Show how you would convert the following starting materials to the indicated nitriles:
(b) phenylacetic acid → 3-phenylpropionitrile

Show how you would synthesize octan-2-one from each compound. You may use any necessary reagents.

(e) heptanoic acid

(A true story.) Chemistry lab students added an excess of ethylmagnesium bromide to methyl furoate, expecting the Grignard reagent to add twice and form the tertiary alcohol. After water workup, they found that the product was a mixture of two compounds. One was the expected product having two ethyl groups, but the unexpected product had added three ethyl groups. Propose a mechanism to explain the formation of the unexpected product.

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).

(e)

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).

(g)

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)