To determine: The mechanism for the rearrangement reaction of
Interpretation: The mechanism for the rearrangement reaction of
Concept introduction: Tautomerization is the process in which molecular formula of compounds remain same but connectivity of atoms or substituents in compounds become different. The stability of compound is the major factor that determines the formation of a compound. The compounds that have low energy are energetically favourable.
Conjugated systems possess alternate single and double bonds that results in lower energy of molecule and increase in stability of a molecule.
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Chapter 15 Solutions
Organic Chemistry (9th Edition)
- When 1-chlorocyclohexene reacts with HBr, the major product is 1-bromo- 1-chlorocyclohexane. Propose a mechanism for this reaction, and explain why your proposed intermediate is more stable than the other possible intermediate.arrow_forwardAlkylation of benzene with 1-chlorobutane in the presence of AlCl3 gave not only the expected butylbenzene product but also, as a major product, (1-methylpropyl)benzene. Write an equation for the reaction Propose a mechanism to account for the formation of butylbenzene Propose a mechanism to account for the formation of (1-methylpropyl)benzenearrow_forwardTreatment of trans-2-chlorocyclohexanol with NaOH yields 1, 2-epoxy-cyclohexane, but reaction of the cis isomer under the same conditions yields cyclohexanone. Propose mechanisms for both reactions, and explain why the different results are obtained.arrow_forward
- Treating cyclohexene with HBr in the presence of acetic acid gives bromocyclohexane (85%) and cyclohexyl acetate (15%). Br OCCH CH,COH + HBr Bromocyclohexane Cyclohexyl acetate (15%) Cyclohexene (85%) Propose a mechanism for the formation of the latter product.arrow_forwardBicyclo-2,5-heptadiene can be prepared in two steps from cyclopentadiene and vinyl chloride. Provide a mechanism for each step.arrow_forwardNonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forward
- Aldehydes and ketones react with thiols to yield thioacetals just as they react with alcohols to yield acetals. Predict the product of the following reaction, and propose a mechanism:arrow_forwardWhen 3-bromo-1-methylcyclohexene undergoes solvolysis in hot ethanol, two productsare formed. Propose a mechanism that accounts for both of these productsarrow_forwardWhen cyclohexene is treated with bromine in saturated aqueous sodium chloride, a mixture of trans-2-bromocyclohexanol and trans-1-bromo-2-chlorocyclohexane results.Propose a mechanism to account for these two products.arrow_forward
- On treatment with HBr, 3-Methyl-1-pentene undergoes addition and rearrangement to yield 3-Bromo-3-methylpentenearrow_forwardShow how the following starting material is converted to the given product by a series of two pericyclic reactions. Account for the observed stereochemistry.arrow_forwardTreating 1-methyl-1-vinylcyclopentane with HCl gives mainly 1-chloro-1,2-dimethylcyclohexane. Propose a mechanism for the formation of this product.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning