`MeCH(OH)CH_(2)CH_(2)COOH` when heated produces

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Answer

To solve the problem of what product is formed when `MeCH(OH)CH_(2)CH_(2)COOH` is heated, we can break down the process step by step:

### Step 1: Identify the Structure
The given compound can be represented as:
- A methyl group (Me) attached to a carbon that has a hydroxyl group (OH).
- This carbon is further connected to a CH2 group, which is then connected to another CH2 group, and finally to a carboxylic acid (COOH).

### Step 2: Analyze the Functional Groups
The compound contains:
- A hydroxyl group (OH)
- A carboxylic acid (COOH)
These functional groups suggest that the compound can undergo dehydration when heated.

### Step 3: Heating the Compound
When the compound is heated, it can undergo an intramolecular reaction. The lone pair of electrons on the oxygen atom of the hydroxyl group can attack the carbonyl carbon of the carboxylic acid group. This leads to the formation of a cyclic structure.

### Step 4: Formation of a Five-Membered Ring
The attack of the hydroxyl oxygen on the carbonyl carbon results in the formation of a five-membered ring. This is a common reaction known as intramolecular esterification or cyclization.

### Step 5: Proton Transfer
After the formation of the five-membered ring, an intramolecular proton transfer occurs. This means that a proton (H+) from the hydroxyl group is transferred to the oxygen atom in the ring, resulting in the formation of a neutral molecule and a positively charged hydroxyl group.

### Step 6: Elimination of Water
The negatively charged oxygen can now act as a leaving group. When it leaves, it results in the formation of a double bond between the carbon atoms, leading to the final product.

### Step 7: Final Product
The final product after heating is an unsaturated compound with a double bond and a methyl group. The structure can be represented as:
- A five-membered cyclic compound with a double bond and a methyl group.

### Conclusion
The product formed from the heating of `MeCH(OH)CH_(2)CH_(2)COOH` is a five-membered cyclic compound with a double bond.

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