CH,OH HO НО OH ОН Glucose (а) (b)

Chemistry for Today: General, Organic, and Biochemistry
9th Edition
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Chapter15: Carboxylic Acids And Esters
Section: Chapter Questions
Problem 15.53E: Complete the following reactions: a. b.
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On the left is a stereorepresentation of glucose

Q.Convert the stereorepresentation on the left to a chair conformation. Which substituent groups in the chair conformation are equatorial? Which are axial?

CH,OH
HO
НО
OH
ОН
Glucose
(а)
(b)
Transcribed Image Text:CH,OH HO НО OH ОН Glucose (а) (b)
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Concept introduction:

In the chair conformation, all C-C-C bond angles are 110.9o and the hydrogens on the adjacent carbon atoms are staggered with respect to one another. In the chair conformation, no two atoms are closely present, so, there is a little strain present in chair conformation structure of cyclohexane. The C-H bonds in the chair conformation are arranged in axial and equatorial positions. The bond that are present parallel to the axis are axial bonds and the bonds that are present perpendicular to the axis are equatorial bonds. In cyclohexane, six hydrogens are axial and six hydrogens are equatorial.

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