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In which of the following Hoffmann elimi...

In which of the following Hoffmann elimination product is more ?

A

`CH_(3)-underset(" "CH_(3))underset(|)overset(" "CH_(3))overset(|)(C)-underset(""OH)underset(|)(CH)-CH_(3) " "underset(Delta)overset("conc."H_(2)SO_(4))(rarr)`

B

`CH_(3)-underset(CH_(3))underset(|)overset(H)overset(|)(C)-underset(Br)underset(|)(CH)-CH_(3)" "overset(("potassium"),("ethoxide"))(rarr)`

C

D

`CH_(3)-underset(CH_(3))underset(|)overset(CH_(3))overset(|)(C)-CH_(2)-Cl " "underset(Delta)overset(alc. KOH)(rarr)`

Text Solution

AI Generated Solution

The correct Answer is:
To determine which of the following reactions follows the Hofmann elimination product, we need to analyze each reaction step by step. The Hofmann elimination product is characterized by the formation of the less substituted alkene, which is contrary to the Zaitsev's rule that states that the more substituted alkene is favored. ### Step-by-Step Solution: 1. **Understanding Hofmann Elimination**: - In Hofmann elimination, the major product is the less substituted alkene. This is in contrast to Zaitsev's rule, where the more substituted alkene is the major product. 2. **Analyzing Reaction A**: - The reactant is a tertiary alcohol treated with concentrated H2SO4. - Upon dehydration, a carbocation is formed, which can rearrange to form a more stable tertiary carbocation. - The major product formed is a more substituted alkene. - **Conclusion**: This reaction follows Zaitsev's rule, not Hofmann elimination. 3. **Analyzing Reaction B**: - The reactant is a bromoalkane treated with potassium ethoxide. - Similar to reaction A, a carbocation is formed, which can also rearrange. - The major product formed is again a more substituted alkene. - **Conclusion**: This reaction also follows Zaitsev's rule, not Hofmann elimination. 4. **Analyzing Reaction C**: - The reactant is a tertiary amine treated with a weak base like silver hydroxide. - The NR3 group is a good leaving group and is removed, leading to the formation of a double bond. - The product formed is a less substituted alkene. - **Conclusion**: This reaction follows Hofmann elimination. 5. **Analyzing Reaction D**: - The reactant has three methyl groups on the beta carbon and is treated with KOH. - Upon elimination, a carbocation is formed, which can rearrange to a more stable form. - The product formed is a more substituted alkene. - **Conclusion**: This reaction follows Zaitsev's rule, not Hofmann elimination. ### Final Conclusion: Based on the analysis, the only reaction that follows Hofmann elimination is **Reaction C**. Therefore, the correct answer is **C**.
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