Co,CH,

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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(a) Draw the product of the following [4 + 2] cycloaddition, which was carried out in the early stages of the synthesis of the alkaloid reserpine (Problem 22.83). Indicate the stereochemistry at any newly formed stereogenic centers. (b) Draw the p orbitals of the alkene and the terminal carbons of the conjugated diene, and show how the orientation of the reactants and orbital overlap lead to the observed stereochemistry.

Co,CH,
Transcribed Image Text:Co,CH,
Expert Solution
Step 1

(a)

The given conjugated diene reacts with alkene in the presence of heat to form two fused rings.

The product of the reaction along with the stereochemistry at any newly formed stereogenic centers is shown below.

Chemistry homework question answer, step 1, image 1

Step 2

In the above reaction, the products is formed in the presence of heat.  The conversion of reactants into product results in the loss of two pi bonds and the formation of two new sigma bonds.  The interaction between four pi electrons of first reactant and two pi electrons of second reactant occur.  The stereochemistry of the product indicates that the –COOCH3 group is present below the plane.

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