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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

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.

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?

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

Propose a mechanism for the following reaction:

The second-order rate constant (in units of M-1 s-1) for acid-catalysed hydration at 25 °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 × 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?
See all solutions

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