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Acid catalysed dehydration of 2-pentanol...

Acid catalysed dehydration of 2-pentanol would give

A

1-pentene as a major product

B

cis 2-pentene as a major product

C

trans-2-pentene as a major product

D

cis- and trans - 2-pentene in equal amount.

Text Solution

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The correct Answer is:
To determine the major product of the acid-catalyzed dehydration of 2-pentanol, we can follow these steps: ### Step-by-Step Solution: 1. **Identify the Reactant**: The reactant is 2-pentanol, which has the following structure: \[ \text{CH}_3\text{CH(OH)CH}_2\text{CH}_2\text{CH}_3 \] 2. **Protonation of Alcohol**: In the presence of an acid (H⁺), the hydroxyl group (-OH) of 2-pentanol gets protonated, forming a protonated alcohol: \[ \text{CH}_3\text{CH(OH}_2^+\text{)CH}_2\text{CH}_2\text{CH}_3 \] 3. **Formation of Carbocation**: The protonated alcohol can lose a water molecule (H₂O) to form a carbocation. The loss of water can occur at the carbon adjacent to the hydroxyl group, leading to the formation of a secondary carbocation: \[ \text{CH}_3\text{C}^+\text{HCH}_2\text{CH}_2\text{CH}_3 \] 4. **Carbocation Rearrangement**: The formed carbocation can rearrange to form a more stable carbocation if possible. In this case, there is no rearrangement needed as the secondary carbocation is already stable. 5. **Deprotonation to Form Alkene**: The carbocation can lose a proton (H⁺) to form an alkene. There are two possible alkenes that can form: cis-2-pentene and trans-2-pentene. The reaction can proceed to form both isomers. 6. **Stability of Alkenes**: Between cis-2-pentene and trans-2-pentene, trans-2-pentene is more stable due to less steric hindrance between the larger alkyl groups. 7. **Final Products**: Therefore, the major product of the acid-catalyzed dehydration of 2-pentanol is trans-2-pentene, while cis-2-pentene is the minor product. ### Conclusion: The major product of the acid-catalyzed dehydration of 2-pentanol is **trans-2-pentene**. ---
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