Four isomeric para-disubstituted aromatic compounds `A` to `D` with molecular formula `C_(8)H_(8)O_(2)` were given for identification. Based on the following observations, give structures of the compounds.
Four isomeric para-disubstituted aromatic compounds `A` to `D` with molecular formula `C_(8)H_(8)O_(2)` were given for identification. Based on the following observations, give structures of the compounds.
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To identify the four isomeric para-disubstituted aromatic compounds A to D with the molecular formula C₈H₈O₂, we will analyze the provided observations step by step.
### Step 1: Analyzing Compounds A and B
- **Observation**: Both A and B form a silver mirror with Tollens' reagent.
- **Conclusion**: This indicates that both compounds contain an aldehyde group (−CHO).
### Step 2: Analyzing Compound B
- **Observation**: Compound B gives a positive test with FeCl₃ solution.
- **Conclusion**: This indicates that compound B contains a phenolic hydroxyl group (−OH).
### Step 3: Structuring Compounds A and B
- **Structure of A**: Since A contains an aldehyde and does not react with FeCl₃, we can propose the structure as:
- **A**: p-Methoxybenzaldehyde (4-methoxybenzaldehyde)
- Structure:
```
O
||
C
|
C6H4-OCH3
```
- **Structure of B**: Since B contains both an aldehyde and a phenolic hydroxyl group, we can propose the structure as:
- **B**: 4-Hydroxybenzaldehyde (p-hydroxybenzaldehyde)
- Structure:
```
O
||
C
|
C6H4-OH
```
### Step 4: Analyzing Compound C
- **Observation**: Compound C gives a positive iodoform test.
- **Conclusion**: This indicates that compound C contains a methylated ketone (−COCH₃).
### Step 5: Structuring Compound C
- **Structure of C**: Since C must contain a methylated carbonyl group and be aromatic, we can propose the structure as:
- **C**: 4-Hydroxyacetophenone (p-hydroxyacetophenone)
- Structure:
```
O
||
C
|
C6H4-OH
|
CH3
```
### Step 6: Analyzing Compound D
- **Observation**: Compound D is readily extracted in aqueous NaHCO₃.
- **Conclusion**: This indicates that compound D contains a carboxylic acid group (−COOH).
### Step 7: Structuring Compound D
- **Structure of D**: Since D must contain a carboxylic acid and be aromatic, we can propose the structure as:
- **D**: 4-Methylbenzoic acid (p-toluic acid)
- Structure:
```
COOH
|
C6H4-CH3
```
### Summary of Structures
- **Compound A**: p-Methoxybenzaldehyde
- **Compound B**: p-Hydroxybenzaldehyde
- **Compound C**: p-Hydroxyacetophenone
- **Compound D**: p-Toluic acid
To identify the four isomeric para-disubstituted aromatic compounds A to D with the molecular formula C₈H₈O₂, we will analyze the provided observations step by step.
### Step 1: Analyzing Compounds A and B
- **Observation**: Both A and B form a silver mirror with Tollens' reagent.
- **Conclusion**: This indicates that both compounds contain an aldehyde group (−CHO).
### Step 2: Analyzing Compound B
- **Observation**: Compound B gives a positive test with FeCl₃ solution.
...
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