How to Assign R,S designations to  stereogenic center in glucose ?

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
icon
Related questions
icon
Concept explainers
Question

How to Assign R,S designations to  stereogenic center in glucose ? 

Expert Solution
Step 1

Glucose is a monosaccharide, having formula C6H1206. It is an important simple sugar that circulates in the blood of living beings as blood sugar Glucose, having 6 carbon atoms and an aldehyde group, is an aldo-hexose.

The structure of D-glucose can be written as

Chemistry homework question answer, step 1, image 1

To assign give R, S designations to each stereogenic centre in glucose, follow the given steps

To find the R or S configuration of stereocenters present in D-glucose, priority order needs to be assigned to the compound by using the following CIP (Cahn-Ingold-Prelog) sequence rules

Chirality center: An atom (usually carbon) which is bonded to four different atoms or groups is known as chiral center.

Rule 1: Select the chiral center in the compound and assign priorities to the atoms based on their atomic number. The atom which has highest atomic number gets the first priority and atom which is having least atomic number (usually hydrogen) gets the fourth priority.

Rule 2: If the first atom of each substituent is same then the next atom is considered for assigning the priority This process is continued to the third and fourth atom until the point of difference is reached

Rule 3: If the substituents have multiple bonds, the multiple bonded atoms are considered as same number of single bonded atoms

If the priority order of the substituents from highest to second highest to third highest 1-->2--> 3 is in clock wise direction then the chiral center has R configuration (Latin rectus means right).

If the priority order of the substituents from highest to second highest to third highest 1--> 2--> 3 is counter clock wise direction then the chiral center has S configuration (Latin sinister means left).

If the least priority substituent (usually hydrogen) is present on the horizontal line then its configuration is reversed (that is clockwise becomes S and anticlockwise R).

steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
Knowledge Booster
Carbohydrates
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY