Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 15, Problem 15.61AP
Interpretation Introduction
Interpretation:
The reason corresponding to the fact that
Concept introduction:
Diels Alder reaction is the reaction between a substituted
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True or False: Acetylene is a naturally occurring conjugated diene
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True or False: the mechanism of the Diels-Alder reaction is three π bonds break; one σ bond and two π bonds form.
1. Compare the electron density maps for the two
compounds. (They were both created using the
same color scale.) There is more electron density
around the oxygen in cycloheptatrienone
compared to the oxygen in cyclopentadienone.
Explain the difference.
Cycloheptatrienone
Cyclopentadienone
2. One of your labs in CHM2211L uses
cyclopentadiene as a reagent in a Diels-Alder
reaction. However, before it can be used in that
reaction it must be heated and distilled as the
compound dimerizes while it is stored. Draw the
dimerization reaction in bond line form.
3. Is the following compound aromatic? Detail how it
meets or does not meet the qualifications of
aromaticity. If it is not aromatic, could it easily be
converted into an aromatic compound? How?
H
CX
H
G.165.
Chapter 15 Solutions
Organic Chemistry
Ch. 15 - Prob. 15.1PCh. 15 - Prob. 15.2PCh. 15 - Prob. 15.3PCh. 15 - Prob. 15.4PCh. 15 - Prob. 15.5PCh. 15 - Prob. 15.6PCh. 15 - Prob. 15.7PCh. 15 - Prob. 15.8PCh. 15 - Prob. 15.9PCh. 15 - Prob. 15.10P
Ch. 15 - Prob. 15.11PCh. 15 - Prob. 15.12PCh. 15 - Prob. 15.13PCh. 15 - Prob. 15.14PCh. 15 - Prob. 15.15PCh. 15 - Prob. 15.16PCh. 15 - Prob. 15.17PCh. 15 - Prob. 15.18PCh. 15 - Prob. 15.19PCh. 15 - Prob. 15.20PCh. 15 - Prob. 15.21PCh. 15 - Prob. 15.22PCh. 15 - Prob. 15.23PCh. 15 - Prob. 15.24PCh. 15 - Prob. 15.25PCh. 15 - Prob. 15.26PCh. 15 - Prob. 15.27PCh. 15 - Prob. 15.28PCh. 15 - Prob. 15.29PCh. 15 - Prob. 15.30PCh. 15 - Prob. 15.31PCh. 15 - Prob. 15.32PCh. 15 - Prob. 15.33PCh. 15 - Prob. 15.34PCh. 15 - Prob. 15.35PCh. 15 - Prob. 15.36PCh. 15 - Prob. 15.37PCh. 15 - Prob. 15.38PCh. 15 - Prob. 15.39PCh. 15 - Prob. 15.40PCh. 15 - Prob. 15.41PCh. 15 - Prob. 15.42APCh. 15 - Prob. 15.43APCh. 15 - Prob. 15.44APCh. 15 - Prob. 15.45APCh. 15 - Prob. 15.46APCh. 15 - Prob. 15.47APCh. 15 - Prob. 15.48APCh. 15 - Prob. 15.49APCh. 15 - Prob. 15.50APCh. 15 - Prob. 15.51APCh. 15 - Prob. 15.52APCh. 15 - Prob. 15.53APCh. 15 - Prob. 15.54APCh. 15 - Prob. 15.55APCh. 15 - Prob. 15.56APCh. 15 - Prob. 15.57APCh. 15 - Prob. 15.58APCh. 15 - Prob. 15.59APCh. 15 - Prob. 15.60APCh. 15 - Prob. 15.61APCh. 15 - Prob. 15.62APCh. 15 - Prob. 15.63APCh. 15 - Prob. 15.64APCh. 15 - Prob. 15.65APCh. 15 - Prob. 15.66APCh. 15 - Prob. 15.67APCh. 15 - Prob. 15.68APCh. 15 - Prob. 15.69APCh. 15 - Prob. 15.70APCh. 15 - Prob. 15.71APCh. 15 - Prob. 15.72APCh. 15 - Prob. 15.73APCh. 15 - Prob. 15.74APCh. 15 - Prob. 15.75APCh. 15 - Prob. 15.76APCh. 15 - Prob. 15.77APCh. 15 - Prob. 15.78APCh. 15 - Prob. 15.79APCh. 15 - Prob. 15.80APCh. 15 - Prob. 15.81APCh. 15 - Prob. 15.82APCh. 15 - Prob. 15.83APCh. 15 - Prob. 15.84APCh. 15 - Prob. 15.85APCh. 15 - Prob. 15.86AP
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- The following triene undergoes an intramolecular Diels-Alder reaction to give a bicyclic product. Propose a structural formula for the product. Account for the observation that the Diels-Alder reaction given in this problem takes place under milder conditions (at lower temperature) than the analogous Diels-Alder reaction shown in Problem 20.34.arrow_forward1,3-Butadiene is a gas at room temperature that requires a gas-handling apparatus to use in a Diels-Alder reaction. Butadiene sulfone is a convenient substitute for gaseous 1,3-butadiene. This sulfone is a solid at room temperature (mp 66°C), and when heated above its boiling point of 110°C, it decomposes by a reverse Diels-Alder reaction to give cis-1,3-butadiene and sulfur dioxide. Draw Lewis structures for butadiene sulfone and SO, then show by curved arrows the path of this reaction, which resembles a reverse Diels-Alder reaction. 140°C SO2 Butadiene sulfone 1,3-Butadiene Sulfur dioxidearrow_forwardDraw the reactants that would react to form this cyclohexene derivative in a Diels-Alder reaction. Include any relevant stereochemical configurations. Draw Diene ✔ Iarrow_forward
- | Anthracene readily undergoes a Diels-Alder reaction with tetracyanoethene, even though anthracene is NC CN ? + aromatic. NC CN (a) Draw two possible products that can form from this reaction. (b) Explain why anthracene can readily undergo a Diels-Alder reaction, whereas benzene does not.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_forwardThe following is an example of a hetero Diels-Alder reaction, because a noncarbon atom (in this case, an N atom) is involved in bond formation and bond breaking. Draw the curved arrows necessary to account for this transformation. OCH3 OCH3 + N- Hydroquinone, benzene, 25 °C, 90 min 86%arrow_forward
- Cyclopentadienyl anion (shown) has the following characteristic. O it is an anion with six π electrons, meeting the Hückel rule for aromaticity O it is not aromatic because it has only four electrons and the tetrahedral carbon prevents cyclic conjugation O it is an anion with six electrons, meeting the Hückel rule for anti-aromaticity O it is an anion with four electrons, meeting the Hückel rule for aromaticityarrow_forwardChlordane, like DDT, is an alkyl halide that was used as an insecticide for crops such as corn and citrus and for lawns. In 1983, it was banned for all uses except against termites, and in 1988, it was banned for use against termites as well. Chlordane can be synthesized from two reactants in one step. One of the reactants is hexachlorocyclopentadiene. What is the other reactant?arrow_forwardWhen heated, allyl aryl ethers and allyl vinyl ethers undergo a reaction called a Claisen rearrangement, a concerted reorganization of bonding electrons similar to the Diels-Alder reaction. The reaction proceeds through a six-membered, cyclic transition state. Draw the structure of the expected product when this compound undergoes a Claisen rearrangement. You do not have to consider stereochemistry. For the purposes of this problem, assume that double bonds in an aromatic ring are localized at the positions indicated in the figure. Include isomerization to a phenol IF appropriate.arrow_forward
- When heated, allyl aryl ethers and allyl vinyl ethers undergo a reaction called a Claisen rearrangement, a concerted reorganization of bonding electrons similar to the Diels-Alder reaction. The reaction proceeds through a six-membered, cyclic transition state. Draw the structure of the expected product when this compound undergoes a Claisen rearrangement. You do not have to consider stereochemistry. For the purposes of this problem, assume that double bonds in an aromatic ring are localized at the positions indicated in the figure. Include isomerization to a phenol IF appropriate.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_forwardReaction of HBr with 3-methylcyclohexene yields a mixture of four products: cis-and trans-1-bromo-3-methylcyclohexane and cis-and trans-1-bromo-2-methylcyclohexane. The analogous reaction of HBr with 3-bromocyclohexene yields trans-1, 2-dibromocyclohexane as the soleproduct. Draw structures of the possible intermediates, and then explain why only a single product is formed in this reaction.arrow_forward
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