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PROBLEM 10.71

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Organic Chemistry
Found in: Page 425

Short Answer

Question: Like other electrophiles, carbocations add to alkenes to form new carbocations, which can then undergo substitution or elimination reactions depending on the reaction conditions. With this in mind, consider the following reactions of nerol, a natural product isolated from lemon grass and other plant sources. Treatment of nerol with TsOH forms α-terpineol as the major product, whereas treatment of nerol with chlorosulfonic acid, HSO3Cl , forms a constitutional isomer, α-cyclogeraniol. Write stepwise mechanisms for both processes. Each mechanism involves the addition of an electrophile—a carbocation— to a double bond.

Answer

See the step by step solution

Step by Step Solution

Generation of carbocation

Carbocations are generated on the alkene when any electrophile is substituted for the alkene. Further, carbocations can also be stabilized by 1,2-hydrogen shifting or 1,2-methyl shifting.

Stability of carbocation

The order of the stability of carbocations is

Bezylcarbocation > Allyl carcocation >

The product is obtained according to the stability of the carbocation.

Explanation

TsOH is an acid and a dehydrating agent. Therefore, the carbocation is generated by the elimination of water. Further, a stable carbocation is formed on which the water molecule attacks.

Formation of the product by dehydration and the C-C bond

The proton of chlorosulfuric acid is directly added to the alkene, which generates the carbocation. Another alkene in the compound attacks and forms the final compound.

The mechanism is shown below:

Formation of carbon-carbon bond

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