Question: Emil Fischers determination of the structure of glucose was carried out as the nineteenth century ended and the twentieth began. The structure of no other

Emil Fischer’s determination of the structure of glucose was carried out as the nineteenth century ended and the twentieth began. The structure of no other sugar was known at that time, and none of the spectroscopic techniques that aid organic analysis were then available. All Fischer had was information from chemical transformations, polarimetry, and his own intellect. Fischer realized that (+)-glucose could be represented by 16 possible stereostructures. By arbitrarily assigning a particular configuration to the stereogenic center at C-5, the configurations of C-2, C-3, and C-4 could be determined relative to it. This reduces the number of structural possibilities to eight. Thus, he started with a structural representation shown as follows, in which C-5 of (+)-glucose has what is now known as the D configuration.

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Consider all the individual pieces of information in the order in which they are presented 1 Chain extension of the aldopentose arabinose by way of the derived cyanohydrin gave a mixture of glucose an... View full answer

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