Within each structure, rank the indicated nitrogens by increasing basicity.

(d)

(e)

Within each structure, rank the indicated nitrogens by increasing basicity.

(f)

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

(a) HOCH₂CH₂NH₂ or CH₃CH₂NH₂

(b) PhNH₂ or PhCH₂NH₂

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

(c)

(d)

Which of the following compounds are capable of being resolved into enantiomers?

(a) N-ethyl-N-methylaniline

(b) 2-methylpiperidine

(c) 1-methylpiperidine

Which of the following compounds are capable of being resolved into enantiomers?

(d) 1,2,2-trimethylaziridine

(e)

(f)

Which of the following compounds are capable of being resolved into enantiomers?

(g)

(h)

Complete the following proposed acid–base reactions, and predict whether the reactants or products are favored.

(a)

(b)

Predict the products of the following reactions:

(a) excess NH₃ + Ph–CH₂CH₂CH₂Br →

Predict the products of the following reactions:

(c)

(d)

Predict the products of the following reactions:

(e)

(f)

Predict the products of the following reactions:

(g)

Predict the products of the following reactions:

(i)

Predict the products of the following reactions:

(k)

Predict the products of the following reactions:

(c)

Predict the products of the following reactions:

(d)

Predict the products of the following reactions:

(g)

Predict the products of the following reactions:

(h)

Predict the products of the following reactions:

(i)

Predict the products of the following reactions:

(j)

Show how m-toluidine can be converted to the following compounds, using any necessary reagents.

(a)

Show how m-toluidine can be converted to the following compounds, using any necessary reagents.

(b)

Show how m-toluidine can be converted to the following compounds, using any necessary reagents.

(e)

Show how m-toluidine can be converted to the following compounds, using any necessary reagents.

(f)

The mass spectrum of tert-butylamine follows shows an intense base peak at m/z 58, and very little else. Use a diagram to show the cleavage that accounts for the base peak. Suggest why no molecular ion is visible in this spectrum.

Using any necessary reagents, show how you would accomplish the following syntheses.

(a)

Using any necessary reagents, show how you would accomplish the following syntheses.

(b)

Using any necessary reagents, show how you would accomplish the following syntheses.

(c)

Using any necessary reagents, show how you would accomplish the following syntheses.

(d)

Using any necessary reagents, show how you would accomplish the following syntheses.

(e)

(f)