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When 3,3-dimethyl-2-butanol is heated with H2SO4, the major product is
- a)3,3-dimethyl-1-butene
- b)2,3-dimethyl-2-butene
- c)2,3-dimethyl-1-butene
- d)None of these
Correct answer is option 'B'. Can you explain this answer?
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Understanding the Reaction
When 3,3-dimethyl-2-butanol is heated with concentrated sulfuric acid (H2SO4), dehydration occurs, leading to the formation of alkenes. This reaction is a classic example of an elimination reaction where water is removed from the alcohol.
Mechanism of Dehydration
- Protonation: The hydroxyl group (-OH) of 3,3-dimethyl-2-butanol is protonated by H2SO4, converting it into a better leaving group (water).
- Formation of Carbocation: After water leaves, a carbocation is formed. In this case, the most stable carbocation is a tertiary carbocation due to the presence of two methyl groups, which stabilize the positive charge.
Major Product Formation
The carbocation can undergo rearrangement, but in this specific case, it remains stable as a tertiary carbocation. The elimination of a proton (H+) from an adjacent carbon leads to alkene formation.
Product Analysis
- The major product is 2,3-dimethyl-2-butene because:
- It is formed from the more stable tertiary carbocation.
- The double bond forms between the second and third carbon atoms, resulting in a more substituted double bond, which is favored according to Zaitsev's rule.
- Other Products:
- 3,3-dimethyl-1-butene is less stable and less favored.
- 2,3-dimethyl-1-butene is also less likely to form due to the stability preference of the double bond placement.
Conclusion
Thus, the major product of the reaction between 3,3-dimethyl-2-butanol and H2SO4 upon heating is indeed 2,3-dimethyl-2-butene, confirming that option B is correct.
When 3,3-dimethyl-2-butanol is heated with concentrated sulfuric acid (H2SO4), dehydration occurs, leading to the formation of alkenes. This reaction is a classic example of an elimination reaction where water is removed from the alcohol.
Mechanism of Dehydration
- Protonation: The hydroxyl group (-OH) of 3,3-dimethyl-2-butanol is protonated by H2SO4, converting it into a better leaving group (water).
- Formation of Carbocation: After water leaves, a carbocation is formed. In this case, the most stable carbocation is a tertiary carbocation due to the presence of two methyl groups, which stabilize the positive charge.
Major Product Formation
The carbocation can undergo rearrangement, but in this specific case, it remains stable as a tertiary carbocation. The elimination of a proton (H+) from an adjacent carbon leads to alkene formation.
Product Analysis
- The major product is 2,3-dimethyl-2-butene because:
- It is formed from the more stable tertiary carbocation.
- The double bond forms between the second and third carbon atoms, resulting in a more substituted double bond, which is favored according to Zaitsev's rule.
- Other Products:
- 3,3-dimethyl-1-butene is less stable and less favored.
- 2,3-dimethyl-1-butene is also less likely to form due to the stability preference of the double bond placement.
Conclusion
Thus, the major product of the reaction between 3,3-dimethyl-2-butanol and H2SO4 upon heating is indeed 2,3-dimethyl-2-butene, confirming that option B is correct.
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When 3,3-dimethyl-2-butanol is heated with H2SO4, the major product isa)3,3-dimethyl-1-buteneb)2,3-dimethyl-2-butenec)2,3-dimethyl-1-butened)None of theseCorrect answer is option 'B'. Can you explain this answer?
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