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)

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

(g)

The following drugs are synthesized using the methods in this chapter and in previous chapters. Devise a synthesis for each, starting with any compounds containing no more than six carbon atoms.

(a) Phenacetin, used with aspirin and caffeine in pain-relief medications.

The following drugs are synthesized using the methods in this chapter and in previous chapters. Devise a synthesis for each, starting with any compounds containing no more than six carbon atoms.

(b) Methamphetamine, once considered a safe diet pill, but now known to be addictive and destructive to brain tissue.

The following drugs are synthesized using the methods in this chapter and in previous chapters. Devise a synthesis for each, starting with any compounds containing no more than six carbon atoms.

(c) Dopamine, one of the neurotransmitters in the brain. Parkinson’s disease is thought to result from a dopamine deficiency.

Synthesize Novocaine from benzene and any other reagents of four carbons or fewer.

Synthesize from benzene. (Hint: All of these require diazonium ions.)

(a) 3-ethylbenzoic acid

Synthesize from benzene. (Hint: All of these require diazonium ions.)

(c) 2-methyl-5-hydroxybenzoic acid

Synthesize from benzene. (Hint: All of these require diazonium ions.)

(d) 4-methoxyaniline

Propose mechanisms for the following reactions.

(a)