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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 (B) is:

A

B

C

D

Text Solution

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The correct Answer is:
To identify the structure of compound (B) among the five isomeric p-substituted aromatic compounds with the molecular formula C8H8O2, we will analyze the given observations step by step. ### Step 1: Analyze the Observations The first observation states that both (A) and (B) form a silver mirror with Tollens' reagent. This indicates that both compounds contain an aldehyde group (–CHO) because Tollens' reagent is used to test for the presence of aldehydes. ### Step 2: Identify the Functional Groups The second part of the observation for compound (B) mentions that it gives a positive test with neutral FeCl3 solution. This indicates the presence of a phenolic –OH group, as phenols react with FeCl3 to form colored complexes. ### Step 3: Determine the Structure of Compound (B) Since compound (B) has both an aldehyde group and a hydroxyl group, we can deduce its structure. The molecular formula C8H8O2 suggests that the compound is likely a para-substituted aromatic compound. - The benzene ring contributes 6 carbon atoms. - The aldehyde group (–CHO) contributes 1 carbon atom. - The hydroxyl group (–OH) does not contribute to the carbon count but does contribute to the overall structure. Thus, we have: - 6 (from benzene) + 1 (from aldehyde) + 1 (from hydroxyl) = 8 carbon atoms. ### Step 4: Visualize the Structure Given that the aldehyde and hydroxyl groups are para to each other, the structure of compound (B) can be drawn as follows: - A benzene ring with a –CHO group at one position and a –OH group at the para position. The structure can be represented as: ``` OH | C6H4 - CHO ``` This corresponds to para-hydroxybenzaldehyde (or p-hydroxybenzaldehyde). ### Conclusion Thus, the structure of compound (B) is para-hydroxybenzaldehyde.

To identify the structure of compound (B) among the five isomeric p-substituted aromatic compounds with the molecular formula C8H8O2, we will analyze the given observations step by step. ### Step 1: Analyze the Observations The first observation states that both (A) and (B) form a silver mirror with Tollens' reagent. This indicates that both compounds contain an aldehyde group (–CHO) because Tollens' reagent is used to test for the presence of aldehydes. ### Step 2: Identify the Functional Groups The second part of the observation for compound (B) mentions that it gives a positive test with neutral FeCl3 solution. This indicates the presence of a phenolic –OH group, as phenols react with FeCl3 to form colored complexes. ...
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