Chapter 21: Problem 499
A chemist possesses succinic anhydride and wants to make \(\beta\) -alanine ( \(\beta\) -aminopropionic acid). How should the synthesis be performed?
Chapter 21: Problem 499
A chemist possesses succinic anhydride and wants to make \(\beta\) -alanine ( \(\beta\) -aminopropionic acid). How should the synthesis be performed?
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Get started for freeCompound A of molecular formula \(\mathrm{C}_{6} \mathrm{H}_{12} \mathrm{~N}_{2} \mathrm{O}_{2}\) reacts with aqueous nitrous acid to give compound \(B\) of formula \(\mathrm{C}_{6} \mathrm{H}_{10} \mathrm{O}_{4}\). Compound B readily loses water on heating to give \(\mathrm{C}, \mathrm{C}_{6} \mathrm{H}_{8} \mathrm{O}_{3}\). Compound A can also react with a solution of bromine and sodium hydroxide in water to give \(\mathrm{D}, \mathrm{C}_{4} \mathrm{H}_{12} \mathrm{~N}_{2}\), which on treatment with nitrous acid and perchloric acid gives methyl ethyl ketone. Write structures of all compounds and the equations involved.
A chemist added water and acid to an unknown ester of formula \(\mathrm{C}_{6} \mathrm{H}_{12} \mathrm{O}_{2}\) to produce an acid \(\mathrm{X}\) and an alcohol \(\mathrm{Y}\). Oxidation of \(\mathrm{Y}\) with chromic acid produced \(\mathrm{X}\). Determine the structure of the original ester. Write equations for all reactions that occur.
Indicating the mechanism, show how ethyl propionate may be prepared from propionic acid.
Methyl ethyl ketone can undergo Claisen condensation with a given ester, for example, ethyl benzoate, to yield either of two products, depending upon experimental conditions. What are these two products? How can one tell which product one has obtained?
a) (-) - Erythrose, \(\mathrm{C}_{4} \mathrm{H}_{8} \mathrm{O}_{4}\), gives tests with Tollens' reagent and Benedict's solution, and is oxidized by bromine water to an optically active acid, \(\mathrm{C}_{4} \mathrm{H}_{8} \mathrm{O}_{5}\). Treatment with acetic anhydride yields \(\mathrm{C}_{10} \mathrm{H}_{14} \mathrm{O}_{7}\). Erythrose consumes three moles of \(\mathrm{HlO}_{4}\), and yields three moles of formic acid and one mole of formaldehyde. Oxidation of erythrose by nitric acid yields an optically inactive compound of formula \(\mathrm{C}_{4} \mathrm{H}_{6} \mathrm{O}_{6}\) (-) - Threose, an isomer of erythrose, shows similar chemical behavior except that nitric acid oxidation yields an optically active compound of formula \(\mathrm{C}_{4} \mathrm{H}_{6} \mathrm{O}_{6}\). On the basis of this evidence what structure or structures are possible for (-) - erythrose? For (-) -threose? (b) When \(\mathrm{R}-\) glyceraldehyde, \(\mathrm{CH}_{2} \mathrm{OHCHOHCHO}\), is treated with cyanide and the resulting product is hydrolyzed, two monocarboxylic acids are formed. These acids are identical with the acids obtained by oxidation with bromine water of (-) - threose and (-) - erythrose. These acids are identical with the acids obtained by oxidation with bromine water of \((-)\) - threose and \((-)\) - erythrose. Assign a single structure to (-) -erythrose and to \((-)-\) threose.
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