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An optically active compound A with mole...

An optically active compound `A` with molecular formula `C_(8)H_(14)` undergoes catalytic hydrogenation to give an optically inactive product. Which of the following structures for A is/are consistent with all the data?

A

B

C

D

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The correct Answer is:
To solve the problem, we need to determine which structure of the compound A (C8H14) is optically active and can yield an optically inactive product upon catalytic hydrogenation. Here’s a step-by-step breakdown: ### Step 1: Understand the requirements - Compound A has the molecular formula C8H14. - It is optically active, meaning it must have a chiral center or a configuration that allows for optical activity. - Upon catalytic hydrogenation, it yields an optically inactive product, which means the product must have a plane of symmetry or be superimposable on its mirror image. **Hint:** Remember that optically active compounds typically have no plane of symmetry, while optically inactive compounds do. ### Step 2: Analyze the options We need to evaluate each given structure to see if it meets the criteria. 1. **Option A:** Check for optical activity. - This structure has a plane of symmetry, making it optically inactive. Thus, it cannot be compound A. **Hint:** Look for a plane of symmetry in the structure to determine optical activity. 2. **Option B:** Check for optical activity and hydrogenation. - This structure does not have a plane of symmetry, making it optically active. Upon hydrogenation, it will still be optically active as it retains chirality. **Hint:** Remember that if a compound is optically active before hydrogenation, it will likely remain so unless it loses chirality. 3. **Option C:** Check for optical activity and hydrogenation. - This structure is also optically active. However, upon hydrogenation, it can lead to a product that has a plane of symmetry (if the groups are arranged in such a way that they can cancel each other out), making the product optically inactive. **Hint:** Visualize the hydrogenation process and how the arrangement of groups might change. 4. **Option D:** Check for optical activity and hydrogenation. - This structure is optically active as well. Similar to option B, after hydrogenation, it will remain optically active. **Hint:** Again, consider the implications of chirality after the addition of hydrogen. ### Step 3: Conclusion Based on the analysis: - Option A is ruled out due to being optically inactive. - Option B is ruled out because it remains optically active after hydrogenation. - Option D is ruled out for the same reason as option B. - Option C is the only structure that can be optically active and yield an optically inactive product upon hydrogenation. Thus, the structure of compound A is **Option C**. **Final Answer:** The structure of compound A is Option C.

To solve the problem, we need to determine which structure of the compound A (C8H14) is optically active and can yield an optically inactive product upon catalytic hydrogenation. Here’s a step-by-step breakdown: ### Step 1: Understand the requirements - Compound A has the molecular formula C8H14. - It is optically active, meaning it must have a chiral center or a configuration that allows for optical activity. - Upon catalytic hydrogenation, it yields an optically inactive product, which means the product must have a plane of symmetry or be superimposable on its mirror image. **Hint:** Remember that optically active compounds typically have no plane of symmetry, while optically inactive compounds do. ...
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