Interpretation:
The structure of the conjugated diene that reacts with HBr to give the carbocation intermediate shown and that of the final products obtained during the reaction are to be given.
Concept introduction:
Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of bromide ion on each of these forms leads to the formation of a mixture of 1, 2- and 1, 4-addition products.
To give:
The structure of the conjugated diene that reacts with HBr to give the carbocation intermediate shown and that of the final product obtained during the reaction.
Trending nowThis is a popular solution!
Chapter 14 Solutions
Bundle: Organic Chemistry, Loose-leaf Version, 9th + LMS Integrated for OWLv2, 4 terms (24 months) Printed Access Card
- The aryl diene undergoes sequential Heck reactions to give a product with the molecular formula C15H18. Propose a structural formula for this product.arrow_forwardBicyclo-2,5-heptadiene can be prepared in two steps from cyclopentadiene and vinyl chloride. Provide a mechanism for each step.arrow_forwardShow the product of the Diels–Alder reaction of the following diene with 3-buten-2-one, H2C = CHCOCH3. Make sure you show the full stereochemistry of the reaction product.arrow_forward
- Following is a retrosynthetic scheme for the synthesis of the tricyclic diene on the left. Show how to accomplish this synthesis from 2-bromopropane, cyclopentadiene, and 2-cyclohexenone.arrow_forwardCarbocations undergo 1,2-methyl shift or 1,2-hydride shift to produce a more stable intermediate. Give the major product(s) obtained from the reaction of the alkene with HBr.SHOW THE FORMATION OF THE CARBOCATION, THE SHIFT THAT MAY OCCUR, AND THE MAJOR PRODUCT FORMED.arrow_forward2,3-Dimethylbutane reacts with bromine in the presence of light to give a mono brominated product. The further reaction gives a good yield of a dibrominated product. Predict the structures of these products, and propose a mechanism for the formation of the mono brominated product.arrow_forward
- What products would you expect from reaction of the following alkenes with NBS? If more than one product is formed, show the structures of all.arrow_forwardWrite the complete and detailed mechanism for THREE EXAMPLES of SN1 reactions. In each example , clearly name and identify the MOLECULES and PRODUCTS at each stage and use curved arrows to show electron movement at each stage of the reaction.arrow_forwardSuppose you were told that each reaction is a substitution reaction, but you were not told the mechanism. Describe how you could conclude from the structure of the haloalkane or cycloalkene, the nucleophile, and the solvent that each reaction is an SN1 reaction.arrow_forward
- In a strongly acidic solution, cyclohexa-1,4-diene tautomerizes to cyclohexa-1,3-diene.Propose a mechanism for this rearrangement, and explain why it is energetically favorablearrow_forwardWhat is the major substitution product for the following reaction? Show the mechanism for the reaction.arrow_forwardFriedel–Crafts alkylations can be carried out with carbocations formed from reactions other than the reaction of an alkyl halide with AlCl3. Propose a mechanism for the following reaction:arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning