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In the esterification of propanoic acid ...

In the esterification of propanoic acid with methanol in the presence
of a mineral acid which of the following are intermediate species?

A

`C_(2)H_(5)-overset(o+)overset(OH)overset(||)C-OH`

B

`C_(2)H_(5)-underset(o+)overset(OH)overset(|)C-OH`

C

`C_(2)H_(5)-underset(OCH_(3))underset(|)overset(OH)overset(|)C-OH`

D

`C_(2)H_(5)-underset(o+)overset(OH)overset(|)C-OCH_(3)`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the question regarding the intermediate species formed during the esterification of propanoic acid with methanol in the presence of a mineral acid, we will follow these steps: ### Step-by-Step Solution: 1. **Identify the Reactants**: - The reactants involved in the reaction are propanoic acid (C2H5COOH) and methanol (CH3OH). 2. **Protonation of the Carboxylic Acid**: - In the presence of a mineral acid (H+), the carbonyl oxygen of the propanoic acid gets protonated, forming a protonated carboxylic acid. This step increases the electrophilicity of the carbonyl carbon. 3. **Formation of the Tetrahedral Intermediate**: - The nucleophilic oxygen of methanol attacks the electrophilic carbon of the protonated carboxylic acid. This results in the formation of a tetrahedral intermediate, which has both the methoxy group (OCH3) and the hydroxyl group (OH) attached to the carbon. 4. **Loss of Water**: - The tetrahedral intermediate can then lose a water molecule (H2O), leading to the formation of a carbocation intermediate. 5. **Proton Transfer**: - A proton transfer occurs, stabilizing the carbocation and resulting in the formation of the final ester product (propyl methanoate or propanoate). 6. **Final Product Formation**: - After the proton transfer and loss of a proton, the final product, which is the ester, is formed. ### Conclusion: The intermediates formed during the reaction include: - Protonated carboxylic acid - Tetrahedral intermediate - Carbocation intermediate Thus, the answer to the question is that the intermediate species are all the mentioned forms.
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