ORGANIC CHEMISTRY-NEXTGEN+BOX (2 SEM.)
4th Edition
ISBN: 9781119761068
Author: Klein
Publisher: WILEY
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Question
Chapter 10.3, Problem 10.14P
Interpretation Introduction
Interpretation:
Major product has to be predicted for the given reaction.
Concept Introduction:
Diels-Alder reaction is the 4+2 addition reaction. Here a total of six pi bonds are involved resulting in formation of one pi bond and two single bonds. Diels-Alder reaction occurs via a single concerted step and not by involvement of ions. If a monosubstituted ethylene is used, the product obtained contains a stereocenter. This can be represented as,
If a cyclic diene is considered, then the product obtained will be a bicyclic compound. Diels-Alder reaction that involves cyclopentadiene results in a bicyclic structure. If the dienophile has a cis configuration, then the two groups have to be in cis configuration to each other. The product obtained will have the groups in endo position. It is a meso compound.
If the dienophile has a trans configuration, then the two groups have to be in trans configuration to each other. The product obtained will have the groups as shown below,
The above two structures are enantiomers.
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Q7.
a. Draw the line-bond structure of the major product for the following reaction, if a reaction
occurs, assume monohalogenation.
b. Calculate the product ratios using the following information (hint: use the number of
hydrogens in each category present to calculate the ratios).
Chlorination: 1° Reactivity=1
2° Reactivity=4
Heat
+ Cl2
3° Reactivity=5
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ORGANIC CHEMISTRY-NEXTGEN+BOX (2 SEM.)
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