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How many chiral centers are present in D-glucose? in D-ribose?

Short Answer

Expert verified
Answer: There are four chiral centers in D-glucose and three chiral centers in D-ribose.

Step by step solution

01

Understanding Chiral Centers

A chiral center (or stereocenter) is an atom within a molecule that has four different groups attached to it. The most common type of chiral center is a carbon atom bonded to four different groups. When a chiral center is present in a molecule, it can exist in two different configurations called enantiomers, which are mirror images of each other and cannot superimpose onto one another.
02

Identifying Chiral Centers in D-Glucose

D-glucose is an aldohexose sugar, which means it has six carbons and one of them is an aldehyde group. The structure of D-glucose is: H | HO-C | HO-C - H | HO-C - H | HO-C - H | CH2OH To determine the chiral centers in D-glucose, we should find the carbon atoms that have four different groups attached to them. D-glucose contains four such carbon atoms (C2, C3, C4, and C5), where each carbon is bonded to one hydroxyl group (OH), one hydrogen atom (H), and two other different carbon atoms. Therefore, there are four chiral centers in D-glucose.
03

Identifying Chiral Centers in D-Ribose

D-ribose is an aldopentose sugar, which means it has five carbons and one of them is an aldehyde group. The structure of D-ribose is: H | HO-C | HO-C - H | HO-C - H | CH2OH To determine the chiral centers in D-ribose, we should find the carbon atoms that have four different groups attached to them. D-ribose contains three such carbon atoms (C2, C3, and C4), where each carbon is bonded to one hydroxyl group (OH), one hydrogen atom (H), and two other different carbon atoms. Therefore, there are three chiral centers in D-ribose.

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Most popular questions from this chapter

Propose structural formulas for the following polysaccharides. (a) Alginic acid, isolated from seaweed, is used as a thickening agent in ice cream and other foods. Alginic acid is a polymer of D-mannuronic acid in the pyranose form joined by \(\beta-1,4\)-glycosidic bonds. (b) Pectic acid is the main component of pectin, which is responsible for the formation of jellies from fruits and berries. Pectic acid is a polymer of D-galacturonic acid in the pyranose form joined by \(\alpha-1,4\)-glycosidic bonds.

Hot water extracts of ground willow and poplar bark are an effective pain reliever. Unfortunately, the liquid is so bitter that most people refuse it. The pain reliever in these infusions is salicin, a \(\beta\)-glycoside of D-glucopyranose and the phenolic - OH group of 2-(hydroxymethyl)phenol. Draw a structural formula for salicin, showing the glucose ring as a chair conformation.

Are \(\alpha\)-D-glucose and \(\beta\)-D-glucose enantiomers? Explain.

Draw Fischer projections for the product(s) formed by reaction of D-galactose with the following. In addition, state whether each product is optically active or inactive. (a) \(\mathrm{NaBH}_{4}\) in \(\mathrm{H}_{2} \mathrm{O}\) (b) \(\mathrm{H}_{2} / \mathrm{Pt}\) (c) \(\mathrm{HNO}_{y}\) warm (d) \(\mathrm{Br}_{2} / \mathrm{H}_{2} \mathrm{O} / \mathrm{CaCO}_{3}\) (e) \(\mathrm{H}_{5} \mathrm{IO}_{6}\) (f) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}\)

Draw a chair conformation for the \(\alpha\) form of a disaccharide in which two units of D-glucopyranose are joined by a \(\beta-1,3\)-glycosidic bond.

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