Asked in ETEA MDCAT 2014 2014Moderate

Which of the following compound will react most readily with bromine in CCl4?

Correct answer: D. 3-Methyl-1-butene

  • A. 1-pentene
  • B. 2-pentene
  • C. 2-Methyl-1-butene
  • D. 3-Methyl-1-butene

Explanation

The reaction of alkenes with bromine proceeds through the formation of a carbocation intermediate. The stability of these carbocations is determined by the number of alkyl substituents; more substituents lead to greater stability. Among the given options, 3-methyl-1-butene forms the most stable carbocation due to its tertiary structure, resulting in the fastest reaction with bromine in CCl4. In contrast, 1-pentene forms the least stable primary carbocation, leading to the slowest reaction, while both 2-pentene and 2-methyl-1-butene form secondary carbocations that are more stable than that of 1-pentene but less stable than that of 3-methyl-1-butene, making them less reactive than the correct answer.

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About Alkenes

Alkenes are unsaturated hydrocarbons containing a carbon-carbon double bond with sigma and pi components and restricted rotation. Their reactions include electrophilic addition of hydrogen, halogens, hydrogen halides and water, with Markovnikov orientation, oxidation, combustion and polymerisation, while their preparation commonly involves elimination from alkyl halides or alcohols.

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