Fundamentals of Organic ChemistryChemistryAmines
Consider the following reaction sequence: Alkene product mixture Alkene product mixture O ₃ / Zn - H ₂ O Final product mixture Which of the following compounds are present in the final product mixture?
Options
- ACH ₃ CHO + HCHO
- BCH ₃ CHO + CH ₃ CH ₂ CH ₃+ HCHO
- CCH ₃ CHO + CH ₃ COCH ₃
- DCH ₃ CHO + CH ₃ COCH ₃+ HCHO
Correct answer
D. CH ₃ CHO + CH ₃ COCH ₃+ HCHO
Step-by-step solution
The given reaction sequence involves Hofmann exhaustive methylation followed by Hofmann elimination, and finally reductive ozonolysis. The starting tertiary amine reacts with excess CH₃I to form a quaternary ammonium iodide. Subsequent treatment with moist Ag₂O replaces the iodide ion with a hydroxide ion, yielding the quaternary ammonium hydroxide: [CH₃-CH(CH₃)-CH₂-N^+(CH₃)₂-CH₂-CH₂-CH₃] OH^- Heating the quaternary ammonium hydroxide causes Hofmann elimination. The hydroxide ion abstracts a -hydrogen to form an al