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Ch. 20 - The Organic Chemistry of Carbohydrates
Bruice - Organic Chemistry 8th Edition
Bruice8th EditionOrganic ChemistryISBN: 9780135213711당신이 사용하는 게 아니라요?교과서 변경
20장, 문제 28c

Name the following compounds and indicate whether or not each is a reducing sugar:
c.

검증된 단계별 안내
1
Step 1: Analyze the structure of the compound. The image shows a five-membered ring with an oxygen atom incorporated into the ring, indicating that this is a furanose form of a sugar. Additionally, there are hydroxyl (-OH) groups and an ethyl group (-CH2CH3) attached to the ring.
Step 2: Identify the functional groups and substituents. The compound has a hydroxymethyl group (-CH2OH) attached to the ring, hydroxyl groups (-OH) on the ring, and an ethoxy group (-OCH2CH3) attached to the ring. These features suggest that the compound is a derivative of a sugar.
Step 3: Determine if the compound is a reducing sugar. Reducing sugars are characterized by the presence of a free anomeric carbon (a carbon attached to the oxygen in the ring and also to a hydroxyl group). In this structure, the anomeric carbon is bonded to an ethoxy group (-OCH2CH3), which means it is not free and cannot act as a reducing agent.
Step 4: Name the compound systematically. The base sugar is likely derived from ribose (a five-carbon sugar), but the ethoxy group substitution modifies the name. The compound can be named as ethyl β-D-ribofuranoside, where 'ethyl' indicates the ethoxy group and 'ribofuranoside' indicates the sugar derivative in the furanose form.
Step 5: Conclude the analysis. The compound is named ethyl β-D-ribofuranoside, and it is not a reducing sugar because the anomeric carbon is not free due to the ethoxy group substitution.

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주요 개념

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Reducing Sugars

Reducing sugars are carbohydrates that can donate electrons to other molecules, typically due to the presence of a free aldehyde or ketone group. This property allows them to reduce certain chemical reagents, such as Benedict's or Fehling's solution, which is a key characteristic in identifying them. Common examples include glucose and fructose, which can participate in redox reactions.
추천 영상:
08:42
Reducing Sugars

Structural Representation of Sugars

Understanding the structural representation of sugars is crucial for identifying their functional groups. Sugars can exist in linear or cyclic forms, and their structure determines their reactivity. Recognizing whether a sugar has a free aldehyde or ketone group in its structure is essential for determining if it is a reducing sugar.
추천 영상:
02:21
Reducing Sugars

Nomenclature of Organic Compounds

Nomenclature refers to the systematic naming of organic compounds based on established rules, such as those set by IUPAC. For sugars, this includes identifying the number of carbon atoms, the type of functional groups, and the stereochemistry. Proper nomenclature is vital for clear communication in organic chemistry and helps in understanding the properties and classifications of compounds.
추천 영상:
01:40
Defining meso compounds.