Chapter 22: Amine Synthesis Worksheet Answers
NOMENCLATURE
Do problems 1 and 2 in Morrison and Boyd. Answers found in the Solutions Manual.
SYNTHESIS
A. Outline a possible laboratory synthesis of each of the following starting with benzene,
toluene, and any alcohols of your choice. You must use a different method for each
synthesis!
1. trimethylamine
Ammonolysis: start with 3 moles of methanol and one mole of PBr3 or 3 moles
HBr.
2. t-butylamine
Hoffman degradation: start with neopentyl alcohol and convert COOHAcid
Chloride.
3. aniline
Nitration/Reduction: start with toluene nitrate toluene.
4. n-propylamine
Nitrile Reduction: start with ethanol +HBr
5. cyclohexylamine
Reductive amination: Start with cyclohexanol and oxidize to cyclohexanone.