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Chapter 6: Q25P (page 256)

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?

Short Answer

Expert verified
  • The solvent CH2Cl2 is utilised to dissolve both reactants but is not involved in the reaction.
  • The intermediate cyclic bromonium ion will react with Br- (nucleophile).

Step by step solution

01

a) If the reaction is carried out in a Dichloromethane medium, Br2 reacts with 1-butene-

  • The solvent CH2Cl2 is utilised to dissolve both reactants but is not involved in the reaction.
  • The intermediate cyclic bromonium ion will react with Br- (nucleophile).

02

If the reaction is carried out in a water medium, Br2 reacts with 1-butene.

  • The first step is the electrophilic assault of H3O+ on the alkene, which results in the formation of a carbocation intermediate.
  • Water reacts with carbocation in the second stage, which is a quick reaction.

The third stage is deprotonation, which produces a neutral product (fast reaction

03

Br2 reacts with 1-butene if the reaction is carried out in the presence of 1-butene-

The first step is the electrophilic assault of H3O+ on the alkene, which results in ethyl alcoholthe formation of a carbocation intermediate.

  • reacts with carbocation in the second stage, which is a quick reaction.
  • The third stage is deprotonation, which produces a neutral product (fast reaction).

04

If the reaction is carried out in methyl alcohol medium, Br2 reacts with 1-butene-

  • The first step is the electrophilic assault of H3O+ on the alkene, which results in the formation of a carbocation intermediate.
  • The second step is when methanol reacts with the carbocation.

The third stage is deprotonation, which produces a neutral product (fast reaction

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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 stereoisomers are obtained when (S)-3-methyl-1-pentene reacts with Cl2?

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?

When fumarate reacts with D2O in the presence of the enzyme fumarase, only one isomer of the product is formed, as shown here. Is the enzyme catalyzing a syn or an anti-addition of D2O?

Each of the following reactions has two nucleophiles that could add to the intermediate formed by the reaction of the alkene with an electrophile. What is the major product of each reaction
See all solutions

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