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In which of the following dehydration by...

In which of the following dehydration by conc. `H_(2)SO_(4)` no rearrangement is favourable ?

A

B

C

D

Text Solution

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The correct Answer is:
To determine which dehydration by concentrated \( H_2SO_4 \) does not favor rearrangement, we need to analyze the carbocation stability formed during the dehydration process. The dehydration of alcohols typically involves the following steps: ### Step 1: Protonation of Alcohol The first step in the dehydration mechanism is the protonation of the alcohol by concentrated sulfuric acid. This converts the alcohol into a better leaving group (water). ### Step 2: Formation of Carbocation After protonation, the alcohol loses a water molecule, leading to the formation of a carbocation. The stability of this carbocation is crucial in determining whether rearrangement is favorable. ### Step 3: Analyzing Carbocation Stability - **Option 1:** If the carbocation formed is a primary carbocation, it is less stable and unlikely to rearrange. - **Option 2:** If the carbocation is secondary or tertiary, it can rearrange to form a more stable carbocation (e.g., from secondary to tertiary). - **Option 3:** If the carbocation is part of a cyclic structure, it may undergo ring expansion or rearrangement to achieve a more stable configuration. ### Step 4: Identify the Correct Option Based on the analysis of the carbocations formed in each option: - In **Option 1**, the carbocation formed is primary and does not favor rearrangement due to its instability. - In **Option 2**, the carbocation can rearrange to a more stable tertiary carbocation. - In **Option 3**, the carbocation can also rearrange due to ring expansion. - In **Option 4**, the carbocation formed is secondary and can rearrange to a more stable tertiary carbocation. ### Conclusion Thus, the option where dehydration by concentrated \( H_2SO_4 \) does not favor rearrangement is **Option 1**. ---
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