Markovnikov Addition To Alkenes
Hydrogen bromide is added to propene in the absence of any peroxide, and the major organic product needs to be identified from the mixture.
Select the correct option:
Solution
2-Bromopropane
Electrophilic addition of HBr to an unsymmetrical alkene follows Markovnikov's rule, which states that the hydrogen of the adding molecule attaches to the doubly bonded carbon that already carries more hydrogen atoms. The mechanism explains why: the proton adds first to give the more stable carbocation. With propene, CH3−CH=CH2, protonation at the terminal carbon produces a secondary carbocation CH3−CH+−CH3, which is stabilized by hyperconjugation and the inductive effect of two alkyl groups, whereas protonation at the internal carbon would give a less stable primary carbocation. Bromide then attacks the secondary cation to give 2-bromopropane as the major product. 1-Bromopropane is the anti-Markovnikov product that forms only in the presence of peroxide, so it is wrong here. 1,2-Dibromopropane would require addition of Br2, not HBr, so it is incorrect. Propan-2-ol involves water, not bromide, so it does not apply. This is the classic NCERT illustration of Markovnikov addition. A plausibility check: the dominant route always passes through the more stable carbocation, confirming the secondary bromide.
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About This Question
- Subject
- chemistry
- Chapter
- hydrocarbons
- Topic
- markovnikov addition to alkenes
- Difficulty
- Easy
- Year
- 2025
Solution
Correct Answer:
2-Bromopropane
Electrophilic addition of HBr to an unsymmetrical alkene follows Markovnikov's rule, which states that the hydrogen of the adding molecule attaches to the doubly bonded carbon that already carries more hydrogen atoms. The mechanism explains why: the proton adds first to give the more stable carbocation. With propene, CH3−CH=CH2, protonation at the terminal carbon produces a secondary carbocation CH3−CH+−CH3, which is stabilized by hyperconjugation and the inductive effect of two alkyl groups, whereas protonation at the internal carbon would give a less stable primary carbocation. Bromide then attacks the secondary cation to give 2-bromopropane as the major product. 1-Bromopropane is the anti-Markovnikov product that forms only in the presence of peroxide, so it is wrong here. 1,2-Dibromopropane would require addition of Br2, not HBr, so it is incorrect. Propan-2-ol involves water, not bromide, so it does not apply. This is the classic NCERT illustration of Markovnikov addition. A plausibility check: the dominant route always passes through the more stable carbocation, confirming the secondary bromide.
This easy difficulty chemistry question is from the chapter hydrocarbons, covering the topic of markovnikov addition to alkenes. It appeared in the 2025 exam.
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