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

Luego H3O+ Br2/hv

MgBr CH3

CH3 — CH — CH3 + HCHO

Mg/éter seco

Br

CH3 — CH — CH3

Br2/hv

CH3CH2CH3

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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 Br2/hv
OH
Mg/éter seco CH3CH3
CH3 — CH —
Luego H30+ CH3 — CHO + — MgBr

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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

OH Br

CH3CHCH2CH3
— CH2 — CH2
Br2/hv
BH3/THF

H2O2/-OH CH3CH2CH2CH3

— CH CH2

H2SO4/calor CH3CH2Br + CH3CH2MgBr

Mg/éter seco
Br2/hv
OH

— CH — CH3 CH3CH3

Luego H3O+

CH3MgBr + CH3Br
— CHO + CH3MgBr

Mg/éter seco

CH3Br

Br2/hv

CH4

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 Secuencias de reacción Mg. Q.F. Agustín Rojas Armas

Br MgBr
CH3CH2CH2CH3 + Br2/hv CH3CH2CHCH3 + Mg/éter seco CH3CH2CHCH3 + CH3CHO

O- +MgBr OH O

CH — CH3 CH — CH3 C — CH3

CH3CH2CHCH3 + H3O+ CH3CH2CHCH3 + CCP CH3CH2CHCH3 + —CH2MgBr

O- +MgBr OH

—CH2 — C — CH3 + H3O+ —CH2 — C — CH3 + CH3COOH

CH3CH2CHCH3 CH3CH2CHCH3

O — C — CH3 OH

—CH2 — C — CH3 + LiAlH4 —CH2 — C — CH3 + PCl5

CH3CH2CHCH3 CH3CH2CHCH3

Cl MgCl

—CH2 — C — CH3 + Mg/éter seco —CH2 — C — CH3 + H30+

CH3CH2CHCH3 CH3CH2CHCH3

Br

—CH2 — CH — CH3 + Br2/hv —CH — CH— CH3

CH3CH2CHCH3 CH3CH2CHCH3

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Secuencias de reacción Mg. Q.F. Agustín Rojas Armas

OH
BH3/THF
CH3 — CH CH2 CH3 — CH2 — CH2 + CrO3/Piridina
-
H202/ 0H

O- +MgBr

CH3CH2CHO + — CH2MgBr CH3CH2 — CH — CH2 — + H3O

OH Cl-

CH3CH2 — CH — CH2 — + PCl5 CH3CH2 — CH — CH2 — + Mg/éter seco

O- +MgCl

MgCl CH — CH3

CH3CH2 CHCH2 — + CH3 — CHO CH3CH2 CHCH2 — + H3O+

OH O

CH — CH3 C — CH3

CH3CH2 CHCH2 — + CCP CH3CH2 CHCH2 — + LiAlH4, luego H3O+

OH

CH — CH3

CH3CH2 CHCH2 —

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Síntesis orgánica Mg. Q.F. Agustín Rojas Armas

A partir de etano, acetona, propan-2-ol y reacciones estudiadas, sintetizar:

CH3 OH

CH3 — CH — C — CH2 — CH2 — CH2

CH3
BH3/THF

H202/-0H

CH3

CH3 — CH — C — CH2 — CH CH2

CH3

CH3 MgBr

CH3 — CH — C — Cl + CH2 — CH CH2

CH3
Mg/éter seco
PCl5
CH3 Br

CH3 — CH — C — OH CH2 — CH CH2

CH3
Br2/hv
Luego H3O+

MgBr O CH3 — CH CH2

CH3 — CH2 + CH3 — C — CH3

H2SO4/180 °C

Mg/éter seco

OH
Br
CH3 — CH — CH2
CH3 — CH2

Br2/hv

CH3CH3

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