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Problem 6.55

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Organic Chemistry
Found in: Page 245

Short Answer

The use of curved arrows is a powerful tool that illustrates even complex reactions.

a. Add curved arrows to show how carbocation A is converted to carbocation B. Label each new bond formed. Similar reactions have been used in elegant synthesis of steroids.

b. Draw the product by following the curved arrows. This reaction is an example of a [3,3] sigma tropic rearrangement, as we will learn in chapter 27.

Answer

a.

Rearrangement of the carbocation A

The formation of the carbocation B

The new sigma bonds in carbocation B

b.

The products of the reaction b

See the step by step solution

Step by Step Solution

Step-by-Step SolutionStep 1: Synthesis of the organic compounds

The synthesis of the organic compounds is done by planning a certain group of reactions by using readily available starting materials. The synthesis happens by using more than one step at a time.

The proper selectivity of the reagents is essential for the synthesis of organic compounds.

Arrows are used to describe chemical reactions. The use of curved arrows demonstrates the movement of the electron pairs for understanding the mechanism of the reactions during organic synthesis.

Step 2: The conversion of carbocation A to carbocation B.

The carbocation A is converted into carbocation B as shown in the following structure:Rearrangement of the carbocation A

The arrows indicate the movement of electrons in the above structure. In the following structure, the carbocation B is finally formed.The formation of the carbocation B

The new sigma bonds in carbocation B

b. The products of the given reaction are as follows:

The products of the reaction b

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