0
$\begingroup$

What is the product of the reaction of 2-methyl-but-1,3-diene with HBr?

2-methyl-but-1,3-diene

What I understand is that carbon (2) will get a positive charge after protonation.

But after this, which should be the major product?

  • 2-bromo-2-methyl-but-3-ene - because in this case the carbocation would be stable because of being tertiary, but the double bond would have less number of hyperconjugated structures and will be less stable

    2-bromo-2-methyl-but-3-ene

  • 1-bromo-3-methyl-2-butene - as the carbocation would be less stable because it would be primary but the double bond would be much more stable because of 8 $\alpha$ hydrogen available

    1-bromo-3-methyl-2-butene

$\endgroup$

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Browse other questions tagged or ask your own question.