Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Question
Chapter 13, Problem 12PP
Interpretation Introduction
Interpretation:
For each case, the formation of two enantiomers in the given reaction and the structural stereochemical relation between the enantiomers formed are to be determined.
Concept introduction:
A Diels Ander reaction is one between a conjugate diene and a reactant containing a double bond (dienophile) to form a product. The product is called adduct.
Diels Ander reactions are highly stereospecific. The configuration of the dienophile is retained in the product, and the reaction is a syn addition reaction.
The dienes react with dienophiles in cis forms rather than trans forms.
Endo and exo refer to the orientation of the dienophile and its electron-withdrawing group when it reacts with a diene in a Diels Ander reaction.
Endo is favored in the transition state of aDiels Ander reaction because it has a lower energy.
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Students have asked these similar questions
The alkene shown undergoes bromination.
H
(a) Draw the product(s) of bromination of this compound, including all expected stereoisomers (if any). Use wedge-and-dash
bonds to designate the stereochemistry at any chirality centers, and make sure to draw an explicit hydrogen if a chirality center
has one. (b) Characterize the starting alkene as having the E or Z configuration. (c) characterize the product(s).
(a)
H
Br₂
Draw the product(s) of bromination.
Br
H
Br
Give reasons for the following:
(i) Benzyl chloride is highly reactive towards the SN1 reaction.
(ii) 2-bromobutane is optically active but 1-bromobutane is optically inactive.
(iii) Electrophilic reactions in haloarenes occur slowly.
Consider the addition of HBr shown here.
HBr
(a) There are three carbocation intermediates possible
from the protonation of this triene. Draw all three of
them and identify the most stable one.
(b) Draw all halogenated products formed by attack of Br on the most stable carbocation.
(c) Which of those products would you expect to be formed in the greatest amount at low temperatures?
(d) Which would you expect to be formed in the greatest amount at high temperatures?
Chapter 13 Solutions
Organic Chemistry
Ch. 13 - Prob. 1PPCh. 13 - Prob. 2PPCh. 13 - Prob. 3PPCh. 13 - Practice Problem 13.4 From each set of resonance...Ch. 13 - Practice Problem 13.5 The following enol (an...Ch. 13 - Prob. 6PPCh. 13 - Practice Problem 13.7
Two compounds, A and B, have...Ch. 13 - Prob. 8PPCh. 13 - Prob. 9PPCh. 13 - Prob. 10PP
Ch. 13 - Prob. 11PPCh. 13 - Prob. 12PPCh. 13 - Prob. 13PPCh. 13 - Prob. 14PPCh. 13 - Prob. 15PPCh. 13 - Practice Problem 13.16
Diels–Alder reactions also...Ch. 13 - Prob. 17PPCh. 13 - Prob. 18PCh. 13 - What product would you expect from the following...Ch. 13 - Prob. 20PCh. 13 - Prob. 21PCh. 13 - Provide the reagents necessary for each of the...Ch. 13 - Prob. 23PCh. 13 - Prob. 24PCh. 13 - Prob. 25PCh. 13 - When 1-pentene reacts with N-bromosuccinimide...Ch. 13 - Prob. 27PCh. 13 - Prob. 28PCh. 13 - Prob. 29PCh. 13 - Prob. 30PCh. 13 - 13.31 Provide a mechanism that explains formation...Ch. 13 - 13.32 Provide a mechanism that explains formation...Ch. 13 - Treating either 1-chloro-3-methyl-2-butene or...Ch. 13 - Prob. 34PCh. 13 - Prob. 35PCh. 13 - Although both 1-bromobutane and 4-bromo-1-butene...Ch. 13 - Prob. 37PCh. 13 - Prob. 38PCh. 13 - Prob. 39PCh. 13 - Prob. 40PCh. 13 - Prob. 41PCh. 13 - Prob. 42PCh. 13 - Prob. 43PCh. 13 - Prob. 44PCh. 13 - 13.44 When furan and maleimide undergo a...Ch. 13 - Two controversial hard insecticides are aldrin and...Ch. 13 - Prob. 47PCh. 13 - Prob. 48PCh. 13 - Prob. 49PCh. 13 - Prob. 50PCh. 13 - Explain the product distribution below based on...Ch. 13 - Mixing furan (Problem 13.44) with maleic anhydride...Ch. 13 - Prob. 53PCh. 13 - Prob. 54PCh. 13 - Prob. 1LGPCh. 13 - Prob. 2LGPCh. 13 - Prob. 1QCh. 13 - Prob. 2QCh. 13 - Prob. 3QCh. 13 - Prob. 4QCh. 13 - Prob. 5Q
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