20 Questions
What type of acids are formed when dicarboxylic/saccharic acids are oxidized?
Aldaric acids
What is the product of the enzymatic oxidation of the primary alcohol end of an aldose?
Alduronic acid
What is the functional group present at the end of an aldose molecule?
Aldehyde group
What is the result of the strong oxidizing agent on a monosaccharide?
Formation of an aldaric acid
What is the type of reaction involved in the conversion of a monosaccharide into an alduronic acid?
Oxidation reaction
What is the name of the product formed when D-Glucose is oxidized with a strong oxidizing agent?
D-Glucaric acid
What is the result of oxidizing glucose?
Gluconic acid
What is the outcome of oxidizing an aldose with a strong oxidizing agent?
A dicarboxylic acid
Which type of sugars can act as reducing agents in oxidation reactions?
Reducing sugars
What is required for the oxidation of ketoses to produce acidic sugars?
A structural rearrangement
What is the reactant that undergoes oxidation to produce an aldonic acid?
A prima alcohol
What is the outcome of reducing an aldonic acid?
A prima alcohol
What type of oxidizing agents can oxidize the aldehyde group of an aldose?
Mild oxidizing agents
What is the common characteristic of all monosaccharides?
They are all reducing sugars
What is the product of reducing a carbonyl group in a monosaccharide using hydrogen as the reducing agent?
A polyhydroxy alcohol
What is the name of the sugar alcohol formed when D-Glucose is reduced?
Sorbitol
What type of reaction occurs when the anomeric hydroxyl group of a monosaccharide undergoes condensation with the hydroxyl group of a second molecule?
Glycosidation
What is the purpose of sorbitol in gum?
To act as a sweetening agent
What is the outcome of the reaction between glucose and methanol in the presence of an acid catalyst?
Formation of a mixture of α- and β-methyl glucopyranosides
What is the role of the hydroxyl group in glycoside formation?
It undergoes condensation with the hydroxyl group of a second molecule
Study Notes
Oxidation to Produce Acidic Sugars
- Aldehyde group is easily oxidized by mild oxidizing agents like Benedict's and Tollens solution.
- Oxidation of prima alcohol produces an aldonic acid.
- Oxidation of glucose produces gluconic acid.
- Reducing sugars are sugars that act as reducing agents in this reaction.
- All monosaccharides are reducing sugars.
- Ketoses are also reducing sugars and undergo a structural rearrangement to produce an aldose.
- Strong oxidizing agents can oxidize both prima alcohol and aldehyde groups to produce a dicarboxylic acid, also known as an aldaric acid.
Enzymatic Oxidation
- Enzymes can oxidize the prima alcohol end of an aldose without oxidizing the aldehyde group to produce an alduronic acid.
Reduction to Produce Sugar Alcohols
- The carbonyl group can be reduced to a hydroxyl group using hydrogen as the reducing agent.
- The product is the corresponding polyhydroxy alcohol or sugar alcohol.
- D-Glucitol, also known as sorbitol, is a sugar alcohol produced by the reduction of glucose.
- Sugar alcohols have an affinity for water, making them useful as moisturizing agents in food and cosmetics.
- Sugar alcohols are also used as sweetening agents in gum, as bacteria cannot use them as a food source.
Glycoside Formation
- Glycosides are formed when the anomeric hydroxyl group of a monosaccharide undergoes condensation with the hydroxyl group of a second molecule, with the elimination of water.
- The linkage resulting from such a reaction is known as a glycosidic bond.
- When glucose reacts with methanol, a mixture of α- and β-methyl glucopyranosides is obtained.
This quiz covers the oxidation of sugars, specifically the formation of acidic sugars through the oxidation of aldehyde groups using mild oxidizing agents. Topics include the conversion of glucose to gluconic acid and the role of reducing sugars.
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