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Markovnikov Addition To Alkenes

Easychemistry

Hydrogen bromide is added to propene in the absence of any peroxide, and the major organic product needs to be identified from the mixture.

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About This Question

Subject
chemistry
Chapter
hydrocarbons
Topic
markovnikov addition to alkenes
Difficulty
Easy
Year
2025
Tags
Markovnikov ruleelectrophilic additioncarbocation stabilityhydrogen halide additionregioselectivity

Solution

Correct Answer:

2-Bromopropane

Electrophilic addition of 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, , protonation at the terminal carbon produces a secondary carbocation , 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 , not , 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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