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Five isomeric p-subsituted aromatic comp...

Five isomeric p-subsituted aromatic compounds (A) to (E ) with molecular formula `C_(8)H_(8)O_(2)` are given for identifyication. Based on the following observition, give the strucctures of the compounds.
i. Both (A) and (B) form a silver mirror with Tollens reagent, (B) also gives a positive test with neutral `FeCl_(3)` solution.
ii. (C ) gives positive iodoform test.
iii. (D) is readily extracted in aqueous `NaHCO_(3)` solution.
iv. (E ) on acid hydrolysis gives 1,4-dihydroxy benzene.
Compound (C ) is:

A

B

C

D

Text Solution

AI Generated Solution

The correct Answer is:
To identify the structure of compound (C) from the five isomeric p-substituted aromatic compounds (A) to (E) with the molecular formula C8H8O2, we will analyze the observations provided step by step. ### Step-by-Step Solution: 1. **Understanding the Iodoform Test**: - The iodoform test is positive for compounds that contain a methyl ketone (R-CO-CH3) or a secondary alcohol that can be oxidized to a methyl ketone. The test involves the reaction of the compound with iodine and sodium hydroxide, producing a yellow precipitate of iodoform (CHI3). - Therefore, we need to find a compound among A to E that contains the structure of a methyl ketone or can be oxidized to one. 2. **Analyzing the Given Compounds**: - We need to check the structures of the compounds A to E to see which one contains the methyl ketone functional group (C=O with a CH3 group attached). - The molecular formula C8H8O2 suggests that we are dealing with aromatic compounds, and we need to look for para-substituted structures. 3. **Identifying Compound (C)**: - From the observations, we know that compound (C) must have the structure that allows it to give a positive iodoform test. - Upon examining the possible structures: - (A) does not have the required methyl ketone structure. - (B) does not have the required structure. - (C) must contain the structure that allows for the iodoform test. - (D) does not have the required structure. - (E) does not have the required structure. 4. **Conclusion**: - The only compound that meets the criteria for the iodoform test is compound (A), which has the structure of a methyl ketone (C=O with a CH3 group). - Therefore, compound (C) is identified as compound (A). ### Final Answer: Compound (C) is: **p-Methylacetophenone (C6H5COCH3)**.

To identify the structure of compound (C) from the five isomeric p-substituted aromatic compounds (A) to (E) with the molecular formula C8H8O2, we will analyze the observations provided step by step. ### Step-by-Step Solution: 1. **Understanding the Iodoform Test**: - The iodoform test is positive for compounds that contain a methyl ketone (R-CO-CH3) or a secondary alcohol that can be oxidized to a methyl ketone. The test involves the reaction of the compound with iodine and sodium hydroxide, producing a yellow precipitate of iodoform (CHI3). - Therefore, we need to find a compound among A to E that contains the structure of a methyl ketone or can be oxidized to one. ...
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