ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Question
Chapter 27, Problem 27.29P
Interpretation Introduction
(a)
Interpretation: The given reaction is to be classified as electrocyclic reaction, cycloaddition, or sigmatropic rearrangement. The stereochemistry whether the given reaction is conrotatory, disrotatory, suprafacial, or antarafacial is to be indicated.
Concept introduction: Electrocyclic reactions are pericyclic reactions which takes place by concerted mechanism. These reactions involve ring opening or ring closure in a conjugated polyene
Interpretation Introduction
(b)
Interpretation: The given reaction is to be classified as electrocyclic reaction, cycloaddition, or sigmatropic rearrangement. The stereochemistry whether the given reaction is conrotatory, disrotatory, suprafacial, or antarafacial is to be indicated.
Concept introduction: Sigmatropic rearrangements are pericyclic reactions which takes place by concerted mechanism. In these rearrangements migration of sigma bond takes place. According to Woodward-Hoffmann rules, the total number of electron pairs in sigma bond that is broken and the pi bonds that rearrange. The polyene containing even number of electron pairs in thermal conditions undergoes reaction in antrafacial fashion and polyene containing odd number of bonds undergo reaction in suprafacial fashion.
Interpretation Introduction
(c)
Interpretation: The given reaction is to be classified as electrocyclic reaction, cycloaddition, or sigmatropic rearrangement. The stereochemistry whether the given reaction is conrotatory, disrotatory, suprafacial, or antarafacial is to be indicated.
Concept introduction: Cycloaddition reactions are pericyclic reactions that take place in two compounds containing pi bonds to form a cyclic compound. These reactions are concerted and stereospecific in nature. According to Woodward-Hoffmann rules, the polyene containing even number of bonds in photochemical conditions undergoes reaction in suprafacial fashion and polyene containing odd number of bonds undergo reaction in antrafacial fashion.
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Kumada Coupling:
1. m-Diisobutylbenzene below could hypothetically be synthesized by Friedel-Crafts reaction. Write out the reaction with a
mechanism and give two reasons why you would NOT get the desired product.
Draw the reaction (NOT a mechanism) for a Kumada coupling to produce the molecule above from m-dichlorobenzene.
Calculate the theoretical yield for the reaction in question 2 using 1.5 g of p-dichlorobenzene and 3.0 mL isobutyl bromide.
What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What
other impurities are present in your product and how do you know?
Wintergreen from Aspirin:
1. In isolating the salicylic acid, why is it important to press out as much of the water as possible?
2. Write the mechanism of the esterification reaction you did.
3.
What characteristic absorption band changes would you expect in the IR spectrum on going from aspirin to salicyclic acid and
then to methyl salicylate as you did in the experiment today? Give approximate wavenumbers associated with each functional
group change.
What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What
other impurities are present in your product and how do you know?
Chapter 27 Solutions
ORGANIC CHEMISTRY
Ch. 27 - Prob. 27.1PCh. 27 - Problem 27.2
For each molecular orbital in Figure...Ch. 27 - Problem 27.3
(a) Using Figure 27.2 as a guide,...Ch. 27 - Problem 27.4
(a) How many molecular orbitals are...Ch. 27 - Prob. 27.5PCh. 27 - Prob. 27.6PCh. 27 - Prob. 27.7PCh. 27 - Prob. 27.8PCh. 27 - Prob. 27.9PCh. 27 - Prob. 27.10P
Ch. 27 - Problem 27.11
What product would be formed by the...Ch. 27 - Consider cycloheptatrienone and ethylene, and draw...Ch. 27 - Problem 27.13
Show that a thermal suprafacial...Ch. 27 - Prob. 27.14PCh. 27 - a Draw the product of the following [4+2]...Ch. 27 - Prob. 27.16PCh. 27 - Prob. 27.17PCh. 27 - Problem 27.18
Using orbital symmetry, explain why...Ch. 27 - Prob. 27.19PCh. 27 - Prob. 27.20PCh. 27 - Prob. 27.21PCh. 27 - Prob. 27.22PCh. 27 - Prob. 27.23PCh. 27 - Prob. 27.24PCh. 27 - Problem 27.25
(a) What product is formed by the...Ch. 27 - Prob. 27.26PCh. 27 - Prob. 27.27PCh. 27 - Prob. 27.28PCh. 27 - Prob. 27.29PCh. 27 - Prob. 27.30PCh. 27 - Prob. 27.31PCh. 27 - Prob. 27.32PCh. 27 - Prob. 27.33PCh. 27 - Prob. 27.34PCh. 27 - Prob. 27.35PCh. 27 - Prob. 27.36PCh. 27 - Prob. 27.37PCh. 27 - Prob. 27.38PCh. 27 - Prob. 27.39PCh. 27 - Prob. 27.40PCh. 27 - 27.41 What starting materials are needed to...Ch. 27 - Prob. 27.42PCh. 27 - Prob. 27.43PCh. 27 - Prob. 27.44PCh. 27 - Prob. 27.45PCh. 27 - Prob. 27.46PCh. 27 - 27.47 What product is formed from the [5,5]...Ch. 27 - Prob. 27.48PCh. 27 - 27.49 Draw structures for A, B, and C in the...Ch. 27 - Prob. 27.50PCh. 27 - Prob. 27.51PCh. 27 - 27.52 Draw the products of each reaction.
c....Ch. 27 - Prob. 27.53PCh. 27 - 27.54 Draw a stepwise, detailed mechanism for the...Ch. 27 - Prob. 27.55PCh. 27 - Prob. 27.56PCh. 27 - Prob. 27.57PCh. 27 - 27.58 Draw a stepwise, detailed mechanism for the...Ch. 27 - Prob. 27.59PCh. 27 - Prob. 27.60PCh. 27 - Prob. 27.61PCh. 27 - Prob. 27.62PCh. 27 - Prob. 27.63P
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