Interpretation:
The order of reactivity of the given compounds in a Diels–Alder reaction is to be ranked along with explanation.
Concept introduction:
舧 Diels–Alder is a type of organic reaction in which substituted
舧 The general reaction of Diels–Alder is as follows:
舧 The Diels–Alder reaction is between a conjugate diene and a reactant containing double bond (dienophile) to form the product and the product is called adduct.
舧 Diels–Alder reactions are highly stereospecific. The configuration of dienophile is retained in the product and the reaction is syn addition.
舧 The dienes react with dienophiles in cis forms rather than trans forms
舧 Endo and exo refers to the orientation of dienophile and its electron withdrawing group, when it reacts with a diene in Diels Alder reaction.
舧 The reaction with orientation of electron withdrawing group of dienophiles under the
舧 The reaction with orientation of electron withdrawing group of dienophiles away from the
舧 Endo is favored in the transition state of Diels–Alder reaction because of its lower energy.
舧 If a compound is stable, it has lower energy and if a compound is unstable, it has higher energy.
Want to see the full answer?
Check out a sample textbook solutionChapter 13 Solutions
ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT
- Rank the following dienes in their rate of reaction with the same dienophile in a Diels-Alder reaction. For example, 1 = fastest or most reactive diene, 4 = slowest or least reactive diene.arrow_forwardTrue or False: Acetylene is a naturally occurring conjugated diene True or False: The Diels-Alder reaction has the stereochemistry of the dienophile is retained in the product. True or False: When looking at kinetic vs. thermodynamic products the kinetic product predominates at low temperature. True or False: the mechanism of the Diels-Alder reaction is three π bonds break; one σ bond and two π bonds form.arrow_forwardAs many as 18 different Diels–Alder products can be obtained by heating a mixture of 1,3-butadiene and 2-methyl-1,3-butadiene. Identify the productsarrow_forward
- Rank the following dienes in order of increasing reactivity in a Diels-Alder reaction.arrow_forwardA2 What is the inverse electron demand Diels–Alder reaction? Please pick a pair of a diene and a dienophile from the following dienes and dienophile that will undergo this type of reaction. Please show how this reaction works using Frontier Molecular Orbitals. What is the reaction product?arrow_forwardMechanism The Diels-Alder reaction is part of a class of reactions known as a cycloaddition reaction. This reaction is specifically a [4+2] cycloaddition which is a concerted (one-step) process in which two new carbon - carbon sigma bonds are formed from two pi bonds. For the first Diels - Alder step of the mechanism fill in the arrows needed for the transformation. The rest of the mechanism is drawn for you. OH Show mechanism arrows for this step! 4 + 2 cycloaddition OH H D- & H+ transfer OH Nuc acyl substitution H L.G.arrow_forward
- 2arrow_forwardOf the three 1,4-diphenyl-1,3-butadiene isomers (E,E or E,Z or Z,Z) indicate the most suitable diene that can be used as a reactant in a Diels-Alder reaction. Explain your choice.arrow_forward7. At room temperature cyclopentadiene reacts with itself to form dicyclopentadiene in a Diels-Alder reaction. a) draw the self reaction of cyclopentadiene 20°C. b) When dicyclopentadiene is heated to boiling (170°C), the retor-Diels-Alder reaction occurs producing 2 moles of cyclopentadiene. Explain this observation in terms of free energy, enthalpy and entropy. c) If the AHxn = -75 kJ/mol and the ASpxn = -226 J/mol K, What temperature would be required for the reaction to be at equilibrium (Keq = 1).arrow_forward
- Name the 2 nonconjugated dienes with formula C6H₁0 that contain an unbranched chain. If there is only one diene, leave the second space blank. Do not use E/Z designators to indicate stereochemistry. Diene #1: Diene #2:arrow_forwardWhat is the diene and dienophile?arrow_forwardThe Diels-Alder reaction is not limited to making six-membered rings with only carbon atoms. Predict the products of the following reaction that produce rings with atoms other than carbon in them.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning