ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
9th Edition
ISBN: 9780137249442
Author: Wade
Publisher: INTER PEAR
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 16.2, Problem 16.4P
Show the product of the Diels-Alder dimerization of cyclobutadiene. (This reaction is similar to the dimerization of cyclopentadiene, discussed in Section15-11.)
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
6) The Diels-Alder reaction of anthracene (which is achiral) and maleic anhydride (also
achiral) results in the formation of an achiral product. This is not always the case (where
two achiral reactants form an achiral product).
a) Propose a Diels-Alder reaction where two achiral starting materials result in the
formation of a chiral product.
b) Would this chiral product be a single enantiomer or a racemic mixture?
Step 6: Now that you have determined the substrates and mechanism of a Diels-Alder reaction, you will learn how to recognize
when you should use the Diels-Alder reaction. In a synthesis reaction, if you are given a cyclohexene product with no other
obvious functional group transformations and an electron-withdrawing group two carbons away from the alkene, it is likely
made via the Diels-Alder reaction.
Deduce the structures of the starting materials to form the Diels-Alder adduct shown.
.....
CN
CN
Diene + Dienophile
The 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%
Chapter 16 Solutions
ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
Ch. 16.2 - Prob. 16.1PCh. 16.2 - Prob. 16.2PCh. 16.2 - a. Draw the resonance forms of benzene,...Ch. 16.2 - Show the product of the Diels-Alder dimerization...Ch. 16.4 - Prob. 16.5PCh. 16.6 - Make a model of cyclooctatetraene in the tub...Ch. 16.6 - Prob. 16.7PCh. 16.6 - Prob. 16.8PCh. 16.7 - Prob. 16.9PCh. 16.8A - a. Draw the molecular orbitals for the...
Ch. 16.8A - Repeat Problem16-10 for the cyclopentadienyl ions....Ch. 16.8C - Explain why each compound or ion should be...Ch. 16.8C - The following hydrocarbon has an unusually large...Ch. 16.8C - Prob. 16.14PCh. 16.8C - Prob. 16.15PCh. 16.9B - Prob. 16.16PCh. 16.9C - Show which of the nitrogen atoms in purine are...Ch. 16.9C - The proton NMR spectrum of 2-pyridone gives the...Ch. 16.9D - Prob. 16.19PCh. 16.9D - Prob. 16.20PCh. 16.10 - Prob. 16.21PCh. 16.12 - Ciprofloxacin is a member of the fluoroquinolone...Ch. 16.13 - Draw and name all the chlorinated benzenes having...Ch. 16.13 - Name the following compounds:Ch. 16.15 - The UV spectrum of 1-phenylprop-2-en-1-ol shows an...Ch. 16 - Prob. 16.26SPCh. 16 - Name the following compounds:Ch. 16 - Draw and name all the methyl, dimethyl, and...Ch. 16 - Four pairs of compounds are shown. In each pair,...Ch. 16 - One of the following hydrocarbons is much more...Ch. 16 - In Kekuls time cyclohexane was unknown, and there...Ch. 16 - Prob. 16.32SPCh. 16 - Azulene is a deep-blue hydrocarbon with resonance...Ch. 16 - Prob. 16.34SPCh. 16 - Prob. 16.35SPCh. 16 - Prob. 16.36SPCh. 16 - Prob. 16.37SPCh. 16 - Prob. 16.38SPCh. 16 - Prob. 16.39SPCh. 16 - Biphenyl has the following structure. a. Is...Ch. 16 - Anions of hydrocarbons are rare, and dianions of...Ch. 16 - How would you convert the following compounds to...Ch. 16 - Prob. 16.43SPCh. 16 - Prob. 16.44SPCh. 16 - A student found an old bottle labeled thymol on...Ch. 16 - Prob. 16.46SPCh. 16 - Prob. 16.47SPCh. 16 - Prob. 16.48SPCh. 16 - The proton NMR chemical shifts of the hydrogens in...Ch. 16 - Prob. 16.50SPCh. 16 - NMR has been used to probe many molecular...
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
- 1. Consider the Diels-Alder cycloaddition reaction below. D heat H D = deuterium = 2H Draw the major regioisomer (or in other words, constitutional isomer) expected to form. Draw appropriate resonance structures and explain why only one constitutional isomer is expected to form. Discuss if this can be drawn with both groups on the dieneophile being endo or one has to be endo and the other has to be exo.arrow_forwardA2 What is the inverse electron demand Diels–Alder reaction? Please pick a pair of a diene and a dienophile from the following dienes and dienophile that will undergo this type of reaction. Please show how this reaction works using Frontier Molecular Orbitals. What is the reaction product?arrow_forwardExp3: Diels-Alder reaction Why does cyclopentadiene regularly form a dimer? How to break the dimer into monomers? Does the diene in this reaction act as the nucleophile or the electrophile? Is the maleic anhydride a nucleophile or an electrophile in this reaction? Explain your reasoning.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_forwardRank the following dienes in order of their reactivity in standard Diels-Alder reactions (1= most reactive, 4= least reactive). Be sure to briefly explain your choices.arrow_forwardTrue or False: Acetylene is a naturally occurring conjugated diene True or False: The Diels-Alder reaction has the stereochemistry of the dienophile is retained in the product. True or False: When looking at kinetic vs. thermodynamic products the kinetic product predominates at low temperature. True or False: the mechanism of the Diels-Alder reaction is three π bonds break; one σ bond and two π bonds form.arrow_forward
- BASED ON THIS EXPERIMENT: The purpose of this experiment is to perform a Diels-Alder reaction between E,E-2,4-hexadien-1-ol and maleic anhydride in a "neat" or solventless condition. The Diels-Alder reaction is a [4+2] cycloaddition that forms a six-membered ring, typically a derivative of cyclohexene. The diene, E,E-2,4-hexadien-1-ol, and the dienophile, maleic anhydride, will be mixed and ground together, resulting in a eutectic mixture. The reaction is unique as it occurs without a solvent, contributing to a "greener" experiment. After the reaction, the product will be analyzed through mass measurements, and the mechanism involves a subsequent nucleophilic acyl substitution. QUESTION: how many carbon atoms does a dienophile contribute to the Diels-Alderadduct? How many carbon atoms does a diene contribute? draw andlabel which reagent is the diene, and which is the dienophile.arrow_forwardWrite a general rule that can be used to predict the major product of a Diels–Alder reaction between an alkene with an electron-withdrawing substituent and a diene with a substituent that can donate electrons by resonance depending on the location of the substituent on the diene.arrow_forwardThe Diels–Alder reaction between butadiene and dimethyl maleate yields a ring structure, as shown in the product. Complete the structure by drawing any missing bonds and indicating the stereochemistry of the new stereocenters.arrow_forward
- Predict the product of the following Diels-Alder reactions.arrow_forward4. Show using resonance which of the molecules below is considered an electron-donating group (EDG) and which the electron-withdrawing group (EWG): Он он vs. (a) Which dienophile above will cause a Diels-Alder reaction to proceed more rapidly with a higher yield? Briefly explain why this is the case.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 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.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
Coenzymes and cofactors; Author: CH15 SWAYAM Prabha IIT Madras;https://www.youtube.com/watch?v=bubY2Nm7hVM;License: Standard YouTube License, CC-BY
Aromaticity and Huckel's Rule; Author: Professor Dave Explains;https://www.youtube.com/watch?v=7-BguH4_WBQ;License: Standard Youtube License