NEETChemistryGeneral Organic Chemistry
The heterolytic cleavage of the C - Br bond in 2-bromo-2-methylbutane yields a carbocation intermediate. What is the number of hyperconjugative structures possible for this resulting carbocation?
Options
- A9
- B6
- C5
- D8
Correct answer
D. 8
Step-by-step solution
First, deduce the structure of the starting compound. 2-Bromo-2-methylbutane is CH ₃- C ( Br )( CH ₃)- CH ₂- CH ₃ . Heterolytic cleavage of the C - Br bond results in the formation of the 2-methylbutan-2-yl carbocation: CH ₃- C ^+( CH ₃)- CH ₂- CH ₃ . To find the number of hyperconjugative structures, count the number of -hydrogens attached to the carbons directly bonded to the positively charged carbon. The -carbons are: - C1 methyl group: 3 -hydrogens - C2 methyl branch: 3 -hydrogens - C3 methylene group: 2 -hydr