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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 observation, give the structures 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 (A) is:

A

B

C

D

Text Solution

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The correct Answer is:
To identify the structure of compound (A) based on the given observations, we can follow these steps: ### Step 1: Analyze the Observations The molecular formula provided is C8H8O2, indicating that we are dealing with an aromatic compound that has two oxygen atoms. The observations provided are crucial for determining the nature of compound (A). ### Step 2: Identify the Functional Group The first observation states that both (A) and (B) form a silver mirror with Tollens' reagent. This test is characteristic of aldehydes, which means that compound (A) must contain a carbonyl group (C=O) in the form of an aldehyde (CHO). ### Step 3: Determine the Structure of Compound (A) Since we know that compound (A) is an aldehyde and must have a total of 8 carbon atoms, we can deduce the possible structures. The presence of the aldehyde group suggests that it could be a para-substituted aromatic compound. ### Step 4: Check the Isomer Options We need to check the options provided to find a structure that fits the criteria: - It must have 8 carbon atoms. - It must contain an aldehyde functional group. Assuming the options are: - Option A: p-Toluic acid (C8H8O2) - Option B: p-Hydroxybenzaldehyde (C8H8O2) - Option C: p-Methoxybenzaldehyde (C8H8O2) - Option D: p-Acetylphenol (C8H8O2) - Option E: p-Dimethylbenzaldehyde (C8H8O2) From these options, we can see that: - Option C (p-Methoxybenzaldehyde) has the aldehyde group and fits the molecular formula C8H8O2. ### Step 5: Confirm the Structure Given that compound (A) is an aldehyde and fits the criteria, we can conclude that the structure of compound (A) is p-Methoxybenzaldehyde. ### Conclusion Thus, the structure of compound (A) is p-Methoxybenzaldehyde. ---
To identify the structure of compound (A) based on the given observations, we can follow these steps: ### Step 1: Analyze the Observations The molecular formula provided is C8H8O2, indicating that we are dealing with an aromatic compound that has two oxygen atoms. The observations provided are crucial for determining the nature of compound (A). ### Step 2: Identify the Functional Group The first observation states that both (A) and (B) form a silver mirror with Tollens' reagent. This test is characteristic of aldehydes, which means that compound (A) must contain a carbonyl group (C=O) in the form of an aldehyde (CHO). ...
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