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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One step in the synthesis of dodecahedrane involves reaction of the tetraene C with dimethylacetylene dicarboxylate (D) to afford two compounds having molecular formula C16H16O4. This reaction has been called a domino Diels–Alder reaction. Identify the two products formed.
When anthracene is added to the reaction of chlorobenzene with concentrated NaOH at 350 °C, an interesting Diels–Alderadduct of formula C20H14 results. The proton NMR spectrum of the product shows a singlet of area 2 around d 3 and abroad singlet of area 12 around d 7. Propose a structure for the product, and explain why one of the aromatic rings ofanthracene reacted as a diene
Following 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.
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 0"C Diels-Alder adductarrow_forwardcis-1-Bromo-4-tert-butylcyclohexane and trans-1-bromo-4-tert-butylcyclohexane both react with sodium ethoxide in ethanol to form 4-tert-butylcyclohexene. Explain why the cis isomer reacts much more rapidly than the trans isomer.arrow_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_forward
- Draw the reactants that would be used to form this cyclohexene derivative in a Diels- Alder reaction. Include any relevant stereochemical configurations. Draw Diene + ·00 aarrow_forwardDraw the reactants that would react to form this cyclohexene derivative in a Diels-Alder reaction. Include any relevant stereochemical configurations. Draw Diene ✔ Iarrow_forwardCyclopentadienyl 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_forward
- Chlordane, 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_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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