Chapter 18: Problem 29
Treating choline with acetic anhydride gives acetylcholine, a neurotransmitter. Write an equation for the formation of acetylcholine.
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Draw a structural formula for the principal product formed when benzamide is treated with cach reagent. (a) \(\mathrm{H}_{2} \mathrm{O}, \mathrm{HCl}\), heat (b) \(\mathrm{NaOH}, \mathrm{H}_{2} \mathrm{O}\), heat (c) \(\mathrm{LiAlH}_{4}\), then \(\mathrm{H}_{2} \mathrm{O}\)
Following is an outline of a synthesis of bombykol, the sex attractant of the male silkworm moth. Of the four stereoisomers possible for this conjugated diene, the 10 -trans12-cis isomer shown here is over \(10^{6}\) times more potent as a sex attractant than any of the other three possible stereoisomers.
We have seen two methods for converting a carboxylic acid and an amine into an amide. Suppose that you start instead with a dicarboxylic acid such as hexanedioic acid and a diamine such as 1,6 -hexanediamine. Show how amide formation in this case can lead to a polymer (a macromolecule of molecular weight several thousands times that of the starting materials). As we shall see in Section 29.5A, the material produced in this reaction is the highmolecular-weight polymer nylon 66 , so named because it is synthesized from two 6 -carbon starting materials.
Draw a structural formula of the principal product formed when benzonitrile is treated with each reagent. (a) \(\mathrm{H}_{2} \mathrm{O}\) (one equivalent), \(\mathrm{H}_{2} \mathrm{SO}_{4}\), heat (b) \(\mathrm{H}_{2} \mathrm{O}\) (excess), \(\mathrm{H}_{2} \mathrm{SO}_{4}\), heat (c) \(\mathrm{NaOH}, \mathrm{H}_{2} \mathrm{O}\), heat (d) \(\mathrm{LiAlH}_{4}\), then \(\mathrm{H}_{2} \mathrm{O}\)
Reaction of a primary or secondary amine with diethyl carbonate under controlled conditions gives a carbamic ester. Propose a mechanism for this reaction.
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