Organic Chemistry-Package(Custom)
Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 16, Problem 16.54P

Diels–Alder reaction of a monosubstituted diene (such as CH 2 = CH CH = CHOCH 3 ) with a monosubstituted dienophile (such as CH 2 = CHCHO ) gives a mixture of products, but the 1 , 2 disubstituted product of ten 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.

Chapter 16, Problem 16.54P, 16.53 Diels–Alder reaction of a monosubstituted diene (such as ) with a monosubstituted dienophile

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True 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.
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.
The Diels-Alder reaction is not limited to making six-membered rings with only carbon atoms. Predict the products of the following reaction  that produce rings with atoms other than carbon in them.

Chapter 16 Solutions

Organic Chemistry-Package(Custom)

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
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