Chapter 32: Problem 730
Suggest a way to separate a mixture of amino acids into three fractions: monoamino monocarboxylic acids, monoamino dicarboxylic acids (the acidic amino acids), and diamino monocarboxylic acids (the basic amino acids).
Chapter 32: Problem 730
Suggest a way to separate a mixture of amino acids into three fractions: monoamino monocarboxylic acids, monoamino dicarboxylic acids (the acidic amino acids), and diamino monocarboxylic acids (the basic amino acids).
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Give formulas for compounds \(\mathrm{A}-\mathrm{G}\), and tell what is happening in each reaction. polystyrene \(+\mathrm{CH}_{3} \mathrm{OCH}_{2} \mathrm{Cl}(\mathrm{SnCl} 4) \rightarrow \mathrm{A}+\mathrm{CH}_{3} \mathrm{OH}\) \(\mathrm{A}+\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{OCONHCH}_{2} \mathrm{COO}^{-+} \mathrm{NHEt}_{3} \rightarrow \mathrm{B}+\mathrm{Et}_{3} \mathrm{NHCl}\) \(\mathrm{B}+\) dil. \(\mathrm{HBr} \rightarrow \mathrm{C}+\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{Br}+\mathrm{CO}_{2}\) \(\mathrm{C}+\) carbobenzoxyalanylchloride \(\rightarrow \mathrm{D}\) \(\mathrm{D}+\) dil \(\mathrm{HBr} \rightarrow \mathrm{E}+\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{Br}+\mathrm{CO}_{2}\) \(\mathrm{E}+\mathrm{HBr}\left(\mathrm{CF}_{3} \mathrm{COOH}\right)^{\rightarrow} \mathrm{F}\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{Br}\right)^{\rightarrow}+\mathrm{G}\)
A pentapeptide on complete hydrolysis yields 3 moles of glycine, 1 mole of alanine, and 1 mole of phenylalanine. Among the products of partial hydrolysis are found \(\mathrm{H} \cdot \mathrm{Ala} \cdot \mathrm{Gly} \cdot \mathrm{OH}\) and \(\mathrm{H} \cdot \mathrm{Gly} \cdot \mathrm{Ala} \cdot \mathrm{OH}\). What structures are possible for this substance on the basis of its giving no nitrogen in the Van Slyke determination?
Many years before the Hofmann degradation of optically active a-phenylpropionamide was studied, the following observations were made: when the cyclopentane derivative, \(\mathrm{I}\), in which the \(-\mathrm{COOH}\) and \(-\mathrm{CONH}_{2}\) groups are cis to each other, was treated with hypobromite, compound II was obtained; compound II could be converted by heat into the amide III (called a lactam). What do these results show about the mechanism of the rearrangement? (Use models.)
Write a mechanism for the reaction of glycine with N- carboethoxyphthalimide involving a sequence of carbony1 addition, ring opening, ring closure and elimination. Would you expect a similar reaction with L-phenylalanine to yield the \(L\), the \(D\), or the D,L-product?
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