Draw all structurally isomeric `2^(@)` chlorides with molecular formula `C_(5)H_(11)Cl`

Answer

To solve the problem of drawing all structurally isomeric secondary chlorides with the molecular formula C5H11Cl, we will follow these steps:

### Step 1: Understand the Definition of Secondary Chlorides
Secondary chlorides are those chlorides where the chlorine atom is attached to a secondary carbon. A secondary carbon is defined as a carbon atom that is bonded to two other carbon atoms.

### Step 2: Identify the Carbon Skeleton
For the molecular formula C5H11Cl, we need to consider a carbon skeleton with five carbon atoms. The main chain can be a straight chain (pentane) or branched.

### Step 3: Draw the Straight Chain Isomers
1. **2-Chloropentane**:
- Draw a straight chain of 5 carbon atoms.
- Place the chlorine atom on the second carbon.
- The structure will look like this:
```
CH3-CHCl-CH2-CH2-CH3
```
- Verify the hydrogen count: 3 + 1 + 2 + 2 + 3 = 11 H.

2. **3-Chloropentane**:
- Again, draw a straight chain of 5 carbon atoms.
- Place the chlorine atom on the third carbon.
- The structure will look like this:
```
CH3-CH2-CHCl-CH2-CH3
```
- Verify the hydrogen count: 3 + 2 + 1 + 2 + 3 = 11 H.

### Step 4: Draw the Branched Isomers
1. **2-Chloro-3-methylbutane**:
- Start with a butane chain (4 carbons) and add a methyl group (1 carbon) to the second carbon.
- Place the chlorine atom on the second carbon of the butane.
- The structure will look like this:
```
CH3-CHCl-CH(CH3)-CH3
```
- Verify the hydrogen count: 3 + 1 + 2 + 3 + 1 = 11 H.

### Step 5: List the Isomers
Now we have identified the following three isomers:
1. 2-Chloropentane
2. 3-Chloropentane
3. 2-Chloro-3-methylbutane

### Final Structures
1. **2-Chloropentane**: CH3-CHCl-CH2-CH2-CH3
2. **3-Chloropentane**: CH3-CH2-CHCl-CH2-CH3
3. **2-Chloro-3-methylbutane**: CH3-CHCl-CH(CH3)-CH3