22. Carboxylic Acid Derivatives: NAS

Show how you would convert the following starting materials to the indicated nitriles:

(b) phenylacetic acid → 3-phenylpropionitrile

Show how you would convert the following starting materials to the indicated nitriles:

(c) p-chloronitrobenzene → p-chlorobenzonitrile

Show how you would accomplish the following syntheses in good yields.

(a)

Show how you would accomplish the following syntheses in good yields.

(b)

Show how you would accomplish the following syntheses in good yields.

(h)

Show how you would accomplish the following multistep syntheses, using the indicated starting material and any necessary reagents.

(c)

Show how you would accomplish the following multistep syntheses, using the indicated starting material and any necessary reagents.

(d)

Peroxyacetic acid (bp = 105 °C) has a lower boiling point than acetic acid (bp = 118 °C), even though peroxyacetic acid has a higher molecular weight. Explain why peroxyacetic acid is more volatile than acetic acid.