Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Textbook Question
Chapter 14, Problem 58P
A transannular Diels–Alder reaction is an intramolecular reaction that occurs when the diene and dienophile are contained in one ring, resulting in the formation of a tricyclic ring system. Draw the product formed when the following triene undergoes a transannular Diels–Alder reaction.
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A possible side reaction is butadiene reacts with another butadiene via a Diels‐Alder reaction. Draw the structure of that 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.
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
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for this step!
4 + 2 cycloaddition
OH
H
D- &
H+ transfer
OH
Nuc acyl
substitution
H
L.G.
Chapter 14 Solutions
Organic Chemistry (6th Edition)
Ch. 14.1 - Prob. 2PCh. 14.2 - Problem 16.3 Draw a second resonance structure for...Ch. 14.2 - Prob. 4PCh. 14.2 - Problem 16.5 Farnesyl diphosphate is synthesized...Ch. 14.3 - Prob. 6PCh. 14.4 - Prob. 7PCh. 14.4 - Prob. 8PCh. 14.8 - Problem 16.12 Using hybridization, predict how the...Ch. 14.8 - Problem 16.13 Use resonance theory to explain why...Ch. 14.9 - Prob. 15P
Ch. 14.9 - Prob. 16PCh. 14.10 - Problem 16.17 Draw a stepwise mechanism for the...Ch. 14.11 - Prob. 19PCh. 14.12 - Problem 16.19 Draw the product formed when each...Ch. 14 - Prob. 32PCh. 14 - 16.31 Which of the following systems are...Ch. 14 - 16.32 Draw all reasonable resonance structures for...Ch. 14 - Prob. 35PCh. 14 - 16.35 Explain why the cyclopentadienide anion A...Ch. 14 - Prob. 38PCh. 14 - 16.37 Draw the structure of each compound.
a. in...Ch. 14 - 16.41 Draw the products formed when each compound...Ch. 14 - Prob. 44PCh. 14 - 16.43 Treatment of alkenes A and B with gives the...Ch. 14 - 16.44 Draw a stepwise mechanism for the following...Ch. 14 - Prob. 47PCh. 14 - 16.57 A transannular Diels–Alder reaction is an...Ch. 14 - Draw a stepwise mechanism for the following...Ch. 14 - Prob. 62PCh. 14 - Prob. 63PCh. 14 - Prob. 64PCh. 14 - Prob. 65PCh. 14 - 16.65 The treatment of isoprene with one...
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- Predict the major product of the following Diels-Alder reactions with the correct regiochemistry and stereochemistry. If an enantiomer is also made, indicate the enantiomer by adding “+ EN” beside the major product. Please explain step by step.arrow_forwardDraw structural formulas for the diene and dienophile that combine in a Diels-Alder reaction to form the product shown. CN Diene + Dienophile CH₂O • Consider E/Z stereochemistry of alkenes. CNarrow_forwardPredict the product(s) of the following Diels-Alder reaction. Include stereochemistry if appropriate.arrow_forward
- Draw the structures of the diene and dienophile that would be used in the diels alder reaction to synthesize the following compounds.arrow_forwardFor the Diels-Alder reaction, identify the diene, the dienophile, and the Diels-Alder adduct. H3CO. R OCH3 LOCH3 R H3CO R compound A compound B compound C Compound A is a: Compound B is a: Compound C is a:arrow_forwardRadical bromination of cyclohexene using NBS gives 3-bromo-1-cyclohexene. Draw the allylic radical intermediate formed during this reaction, showing both resonance structures.arrow_forward
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