Chapter 18: Problem 1
Draw a structural formula for each compound. (a) \(\mathrm{N}\)-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) \(\mathrm{N}\)-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 freeUsing your reaction roadmap as a guide, show how to convert 1-bromopropane and carbon dioxide into 4-heptanone. You must use 1-bromopropane and carbon dioxide as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way.
Barbiturates 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?
The following compound is one of a group of \(\beta\)-chloroamines, many of which have antitumor activity. Describe a synthesis of this compound from anthranilic acid and ethylene oxide.
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.
Synthesis of nitriles by nucleophilic displacement of halide from a haloalkane (also called an alkyl halide) is practical only with primary and secondary haloalkanes. It fails with tertiary haloalkanes. Why? What is the major product of the following reaction?
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