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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+.)

The second-order rate constant (in units of M-1 s-1) for acid-catalysed hydration at 25 掳C is given for each of the following alkenes:

a. Calculate the relative rates of hydration of the alkenes. (Hint: Divide each rate constant by the smallest rate constant of the series: 3.51 脳 10-8.)

b. Why does (Z)-2-butene react faster than (E)-2-butene?

c. Why does 2-methyl-2-butene react faster than (Z)-2-butene?

d. Why does 2,3-dimethyl-2-butene react faster than 2-methyl-2-butene?

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?

The reaction of 2-ethyl-1-pentene with Br2, with H2 + Pd/C, or with R2BH/THF followed by aqueous HO- + H2O2 leads to a racemic mixture. Explain why a racemic mixture is obtained in each case.
See all solutions

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