Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 14.SE, Problem 51AP
Draw the resonance forms that result when the dienes below are protonated. If the resonance forms differ in energy, identify the most stable one.
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Diels–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 often predominates. Draw the resonance hybrid for each reactant, and use the charge distribution of the hybrids to explain why the 1,2-disubstituted product is the major product.
Diels–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.
Fill in the blank with either cumulated, conjugated, or isolated.
a
Compound a is a
diene.
Compound b is a
diene.
Compound c is a
diene.
The most stable compound is the
diene.
Chapter 14 Solutions
Organic Chemistry
Ch. 14.1 - Prob. 1PCh. 14.2 - Give the structures of both 1, 2 and 1, 4 adducts...Ch. 14.2 - Prob. 3PCh. 14.2 - Give the structures of both 1, 2 and 1, 4 adducts...Ch. 14.3 - Prob. 5PCh. 14.3 - Prob. 6PCh. 14.5 - Predict the product of the following Diels–Alder...Ch. 14.5 - Prob. 8PCh. 14.5 - Which of the following dienes have an s-cis...Ch. 14.5 - Predict the product of the following Diels–Alder...
Ch. 14.6 - Prob. 11PCh. 14.6 - Prob. 12PCh. 14.7 - Prob. 13PCh. 14.7 - Prob. 14PCh. 14.8 - Which of the following compounds would you expect...Ch. 14.SE - Prob. 16VCCh. 14.SE - Show the product of the Diels–Alder reaction of...Ch. 14.SE - Prob. 18VCCh. 14.SE - Prob. 19VCCh. 14.SE - Prob. 20MPCh. 14.SE - Prob. 21MPCh. 14.SE - In light of your answer to Problem 14-21 propose...Ch. 14.SE - Luminol, which is used by forensic scientists to...Ch. 14.SE - Prob. 24MPCh. 14.SE - Give IUPAC names for the following compounds:Ch. 14.SE - Prob. 26APCh. 14.SE - Prob. 27APCh. 14.SE - Electrophilic addition of Br2 to isoprene...Ch. 14.SE - Prob. 29APCh. 14.SE - Prob. 30APCh. 14.SE - Predict the products of the following...Ch. 14.SE - 2,3-Di-tert-butyl-1,3-butadiene does not undergo...Ch. 14.SE - Prob. 33APCh. 14.SE - Prob. 34APCh. 14.SE - Prob. 35APCh. 14.SE - Prob. 36APCh. 14.SE - Rank the following dienophiles in order of their...Ch. 14.SE - Prob. 38APCh. 14.SE - Prob. 39APCh. 14.SE - Prob. 40APCh. 14.SE - Although the Diels–Alder reaction generally...Ch. 14.SE - Prob. 42APCh. 14.SE - Tires whose sidewalls are made of natural rubber...Ch. 14.SE - Prob. 44APCh. 14.SE - Prob. 45APCh. 14.SE - Prob. 46APCh. 14.SE - Would you expect allene, H2C = C = CH2, to show a...Ch. 14.SE - The following ultraviolet absorption maxima have...Ch. 14.SE - Prob. 49APCh. 14.SE - -Ocimene is a pleasant-smelling hydrocarbon found...Ch. 14.SE - Draw the resonance forms that result when the...Ch. 14.SE - Prob. 52APCh. 14.SE - Treatment of 3,4-dibromohexane with strong base...Ch. 14.SE - Prob. 54APCh. 14.SE - Prob. 55APCh. 14.SE - Prob. 56APCh. 14.SE - Prob. 57APCh. 14.SE - Prob. 58APCh. 14.SE - Hydrocarbon A, C10H14, has a UV absorption at...Ch. 14.SE - Prob. 60APCh. 14.SE - Prob. 61APCh. 14.SE - Prob. 62APCh. 14.SE - Prob. 63APCh. 14.SE - Prob. 64APCh. 14.SE - The double bond of an enamine (alkene + amine) is...Ch. 14.SE - Prob. 66AP
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- 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_forwardWhich diene would you expect to be more stable? Which diene would you expect to be more stable? 2 H₂ Pt 2 H₂ Pt MacBook Airarrow_forwardWhich one of these dienes is least stable? H3C C=c=c CH3 H H3C A B Earrow_forward
- Which of the following is an isolated diene? A A B C C D D E E ad A B C D B.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_forward2) Rank the following dienes in order of increasing rate of Diels-Alder reaction with maleic anhydride. You do not need to explain your ranking. H3C. H3CO Diene A Diene B Diene Carrow_forward
- Draw the major product of the following Diels-Alder reaction. Use the Bicyclic ring tool and guide points to draw bicyclic molecules. NC CN A Click and drag to start drawing a structure. X Ö 4 Sarrow_forwardWhat is a reactant for the following Diels Alder reaction? Y NO CN ON temp CN D NCarrow_forwardName 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_forward
- 9. Which of the following dienes could react with acrylonitrile (dienophile in the reaction) in a Diels-Alder reaction? CH, A acrylonitrile B B. pCH, HC C CH Nal 3- Brarrow_forward3 Please give one example for the classes of different dienes. Please explain why the conjugated diene is most stable.arrow_forwardDetermine the starting material (diene and dienophile) for the following compound.arrow_forward
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