Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Question
Chapter 6, Problem 6.53P
Interpretation Introduction
Interpretation:
Considering the given example which depicts the Diels-Alder reaction it should be predicted that whether the reaction is exothermic or endothermic reaction.
Concept Introduction:
Exothermic reaction: Exothermic reactions are those reactions in which heat energy is released during the reaction.
Endothermic reaction: Endothermic reactions are those in which heat is absorbed during any
Diels-Alder reaction: It is the reaction between the conjugated diene and dienophile which results in the formation of new compound which is substituted cyclohexene derivative.
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The 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.
True 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.
Mechanism
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.
Chapter 6 Solutions
Organic Chemistry
Ch. 6.2 - Using the BDE values from Appendix 3, calculate...Ch. 6.3 - Name and draw a structural formula for the product...Ch. 6.3 - Prob. 6.3PCh. 6.3 - Propose a mechanism for the addition of HI to...Ch. 6.3 - Prob. 6.5PCh. 6.3 - Propose a mechanism for the acid-catalyzed...Ch. 6.3 - The acid-catalyzed hydration of...Ch. 6.3 - Complete these reactions. (a) (b)Ch. 6.3 - Draw the structure of the chlorohydrin formed by...Ch. 6.4 - Draw structural formulas for the alkene that gives...
Ch. 6.5 - Prob. 6.11PCh. 6.5 - Prob. 6.12PCh. 6.5 - What alkene with the molecular formula C6H12, when...Ch. 6 - Prob. 6.15PCh. 6 - Prob. 6.16PCh. 6 - Predict the organic product(s) of the reaction of...Ch. 6 - Prob. 6.18PCh. 6 - Prob. 6.20PCh. 6 - Draw a structural formula for an alkene with the...Ch. 6 - Account for the fact that addition of HCl to...Ch. 6 - Account for the fact that treating propenoic acid...Ch. 6 - Draw a structural formula for the alkene with the...Ch. 6 - Draw the alternative chair conformations for the...Ch. 6 - Draw a structural formula for the cycloalkene with...Ch. 6 - Reaction of this bicycloalkene with bromine in...Ch. 6 - Terpin, prepared commercially by the...Ch. 6 - Propose a mechanism for this reaction and account...Ch. 6 - Treating 2-methylpropene with methanol in the...Ch. 6 - When 2-pentene is treated with Cl2 in methanol,...Ch. 6 - Treating cyclohexene with HBr in the presence of...Ch. 6 - Propose a mechanism for this reaction. 1-Pentane...Ch. 6 - Treating 4-penten-1-ol with bromine in water forms...Ch. 6 - Prob. 6.35PCh. 6 - Prob. 6.36PCh. 6 - Reaction of -pinene with borane followed by...Ch. 6 - Write structural formulas for the major organic...Ch. 6 - Draw the structural formula of the alkene that...Ch. 6 - Consider the following reaction. (a) Draw a...Ch. 6 - Prob. 6.42PCh. 6 - Prob. 6.43PCh. 6 - Show how to convert ethylene to these compounds....Ch. 6 - Show how to convert cyclopentene into these...Ch. 6 - Prob. 6.46PCh. 6 - Describe the stereochemistry of the bromohydrin...Ch. 6 - Prob. 6.49PCh. 6 - Treating 1,3-butadiene with 1 mole of HBr gives a...Ch. 6 - In this chapter, we studied the mechanism of the...Ch. 6 - As we have seen in this chapter, carbon-carbon...Ch. 6 - Prob. 6.53PCh. 6 - Prob. 6.54P
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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- A chemist is attempting to synthesize a complex natural product with a highly strained cyclohexene ring system. Which type of reactants would be most suitable for achieving this goal, and why? Provide a detailed explanation of the choice of reactants and the expected outcome in terms of the Diels-Alder reaction.arrow_forwardUemura and coworkers studied a time dependent Diels-Alder reaction which first formed the endo product as the major organic product and with time produced the exo product (J. Org. Chem. 2018, 83, 9300−9304). Show the endo and exo product for the reaction below. Which is the thermodynamic product and which is the kinetic product? Explain your reasoning.arrow_forwardWhich of these dienes can undergo a Diels-Alder reaction? II III IV O Ll and V O l and V O l and IVarrow_forward
- A Diels-Alder reaction calls for the use of 5.9 mL of a 4.0 M solution of cyclopentadiene in methanol. Calculate the number of moles of cyclopentadiene present in this volume. mol number of moles of cyclopentadiene:arrow_forwardFollowing is an example of a type of reaction known as a Diels-Alder reaction 1,3-Pentadiene Ethylene 3-Methylcyclohexene (a racemic mixture) The Diels-Alder reaction between a diene and an alkene is quite remarkable in that it is one of the few ways that chemists have to form two new carbon-carbon bonds in a single reaction. Given what you know about the relative strengths of carbon-carbon sigma and pi bonds, would you predict the Diels-Alder reaction to be exothermic or endothermic? Explain your reasoning.arrow_forward4B2 Write the possible reactants that gave the following products in the Diels-Alder reaction -H O OEtarrow_forward
- Which combination of reactants would react to give the following Diels-Alder produc CN +. CN CN II OH CN ČN IV IIIarrow_forward70 ins210 V16225050 panx qalborgo 3) In a recently-published synthesis of yohimbine (used in folk medicine as an aphrodisiac), the Diels-Alder reaction was used to form a new ring during a key step. R OtBu Diels-Alder a. Draw a circle around the four atoms of the diene group in this molecule. b. Draw a square around the two atoms of the best dienophile group in this molecule. c. Draw the product of this reaction, ignoring stereochemistry.arrow_forwardDiels–Alder reaction of a monosubstituted diene (such as CH2=CH–CH=CHOCH3) with a monosubstituted dienophile (such as CH2=CHCHO)gives a mixture of products, but the 1,2-disubstituted product oftenpredominates. Draw the resonance hybrid for each reactant, and use thecharge distribution of the hybrids to explain why the 1,2-disubstitutedproduct is the major product.arrow_forward
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