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This problem is based upon the ideas used in the classic Fisher glucose proof.
Suppose you had four unknown D-aldohexoses, compounds A, B, C and D. The following reactions were run to identify compounds.
a. The Ruff degradation of a aldohexose removes the C-2 carbon and yields an aldopentose. The Ruff degradation of A and B gave the same pentose W. NaBH4 reduction of pentose W gave an achiral alditol X.
b. The Ruff degradation of C and D gave the same pentose Y. NaBH4 reduction of pentose Y also gave an achiral alditol Z.
c. NaBH4 reduction of C gave an achiral alditol, T.
d. Fisher developed a method for interchanging the ends of an aldohexose. Applying this procedure to aldohexose A gave back the same compound A.
Identify the four compounds A, B, C and D. On the answer form fill in the blanks using the numbers given under the structure names in the figure at the top of this page.
Suppose you had four unknown D-aldohexoses, compounds A, B, C and D. The following reactions were run to identify compounds.
a. The Ruff degradation of a aldohexose removes the C-2 carbon and yields an aldopentose. The Ruff degradation of A and B gave the same pentose W. NaBH4 reduction of pentose W gave an achiral alditol X.
b. The Ruff degradation of C and D gave the same pentose Y. NaBH4 reduction of pentose Y also gave an achiral alditol Z.
c. NaBH4 reduction of C gave an achiral alditol, T.
d. Fisher developed a method for interchanging the ends of an aldohexose. Applying this procedure to aldohexose A gave back the same compound A.
Identify the four compounds A, B, C and D. On the answer form fill in the blanks using the numbers given under the structure names in the figure at the top of this page.