ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
9th Edition
ISBN: 9780137249442
Author: Wade
Publisher: INTER PEAR
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Question
Chapter 15.12C, Problem 15.20P
(a)
Interpretation Introduction
Interpretation:
The
Concept introduction:
When ultraviolet light is used rather than heat for
(b)
Interpretation Introduction
Interpretation:
The reaction of thermally allowed cycloaddition of two butadiene molecules is to be shown and an explanation corresponding to the fact that it is thermally allowed is to be stated.
Concept introduction:
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 the diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.
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Draw the structure consistent with each description.
a.(2E,4E)-octa-2,4-diene in the s-trans conformation
b.(3E,5Z)-nona-3,5-diene in the s-cis conformation
c.(3Z,5Z)-4,5-dimethyldeca-3,5-diene. Draw both the s-cis and s-trans conformations.
6.) For the following reactions, please draw the structures of both the diene and dienophile that
would afford the depicted Diels Alder adducts.
1.
? + ?
Diene
Dienophile
CH3 O
CH3
? + ?
CH3
Diene
Dienophile
CH
? + ?
Diene
Dienophile
? + ?
Dienophile
Diene
CHa
1. Consider the Diels-Alder cycloaddition reaction below.
D
heat
H
D = deuterium = 2H
Draw the major regioisomer (or in other words, constitutional isomer) expected to form. Draw
appropriate resonance structures and explain why only one constitutional isomer is expected to
form. Discuss if this can be drawn with both groups on the dieneophile being endo or one has to
be endo and the other has to be exo.
Chapter 15 Solutions
ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
Ch. 15.2 - Prob. 15.1PCh. 15.2 - Prob. 15.2PCh. 15.2 - Prob. 15.3PCh. 15.4 - Prob. 15.4PCh. 15.4 - Prob. 15.5PCh. 15.5 - Treatment of an alkyl halide with AgNO3 in alcohol...Ch. 15.5 - Propose a mechanism for each reaction, showing...Ch. 15.6 - When Br2 is added to buta-1,3-diene at 15 C, the...Ch. 15.7 - Prob. 15.9PCh. 15.7 - When N-bromosuccinimide is added to hex-1-ene in...
Ch. 15.7 - Prob. 15.11PCh. 15.9 - Addition of 1-bromobut-2-ene to magnesium metal in...Ch. 15.10 - Show how you might synthesize the following...Ch. 15.11 - Predict the products of the following proposed...Ch. 15.11 - Prob. 15.15PCh. 15.11A - Prob. 15.16PCh. 15.11B - Prob. 15.17PCh. 15.11B - Predict the products of the following Diels-Alder...Ch. 15.12C - Prob. 15.19PCh. 15.12C - Prob. 15.20PCh. 15.13C - Prob. 15.21PCh. 15.13D - Using the examples in Table15-2 to guide you,...Ch. 15.14 - Phenolphthalein is an acid-base indicator that is...Ch. 15 - Prob. 15.24SPCh. 15 - Prob. 15.25SPCh. 15 - Show how the reaction of an allylic halide with a...Ch. 15 - Prob. 15.27SPCh. 15 - A solution was prepared using 0.0010 g of an...Ch. 15 - Prob. 15.29SPCh. 15 - Prob. 15.30SPCh. 15 - Prob. 15.31SPCh. 15 - Prob. 15.32SPCh. 15 - Prob. 15.33SPCh. 15 - Give the structures of the products represented by...Ch. 15 - Furan and malemide undergo a Diels-Alder reaction...Ch. 15 - Prob. 15.36SPCh. 15 - Prob. 15.37SPCh. 15 - Prob. 15.38SPCh. 15 - Prob. 15.39SPCh. 15 - Determine whether each structure is likely to be...Ch. 15 - An important variation of the Diels-Alder reaction...
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