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Magazine Chapter 20: Q69P (page 985)
Predict whether d-altrose exists preferentially as a pyranose or a furanose.
Short Answer
D-altrose exists preferentially as a furanose.
Step by step solution
Pyranose and furanose
A pyranose constitutes a six-memebered ring comprising of one oxygen and five carbon atoms. A furanose is a five-membered ring comprising of one oxygen and four carbon atoms.
Predicting whether d-altrose exists preferentially as a pyranose or a furanose
An altrose exists in two forms鈥攑yranose and furanose. Pyranose and furanose are six-membered and five-membered rings respectively.
The compound becomes a stable compound if the adjacent substituents are trans to each other as this arrangement does not cause steric hinderance. D-altrose exists in furanose form as the substituents are in trans position in this form.
The structures of furanose and pyranose form are shown below.
Furanose and pyranose form of D-altrose
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