22. Carboxylic Acid Derivatives: NAS

The structures of four useful polymers are shown, together with some of their best-known products. In each case,

(i) determine the kind of polymer (polyamide, polyester, etc.).

(c) <IMAGE>

(d) <IMAGE>

Which of the following are considered carboxylic acid derivatives?

(a) <IMAGE>

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) <IMAGE>

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) <IMAGE>

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) <IMAGE>

Predict the products (if any) of the following acid–base reactions.

(a) acetic acid + ammonia

(b) phthalic acid + excess NaOH

(c) p-toluic acid + potassium trifluoroacetate

Arrange each group of compounds in order of increasing acidity.

(a) phenol, ethanol, acetic acid

(b) p-toluenesulfonic acid, acetic acid, chloroacetic acid

(c) benzoic acid, o-nitrobenzoic acid, m-nitrobenzoic acid

(d) butyric acid, a-bromobutyric acid, b-bromobutyric acid

(e) <IMAGE>

The structures of four useful polymers are shown, together with some of their best-known products. In each case,

(i) determine the kind of polymer (polyamide, polyester, etc.).

(ii) draw the structures of the monomers that would be released by complete hydrolysis.

(iii) suggest what monomers or stable derivatives of the monomers might be used to make these polymers.

(a) <IMAGE>

The structures of four useful polymers are shown, together with some of their best-known products. In each case,

(i) determine the kind of polymer (polyamide, polyester, etc.).

(ii) draw the structures of the monomers that would be released by complete hydrolysis.

(iii) suggest what monomers or stable derivatives of the monomers might be used to make these polymers.

(b) <IMAGE>

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.

<IMAGE of reactions>

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

(e) <IMAGE>

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

(g) <IMAGE>

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) <IMAGE>

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

(b) <IMAGE>

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

(h) <IMAGE>

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

(c) <IMAGE>

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

(d) <IMAGE>