To solve the question about the wrong order with respect to the indicated property (acidic strength or basic strength), we will analyze each option step by step.
### Step 1: Understand the Compounds and Their Functional Groups
1. **Benzoic Acid (C6H5COOH)**: This is a carboxylic acid, which is generally more acidic due to the presence of the carboxyl group (-COOH).
2. **Phenol (C6H5OH)**: This is an alcohol with a hydroxyl group (-OH) attached to a benzene ring. It is less acidic than carboxylic acids.
3. **Cyclohexanol (C6H11OH)**: This is also an alcohol, but it does not have the resonance stabilization that phenol has, making it less acidic than phenol.
### Step 2: Compare Acidic Strength
- The order of acidic strength based on the functional groups is:
- **Benzoic Acid > Phenol > Cyclohexanol**
- This order is correct because the carboxylic acid can stabilize the negative charge after deprotonation through resonance, while phenol can stabilize it to a lesser extent, and cyclohexanol cannot stabilize it at all.
### Step 3: Analyze the Basic Strength of Aniline, Cyclohexylamine, Benzene, and Benzamide
1. **Aniline (C6H5NH2)**: This compound has an amino group (-NH2) attached to a benzene ring. The lone pair on nitrogen is involved in resonance with the benzene ring, reducing its basicity.
2. **Cyclohexylamine (C6H11NH2)**: This compound has an amino group attached to a cyclohexane ring. The lone pair on nitrogen is not involved in resonance, making it more basic than aniline.
3. **Benzene (C6H6)**: This is a non-basic compound as it does not have any functional group that can donate a proton.
4. **Benzamide (C6H5CONH2)**: The amide group (-CONH2) has resonance that delocalizes the lone pair on nitrogen, making it less basic than aniline.
### Step 4: Compare Basic Strength
- The expected order of basic strength is:
- **Cyclohexylamine > Aniline > Benzamide > Benzene**
- This order is correct because cyclohexylamine has the most available lone pair on nitrogen, while benzene is non-basic.
### Step 5: Evaluate the Given Orders
- The orders for acidic strength (Benzoic Acid > Phenol > Cyclohexanol) and basic strength (Cyclohexylamine > Aniline > Benzamide > Benzene) are correct.
- The question asks for the wrong order, and based on the analysis, the order involving aniline, cyclohexylamine, benzene, and benzamide is the one that is incorrectly stated in the question.
### Conclusion
The wrong order with respect to the indicated property is the one involving aniline, cyclohexylamine, benzene, and benzamide.
### Final Answer
The wrong order is: **Cyclohexylamine > Aniline > Benzamide > Benzene** (this is the correct order, but if stated otherwise, it would be wrong).
