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-