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of benzene with 2-chloro-1-phenylpropane, the expected product is not produced.  Instead of 1,2-diphenylpropane (expected product), the product 1,1-diphenylpropane (observed product) is produced (see below).  Explain why this product is produced.

of benzene with 2-chloro-1-phenylpropane, the expected product is not produced.  Instead of 1,2-diphenylpropane (expected product), the product 1,1-diphenylpropane (observed product) is produced (see below).  Explain why this product is produced.

Chemistry
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
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  1. In the Friedel Crafts Alkylation of benzene with 2-chloro-1-phenylpropane, the expected product is not produced.  Instead of 1,2-diphenylpropane (expected product), the product 1,1-diphenylpropane (observed product) is produced (see below).  Explain why this product is produced.  
## Friedel-Crafts Alkylation Reaction Explanation ### Reaction Overview In the Friedel-Crafts Alkylation of benzene with 2-chloro-1-phenylpropane, the expected product is not produced. Instead of 1,2-diphenylpropane (expected product), the product 1,1-diphenylpropane (observed product) is produced. The following reaction diagram illustrates this process: **Reactants:** - Benzene - 2-chloro-1-phenylpropane - \(\text{AlCl}_3\) (Aluminum Chloride) ### Chemical Structures and Reaction Pathway **Initial Reactants and Catalyst:** 1. **2-chloro-1-phenylpropane:** The structure includes a three-carbon chain with a chlorine and phenyl group attached to the first carbon. 2. **AlCl3:** A Lewis acid catalyst used in the reaction. The diagram presents: - **Reactant Structure:** - A benzene ring (hexagon with alternate double bonds). - A chain with a chlorine atom (Cl) and a phenyl group (benzene ring) attached at the first carbon. ``` Reactant structure: Cl | Ph-CH-CH-CH3 ``` **Reaction Intermediate:** This stage involves the interaction of the reactant with \(\text{AlCl}_3\), which facilitates the alkylation process. ### Expected Product **1,2-Diphenylpropane:** - Chemical Structure: ``` Expected product: Ph | Ph-CH-CH2-CH3 ``` - Explanation: It consists of two phenyl groups (Ph) attached to the first and second carbons of the propane chain. ### Observed Product **1,1-Diphenylpropane:** - Chemical Structure: ``` Observed product: Ph | Ph-C-CH2-CH3 ``` - Explanation: Both phenyl groups are attached to the same carbon (the first carbon) of the propane chain, which leads to the formation of a more stable carbocation intermediate during the reaction. ### Explanation The observed product is favored due to the stability of the carbocation intermediate during the reaction mechanism. When the aluminum chloride catalyst facilitates the removal of the chlorine atom from 2-chloro
Transcribed Image Text:## Friedel-Crafts Alkylation Reaction Explanation ### Reaction Overview In the Friedel-Crafts Alkylation of benzene with 2-chloro-1-phenylpropane, the expected product is not produced. Instead of 1,2-diphenylpropane (expected product), the product 1,1-diphenylpropane (observed product) is produced. The following reaction diagram illustrates this process: **Reactants:** - Benzene - 2-chloro-1-phenylpropane - \(\text{AlCl}_3\) (Aluminum Chloride) ### Chemical Structures and Reaction Pathway **Initial Reactants and Catalyst:** 1. **2-chloro-1-phenylpropane:** The structure includes a three-carbon chain with a chlorine and phenyl group attached to the first carbon. 2. **AlCl3:** A Lewis acid catalyst used in the reaction. The diagram presents: - **Reactant Structure:** - A benzene ring (hexagon with alternate double bonds). - A chain with a chlorine atom (Cl) and a phenyl group (benzene ring) attached at the first carbon. ``` Reactant structure: Cl | Ph-CH-CH-CH3 ``` **Reaction Intermediate:** This stage involves the interaction of the reactant with \(\text{AlCl}_3\), which facilitates the alkylation process. ### Expected Product **1,2-Diphenylpropane:** - Chemical Structure: ``` Expected product: Ph | Ph-CH-CH2-CH3 ``` - Explanation: It consists of two phenyl groups (Ph) attached to the first and second carbons of the propane chain. ### Observed Product **1,1-Diphenylpropane:** - Chemical Structure: ``` Observed product: Ph | Ph-C-CH2-CH3 ``` - Explanation: Both phenyl groups are attached to the same carbon (the first carbon) of the propane chain, which leads to the formation of a more stable carbocation intermediate during the reaction. ### Explanation The observed product is favored due to the stability of the carbocation intermediate during the reaction mechanism. When the aluminum chloride catalyst facilitates the removal of the chlorine atom from 2-chloro
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