlace: Genera tencin en el anillo

CH3-CH-CH2-CH2-CH-CH3

CH3-CH2-CH2-CH3

CH2

2,5- Dimetilhexano

CH3

CH2

H H
H-C C CH2H
H H

H
C - C H

CH3 CH3

CH2

Propano

CH2

2,2,3,3- Tetrametilbutano

CH2N2 o CH2CO Luz u.v

H
C: + N-N

Ejemplo:

CH3

CH2

C: :N-N

Ejemplo:
Isobutano

CH2

Mecanismo alcanos o alquenos

SO2Cl2
perxidos

CH2

Cloruro de Sulfurilo: Halogenacin primario (a C primarios (CH3) nicamente)

CH3-CH2-CH3

Ejemplo:

Cl
Cl2

Cl y Br

H
Estructura spiro (espiro)
10
11

16

H-C C-H
H H
15 vinil-dispiro [5.1.7.2]-1,10-heptodecadieno

17
5

12
13

15
14 CH2-CH
7

6
1

Posiciones de adicin Markovnikov

Halogenacin de alquilo: Cuando hay una materia prima

Cl

X
CH3-CH2-CH2

KOH
EtOH

Ejemplo:

2,3-Dimetil-1-buteno
CH3

CH3-CH2-CH3

Ms estables

ter,

SO2Cl2

1)Li/ ter,
2)CuI

CH3-CH2-CH2-Cl (A)

CH3-CH2-CH2-CH2
H2O

Br
CH3-C-CH2-CH2-CH3
CH3

CH3-CH2-CH=CH2

CH3
H2 exceso
2H2

CH2=CH2-CH-CH-CH2=CH2

Ni

Cl Cl

Transposicin de grupo
Cl

CH3

CH3
H2O

CH3-C-CH-CH2 + :Cl -

CH3-C=CH-CH3

EtOH o
MeOH,

H H

2-Metil-2-buteno

CH3

Br:

Br

H
CH3-CH=CH-CH3+ZnX2

CH3

CH3

H2O

CH3-CH-CH2-CH-CH3

CH3-C-CH-CH2

CH3

CH2=CH-CH=CH2

CH3-C-CH2-CH2

2,3,6,7-Tetrametil-2,4,6-octatrieno
CH3
CH3
CH3-C=C-CH=CH-C=CH-CH3

Propano

CH3-CH2-CH3
Br2

CH3

u.v

CH3-CH-Br

ter,

u.v

CH3 CH3

CH3 CH3

Na

CH3 -C=C-CH2-CH2-C=C-CH3

ter,

CH2-C=C-CH3

Br Br
CH3
BrCH3 -C=C-CH-CH-C=C-CH3

SO2Cl2, perxido

acetona

acetona

KOH
EtOH

CH2-C -CH-CH3

CH2-CH-C-CH3

CH2-C -CH-CH3

CH2-CH-C-CH3

NBS

Cl CH3

Cl CH3
CH2-CH-C-CH3

CH2-CH-C-CH3
CH3 CH3
CH3
CH3

Na

2)HCl conc.

CH2=CH-C-CH3

ter,

2HBr

2HCl

CH3 CH3

CH3 CH3

Br CH3CH3

CH3-CH=C - C-CH3
CH3

HBr
Perxidos

CH3-CH-CH-C-CH3
CH3

Sntesis de alcoholes a partir de alquenos

OH

Forma el alqueno

CH3-CH=CH2+ HCl
H3O O H

CH3-CH=CH2-+H2O+H+

Zn,NaI(a.c.)
EtOH,

Br
CH2-CH2-C-CH3
CH2-CH2-C-CH3

:Cl Cl:

CH-CH3

CH3-CH-CH2

H-Cl

:OH

Roba

CH3-CH-CH2+Cl

CH3-CH-CH2

Puede ver transposicin

se genera un carbocatin por el robo

Ejemplo:

CH3
OH

OH CH3
CH3-CH-C-CH3

CH3
H+

CH3-C=C-CH3
CH3

CH3

Cl
CH2-CH-CH3

CH2

Covalente polar
+
-

H
:OH

X
X

CH3 CH3

CH3 CH3

perxidos

CH3

CCl4

EtOH,

CH3-CH2-CH2

CH3

Br

CH2-CH

Na
ter,

CH3-C C-CH3

Markovnikov

X2

Br2

Br-CH2-C C-CH3

CH3

CH3

Cl

CH2=CH-CH3

H2O

H CH3 CH3
H
CH-C
C-CH3

CH2=CH-C-CH3

Anti-Markovnikov

Tetracloruro de carbono

CH3-C-Br
CH3

CH3 CH3

1)HBr(dilu.)

Cl CH3

Cl CH3

Br2

CH2-CH-C-CH3

CH3

CH3-CH-CH3

CH3 CH3

CH2-CH-C-CH3

CH3

CH3

CH3

CH2=CH-C-CH3
Br
CH3

Cl CH3

CH3 Cl

CH3-CH-CH-C-CH3

1-Cloro-3-metilbutano

Br CH3

CH3 Br

2-Bromo-3,4,4-trimetilpentano
Br CH3CH3

CH3

CH2=CH-CH-CH3

C 2

CH3

CH3

Ejemplo:

Alilica

CH3-C-CH-CH3

CH3 H

CH3-CH-CH3

Zn

CH3

CH3-C-C-CH2

CH3

NOTA: EL HIDRURO ES PRIMERO

CH3:

Isobutano

CH3-C=C-CH3

CH3

CH3-C-CH-CH2

Ejemplo:

CH3 CH3

CH3

CH3

CH3

Cl

CH3 CH3
CH3-C=C-CH=CH-C=CH-CH3
CH
CH2-C C-CH3
CH3
3

X
CH2=CH-CH2

X2, u.v, NBS,

Cl-CH2-CH2-CH-CH3

Zn

CH3

Halogenacin de alquenos
CH2=CH-CH2

H2O2

Br

CH3

CH3

CH3

SO2Cl2

CH3

CH3- C - C-CH3
Br

Cl CH3CH3

H H

CH2

CH3

CH3 CH3
2Br2

CH3-C=C-CH2

MeOH,

CH3-C-CH-CH2

CH3 CH3
CH3-CH-CH-CH3

Na

CH3-C-CH-CH2

Cl:

CH3

CH3

H2O

CH3

Ejemplo:

CH3

CH3

Cl

EtOH

CH3-CH=CH-CH-CH3

EtOH,

Ms estable

2KOH

Ante dos C Halogenados adyacentes

no se ciclan, se transpone de un C
cuaternario.

Puede competir con el H

Ni P.T.

1-Cloro-3-metilbutano

2Br2

Cl
por el tamao

CH3-CH-CH2-CH2

CH3-CH-CH-CH2

CH-CH3

Rxn homoltica

CH

C=C

CH2=CH2-CH-CH-CH2=CH2
Cl Cl
CH3

Br

Ejemplo:

CH3-CH-CH-CH2 +:X

Vecinal
Zn
acetona

Ni o Pd
o Pt

EtOH

EtOH o MeOH

CH3-CH-CH-CH3

Adicin
H2

KOH

Br2

CH-CH3

(Perxidos)

H-C=C-H

EtOH

CH3-CH-CH2-CH2-CH3
CH3
X

Eliminacin en medio altamente polar

CH2-CH-CH3

H + Br

Con alquinos para obtener alquenos

KOH

3) (A)

H Br

Cl2
calor

CH3
CH3

CH3
CH3
CH3-CH-Cl

HBr
R-O - O-R

CH2-CH-CH-CH3

perxido

CH3-C=CH-CH2-CH3

CH3-CH2-CH3

CH2
H

H Br
CH2-CH-CH3

CH2

Cl

CH3
2-Metil-2-pentano

Propano

Br
CH2=CH-CH3

CH2

Anti-Markovnikov
Por radicales
libres

EtOH

CH3
CH3-CH-CH-CH3

Na

CH3-CH=CH-CH3

EtOH

CH3

CH3-CH-Br

KOH

H Cl
CH2-CH-CH3

HCl conc.
HBr cou.

CH3-CH=CH2 CH2=CH-CH3

EtOH

KOH

CH2=C-CH-CH3

CH3

Br2

Br
CH3-CH-CH2-CH3

MeOH

Propano

KOH

CH3-CH=CH2 + HX CH3-CH-CH3

X-

OH2 CH3
CH3-CH-C-CH3
CH3

CH3
CH3-CH-C-CH3
CH3

H CH3
CH3-C - C-CH3
CH3

CH3
H
CH3-CH-CH=CH2

CH3

CH3

OH-

CH-CH2
Cl Cl

El nombre va a estar dado por la cadena ms larga que tenga el OHCH3

CH3 OH OH

X2

CH3-CH=CH2
Cl
B
CH2- CH2-CH2-CH
2
Cl

CH3-CH2-Br

CH3-CH2-CH3

OH Br

CH3- CH2-CH2-CH3

ter,

CH3- CH2-CH2-Cl (A)

CH3

Br

KMnO4

Br2

KOH

Fro

n-Butano

CH3-C- C-CH2 -CH3

SO2Cl2 / Perxido

EtOH

Br2

CH3-CH-Br

Br

3) (A)

CH3

OH Br

CH3-CH2-CH2-CH2-Cl

Perxido

CH3

OH CH3
CH3-CH-CH-CH-CH=CH2

OH
H2
Ni

H2 (exceso)

Na

Pd (P.T.)

U.V

ter,

Br2

CH3-CH2-CH-Br

Na
ter,

KOH

CH3-CH2-C = C-CH2-CH3

EtOH

CH3 CH3
CH3-CH -C = C-CH2-CH3

H2

Br CH CH
3
3
CH3-CH-CH-CH-CH2-CH3
OH

Ni

Br
CH3CH3
CH3-CH -CH-CH-CH2-CH3
2)H2O2,OH-

Acetona

Cl2

OH

Br
KOH
EtOH

Br2

KOH
EtOH

CH3 CH3

CH3-CH=C -CH-CH2-CH3

Ozonlisis: oxidacin en el doble enlace

Alquenos

H
H
H
H

O3,THF
Agua,Zn

Facilita la disolucin de gas

H
Ejemplo
CH3
O3,THF
CH2=C-CH=CH-CH2-CH=CH2

Agua,Zn

n-Butano

CH3-C

CH3-CH2-CH2-CH3

Br2

Br

2H-C

Br

+ O=C-C + C-CH2-C
H H
Zn

CH3-CH-CH-CH3 acetona

CH3-CH=CH-CH3

=O

Benceno: aromaticidad, Rxn de sustitucin electrofilica

H
3H2 H2(exceso)

H
H

Ciclohexanona

H
H
H

H
H
H

1)Br2/calor
CH3-CH2-CH2-CH2-CH2-CH3

1)SO2Cl2/ H2O2

2)Na/ter,

2)Zn,NaI(a.c)/EtOH,

3)Br2/u.v

O3 Agua,Zn

2CH3-C

Ni o Pd o Pt
Presin,Temperatura(P.T)

n-Hexano

H
H

=O

Br2

H2 Ni

H2O

CH3 CH3
CH3-CH2-CHCH-CH2-CH3

Br

Zn

Fro

Cl

CH3-CH2-CCH-CH2-CH3

1)(BH3)2

KMnO4

OH

CH3 CH3

CH3 CH3

Br2
Calor

OH

CH3

OH
CH3

Br2
Br2

CH3 CH3
CH3-CH-CH-CH-CH2-CH3

3) CH3-CH2-CH2-CH3

Br2

CH3-CH-CH-CH-CH2-CH3
CH3

CH3

CH3-CH2-CH2-CH3

Br

Br-CH-CH=CH2

ter,

CH3

2)NaBH4

Pone un OH y Br con esta Rxn

CH3-CH2-CH=CH2

EtOH

CH3
Na

CH2=CH-CH-CH-CH=CH2

1) Hg(AcO)2

CH3-C=CH2-CH2-CH3

H2O

KOH

SO2Cl2

CH3-CH2-CH2-CH3

EtOH,

KOH

CH3

Br2

CH3-C- C-CH2 -CH3

2)

CH3-CH=C-CH-CH2-CH3
CH3

CH3

CH3-CH2-CH2-CH3

CH3-CH-CH2-CH2-CH3

CH3
CH3-CH-CH2-CH2-CH3

1)Li/ter
2)CuI

3,4-Dimetil-2-hexanol

CH3
Br2

O3,THF
Agua,Zn

H Br
Br
Zn
acetona

OH

HO

3-Bromo-2-metil-2-pentanol
CH3

Anti-Markovnikov

CH3-CH3

acetona

Markovnikov

Ejemplo: 1)Propano

Zn,NaI (a.c.) EtOH,

Na

Zn

Cl

OH
2SO2Cl2 H2O2

Br2

CH3-CH-CH2

H2O

1) Etano

2)

Cl

Etilciclohexano

OH

3-Metil-1,2-bunanodiol

HO

CH=CH2

Sntesis de habhidrina

CH3-2CH-3CH-4CH2

Ejemplo:

H
H

Alcoholes Halogenados

2-Metil-2butanol

CH-CH2

H2 (exceso)

Acta sobre el doble enlace

Ni,P.T

CH3-2CH-3CH2-4CH2

CH2-CH3

Fro

OH

Ni

1,2-Diales(glicoles)vecinos

CH3 OH OH
CH3-CH-CH-CH2

CCl4

CH3
CH3-CH-CH2-CH2

H2O2

BH2

Se une al C con ms H

H2 (exceso)
Cl2

OH

Se une al C con menos H

CH3-CH-CH-CH2

CH3
KMnO4
CH3-CH-CH=CH2

CH3 OH
transposicin
CH3-CH-CH-CH2

Anti-Markovnikov

Etilbencen
o

Ni

VINILO

HgAcO

Ms H

(BH3)2

CH3-CH-CH=CH2

OH
No hay

NaBH4

CH3-CH-CH-CH2

CH3

CH=CH2

H2O

CH3-CH-CH=CH2

H2 (exceso)

CH3-C-CH2-CH3+H2SO4

CH3 OH
Hg(AcO)2

CH-CH2

Estereno

CH3
H2O

OSO3H

Markovnikov

transposicin

H2SO4 conc.

CH3
CH3-CH-CH=CH2

Hay carbocatin y puede haber

Sntesis de alcoholes a partir de alquenos

Onolisis: rompe el doble enlace creando un carboxilo y un

ferinas (ambos son carboxilos)

CASO ESPECIAL
H

HO
OH
CH3-C=O + C-C + CO2

KMnO4

CH3 -C=CH-CH=CH2

OH-,

H C

Cetona

CH3-CH2-CH3

CH2N2
Luz u.v

CH3-CH2-C

KOH

CH3-CH2 -CH=CH2

OH-,

EtOH

CH3

Benceno

CH3

Condensacin de Diels Alder: se genera con C=C-C=C y

Los puntos ( )forman el
con un C=C, para formar un ciclohexgono
H

El enlace ataca

C
+
C
H
H

H C
H C
H

clicohexeno

H
H

H
Benceno

Dienfilo (alqueno simple)

Dieno conjugado

Aducto de Diels-Alder

Ejemplo:
1,3-Butaeno y
propileno

4-Metilciclohexeno
CH3

CH2=CH-CH=CH2 + CH2=CH-CH3
H

CH3

H
C

H C
H

CH3

Benceno

C
H

1)Br2/calor
2)Na/ter,

Isobutano

1) CH3

2) CH3

CH3-C-CH3

CH3-C-CH3

Br

CH3-C-CH3

3)

CH3-C-CH3
CH2

2) KOH,EtOH
3) NBS
4) KOH,EtOH

CH3-C-CH3

CH3-C-CH3

C-CH3
Br-CH2-CH

C-CH3

2)

CH3

CH2=CH

CH3-C-CH3
H-C-CH3
H
Br-CH2-CH

C=CH2

CH2=CH
CH3
C

2)

CH3
CH3-C-CH3 B
CH-CH3

CH2=CH

CH
CH2

CH3

Br-C-CH3

CH2

2) KOH,EtOH

4)

CH3

CH3-C-CH3

1) H2, Ni

2) NBS

CH3-C-CH3

CH-CH3

H-C-CH3
H
Br-CH2-CH

CH3

3)

CH3

Br
1) H2O,MeOH,

CH3-CH2

CH3-C-CH3

CH3-C-CH3

1)

1) CH3

2) CH3

1) H2, Ni

1)

CH3

CH3-C-CH3

CH3
3)Br2/u.v

CH3
CH3-CH-CH3

H
Benceno

H
H

Cl
CH3-CH2 -CH2-CH2

SO2Cl2
H2O2

KMnO4

+CO
OH

+ CH3-CH=CH-CH3

reacciona primero el doble enlace y el eterotomo se pone como sustituyente

CH3-CH2 -CH2-CH3

Diels - Alder

CH3-CH2-C
OH

CH3-CH2-CH3

H C

cido propanoico

Formaldehido (metanol)

cidos carboxlicos

Propano

=O

CH3

CH3

CH3-C-CH3

CH2=CH
CH3
CH3-C-CH3

CH-CH3 +
CH
CH2

CH-CH3
CH3-C-CH3
CH3

Carbono

Nombre

Forma natural
(n)

Estructura

Metano

CH4

Etano

CH3-CH3

Propano

4
5
6
7

Butano
Pentano
Hexano
Heptano

n-Butano
n-Pentano
n- Hexano
n- Heptano

CH3-(CH2)2-CH3
CH3-(CH2)3-CH3
CH3-(CH2)4-CH3
CH3-(CH2)5-CH3

8
9
10
11
12

Octano
Nonano
Decano
Undecano
Dodecano

n- Octano
n- Nonano
n- Decano
n- Undecano
n- Dodecano

CH3-(CH2)6-CH3
CH3-(CH2)7-CH3
CH3-(CH2)8-CH3
CH3-(CH2)9-CH3
CH3-(CH2)10-CH3

13

Tridecano

n- Tridecano

CH3-(CH2)11-CH3

14

Tetradecano

n- Tetradecano

CH3-(CH2)12-CH3

15

Pentadecano

n-Pentadecano

CH3-(CH2)13-CH3

16

Hexadecano

n- Hexadecano

CH3-(CH2)14-CH3

17

Heptadecano

n- Heptadecano

CH3-(CH2)15-CH3

18

Octadecano

n- Octadecano

CH3-(CH2)16-CH3

19

Nonadecano

n- Nonadecano

CH3-(CH2)17-CH3

20

Eicosano

n- Eicosano

CH3-(CH2)18-CH3

CH3-CH2-CH3