Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Question
Chapter 15, Problem 15.29SP
(a)
Interpretation Introduction
To determine: The product that is formed when given diene reacts with methyl acetylenecarboxylate, a strong dienophile.
Interpretation: The product that is formed when given diene reacts with methyl acetylenecarboxylate, a strong dienophile is to be stated.
Concept introduction: Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and the diene adds to the one side of the dienophile. Thus, they have syn stereochemistry. In Diels-Alder reaction, the diene behaves like an electron rich species, whereas the dienophile behaves like an electron poor species.
(b)
Interpretation Introduction
To determine: The path by which the strongly exothermic decarboxylation takes place.
Interpretation: The path by which the strongly exothermic decarboxylation takes place is to be stated.
Concept introduction: Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and the diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.
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Exp3: Diels-Alder reaction
Why does cyclopentadiene regularly form a dimer? How to break the dimer into monomers?
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The diene shown below will NOT react in a Diels-Alder reaction. Why not?
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O A. The compound is lacking in electron donating groups.
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The diene shown below will NOT react in a Diels-Alder reaction. Why not?
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OA. The compound is lacking in electron withdrawing groups.
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Chapter 15 Solutions
Organic Chemistry (9th Edition)
Ch. 15.2 - Prob. 15.1PCh. 15.2 - Prob. 15.2PCh. 15.2 - Prob. 15.3PCh. 15.4 - Prob. 15.4PCh. 15.4 - Prob. 15.5PCh. 15.5 - Treatment of an alkyl halide with AgNO3 in alcohol...Ch. 15.5 - Propose a mechanism for each reaction, showing...Ch. 15.6 - When Br2 is added to buta-1,3-diene at 15 C, the...Ch. 15.7 - Prob. 15.9PCh. 15.7 - When N-bromosuccinimide is added to hex-1-ene in...
Ch. 15.7 - Prob. 15.11PCh. 15.9 - Addition of 1-bromobut-2-ene to magnesium metal in...Ch. 15.10 - Show how you might synthesize the following...Ch. 15.11 - Predict the products of the following proposed...Ch. 15.11 - Prob. 15.15PCh. 15.11A - Prob. 15.16PCh. 15.11B - Prob. 15.17PCh. 15.11B - Predict the products of the following Diels-Alder...Ch. 15.12C - Prob. 15.19PCh. 15.12C - Prob. 15.20PCh. 15.13C - Prob. 15.21PCh. 15.13D - Using the examples in Table15-2 to guide you,...Ch. 15.14 - Phenolphthalein is an acid-base indicator that is...Ch. 15 - Prob. 15.24SPCh. 15 - Prob. 15.25SPCh. 15 - Show how the reaction of an allylic halide with a...Ch. 15 - Prob. 15.27SPCh. 15 - A solution was prepared using 0.0010 g of an...Ch. 15 - Prob. 15.29SPCh. 15 - Prob. 15.30SPCh. 15 - Prob. 15.31SPCh. 15 - Prob. 15.32SPCh. 15 - Prob. 15.33SPCh. 15 - Give the structures of the products represented by...Ch. 15 - Furan and malemide undergo a Diels-Alder reaction...Ch. 15 - Prob. 15.36SPCh. 15 - Prob. 15.37SPCh. 15 - Prob. 15.38SPCh. 15 - Prob. 15.39SPCh. 15 - Determine whether each structure is likely to be...Ch. 15 - An important variation of the Diels-Alder reaction...
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