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Ch.13 Carbohydrates
Timberlake - Chemistry: An Introduction to General, Organic, and Biological Chemistry 14th Edition
Timberlake14th EditionChemistry: An Introduction to General, Organic, and Biological ChemistryISBN: 9781292472249당신이 사용하는 게 아니라요?교과서 변경
모든 교과서Timberlake 14th EditionCh.13 Carbohydrates문제 69b
13장, 문제 69b

The sugar d-gulose is a sweet-tasting syrup.
Haworth structure of d-gulose, a sweet syrup, showing its cyclic monosaccharide form.
b. Draw the Haworth structures for α− and β-D-gulose.

검증된 단계별 안내
1
Understand that d-gulose is a monosaccharide, specifically an aldohexose, meaning it contains six carbon atoms and an aldehyde functional group. The Haworth structure represents the cyclic form of the sugar, which forms when the aldehyde group reacts with a hydroxyl group on the same molecule to create a hemiacetal.
Identify the key components of d-gulose: the aldehyde group at the top (C1) and the hydroxyl groups attached to the other carbons. The stereochemistry of d-gulose determines the orientation of these hydroxyl groups. For d-gulose, the hydroxyl groups on C2 and C4 are on the right in the Fischer projection, while the hydroxyl group on C3 is on the left.
To draw the Haworth structure, first form a six-membered ring (a pyranose) by connecting the oxygen of the hydroxyl group on C5 to the carbon of the aldehyde group (C1). This creates a new chiral center at C1, leading to two possible anomers: α and β.
For the α-anomer, place the hydroxyl group on C1 (the anomeric carbon) pointing downward (opposite to the CH2OH group on C5). For the β-anomer, place the hydroxyl group on C1 pointing upward (same side as the CH2OH group on C5).
Complete the structure by ensuring the correct orientation of the hydroxyl groups on C2, C3, and C4 based on the stereochemistry of d-gulose. The CH2OH group on C5 should always point upward in the d-configuration. Label the structures as α-d-gulose and β-d-gulose accordingly.

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3m

주요 개념

질문에 올바르게 답하기 위해 반드시 이해해야 하는 핵심 개념들은 다음과 같습니다.

Haworth Structure

The Haworth structure is a way of representing the cyclic form of monosaccharides, where the sugar is depicted in a ring form. This representation highlights the anomeric carbon, which is the carbon that was part of the carbonyl group in the open-chain form. The orientation of the hydroxyl groups around this carbon determines whether the sugar is in the alpha (α) or beta (β) configuration.
추천 영상:
가이드 코스
2:18
Intro to Haworth Projections Concept 1

Anomeric Carbon

The anomeric carbon is the carbon atom in a sugar that was part of the carbonyl group (aldehyde or ketone) before the sugar cyclizes. In the case of d-gulose, this carbon is crucial for determining the sugar's anomeric form. The configuration of the hydroxyl group attached to the anomeric carbon defines whether the sugar is in the α or β form, influencing its chemical properties and reactivity.
추천 영상:
가이드 코스
5:36
Amino Acid Catabolism: Carbon Atoms Concept 2

D- and L- Configuration

The D- and L- configuration refers to the stereochemistry of sugars based on the orientation of the hydroxyl group on the penultimate carbon (the second-to-last carbon). In d-gulose, the 'D' designation indicates that the hydroxyl group on this carbon is on the right side in the Fischer projection. This configuration is essential for distinguishing between different sugars and understanding their biochemical roles.
추천 영상:
가이드 코스
1:30
D vs L Enantiomers Concept 1
관련 실천
교과서 질문

 Identify each of the following pairs of Fischer projections as enantiomers or identical compounds:

c.

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교과서 질문

Use the Fischer projection for D-gulose in problem 13.69 to answer each of the following:

b. Draw the Fischer projection and name the product formed by the oxidation of D-gulose.

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교과서 질문

Use the Fischer projection for d-gulose in problem 13.69 to answer each of the following:

a. Draw the Fischer projection and name the product formed by the reduction of D-gulose.

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교과서 질문

D-Erythritol is 70% as sweet as sucrose and contains only hydroxyl functional groups. When d-erythritol is oxidized it forms D-erythrose. Draw the Fischer projection for D-erythritol.

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교과서 질문

The sugar d-gulose is a sweet-tasting syrup.

a. Draw the Fischer projection for L-gulose.

546
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교과서 질문

What are the differences in the Fischer projections of d-fructose and d-galactose?

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