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Chapter 15: Q5P. (page 760)

Question: When 3-bromo-1-methylcyclohexene undergoes solvolysis in hot ethanol, two products are formed. Propose a mechanism that accounts for both of these products.

Short Answer

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Answer

The mechanism of the reaction when 3-bromo-1-methylcyclohexene undergoes solvolysis in hot ethanol is:

Step by step solution

01

Solvolysis

Solvolysis is a chemical reaction in the presence of solvents like water and alcohol.These reagents are presently greater than required for the reaction to occur.

02

Mechanism when 3-bromo-1-methylcyclohexene undergoes solvolysis

When 3-bromo-1-methylcyclohexene is heated, bromine anion and 1-methylcyclohexene cation is formed. This allylic cation has resonance forms, and when treated with ethanol, the nucleophile attacks the positive charge. In the reaction mixture, the most basic species remove the proton, and the oxygen of the ethanol molecule is more basic than the bromide ion. The two products are formed from the reaction with hot ethanol.

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Most popular questions from this chapter

Question: Predict the product(s) of light-initiated reaction with NBS in CCl4 for the following starting materials.

  1. cyclohexene
  2. 3,4-dimethylhex-3-ene

Show that the [4+2] Diels-Alder reaction is photochemically forbidden.

When methylenecyclohexane is treated with a low concentration of bromine under irradiation by a sunlamp, two substitution products are formed.

  1. Propose structures for these two products.
  2. Propose a mechanism to account for their formation.

Show how you might synthesize the following compounds starting with bromobenzene, and alkyl or alkenyl halides of four carbon atoms or fewer.

a. 3-phenylprop-1-ene

b.5-methylhex-2-ene

c. dec-5-ene

Propose a mechanism for each reaction, showing explicitly how the observed mixtures of products are formed.

a) 3-methyl-but-2-en-1-ol+HBr→1-bromo-2-ene+3-bromo-3-methyl-1-ene

b)2-methyl-but-3-en-2a-ol+HBr→1-bromo-2-ene+3-bromo-3-methyl-1-enec)cyclopenta-1,3-diene+Br2→3,4-dibromocyclopent-1-ene+3,5-dibromocyclopent-1-ene

d)1-cholorobut-2-ene+AgNO3+H2O→but-2-en-1-ol+but-3-en-2-ol

e)3-cholorobut-1-ene+AgNO3+H2O→but-2-en-1-ol+but-3-en-2-ol
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