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In the reaction of p-chlorotoluene with ...

In the reaction of p-chlorotoluene with `KNH_(2)` is liguid `NH_(3)` the major product is .

A

o-Toluidine

B

m-Toluidine

C

p-Toluidine

D

p-Chloroaniline

Text Solution

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The correct Answer is:
To solve the problem of determining the major product in the reaction of p-chlorotoluene with KNH2 in liquid NH3, we can follow these steps: ### Step-by-Step Solution: 1. **Identify the Structure of p-Chlorotoluene**: - p-Chlorotoluene is a benzene ring with a chlorine (Cl) atom and a methyl (CH3) group attached to it. The chlorine is located at the para position relative to the methyl group. - The structure can be represented as follows: ``` Cl | C6H4 - CH3 ``` 2. **Understand the Reaction Conditions**: - The reaction involves the use of KNH2 (potassium amide), which provides the NH2- (amide ion) in liquid ammonia (NH3). - The amide ion is a strong nucleophile and will attack the aromatic ring. 3. **Formation of Benzyne Intermediate**: - The chlorine atom is a good leaving group, and under the reaction conditions, it can be displaced, leading to the formation of a benzyne intermediate. This intermediate has a triple bond between two carbon atoms in the benzene ring. - The reaction can be represented as: ``` p-Chlorotoluene → Benzyne + Cl^- ``` 4. **Nucleophilic Attack by NH2-**: - The NH2- ion can attack the benzyne intermediate at two possible positions: the carbon adjacent to the methyl group (ortho position) or the carbon opposite to the methyl group (meta position). - The attack at the ortho position would lead to a less stable product due to steric hindrance from the methyl group. 5. **Determine the Major Product**: - The more stable product will be formed when NH2- attacks the meta position. This is because the negative charge resulting from the nucleophilic attack will be further away from the electron-donating methyl group, leading to increased stability. - The product formed from the meta attack is called meta-toluidine (or meta-aminotoluene). 6. **Conclusion**: - The major product of the reaction of p-chlorotoluene with KNH2 in liquid NH3 is **meta-toluidine**. ### Final Answer: The major product is **meta-toluidine**.

To solve the problem of determining the major product in the reaction of p-chlorotoluene with KNH2 in liquid NH3, we can follow these steps: ### Step-by-Step Solution: 1. **Identify the Structure of p-Chlorotoluene**: - p-Chlorotoluene is a benzene ring with a chlorine (Cl) atom and a methyl (CH3) group attached to it. The chlorine is located at the para position relative to the methyl group. - The structure can be represented as follows: ``` ...
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When three isomeric chlorotounes are treated with KNH_(2) in liquid NH_(3) , they yield different toluidines as shown below. Explain these observations. ltrgt a. o- Chlorotouene rarr (o : m)- Toluidine b. m- Chlorotouene rarr (o + m + p)- Touidine c. p- Chlorotouene rarr (m +p)- Touidine

In the reaction p-chlorotoluene with KNH_2 in liq. NH_3 , the major product is

Knowledge Check

  • In the reaction of p-chlorotoluene with KNH_(2) in liquid NH_(3) , the major product is

    A
    o-toluidine
    B
    m-toluidine
    C
    p-toluidine
    D
    p-chloroaniline
  • In the reaction of p-chlorotoluene with KNH_(2) in liq. NH_(3) , the major product is

    A
    o-toluidine
    B
    m-toluidine
    C
    p-toluidine
    D
    o-chloroaniline
  • In the reaction of p- chlorotoluene with KNH_(2) in liq NH_(3) , the major product is

    A
    o- toluidine
    B
    p-toluidine
    C
    p-chlooroaniline
    D
    m-toluidine
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