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Give an IUPAC or common name for each compound. a. \(\left(\mathrm{CH}_{3} \mathrm{CH}_{2}\right)_{2} \mathrm{CHCOCl}\) b. \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COOCH}_{3}\) c. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CON}\left(\mathrm{CH}_{3}\right) \mathrm{CH}_{2} \mathrm{CH}_{3}\)

Draw the structure corresponding to each name. a. 5 -methylheptanoyl chloride e. 3-methylpentanenitrile b. isopropyl propanoate f. o-cyanobenzoic acid c. acetic formic anhydride g. sec-butyl 2-methylhexanoate d. \(N\) -isobutyl-N-methylbutanamide h. \(N\) -ethylhexanamide

Without reading ahead in Chapter 22, state whether it should be possible to carry out each of the following nucleophilic substitution reactions. a. \(\mathrm{CH}_{3} \mathrm{COCl}\) \(\mathrm{CH}_{3} \mathrm{COOH} \quad\) c. \(\mathrm{CH}_{3} \mathrm{COOCH}_{3} \longrightarrow \mathrm{CH}_{3} \mathrm{COCl}\) b. \(\mathrm{CH}_{3} \mathrm{CONHCH}_{3} \longrightarrow \mathrm{CH}_{3} \mathrm{COOCH}_{3}\)

Rank the compounds in each group in order of increasing reactivity in nucleophilic acyl substitution. a. \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COOCH}_{3}, \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COCl}, \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CONH}_{2}\) b. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOH},\left(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CO}\right)_{2} \mathrm{O}, \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CONHCH}_{3}\)

Explain why trichloroacetic anhydride \(\left[\left(\mathrm{Cl}_{3} \mathrm{CCO}\right)_{2} \mathrm{O}\right]\) is more reactive than acetic anhydride \(\left[\left(\mathrm{CH}_{3} \mathrm{CO}\right)_{2} \mathrm{O}\right]\) in nucleophilic acyl substitution reactions.

Draw the products formed when benzoyl chloride \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COCl}\right)\) is treated with each nucleophile: (a) \(\mathrm{H}_{2} \mathrm{O}\), pyridine; (b) \(\mathrm{CH}_{3} \mathrm{COO}^{-}\); (c) \(\mathrm{NH}_{3}\) (excess); (d) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\) (excess).

Draw the products formed when benzoic anhydride \(\left[\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CO}\right)_{2} \mathrm{O}\right]\) is treated with each nucleophile: (a) \(\mathrm{H}_{2} \mathrm{O}\), pyridine; (b) \(\mathrm{CH}_{3} \mathrm{OH} ;\) (c) \(\mathrm{NH}_{3}\) (excess); (d) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\) (excess).

Draw the products formed when benzoic acid \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COOH}\right)\) is treated with \(\mathrm{CH}_{3} \mathrm{OH}\) having its \(\mathrm{O}\) atom labeled with \({ }^{18} \mathrm{O}\left(\mathrm{CH}_{3}{ }^{18} \mathrm{OH}\right)\). Indicate where the labeled oxygen atom resides in the products.

What two monomers are needed to prepare nylon \(6,10 ?\)

Draw the structure of Kodel, a polyester formed from 1,4 -dihydroxymethylcyclohexane and terephthalic acid. Explain why fabrics made from Kodel are stiff and crease resistant.