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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

a. Identify two alkenes that react with HBr to form 1-bromo-1-methylcyclohexane without undergoing a carbocation rearrangement.

b. Would both alkenes form the same alkyl halide if DBr were used instead of HBr? (D is an isotope of H, so D+ reacts like H+.)

What will be the major product obtained from the reaction of Br2 with 1-butene if the reaction is carried out in

a. dichloromethane?

b. water?

c. ethyl alcohol?

d. methyl alcohol?

Why are Na+ and K+ unable to form covalent bonds?

What is the product of the addition of I-Cl to 1-butene? (Hint: Chlorine is more electronegative than iodine [Table 1.3].)

:a. How does the first step in the reaction of propene with Br2 differ from the first step in the reaction of propene with HBr?

b. To understand why Br- adds to a carbon of the bromonium ion rather than to the positively charged bromine, draw the product that would be obtained if Br- did add to bromine.
See all solutions

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