Organic Chemistry
8th Edition
ISBN: 9781337516402
Author: Brown
Publisher: Cengage
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Chapter 20, Problem 20.35P
The following triene undergoes an intramolecular Diels-Alder reaction to give a bicyclic product. Propose a structural formula for the product. Account for the observation that the Diels-Alder reaction given in this problem takes place under milder conditions (at lower temperature) than the analogous Diels-Alder reaction shown in Problem 20.34.
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Problem 64 of 15
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Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product
structures, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s).
Be sure to account for all bond-breaking and bond-making steps.
0:0
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N.
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:O
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H
H.
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Select to Add Arrows
O
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H
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0:0.
S.
H
Select to Add Arrows
S
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H
H
Order the following organic reactions by relative rate. That is, select '1' next to the reaction that will have the fastest initial rate, select '2' next to the reaction
that will have the next fastest initial rate, and so on. If two reactions will have very similar initial rates, you can select the same number next to both.
If a reaction will have zero or nearly zero initial rate, don't select a number and check the box in the table instead.
Note: the "Nu" in these reactions means "a generic nucleophile."
ملی
CI
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3
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Reaction
Relative Rate
(Choose one) ▼
Nu
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zero or nearly zero
Nu
:Nu
bi
(Choose one)
zero or nearly zero
: Nu
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Nu
:H
(Choose one)
zero or nearly zero
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Problem 38 of 15
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Curved arrows are used to illustrate the flow of electrons. Use the reaction conditions provided and follow
the arrows to draw the product formed in this reaction or mechanistic step(s).
Include all lone pairs and charges as appropriate. Ignore inorganic byproducts.
Br2
FeBrз
H
(+)
Br:
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Chapter 20 Solutions
Organic Chemistry
Ch. 20.1 - Prob. 20.1PCh. 20.1 - Estimate the stabilization gained as a result of...Ch. 20.2 - Predict the product(s) formed by addition of one...Ch. 20.3 - Prob. 20.4PCh. 20.3 - Prob. 20.5PCh. 20.4 - Prob. 20.6PCh. 20.5 - Prob. 20.7PCh. 20.5 - Prob. 20.8PCh. 20.5 - Prob. 20.9PCh. 20.6 - Prob. 20.10P
Ch. 20.6 - Prob. 20.11PCh. 20.6 - Prob. 20.12PCh. 20 - If an electron is added to 1,3-butadiene, into...Ch. 20 - Prob. 20.15PCh. 20 - Predict the structure of the major product formed...Ch. 20 - Predict the major product formed by 1,4-addition...Ch. 20 - Predict the structure of the major 1,2-addition...Ch. 20 - Prob. 20.19PCh. 20 - Prob. 20.20PCh. 20 - Prob. 20.21PCh. 20 - Prob. 20.22PCh. 20 - Prob. 20.23PCh. 20 - Pyridine exhibits a UV transition of the type n at...Ch. 20 - Prob. 20.25PCh. 20 - Prob. 20.26PCh. 20 - Prob. 20.27PCh. 20 - Write the frontier molecular orbital analysis for...Ch. 20 - Prob. 20.29PCh. 20 - Draw structural formulas for the products of...Ch. 20 - Propose structural formulas for compounds A and B...Ch. 20 - Under certain conditions, 1,3-butadiene can...Ch. 20 - Prob. 20.33PCh. 20 - Prob. 20.34PCh. 20 - The following triene undergoes an intramolecular...Ch. 20 - Prob. 20.36PCh. 20 - Prob. 20.37PCh. 20 - Prob. 20.38PCh. 20 - Prob. 20.39PCh. 20 - The Diels-Alder reaction is not limited to making...Ch. 20 - The first step in a synthesis of dodecahedrane...Ch. 20 - Bicyclo-2,5-heptadiene can be prepared in two...Ch. 20 - Prob. 20.43PCh. 20 - Prob. 20.44PCh. 20 - Following is a retrosynthetic scheme for the...Ch. 20 - Prob. 20.46PCh. 20 - Prob. 20.47PCh. 20 - Prob. 20.48PCh. 20 - Prob. 20.49PCh. 20 - Prob. 20.50PCh. 20 - What reaction presented in this chapter is...Ch. 20 - Claisen rearrangement of an allyl phenyl ether...Ch. 20 - Prob. 20.53PCh. 20 - Prob. 20.54PCh. 20 - We now continue the use of organic chemistry...Ch. 20 - Write the products of the following sequences of...
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