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b)
ηCH 2 = CH
–
CN
(+)
Cl2 Li
CH4 CH3 – Cl CH3 – Li CuX CH3
∆,λ CuLi
CH3
CH3 – CH3
–– Br
C–N KOH Br2
–
CH2 = CH CH2 – CH2 CH3 – CH2
Et OH ∆
–
CN
NaNH2 NH3 Liq.
(-) (+)
ηCH2 = CH
NH2 – CH2 – CH
NH2 – CH2 – CH ˸ Na CH – CH
–
CN
–
–
CN CN CN n
49. Sintetizar los siguientes polímeros desde materias primas sencillas (CH4, , etc.)
Reacción Global
,λ
CH4 + Cl2 CH3 – Cl + HCl
ó∆
Inicio
Partiendo de CH4
λ
– – –
i) Cl • • Cl 2 Cl •
–
– – –
ó∆
Propagación
H H
–
–
–
ii) H – C • • H + • Cl H • • Cl + H – C •
–
–
–
–
H H
H – – H –
–
iii) H – C • + Cl • • Cl –
H – C – Cl + Cl •
–
–
–
– – –
–
–
H H
Terminación
H – H –
–
–
iv) H – C • + • Cl H – C – Cl
–
–
– –
–
–
H H
– –
– –
v) Cl • + • Cl Cl • • Cl
–
–
–
–
– –
– –
H H H H
–
–
–
H H H H
H H
– – – –
–
vii) H – C • + •O–O H–C••O–O
–
– – – –
–
–
H H
CH3
CuI CH3 – Cl
2 CH3 – Cl + 2Li CuLi CH3 – CH3 + CH3 – Cu + LiCl
CH3
–
i) CH3 – Cl + • Li CH3 – Cl
–
–
(+)
Li
(-) (+)
–
ii) CH3 – Cl + • Li CH3 • • Li + LiCl
–
–
(+)
Li
–
– –
CH3
–
– –
CH3 Etano
Mecanismo de Halogenación por radicales libres.
λ
–
i) Cl • • Cl 2 Cl •
–
–
ó∆
H H
–
–
–
ii) CH3 – C • • H + • Cl H – Cl + CH3 – C •
–
–
–
–
H H
H
–
– –
– –
iv) Cl • + • Cl Cl • • Cl
–
–
–
– –
– –
Mecanismo KOH en etanol
Reacción Global
– (-)
KOH/Et. OH
CH3 – CH2 – Cl CH2 = CH2 + H2O + Cl
–
–
(-) (+)
–
i) H2C – CH2 + OHK H2C = CH2
–
–
–
–
H Cl
Mecanismo Sustitución Nucleofílica
(-)
–N
:
(+)
i) H2C = C – H + :C–
– H2C = CH + H
–
•
H CN
(+) (-)
i) NaNH2 + NH3 Liq. Na + NH2 :
(-) (+)
ii) NH2 : + CH2 = CH NH2 – CH2 – CH : Na
–
CN CN
CN
–
(-) (+) (-) (+)
CH2 = CH
iii) NH2 – CH2 – CH : Na NH2 – CH2 – CH – CH2 – CH : Na
–
–
–
CN CN CN
CN CN
–
(-) (+)
–
η CH2 = CH
iv) NH2 – CH2 – CH – CH2 – CH : Na NH2 – CH2 – CH CH – CH
n
–
–
CN CN
a)Poli (metil metacrilato)
CH3
η CH
–
2 =C
–
–
C=O
– –
O
–
–
–
CH3
(+)
Cl 2 Li CuI
CH3 – CH3 CH3 – CH2 – Cl CH3 – CH2 –Li CH3 – CH2
λ
CuLi
CH3 – CH2
S(+) S(-)
–
–
–
CH3 = CH KOH
CH3 – CH Br CH3 – CH2
∆
–
Br
O
–
–
–
=
CH3 – C – O – CH3
– CH3
–
O
–
–
CH3 –
–
C–O
–
(-) (+) –
–
Na NH2
H 3C = C NH2 – CH2– CH : Na NH2 – CH2– CH
NH2 – CH2– CH
CH2– CH
NH3 Liq. –
η
–
– –
–
–
–
C=O – C=O – C=O – C•O
–
–
–
O
–
–
O O O
–
–
–
–
–
–
–
CH3 CH3 CH3 CH3
Mecanismo de Sustitución Nucleofílica
=O
CH3 CH3
–
–
–
–
–
i) H2C = C + CH3 – C – O – CH3 H2C = C + CH4
– –
–
–
H C=O –
– –
O
–
–
CH3
(+) (-)
i) Na NH2 + NH3 Liq. Na + NH2 :
(-) (+)
:
ii) NH2 + CH2 = CH – NH2 – CH2 – CH : Na
–
–
C=O – C=O –
–
O
–
–
O
–
–
–
–
CH3 CH3
COOCH3
–
(-) (+) (-) (+)
CH2 = CH
iii) NH2 – CH2 – CH : Na NH2 – CH2 – CH – CH2 – CH : Na
η veces
–
–
COO CH3 COO CH3 COO CH3
COOCH3 COOCH3
–
(-) (+)
CH2 = CH
iv) NH2 – CH2 – CH – CH2 – CH : Na CH2 – CH
–
Inicio
λ
– –
–
i) Cl • • Cl 2 Cl •
–
–
–
– –
ó∆ –
Propagación
H H
–
–
–
–
–
H H
H H
– – – –
–
–
–
–
–
– – – –
–
–
H H
Propagación
H
– –
–
iv) H3C – C • + • Cl H3C – CH2 – Cl
–
–
– –
– H
– – –
–
v) Cl • + • Cl Cl – Cl
–
–
–
–
– – –
–
Mecanismo Corey House
CH3 – CH2
CH3
CH3 – Cl
–
CuI
2 CH3 – CH2 – Cl + 2Li CuLi CH3 – CH2 + CH3 – CH2 – CuI + LiCl
CH3 – CH2
–
i) CH3 – CH2 – Cl + • Li CH3 – CH2 – Cl
–
–
(+)
Li
(-) (+)
–
ii) CH3 – CH2 – Cl + • Li CH3 – CH2 • • Li + LiCl
–
–
(+)
Li
(+) CH3 – CH2 (-) (+) –
iii) 2 Li : CH2 – CH3 + Cu : I CuLi + Li – Cl
–
–
CH3 – CH2
CH3 – CH2
CH3
S(+) S(-)
– –
–
(-) (+)
iv) CuLi + CH3 – Cl CH3 – CH2 + LiCl
–
– –
CH3 – CH2
λ
– – –
i) Cl • • Cl 2 Cl •
–
– – –
ó∆
CH3 CH3
–
–
ii) CH3 – C • • H + • Cl H • • Cl + CH3 – C •
–
–
–
–
H H
CH3 CH3
–
–
–
–
–
H
Mecanismo KOH en etanol
–
–
–
i) H2C – CH + OHK H2C = CH
– –
–
–
H Cl