**Substitution Reaction Mechanism Proposal****Instruction:**Propose a mechanism for the SUBSTITUTION reaction below. HINT: AlCl₃ is an ELECTROPHILE.**Reaction:**1. **Reactants:** - Benzaldehyde (C₆H₅CHO) - 1-Chloro-2-methylpropane (CH₃CH(CH₃)CH₂Cl) - Aluminum chloride (AlCl₃)2. **Product:** - 3,5-Dimethylbenzaldehyde**Explanation:**The reaction involves the substitution of the chlorine atom in 1-chloro-2-methylpropane with the aromatic ring, resulting in the formation of a dimethylated aromatic compound. Aluminum chloride (AlCl₃) acts as a catalyst by generating a more reactive electrophile from the alkyl chloride, facilitating its addition to the benzaldehyde ring.

Answered: 4. Propose a mechanism for the…

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

Section: Chapter Questions

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

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Question

**Substitution Reaction Mechanism Proposal**

**Instruction:**

Propose a mechanism for the SUBSTITUTION reaction below. HINT: AlCl₃ is an ELECTROPHILE.

**Reaction:**

1. **Reactants:**
- Benzaldehyde (C₆H₅CHO)
- 1-Chloro-2-methylpropane (CH₃CH(CH₃)CH₂Cl)
- Aluminum chloride (AlCl₃)

2. **Product:**
- 3,5-Dimethylbenzaldehyde

**Explanation:**

The reaction involves the substitution of the chlorine atom in 1-chloro-2-methylpropane with the aromatic ring, resulting in the formation of a dimethylated aromatic compound. Aluminum chloride (AlCl₃) acts as a catalyst by generating a more reactive electrophile from the alkyl chloride, facilitating its addition to the benzaldehyde ring.

Expert Solution

Step 1

The given reaction is a Friedel - Crafts alkylation reaction.

In this reaction alkylation of aromatic ring takes place with the help of alkyl halide & using strong Lewis acid such as aluminum trichloride (AlCl3) as a catalyst.

This reaction proceed by electrophilic aromatic substitution mechanism.

In this reaction removal of -Cl from N-propyl chloride to form primary carbocation i.e, electrophile species. After rearrangement it convert into more stable carbocation secondary carbocation formed.

Double bond of aromatic ring attacks on this carbocation ,so aromaticity is break, & aromatic carbocation formed.Now, -(H+) on carbocation remove so, aromaticity is restored.

Now, H+ reacts with AlCl4- to give back HCl and AlCl3.