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Reduction of hexose A (molecular formula...

Reduction of hexose A (molecular formula `C_(6)H_(12)O_(6)`) with sodium borohydride gives compound B and C. Compound B is optically inactive, whereas compound C is optically active. Which of the following is compound A?

A

D - fructose

B

D - glucose

C

D - mannose

D

D - galactose

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The correct Answer is:
To solve the problem, we need to identify the hexose (compound A) that, when reduced with sodium borohydride (NaBH4), gives one optically inactive compound (B) and one optically active compound (C). ### Step-by-Step Solution: 1. **Understanding the Structure of Hexoses**: - Hexoses are monosaccharides with the formula C6H12O6. Common hexoses include glucose, fructose, galactose, and mannose. 2. **Identifying the Type of Reaction**: - Sodium borohydride is a reducing agent that reduces carbonyl groups (aldehydes and ketones) to alcohols. In the case of hexoses, the carbonyl group can be either an aldehyde (as in glucose) or a ketone (as in fructose). 3. **Analyzing the Options**: - We need to analyze the structures of the common hexoses to see which one can produce two different products upon reduction: - **D-Fructose**: A ketose (C=O in the second carbon). - **D-Glucose**: An aldose (C=O at the first carbon). - **D-Galactose**: An aldose (similar to glucose but with different hydroxyl group arrangements). - **D-Mannose**: Another aldose. 4. **Reduction of D-Fructose**: - D-Fructose, when reduced by NaBH4, will yield two products: - One product will be a secondary alcohol (B) and will be optically inactive due to symmetry. - The other product will be a different stereoisomer (C) that is optically active due to the presence of an asymmetric carbon. 5. **Conclusion**: - Since D-Fructose can produce one optically inactive compound (B) and one optically active compound (C) upon reduction, it fits the criteria given in the question. Therefore, compound A is **D-Fructose**. ### Final Answer: Compound A is **D-Fructose**.
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