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Chapter 6: Q62P (page 283)

When 3-methyl-1-butene reacts with HBr, two alkyl halides are formed: 2-bromo-3-methylbutane and 2-bromo-2-methylbutane. Propose a mechanism that explains the formation of these two products.

Short Answer

Expert verified

In this markoniv addition takes place.

Markoniv addition= Positive ion will go to that double bonded carbon which has more no of hydrogens attached and negative ion will go towards that carbon which has less number of hydrogens attached.

Step by step solution

01

Step 1: How the reaction proceed

In this markoniv addition takes place.

Markoniv addition= Positive ion will go to that double bonded carbon which has more no of hydrogens attached and negative ion will go towards that carbon which has less number of hydrogens attached.

02

Final answer

Here first double bond attack on H and HBr releases Br- ion. Then it will form carbonation which on hydride shift form 3掳 carbocation. Which is more stable than 2掳 carbocation. Br- reacts on both 2掳 and 3掳 carbocation and form two products i.e. 2-bromo-3-methylbutane and 2-bromo-2-methylbutane.

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Most popular questions from this chapter

What aspect of the structure of the alkene does ozonolysis not tell you ?

What stereoisomers would you expect to obtain from each of the following reactions

Which electrophilic addition reactions

a. form a carbocation intermediate? c. form a three-membered ring intermediate?

b. form no intermediate? d. form a five-membered ring intermediate?

Propose a mechanism for each of the following reactions:

a. How many s bond orbitals are available for overlap with the vacant p orbital in the methyl cation?

b. Which is more stable: a methyl cation or an ethyl cation? Why?
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