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Dehydration of 1-butanol gives 2-butane ...

Dehydration of 1-butanol gives 2-butane as a major product, by which of the following intermediate the compound 2-butene obtained.

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Text Solution

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The correct Answer is:
To solve the question regarding the dehydration of 1-butanol to form 2-butene and identify the intermediate involved, we can follow these steps: ### Step-by-Step Solution: 1. **Identify the Structure of 1-Butanol**: The molecular structure of 1-butanol (butan-1-ol) is: \[ CH_3-CH_2-CH_2-CH_2OH \] Here, the hydroxyl (-OH) group is attached to the first carbon. **Hint**: Remember that 1-butanol has a four-carbon chain with the -OH group on the first carbon. 2. **Dehydration Reaction**: The dehydration of 1-butanol involves the removal of a water molecule (H2O). This reaction is typically facilitated by a dehydrating agent, such as concentrated sulfuric acid (H2SO4), which generates protons (H+). **Hint**: Concentrated sulfuric acid acts as a catalyst and helps in protonating the alcohol group. 3. **Formation of Oxonium Ion**: The alcohol group (-OH) is protonated to form an oxonium ion: \[ CH_3-CH_2-CH_2-CH_2OH_2^+ \] This oxonium ion is unstable and leads to the elimination of water. **Hint**: The oxonium ion is formed when the -OH group is protonated, making it a better leaving group. 4. **Formation of Carbocation**: Upon the elimination of water, a carbocation is formed. In this case, the initial carbocation formed is a primary carbocation: \[ CH_3-CH_2-CH_2-CH_2^+ \] **Hint**: Primary carbocations are less stable and may undergo rearrangement to form more stable carbocations. 5. **Carbocation Rearrangement**: The primary carbocation undergoes a 1,2-hydride shift to form a more stable secondary carbocation: \[ CH_3-CH^+-CH_2-CH_3 \] Here, the positive charge has shifted to the second carbon, creating a secondary carbocation. **Hint**: Carbocation rearrangement occurs to achieve greater stability; secondary carbocations are more stable than primary ones. 6. **Formation of 2-Butene**: The secondary carbocation can lose a proton (H+) to form 2-butene. According to Zaitsev's rule, the more substituted alkene is favored: \[ CH_3-CH=CH-CH_3 \] **Hint**: Zaitsev's rule states that the more substituted alkene is the major product in elimination reactions. 7. **Identify the Intermediate**: The intermediate that leads to the formation of 2-butene is the secondary carbocation formed after the rearrangement. **Final Answer**: The intermediate involved in the dehydration of 1-butanol to form 2-butene is the **secondary carbocation**.

To solve the question regarding the dehydration of 1-butanol to form 2-butene and identify the intermediate involved, we can follow these steps: ### Step-by-Step Solution: 1. **Identify the Structure of 1-Butanol**: The molecular structure of 1-butanol (butan-1-ol) is: \[ CH_3-CH_2-CH_2-CH_2OH ...
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