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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° carbocation. Which is more stable than 2° carbocation. Br- reacts on both 2° and 3° 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

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?

What is the major product of each of the following reactions?

What are the products of the following reactions? Indicate whether each reaction is an oxidation or a reduction.

a.What alkene is required to synthesize each of the following compounds?

b. What other epoxide would be formed?

c. Assign an Ror Sconfiguration to each asymmetric center.

What stereoisomers are obtained from each of the following reactions?
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