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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

Addition of 1-bromobut-2-ene to magnesium metal in dry ether results in formation of a Grignard reagent. Addition of water to this Grignard reagent gives a mixture of but-1-ene and but-2-ene (cis and trans). When the Grignard reagent is made using 3-bromobut-1-ene, addition of water produces exactly the same mixture of products in the same ratios. Explain this curious result.

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

In Solved Problem 15-2, we simply predicted that the products would have a 1, 2-or 1, 4-relationship of the proper substitutents. Draw the charge-separated resonance forms of the reactants to support these predictions.

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

Question: When N-bromosuccinimide is added to hex-1-ene in CCl4and a sunlamp is shone on the mixture, three products result.

  1. Give the structures of these three products.
  2. Propose a mechanism that accounts for the formation of these three products.
See all solutions

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