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Ch.6 Carbohydrates Life's Sweet Molecules
Frost - General, Organic and Biological Chemistry 4th Edition
Frost4th EditionGeneral, Organic and Biological ChemistryISBN: 9780134988696Not the one you use?Change textbook
Chapter 3, Problem 29

The sugar alcohol ribitol is a component of the vitamin riboflavin and the energy transfer molecule FAD. Ribitol is formed when the monosaccharide ribose undergoes reduction at carbon 1. Draw the structure of ribitol.

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1
Understand the problem: Ribitol is formed by the reduction of d-ribose at carbon 1. Reduction involves the addition of hydrogen atoms to the aldehyde group at carbon 1, converting it into a primary alcohol group.
Examine the structure of d-ribose: d-Ribose is a monosaccharide with five carbon atoms. It contains an aldehyde group (-CHO) at carbon 1 and hydroxyl groups (-OH) attached to carbons 2, 3, 4, and 5.
Apply the reduction process: During reduction, the aldehyde group (-CHO) at carbon 1 is converted into a primary alcohol group (-CH₂OH). This involves the addition of hydrogen atoms to the carbon and oxygen in the aldehyde group.
Draw the structure of ribitol: After reduction, ribitol will have a chain of five carbon atoms, each bonded to a hydroxyl group (-OH). The carbon 1 will now have a primary alcohol group (-CH₂OH) instead of an aldehyde group.
Verify the structure: Ensure that the resulting structure has five carbons, each with a hydroxyl group (-OH), and that carbon 1 has been correctly reduced to a primary alcohol group (-CH₂OH). This structure represents ribitol.

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Key Concepts

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

Ribitol Structure

Ribitol is a sugar alcohol derived from ribose, specifically formed by the reduction of the aldehyde group at carbon 1 of ribose to a hydroxyl group. This structural change transforms ribose, a five-carbon sugar, into ribitol, which is characterized by its alcohol functional group. Understanding the structural formula of ribitol is essential for visualizing its role in biological molecules.
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Riboflavin and FAD

Riboflavin, also known as vitamin B2, is a vital nutrient that plays a crucial role in energy metabolism. It is a precursor to flavin adenine dinucleotide (FAD), a coenzyme involved in various biochemical reactions, including the Krebs cycle. Ribitol is a component of riboflavin, highlighting its importance in cellular energy transfer processes.
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Reduction Reaction

A reduction reaction involves the gain of electrons or hydrogen by a molecule, resulting in a decrease in oxidation state. In the case of ribitol formation, ribose undergoes reduction at its carbon 1, converting the aldehyde group into a hydroxyl group. This process is fundamental in organic chemistry and biochemistry, as it alters the properties and reactivity of the molecule.
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