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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

Text Solution

AI Generated Solution

The correct Answer is:
To determine which hexose (compound A) corresponds to the molecular formula C6H12O6 and fits the given conditions of the problem, we can follow these steps: ### Step 1: Identify the Structure of Hexose A Hexose A has the molecular formula C6H12O6, which indicates it is a monosaccharide with six carbon atoms. Common hexoses include D-glucose, D-fructose, D-mannose, and D-galactose. ### Step 2: Analyze the Reduction with Sodium Borohydride Sodium borohydride (NaBH4) is a reducing agent that reduces carbonyl groups (aldehydes and ketones) to alcohols. ### Step 3: Consider the Structures of the Options 1. **D-Fructose**: It is a ketose (contains a ketone group). - Structure: CH2OH-CO-(CHOH)3-CHO - Upon reduction, it can form two products: - **Sorbitol** (optically active) - **Mannitol** (optically inactive) 2. **D-Glucose**: It is an aldose (contains an aldehyde group). - Structure: CHO-(CHOH)4-CH2OH - Upon reduction, it forms only one product, which is optically active. 3. **D-Mannose**: It is also an aldose. - Structure: Similar to glucose but with different configurations. - Upon reduction, it forms only one product, which is optically active. 4. **D-Galactose**: It is also an aldose. - Structure: Similar to glucose but with different configurations. - Upon reduction, it forms only one product, which is optically active. ### Step 4: Determine the Optical Activity of the Products - For **D-Fructose**: - The reduction yields both an optically active compound (sorbitol) and an optically inactive compound (mannitol). - For **D-Glucose, D-Mannose, and D-Galactose**: - The reduction yields only optically active products. ### Conclusion Since compound B is optically inactive and compound C is optically active, the only hexose that fits this description is **D-Fructose**. ### Final Answer Compound A is **D-Fructose**. ---
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