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PROBLEM 10.60

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Organic Chemistry
Found in: Page 423

Short Answer

Question: Less stable alkenes can be isomerized to more stable alkenes by treatment with strong acid. For example, 2,3-dimethylbut-1-ene is converted to 2,3-dimethylbut-2-ene when treated with . Draw a stepwise mechanism for this isomerization process.

Answer

See the step by step solution

Step by Step Solution

Isomerization process

The isomerization process explains the formation of different structures (with variable orientations of groups) from one structure. Both structures (initial and final) have the same chemical composition.

Consequences of isomerization process

The isomerization process gives a more stable product by changing either the position of double or triple bond or the functional groups.

Explanation

The given alkene 2,3-dimethyl-1-butene isomerizes to 2,3-dimethyl-2-butene. In this, the initial alkene changes the position of its double bond. The mechanism followed is given below:

The protonation of alkene occurs in the presence of H2SO4 to generate a carbocation. The base formed by the protonation process again abstracts the proton from another carbon and forms a new alkene.

Reaction mechanism

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