Skip to main content
Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
All textbooksMullins 1st EditionCh. 27 - Carbohydrates, Nucleic Acids, and LipidsProblem 69
Chapter 26, Problem 69

Upon dissolving α-D-glucose or β-D-glucose in water, the specific rotation gradually changes, eventually reaching +52.6° for both solutions. Explain what is happening here.

Verified step by step guidance
1
Understand the concept of mutarotation: Mutarotation is the change in the optical rotation of a solution due to the interconversion between different anomers of a sugar (α and β forms) in aqueous solution. This occurs because the sugar exists in equilibrium between its cyclic and open-chain forms.
Recognize the structure of α-d-glucose and β-d-glucose: Both are cyclic forms of glucose, differing in the orientation of the hydroxyl group (-OH) on the anomeric carbon (C1). In α-d-glucose, the -OH group is on the opposite side of the ring relative to the CH2OH group, while in β-d-glucose, the -OH group is on the same side as the CH2OH group.
Describe the equilibrium process: When α-d-glucose or β-d-glucose is dissolved in water, the cyclic forms open up to form the linear chain structure. The linear chain then closes back into cyclic forms, allowing interconversion between the α and β anomers. This process establishes an equilibrium mixture of α-d-glucose, β-d-glucose, and a small amount of the open-chain form.
Explain the change in specific rotation: The specific rotation of a solution depends on the proportions of the α and β anomers present. Initially, the specific rotation reflects the predominant form (α or β) in the solution. As equilibrium is reached, the specific rotation stabilizes at +52.6°, which corresponds to the equilibrium mixture of α-d-glucose and β-d-glucose in water.
Conclude with the significance of the equilibrium: The final specific rotation of +52.6° is a characteristic property of the equilibrium mixture of α-d-glucose and β-d-glucose in water. This demonstrates the dynamic nature of mutarotation and the ability of glucose to interconvert between its anomeric forms in aqueous solution.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above.
Was this helpful?

Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Anomeric Effect

The anomeric effect refers to the preference of certain anomers (α and β forms of sugars) to adopt specific conformations in solution. In the case of glucose, the α and β anomers can interconvert in water, leading to a mixture of both forms. This phenomenon affects the optical rotation of the solution as the equilibrium shifts between the two anomers.
Recommended video:
2:02
Directing Effects in Substituted Pyrroles, Furans, and Thiophenes Concept 1

Optical Activity

Optical activity is the ability of a substance to rotate the plane of polarized light. This property is significant in carbohydrates like glucose, where the specific rotation is a measure of how much the light is rotated by a solution of the sugar. The specific rotation can change as the concentration of different anomers in solution varies, reflecting the dynamic equilibrium between them.
Recommended video:
Guided course
08:17
Mutorotation and Optical Activity

Mutarotation

Mutarotation is the process by which the optical rotation of a sugar solution changes over time as the anomers interconvert. For glucose, this involves the conversion between α-d-glucose and β-d-glucose in water, leading to a gradual change in specific rotation until it stabilizes at a constant value. This process is crucial for understanding the behavior of sugars in solution.
Recommended video:
Guided course
03:06
Mechanism
Related Practice
Textbook Question

Starting with a Fischer projection of d-glucose (and other sugars), switch only the stereocenter that gave it the designation of d. What new sugar have you made? [Hint: The answer is not l-glucose.]

Textbook Question

Suggest a mechanism by which TXB2 might be formed from TXA2 in an acid-catalyzed hydrolysis reaction. [The structure has been simplified.]

6
views
Textbook Question

(a) Suggest an arrow-pushing mechanism for the mutarotation of α-d-glucose to β-d-glucose in the presence of acid. Acid isn’t necessary, but it does increase the rate of the process.

(b) What is the role of acid in your mechanism?

4
views
Textbook Question

The α- and β-anomers of glucose are shown here.

In solution, these two epimers can interconvert through a process called mutarotation. What is the ratio of anomers (α:β) when the specific rotation is +52.6°

1
views
Textbook Question

The α- and β-anomers of glucose are shown here. In solution, these two epimers can interconvert through a process called mutarotation.

Given that α-D-glucose has a specific rotation of + 112.2° , why is the specific rotation of β-D-glucose not -112.2°? What molecule would have a specific rotation of -112.2°?

1
views
Textbook Question

Is the compound d or l?

1
views