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A compound of molecular formula C(8)H(...

A compound of molecular formula ` C_(8)H_(8)O_(2)` reacts with acetophenone is form a single cross-aldol product in the presence of base. The same compound on reaction with conc. NaOH forms benzyl alcohol as one of the products. The structure of the compounds is :

A

B

C

D

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To solve the problem, we need to determine the structure of a compound with the molecular formula C8H8O2 that reacts with acetophenone to form a single cross-aldol product and also yields benzyl alcohol when reacted with concentrated NaOH. ### Step-by-Step Solution: 1. **Identify the Molecular Formula**: The compound has the molecular formula C8H8O2. This indicates that it contains 8 carbon atoms, 8 hydrogen atoms, and 2 oxygen atoms. 2. **Understand the Reaction Conditions**: The compound reacts with acetophenone (which has the structure C6H5C(O)CH3) in the presence of a base to form a single cross-aldol product. This suggests that the compound does not have an alpha hydrogen atom, which is necessary for self-condensation. 3. **Consider the Aldehyde Group**: The compound must contain an aldehyde group (-CHO) because it undergoes a cross-aldol reaction. In addition, it should not have any alpha hydrogen atoms to prevent self-condensation. 4. **Analyze the Canizaro Reaction**: The compound also reacts with concentrated NaOH to form benzyl alcohol, indicating that it undergoes a Canizaro reaction. For a compound to undergo this reaction, it must have an aldehyde group and no alpha hydrogens. 5. **Propose Possible Structures**: Given the requirements, we can propose the structure of the compound. The structure that fits all the criteria is 4-methoxybenzaldehyde (4-methoxybenzylaldehyde), which has the structure: - A benzene ring with a methoxy group (-OCH3) at the para position and an aldehyde group (-CHO). 6. **Verify the Structure**: - The structure of 4-methoxybenzaldehyde is C8H8O2. - It does not have alpha hydrogens, satisfying the condition for a single cross-aldol product. - It can undergo the Canizaro reaction, yielding benzyl alcohol as one of the products. 7. **Write the Reactions**: - **Cross-Aldol Reaction**: 4-methoxybenzaldehyde + acetophenone → Cross-aldol product. - **Canizaro Reaction**: 4-methoxybenzaldehyde + NaOH → Benzyl alcohol + Sodium salt of 4-methoxybenzaldehyde. ### Conclusion: The structure of the compound is **4-methoxybenzaldehyde**.
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