26. Amines

Predict the products of the following reactions.

(d)

Guanidine (shown) is about as strong a base as hydroxide ion. Explain why guanidine is a much stronger base than most other amines.

Explain why N,N,2,6-tetramethylaniline (shown) is a much stronger base than N,N-dimethylaniline.

Rank each set of compounds in order of increasing boiling points.

(a) triethylamine, di-n-propylamine, n-propyl ether

(b) ethanol, dimethylamine, dimethyl ether

(c) diethylamine, diisopropylamine, trimethylamine

In each pair of compounds, select the stronger base, and explain your choice.

(c)

(d)

Triethylenemelamine (TEM) is an antitumor agent. Its activity is due to its ability to cross-link DNA.

b. Explain why it can cross-link DNA.

Explain why the reaction of an alkyl halide with ammonia gives a low yield of primary amine.

Rank each set of compounds in order of increasing basicity.

(d) pyrrole, imidazole, 3-nitropyrrole

Predict the products of the following reactions.

(c)

Show how you would use direct alkylation to synthesize the following compounds.

(a) benzyltrimethylammonium iodide 

(b) pentan-1-amine 

(c) benzylamine