15-20-SÍNTESIS-y-SECUENCIA

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Síntesis orgánica
Mg. Q.F. Agustín Rojas Armas
A partir de formaldehído, tolueno, propano y reacciones estudiadas, sintetizar:
CH3 — CH — CH
CH —
CH3
H2SO4/calor
OH
CH3 — CH — CH — CH2 —
CH3
Luego H3O+
CH3 — CH — CHO
+
BrMgCH2 —
CH3
Mg/éter seco
CrO3/Piridina/HCl
CH2 Br
CH3 — CH — CH2OH
+
CH3
Br2/hv
Luego H3O+
CH3
MgBr
CH3 — CH — CH3
+
HCHO
Mg/éter seco
Br
CH3 — CH — CH3
Br2/hv
CH3CH2CH3
-15-
Síntesis orgánica
Mg. Q.F. Agustín Rojas Armas
A partir de formaldehído, acetaldehído, ciclobutano, etano y reacciones estudiadas, sintetizar:
CH3 — C
CH — CH2 — CH2 — CH3
H2SO4/calor
OH
CH3 — CH — CH — CH2 — CH2 — CH3
Luego H3O+
MgCl
CH3 — CH — CHO
+
CH2 — CH2 — CH3
Mg/éter seco
CCP
OH
Cl
CH3 — CH — CH2
CH2 — CH2 — CH3
PCl5
Luego H3O+
OH
CH3 — CH — MgCl + HCHO
CH2 — CH2 — CH3
Luego H3O+
Mg/éter seco
HCHO + CH3CH2MgBr
CH3 — CH — Cl
Mg/éter seco
Br2/hv
CH3CH2Br
PCl5
— Br
OH
Br2/hv
CH3CH3
Mg/éter seco
CH3 — CH —
Luego H30+
CH3 — CHO +
-16-
— MgBr
Síntesis orgánica
Mg. Q.F. Agustín Rojas Armas
A partir de metano, benzaldehído y reacciones estudiadas, sintetizar:
OH
— CH2 — CH — CH — CH2 — CH3
CH3
Luego H3O+
MgBr
— CH2 — CHO
+
CH3 — CH — CH2 — CH3
Mg/éter seco
CrO3/Piridina
Br
OH
CH3CHCH2CH3
— CH2 — CH2
Br2/hv
BH3/THF
H2O2/-OH
— CH
CH3CH2CH2CH3
CH2
CH3CH2Br
H2SO4/calor
— CH — CH3
CH3CH2MgBr
Mg/éter seco
Br2/hv
OH
+
CH3CH3
Luego H3O+
CH3MgBr + CH3Br
— CHO + CH3MgBr
Mg/éter seco
CH3Br
Br2/hv
CH4
-17-
Secuencias de reacción
Mg. Q.F. Agustín Rojas Armas
Br
CH3CH2CH2CH3 + Br2/hv
MgBr
CH3CH2CHCH3 + Mg/éter seco
CH3CH2CHCH3 + CH3CHO
O- +MgBr
OH
O
CH — CH3
CH — CH3
C — CH3
CH3CH2CHCH3 + H3O+
CH3CH2CHCH3 + CCP
O- +MgBr
CH3CH2CHCH3 +
—CH2MgBr
OH
—CH2 — C — CH3 + H3O+
—CH2 — C — CH3 + CH3COOH
CH3CH2CHCH3
CH3CH2CHCH3
O
OH
O — C — CH3
—CH2 — C — CH3
+
LiAlH4
—CH2 — C — CH3 + PCl5
CH3CH2CHCH3
CH3CH2CHCH3
Cl
MgCl
—CH2 — C — CH3 + H30+
—CH2 — C — CH3 + Mg/éter seco
CH3CH2CHCH3
CH3CH2CHCH3
Br
—CH2 — CH — CH3
+
Br2/hv
—CH — CH— CH3
CH3CH2CHCH3
CH3CH2CHCH3
-18-
Secuencias de reacción
Mg. Q.F. Agustín Rojas Armas
OH
CH3 — CH
BH3/THF
CH2
-
CH3 — CH2 — CH2 + CrO3/Piridina
H202/ 0H
O- +MgBr
+ H3O
CH3CH2 — CH — CH2 —
— CH2MgBr
CH3CH2CHO +
Cl-
OH
CH3CH2 — CH — CH2 —
+ PCl5
+ Mg/éter seco
CH3CH2 — CH — CH2 —
O- +MgCl
CH — CH3
MgCl
CH3CH2 CHCH2 —
+ CH3 — CHO
CH3CH2 CHCH2 —
OH
O
CH — CH3
C — CH3
CH3CH2 CHCH2 —
CH3CH2 CHCH2 —
+ CCP
OH
CH — CH3
CH3CH2 CHCH2 —
-19-
+ H3O+
+ LiAlH4, luego H3O+
Síntesis orgánica
Mg. Q.F. Agustín Rojas Armas
A partir de etano, acetona, propan-2-ol y reacciones estudiadas, sintetizar:
OH
CH3
CH3 — CH — C — CH2 — CH2 — CH2
CH3
BH3/THF
H202/-0H
CH3
CH3 — CH — C — CH2 — CH
CH2
CH3
MgBr
CH3
CH3 — CH — C — Cl
+
CH2 — CH
CH2
CH3
Mg/éter seco
PCl5
Br
CH3
CH2 — CH
CH3 — CH — C — OH
CH2
CH3
Br2/hv
Luego H3O+
MgBr
CH3 — CH2
O
+
CH3 — CH
CH2
CH3 — C — CH3
H2SO4/180 °C
Mg/éter seco
OH
Br
CH3 — CH — CH2
CH3 — CH2
Br2/hv
CH3CH3
-20-
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