Chapter 21: Problem 502
Indicating the mechanism, show how ethyl propionate may be prepared from propionic acid.
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Chapter 21: Problem 502
Indicating the mechanism, show how ethyl propionate may be prepared from propionic acid.
These are the key concepts you need to understand to accurately answer the question.
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A chemist possesses succinic anhydride and wants to make \(\beta\) -alanine ( \(\beta\) -aminopropionic acid). How should the synthesis be performed?
Compound 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.
Fumaric and maleic acid give the same anhydride on heating, but fumaric acid must be heated to much higher temperatures than maleic acid to effect the same change. Explain. Write reasonable mechanism for both reactions.
What are the carboxylic acid derivatives? Discuss their nomenclature. Give examples.
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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