Chapter 18: Problem 1
Draw a structural formula for each compound. (a) \(N\)-Cyclohexylacetamide (b) 1-Methylpropyl methanoate (c) Cyclobutyl butanoate (d) \(N\)-(1-Methylheptyl) succinimide (e) Diethyl adipate (f) 2-Aminopropanamide
Chapter 18: Problem 1
Draw a structural formula for each compound. (a) \(N\)-Cyclohexylacetamide (b) 1-Methylpropyl methanoate (c) Cyclobutyl butanoate (d) \(N\)-(1-Methylheptyl) succinimide (e) Diethyl adipate (f) 2-Aminopropanamide
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Get started for freeBarbiturates are prepared by treating a derivative of diethyl malonate with urea in the presence of sodium ethoxide as a catalyst. Following is an equation for the preparation of barbital, a long-duration hypnotic and sedative, from diethyl diethylmalonate and urea. Barbital is prescribed under one of a dozen or more trade names. (a) Propose a mechanism for this reaction. (b) The \(\mathrm{p} K_{\mathrm{a}}\) of barbital is 7.4. Which is the most acidic hydrogen in this molecule? How do you account for its acidity?
Show how to synthesize 5-nonanone from 1-bromobutane as the only organic starting material.
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. Show how this synthesis might be accomplished and explain how your proposed synthesis is stereoselective for the 10 -trans-12-cis isomer.
Draw a structural formula of the principal product formed when ethyl benzoate is treated with each reagent. (a) \(\mathrm{H}_{2} \mathrm{O}, \mathrm{NaOH}\), heat (b) \(\mathrm{H}_{2} \mathrm{O}, \mathrm{H}_{2} \mathrm{SO}_{4}\), heat (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}\) (d) DIBALH \(\left(-78^{\circ} \mathrm{C}\right)\), then \(\mathrm{H}_{2} \mathrm{O}\) (e) \(\mathrm{LiAlH}_{4}\), then \(\mathrm{H}_{2} \mathrm{O}\) (f) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{MgBr}\) (two equivalents), then \(\mathrm{HCl} / \mathrm{H}_{2} \mathrm{O}\)
Treating choline with acetic anhydride gives acetylcholine, a neurotransmitter. Write an equation for the formation of acetylcholine. $$ \left(\mathrm{CH}_{3}\right)_{3} \mathrm{NCH}_{2} \mathrm{CH}_{2} \mathrm{OH} $$ Choline
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