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Magazine Chapter 13: Problem 38
Draw the Fischer projection for the oxidation and the reduction products of \(\mathrm{D}\) -mannose. What are the names of the sugar acid and the sugar alcohol produced?
Short Answer
Expert verified
The oxidation product is D-Mannonic Acid; the reduction product is D-Mannitol.
Step by step solution
01
- Understand \(\textbf{D}\text{-mannose}
\( \textbf{D-Mannose} \) is an aldohexose, which means it is a six-carbon sugar with an aldehyde group. It is a simple sugar found naturally in fruits and vegetables.
02
- Draw Fischer Projection for \(\textbf{D}\text{-mannose}
The Fischer projection of \( \textbf{D-Mannose} \) has the following structure:\[ \begin{array}{c} \text{CHO} \ \text{|} \ \text{HCOH} \ \text{|} \ \text{HOCH} \ \text{|} \ \text{HCOH} \ \text{|} \ \text{HCOH} \ \text{|} \ \text{CH2OH} \end{array} \]
03
- Understand oxidation product \(\textbf{D-Mannonic Acid}\text
Oxidizing \( \textbf{D-Mannose} \) converts the aldehyde group (\( \text{CHO} \)) to a carboxylic acid group (\( \text{COOH} \)), forming \( \textbf{D-Mannonic Acid} \).Fischer projection for \( \textbf{D-Mannonic Acid} \) is:\[ \begin{array}{c} \text{COOH} \ \text{|} \ \text{HCOH} \ \text{|} \ \text{HOCH} \ \text{|} \ \text{HCOH} \ \text{|} \ \text{HCOH} \ \text{|} \ \text{CH2OH} \end{array} \]
04
- Understand reduction product \(\textbf{D-Mannitol}\text
Reducing \( \textbf{D-Mannose} \) converts the aldehyde group (\( \text{CHO} \)) to an alcohol group (\( \text{CH2OH} \)), forming \( \textbf{D-Mannitol} \).Fischer projection for \( \textbf{D-Mannitol} \) is:\[ \begin{array}{c} \text{CH2OH} \ \text{|} \ \text{HCOH} \ \text{|} \ \text{HOCH} \ \text{|} \ \text{HCOH} \ \text{|} \ \text{HCOH} \ \text{|} \ \text{CH2OH} \end{array} \]
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Fischer Projection
Fischer projections are a way to represent 3D molecules in 2D. They are especially useful for showing sugars and amino acids. A Fischer projection places the molecule in a specific orientation:
- The vertical lines represent bonds going \textbf{away} from the viewer.
- The horizontal lines represent bonds coming \textbf{towards} the viewer.
Sugar Acid
Sugar acids, also called aldonic acids, are formed when the aldehyde group (\text{CHO}) in a sugar gets oxidized to a carboxylic acid group (\text{COOH}). In this case, oxidizing \textbf{D-Mannose} gives \textbf{D-Mannonic Acid}. The transformation is easy to see in the Fischer projection:
\[ \text{COOH} \ \text{|} \ \text{HCOH} \ \text{|} \ \text{HOCH} \ \text{|} \ \text{HCOH} \ \text{|} \ \text{HCOH} \ \text{|} \ \text{CH2OH} \] Oxidation to form sugar acids is common in metabolism and biochemistry.
- Original aldehyde group \text{CHO} at the top.
- Changed to carboxylic acid group \text{COOH} after oxidation.
\[ \text{COOH} \ \text{|} \ \text{HCOH} \ \text{|} \ \text{HOCH} \ \text{|} \ \text{HCOH} \ \text{|} \ \text{HCOH} \ \text{|} \ \text{CH2OH} \] Oxidation to form sugar acids is common in metabolism and biochemistry.
Sugar Alcohol
Sugar alcohols, also called alditols, are produced when the aldehyde group (\text{CHO}) of a sugar is reduced to an alcohol group (\text{CH2OH}). For \textbf{D-Mannose}, the reduction forms \textbf{D-Mannitol}.
- Original aldehyde group \text{CHO} is reduced.
- This group turns into \text{CH2OH}.
Oxidation
Oxidation reactions in sugars involve the loss of electrons, typically converting an aldehyde group (\text{CHO}) to a carboxylic acid group (\text{COOH}). For example, oxidizing \textbf{D-Mannose} produces \textbf{D-Mannonic Acid}. The general steps in oxidation are:
- Identify the aldehyde group \text{CHO}.
- Transform it to carboxylic acid \text{COOH}.
Reduction
Reduction reactions in sugars involve the gain of electrons, commonly turning an aldehyde group (\text{CHO}) into an alcohol group (\text{CH2OH}). For \textbf{D-Mannose}, reduction creates \textbf{D-Mannitol}. Steps in the reduction:
- Identify the aldehyde group \text{CHO}.
- Convert it into an alcohol group \text{CH2OH}.
