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

(c) p-chloronitrobenzene → p-chlorobenzonitrile

Show how each transformation may be accomplished by using a nitrile as an intermediate. You may use any necessary reagents.

(a) hexan-1-ol → heptan-1-amine

Show how each transformation may be accomplished by using a nitrile as an intermediate. You may use any necessary reagents.

(b) cyclohexanecarboxamide → cyclohexyl ethyl ketone

Show how each transformation may be accomplished by using a nitrile as an intermediate. You may use any necessary reagents.

(c) octan-1-ol → decan-2-one

Propose a mechanism for the reaction of methyl isocyanate with 1-naphthol to give Sevin® insecticide.

For each heterocyclic compound,

(ii) show what compounds would result from complete hydrolysis.

(a)

(b)

(c)

For each heterocyclic compound,

(iii) are any of the rings aromatic? Explain.

(a)

(b)

(c)

For each heterocyclic compound,

(i) explain what type of acid derivative is present.

(a)

(b)

(c)

For each heterocyclic compound,

(i) explain what type of acid derivative is present.

(ii) show what compounds would result from complete hydrolysis.

(iii) are any of the rings aromatic? Explain.

(d)

For each heterocyclic compound,

(i) explain what type of acid derivative is present.

(ii) show what compounds would result from complete hydrolysis.

(iii) are any of the rings aromatic? Explain.

(e)

For each heterocyclic compound,

(i) explain what type of acid derivative is present.

(ii) show what compounds would result from complete hydrolysis.

(iii) are any of the rings aromatic? Explain.

(f)

Draw structures to correspond with the following common and systematic names:

(a) phenyl formate 

(b) cyclohexyl benzoate 

(c) cyclopentyl phenylacetate

Draw structures to correspond with the following common and systematic names:

(d) N-butylacetamide

(e) N,N-dimethylformamide

Draw structures to correspond with the following common and systematic names:

(f) benzoic propionic anhydride

(g) benzamide

Draw structures to correspond with the following common and systematic names:

(h) γ-hydroxyvaleronitrile

Draw structures to correspond with the following common and systematic names:

(k) phenyl isocyanate

(l) cyclobutyl ethyl carbonate

Draw structures to correspond with the following common and systematic names:

(m) δ-caprolactam

Draw structures to correspond with the following common and systematic names:

(n) trichloroacetic anhydride

(o) ethyl N-methyl carbamate

Give appropriate names for the following compounds:

(a)

(b)

Give appropriate names for the following compounds:

(c)

(d)

Give appropriate names for the following compounds:

(e)

(f)

Give appropriate names for the following compounds:

(g)

(h)

Give appropriate names for the following compounds:

(i)

(j)

Give appropriate names for the following compounds:

(k)

(l)

Predict the major products formed when benzoyl chloride (PhCOCl) reacts with the following reagents.

(a) ethanol

(b) sodium acetate

(c) aniline

Predict the major products formed when benzoyl chloride (PhCOCl) reacts with the following reagents.

(d) anisole and aluminum chloride

(e) excess phenylmagnesium bromide, then dilute acid

(f) LiAlH(O-t-Bu)₃

Predict the products of the following reactions.

(a) phenol + acetic anhydride

(b) phenol + acetic formic anhydride

(c) aniline + phthalic anhydride

Predict the products of the following reactions.

(d) anisole + succinic anhydride and aluminum chloride

Predict the products of the following reactions.

(e)

(f)

Acid-catalyzed transesterification and Fischer esterification take place by nearly identical mechanisms. Transesterification can also take place by a base-catalyzed mechanism, but all attempts at base-catalyzed Fischer esterification (using –OR″, for example) seem doomed to failure. Explain why Fischer esterification cannot be catalyzed by base.