Explain why I and II are not likely to be the major products of the following reaction. + AICI3

Chemistry
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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
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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**Question:**

Explain why I and II are not likely to be the major products of the following reaction.

**Reaction:**

The starting material is toluene, which is a benzene ring with a methyl group attached to it. It reacts with a Cl group and AlCl₃ as a catalyst.

**Products:**

- Product I: A benzene ring with a propyl group attached to the ortho position relative to the methyl group.

- Product II: A benzene ring with a propyl group attached to the para position relative to the methyl group.

**Explanation of Diagram:**

The diagram shows the structure of toluene and illustrates the Friedel-Crafts alkylation reaction using AlCl₃ as a catalyst. The products, labeled as I and II, are ortho- and para-substituted propylbenzene derivatives.

**Analysis:**

The reaction is a Friedel-Crafts alkylation, and the intermediate carbocation formed may rearrange. The linear propyl group can rearrange to form a more stable secondary carbocation, leading to isopropylbenzene, which is more likely to be the major product than the linear propyl derivatives shown as I and II.
Transcribed Image Text:**Question:** Explain why I and II are not likely to be the major products of the following reaction. **Reaction:** The starting material is toluene, which is a benzene ring with a methyl group attached to it. It reacts with a Cl group and AlCl₃ as a catalyst. **Products:** - Product I: A benzene ring with a propyl group attached to the ortho position relative to the methyl group. - Product II: A benzene ring with a propyl group attached to the para position relative to the methyl group. **Explanation of Diagram:** The diagram shows the structure of toluene and illustrates the Friedel-Crafts alkylation reaction using AlCl₃ as a catalyst. The products, labeled as I and II, are ortho- and para-substituted propylbenzene derivatives. **Analysis:** The reaction is a Friedel-Crafts alkylation, and the intermediate carbocation formed may rearrange. The linear propyl group can rearrange to form a more stable secondary carbocation, leading to isopropylbenzene, which is more likely to be the major product than the linear propyl derivatives shown as I and II.
Expert Solution
Step 1

Friedel-Craft alkylation reaction:
When the benzene reacts with an alkyl halide in presence of Lewis acid catalyst alkyl benzene is formed. The reaction follows an aromatic electrophilic substitution reaction mechanism. Benzene gives an aromatic electrophilic substitution reaction. The reaction completes in two steps. In the first and rate-determining step, the electrophilic adds to the benzene to give the arenium ion intermediate. In the second step of the reaction, a proton is removed from the arenium ion and the aromaticity is regenerated.

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