Question

For each addition route of the reaction, draw the structures of the possible products, including stereochemistry....

For each addition route of the reaction, draw the

For each addition route of the reaction, draw the structures of the possible products, including stereochemistry. Note that more than one product is produced in each case since stereochemistry must be considered.

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Answer #1
Concepts and reason

In the given reaction, a diene is reacting with chlorine molecule in chloroform. The given problem is based on 1,2 and 1,4-addition reaction of the halogens to dienes hence, draw the products of the given reaction with the correct stereochemistry.

Fundamentals

Conjugated dienes undergo addition reaction on the double bond with the halogens and tend to form two types of product as shown below:

1,2additionproduct1,2 - {\rm{addition product}} : In this addition product, addition of reagent takes place at the adjacent positions.

1,4additionproduct1,4 - {\rm{addition product}} : In this addition product, addition of one part of the reagent takes place at first position while that of another part of the reagent gets attached to the fourth position with respect to the first addition. E configuration is the favored product over the z configuration product.

Consider 1,2additionproduct1,2 - {\rm{addition product}} of the given reaction by anti-addition of the chlorine molecule as shown below:

Cl2
CCI4
2
+
С
1,2-addition product

Consider 1,4additionproduct1,4 - {\rm{addition product}} of the given reaction by delocalization of the double bond as shown below:

3
Cl2
CCI
2
CI
E-configuration
+
Н
Cl
4
1,4-addition products
Z-configuration

Ans:

Hence, 1,2additionproduct1,2 - {\rm{addition product}} of the given reactant is as follows:

1,2-addition product
Cl
Cl2
CCI
+

Hence, 1,4additionproduct1,4 - {\rm{addition product}} of the given reactant is as follows:

3
Cl2
CC4
E-configuration
(major due to more
stable)
2
CI
+
Н
Cl
4
1,4-addition products
Z-configuration

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