Interpretation: In the given intramolecular Diels-Alder reaction, the structural formula of the product has to be predicted.
Concept Introduction:
Diels-Alder reaction:
It is the reaction of conjugated dienes with double or triple bonded compounds which are known as “dienophiles”. The reaction is a
Example:
This mechanism shown that three
Diels-Alder reaction to form bicyclic system:
The Diels-Alder adduct formed in the Diels-Alder reaction can also be a bicyclic system which will be obtained when cylopentadiene is used as the diene as shown here:
In this reaction, the cylopentadiene acts as both diene and dienophile and formed a bicyclic system. When it is heated to
Intramolecular reaction:
In the word “Intramolecular”- “Intra”- means “within” or “in”. So an intramolecular reaction means the reaction is taking place within one molecule itself without the involvement of any other molecules.
Trending nowThis is a popular solution!
Chapter 20 Solutions
Organic Chemistry
- 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_forwardClaisen rearrangement of an allyl phenyl ether with substituent groups in both ortho positions leads to the formation of a para-substituted product. Propose a mechanism for the following rearrangement.arrow_forwardBicyclo-2,5-heptadiene can be prepared in two steps from cyclopentadiene and vinyl chloride. Provide a mechanism for each step.arrow_forward
- Show how the following starting material is converted to the given product by a series of two pericyclic reactions. Account for the observed stereochemistry.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_forwardDraw the structure of each product from the reaction of benzene with 2-chloro-1-methylcyclohexane using AlCl 3 as the catalyst and Identify the major product.arrow_forward
- What is the major product formed from reacting cyclohexene in aqueous Br2, followed by treatment with potassium tert-butoxide?arrow_forwardIdentify products A and B from the given 1H NMR data. Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1H) ppm. What is the structure of B?arrow_forwardAn alkene is treated with OsO4 followed by H2O2. When the resulting diol is treated with HIO4, the only product obtained is an unsubstituted cyclic ketone with molecular formula C6H10O. What is the structure of the alkene?arrow_forward
- Aldehydes and ketones undergo acid-catalyzed reaction with alcohols to yield hemiacetals, compounds that have one alcohol-like oxygen and one ether-like oxygen bonded to the same carbon. Further reaction of a hemiacetal with alcohol then yields an acetal, a compound that has two ether-like oxygens bonded to the same carbon. Show the structure of the acetal that you would obtain by reaction of acetophenone with 2-propanol. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. Do not include lone pairs in your answer. They will not be considered in the grading. ?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_forwardWhen cis-4-chlorocyclohexanol is treated with sodium hydroxide in ethanol, it gives mainly the substitution product trans-1,4-cyclohexanediol (1). Under the same reaction conditions, trans-4-chlorocyclohexanol gives 3-cyclohexenol (2) and the bicyclic ether (3). (a) Propose a mechanism for formation of product (1), and account for its configuration. (b) Propose a mechanism for formation of product (2). (c) Account for the fact that the bicyclic ether (3) is formed from the trans isomer but not from the cis isomer.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning