ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 16, Problem 16.21P
Interpretation Introduction
Interpretation: The diene that reacts faster in the Diels-Alder reaction is to be stated with an explanation.
Concept introduction: Diene is a hydrocarbon that contains two
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 diene adds to the one side of the dienophile. Thus, they have syn or cis stereochemistry.
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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.
2) Rank the following dienes in order of increasing rate of Diels-Alder reaction with maleic
anhydride. You do not need to explain your ranking.
H3C.
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Diene B
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Write 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.
Chapter 16 Solutions
ORGANIC CHEMISTRY
Ch. 16 - Prob. 16.1PCh. 16 - Prob. 16.2PCh. 16 - Problem 16.3 Draw a second resonance structure for...Ch. 16 - Prob. 16.4PCh. 16 - Problem 16.5 Farnesyl diphosphate is synthesized...Ch. 16 - Prob. 16.6PCh. 16 - Prob. 16.7PCh. 16 - Prob. 16.8PCh. 16 - Problem 16.9 Determine the hybridization of the...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. 16.14PCh. 16 - Prob. 16.15PCh. 16 - Problem 16.16 Draw the products formed when each...Ch. 16 - Problem 16.17 Draw a stepwise mechanism for the...Ch. 16 - Prob. 16.18PCh. 16 - Problem 16.19 Draw the product formed when each...Ch. 16 - Prob. 16.20PCh. 16 - Prob. 16.21PCh. 16 - Problem 16.22 Rank the following dienophiles in...Ch. 16 - Prob. 16.23PCh. 16 - Prob. 16.24PCh. 16 - Problem 16.25 What diene and dienophile are needed...Ch. 16 - Prob. 16.26PCh. 16 - Problem 16.27 Which compound in each pair absorbs...Ch. 16 - Prob. 16.28PCh. 16 - 16.29 Name each diene and state whether the...Ch. 16 - Prob. 16.30PCh. 16 - 16.31 Which of the following systems are...Ch. 16 - 16.32 Draw all reasonable resonance structures for...Ch. 16 - Prob. 16.33PCh. 16 - Prob. 16.34PCh. 16 - 16.35 Explain why the cyclopentadienide anion A...Ch. 16 - Prob. 16.36PCh. 16 - 16.37 Draw the structure of each compound.
a. in...Ch. 16 - Prob. 16.38PCh. 16 - 16.39 Label each pair of compounds as...Ch. 16 - Prob. 16.40PCh. 16 - 16.41 Draw the products formed when each compound...Ch. 16 - Prob. 16.42PCh. 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. 16.45PCh. 16 - 16.46 Explain, with reference to the mechanism,...Ch. 16 - Prob. 16.47PCh. 16 - Prob. 16.48PCh. 16 - Prob. 16.49PCh. 16 - Prob. 16.50PCh. 16 - Prob. 16.51PCh. 16 - Prob. 16.52PCh. 16 - 16.53 Diels–Alder reaction of a monosubstituted...Ch. 16 - Prob. 16.54PCh. 16 - 16.55 Devise a stepwise synthesis of each compound...Ch. 16 - Prob. 16.56PCh. 16 - 16.57 A transannular Diels–Alder reaction is an...Ch. 16 - Prob. 16.58PCh. 16 - Draw a stepwise mechanism for the following...Ch. 16 - Prob. 16.60PCh. 16 - Prob. 16.61PCh. 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 - Prob. 16.67PCh. 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. 16.74PCh. 16 - Prob. 16.75P
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