Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 16, Problem 16.59P
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.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
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
Show mechanism arrows
for this step!
4 + 2 cycloaddition
OH
H
D- &
H+ transfer
OH
Nuc acyl
substitution
H
L.G.
Chapter 16 Solutions
Organic Chemistry-Package(Custom)
Ch. 16 - Prob. 16.1PCh. 16 - Prob. 16.2PCh. 16 - Draw a second resonance structure for each...Ch. 16 - Prob. 16.4PCh. 16 - Prob. 16.5PCh. 16 - Prob. 16.6PCh. 16 - Prob. 16.7PCh. 16 - Determine the hybridization of the labeled atom in...Ch. 16 - Problem 16.10 Draw the structure consistent with...Ch. 16 - Problem 16.11 Neuroprotectin D1 (NPD1) is...
Ch. 16 - Problem 16.12 Using hybridization, predict how the...Ch. 16 - Problem 16.13 Use resonance theory to explain why...Ch. 16 - Prob. 16.13PCh. 16 - Prob. 16.14PCh. 16 - Prob. 16.15PCh. 16 - Problem 16.17 Draw a stepwise mechanism for the...Ch. 16 - Prob. 16.17PCh. 16 - Problem 16.19 Draw the product formed when each...Ch. 16 - Prob. 16.19PCh. 16 - Prob. 16.20PCh. 16 - Rank the following dienophiles in order of...Ch. 16 - Prob. 16.22PCh. 16 - Prob. 16.23PCh. 16 - Prob. 16.24PCh. 16 - Prob. 16.25PCh. 16 - Problem 16.27 Which compound in each pair absorbs...Ch. 16 - Prob. 16.27PCh. 16 - 16.29 Name each diene and state whether the...Ch. 16 - Prob. 16.29PCh. 16 - Prob. 16.30PCh. 16 - Prob. 16.31PCh. 16 - Prob. 16.32PCh. 16 - Prob. 16.33PCh. 16 - Prob. 16.34PCh. 16 - 16.35 Explain why the cyclopentadienide anion A...Ch. 16 - Explain each statement using resonance theory. a....Ch. 16 - 16.37 Draw the structure of each compound.
a. in...Ch. 16 - Draw and name all dienes of molecular formula...Ch. 16 - Prob. 16.39PCh. 16 - 16.39 Label each pair of compounds as...Ch. 16 - Prob. 16.41PCh. 16 - 16.41 Draw the products formed when each compound...Ch. 16 - Prob. 16.43PCh. 16 - 16.43 Treatment of alkenes A and B with gives the...Ch. 16 - 16.44 Draw a stepwise mechanism for the following...Ch. 16 - Prob. 16.46PCh. 16 - 16.46 Explain, with reference to the mechanism,...Ch. 16 - Prob. 16.48PCh. 16 - Prob. 16.49PCh. 16 - Prob. 16.50PCh. 16 - Prob. 16.51PCh. 16 - Prob. 16.52PCh. 16 - Prob. 16.53PCh. 16 - 16.53 Diels–Alder reaction of a monosubstituted...Ch. 16 - Prob. 16.55PCh. 16 - Prob. 16.56PCh. 16 - 16.55 Devise a stepwise synthesis of each compound...Ch. 16 - Prob. 16.58PCh. 16 - 16.57 A transannular Diels–Alder reaction is an...Ch. 16 - Draw a stepwise mechanism for the following...Ch. 16 - Draw the products of each reaction. Indicate the...Ch. 16 - Prob. 16.62PCh. 16 - Prob. 16.63PCh. 16 - Prob. 16.64PCh. 16 - 16.65 The treatment of isoprene with one...Ch. 16 - 16.66 The treatment of with forms B (molecular...Ch. 16 - Rank the following compounds in the order of...Ch. 16 - Prob. 16.68PCh. 16 - Prob. 16.69PCh. 16 - Prob. 16.70PCh. 16 - Prob. 16.71PCh. 16 - Prob. 16.72PCh. 16 - Prob. 16.73PCh. 16 - Prob. 16.74P
Knowledge Booster
Learn more about
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
- What kind of compounds are prepared using the Diels Alder reaction?arrow_forwardDraw 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_forwardThe Diels–Alder Reaction – A [4+2] Cycloaddition Experiment. During the experiment we used Maleic Anhydride and Furan. Draw a mechanism for the [4+2] cycloaddition.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_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_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_forward
- 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
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Alcohols, Ethers, and Epoxides: Crash Course Organic Chemistry #24; Author: Crash Course;https://www.youtube.com/watch?v=j04zMFwDeDU;License: Standard YouTube License, CC-BY