Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Question
Chapter 16, Problem 16.39SP
(a)
Interpretation Introduction
Interpretation:
The Kekule structure that shows the reactive positions of anthracene that are the ends of a diene, appropriate for a Diels-Alder reaction is to be drawn.
Concept introduction:
Diels-Alder reaction is used for the formation of rings or bicyclic compounds by the cycloaddition reaction between a diene and a dienophile.
(b)
Interpretation Introduction
Interpretation:
The information regarding the reaction of anthracene with maleic anhydride is given. The product of Diels-Alder reaction of anthracene with maleic anhydride is to be stated.
Concept introduction:
Diels-Alder reaction is used for the formation of rings or bicyclic compounds by the cycloaddition reaction between a diene and a dienophile.
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Students have asked these similar questions
10. The following compound was produced in a Diels-Alder reaction.
COOH
a) How many sp³ hybridized carbons are in this molecule?
b) Is this molecule chiral?
c) Are the carboxylic acid substituents electron donating group or electron withdrawing group?
d) Draw the diene and dienophile which would react together to give this product.
3) In a recently-published synthesis of yohimbine (used in folk medicine as an aphrodisiac), the
Diels-Alder reaction was used to form a new ring during a key step.
7
R
N-
-CVI
O
Spring
OtBu
Diels-Alder
a. Draw a circle around the four atoms of the diene group in this molecule.
b. Draw a square around the two atoms of the best dienophile group in this molecule.
c. Draw the product of this reaction, ignoring stereochemistry.
Draw structural formulas for the diene and dienophile that combine in a Diels-Alder reaction to form the
product shown.
Diene + Dienophile
?
CH3
Consider E/Z stereochemistry of alkenes.
• Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the
bottom right corner.
Separate multiple products using the + sign from the drop-down menu.
Lits
O. Sn [F
CH3
Chapter 16 Solutions
Organic Chemistry (9th Edition)
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...
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