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15240672380's Question
Chemistry
Posted 9 months ago

A newly synthesized organic compound, C8H10O2 N2\mathrm{C} 8 \mathrm{H} 10 \mathrm{O} 2 \mathrm{~N} 2, exhibits intriguing reactivity and structural properties. The compound undergoes nitration much faster than benzene, suggesting an activated aromatic ring. Additionally, it forms a diethyl acetal when treated with ethanol in the presence of an acid catalyst, indicating the presence of a carbonyl group. Utilizing these clues and the principles of organic chemistry, what is the most probable structure for this compound? Options: a) 4nitroaniline b) 3,4-dimethoxyaniline c) N,N-dimethyl-p-aminobenzaldehyde d) 2,4dinitrophenol
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Answer from Sia
Posted 9 months ago
C
Key Concept
Activated aromatic ring and carbonyl group reactivity
Explanation
The compound's faster nitration than benzene indicates an activated aromatic ring, which is consistent with an electron-donating group attached to the ring, such as an amino group. The formation of a diethyl acetal suggests the presence of an aldehyde group, as ketones generally do not form acetals as readily. Therefore, the most probable structure is N,N-dimethyl-p-aminobenzaldehyde, which has both an activated aromatic ring due to the amino group and a reactive aldehyde group that can form an acetal.

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