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954 CHAPTER TWENTY-TWO = Amines 22.30 Describe procedures for preparing each of the following compounds, using ethanol as the source of all their carbon atoms. Once you prepare a compound, you need not repeat its synthesis in a subsequent part of this problem. (a) Ethylamine (b) N-Ethylacetamide (©) Diethylamine (@) N,N-Diethylacetamide (e) Triethylamine (f) Tetraethylammonium bromide 2291 Show by writing the appropriate sequence of equations how you could carry out each of the following transformations: (a) 1-Butanol to 1-pentanamine (b) tert-Butyl chloride to 2,2-dimethyl-1-propanamine (©) Cyclohexanol to N-methylcyclohexylamine (d) Isopropyl alcohol to 1-amino-2-methyl-2-propanol (e) Isopropyl alcohol to 1-amino-2-propanol (® Isopropyl alcohol to 1-(N,N-dimethylamino)-2-propanol L\ C oe x«K to CsHs CH; | CeHsCHCH3 22.32 Each of the following dihaloalkanes gives an N-(haloalkyl)phthalimide on reaction with one equivalent of the potassium salt of phthalimide. Write the structure of the phthalimide derivative formed in each case and explain the basis for your answer. ABS orn PDF Enhancer HACE CCH, pe © BrCH,CCHsCHBr CH; 22.33 Give the structure of the expected product formed when benzylamine reacts with each of the following reagents: (a) Hydrogen bromide (b) Sulfuric acid (©) Acetic acid (d) Acetyl chloride (©) Acetic anhydride (f) Acetone (g) Acetone and hydrogen (nickel catalyst) (h) Ethylene oxide (i) 1,2-Epoxypropane Excess methyl iodide (&) Sodium nitrite in dilute hydrochloric acid Write the structure of the product formed on reaction of aniline with each of the following: (a) Hydrogen bromide (b) Excess methyl iodide (c) Acetaldehyde 
