Using the Haworth projection, draw the furanose ring that would form between the C₅ hydroxyl group and the ketone at C₂ for the molecule shown.


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Verified step by step guidance

1. Identify the functional groups involved in the cyclization: the C₅ hydroxyl group and the ketone at C₂.
2. Recognize that the reaction involves the formation of a hemiacetal, where the hydroxyl group attacks the carbonyl carbon of the ketone.
3. Determine the stereochemistry of the resulting furanose ring by considering the orientation of substituents in the original linear form.
4. Draw the furanose ring using the Haworth projection, ensuring that the anomeric carbon (C₂) is correctly positioned and the substituents are oriented based on their stereochemistry.
5. Label the carbons in the furanose ring to ensure clarity and accuracy in the representation.

Key Concepts

Haworth Projection

The Haworth projection is a way of representing cyclic sugars in a two-dimensional format that illustrates the cyclic structure of monosaccharides. It shows the orientation of the hydroxyl groups and other substituents around the ring, making it easier to visualize the three-dimensional conformation of the molecule. This representation is crucial for understanding how sugars interact and form glycosidic bonds.

Furanose Ring Structure

A furanose ring is a five-membered cyclic structure formed from a monosaccharide, typically involving four carbon atoms and one oxygen atom. In the context of sugars, the furanose form is often derived from a ketose sugar, where the hydroxyl group on the C₅ carbon reacts with the carbonyl group at C₂, leading to the formation of a stable ring structure. Understanding this formation is essential for predicting the behavior of sugars in biochemical processes.

Ketone and Hydroxyl Group Reactivity

The reactivity of ketones and hydroxyl groups is fundamental in organic chemistry, particularly in carbohydrate chemistry. Ketones contain a carbonyl group (C=O) that can react with alcohols (like hydroxyl groups) to form hemiacetals or acetals. In the case of sugar cyclization, the reaction between the ketone at C₂ and the hydroxyl group at C₅ leads to the formation of the furanose ring, which is a key step in sugar chemistry.