SOLUCIONES - EXAMEN QUMICA ORGNICA - JUNIO 2004 1.

a)
Cl Cl
Trans-(ec)-1,2-diclorociclohexano

b)
CH3 CH3

c)
OH CH3
Trans-(ec)-1,4-dimetilciclohexano Cis-(ec)-1-hidroxi-3-metilciclohexano

2,.
a)
H CH2 OH OH

b)
CH 3

COOH H

c)
H H

COOH

d)
OH H CH3

COOH

(R) (R)
CH 3

(R)
OH OH

(S)
CH2 Cl

(S)
COOH

OH

(S)
H

3.CH3 HCl a) CH2 = CH - CH 3 CH3 - CH - CH 3 Cl

HNO3 / H2 SO4

CH - CH 3

H2SO 4 SO3 H

CH - CH 3

AlCl3

CH3

b)

NO2 Cl2/FeCl3 OH H2SO 4(ac) Cl

NO2

HCl/Zn Cl CH3 C CH3

N2 +ClCuCN Cl OH CH3 - C - CH CH3 CH3

CN

c)

CH2 = CH - CH3 HCl

CH3 - CH - CH 3 Mg/ter

Cu/Calor

O
CH3 - CH - CH 3 Cl CH3 - CH - CH 3 Mg Cl

H2O/H+

CH3

4.a)
O CHO

CH 3

NH 2

CH 3

b)

NaOH

COO- Na+

+
COOH

CH2OH

c)

+
COOH

COOH COOH

5.
Cl2/FeCl3

Cl Mg/ter

Mg - Cl

1)propanal 2) H2O/H+

CH - CH 2 - CH3

OH
Cu/Calor

CO/HCl

CHO

(C)
CH = CH - C

C - CH2 - CH3

(A)
6 y 8. Consultar teora 7.a)
CH 3 C CH2 C CH 3 O O

O
CH2 - CH3

(B)

b)

CH3 - CH - CH 2Cl CH 3