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Consider the following reaction: C6H5-...

Consider the following reaction:
`C_6H_5-underset(H)underset(|)overset(CH_3)overset(|)C-Br+H_2Oto OH-underset(H)underset(|)overset(CH_3)overset(|)C-C_6H_5+HBr`
The reaction proceeds with 98% racemistation. The reaction may follow

A

`S_(N^1)` mechanism

B

`S_(N^2)` mechanism

C

E1 mechanism

D

E2 mechanism

Text Solution

AI Generated Solution

The correct Answer is:
To analyze the given reaction and determine the mechanism it follows, we will break down the steps involved in the reaction and the characteristics of the mechanisms. ### Step-by-Step Solution: 1. **Identify the Reaction Components:** The reaction involves a haloalkane (C6H5C(CH3)Br) and water (H2O) as reactants, producing an alcohol (C6H5C(CH3)OH) and HBr as products. 2. **Understand the Mechanism:** The reaction proceeds with 98% racemization, indicating that the product is a racemic mixture of enantiomers. This is a key characteristic of the SN1 mechanism, which typically results in racemization due to the formation of a planar carbocation intermediate. 3. **Formation of Carbocation:** In the first step of the SN1 mechanism, the bromine (Br) leaves, forming a carbocation (C6H5C(CH3)+). This step is the rate-determining step and is unimolecular, meaning the rate of reaction depends only on the concentration of the haloalkane. 4. **Nucleophilic Attack:** In the second step, water (acting as a nucleophile) attacks the carbocation. Since the carbocation is planar, the nucleophile can attack from either side, leading to the formation of both enantiomers of the alcohol. 5. **Role of Solvent:** The use of water as a solvent is significant because it is a polar protic solvent, which stabilizes the carbocation and facilitates the leaving of the bromide ion (Br-). 6. **Conclusion:** Based on the above analysis, the reaction follows the SN1 mechanism due to the formation of a carbocation and the racemization of the product. ### Final Answer: The reaction may follow the **SN1 mechanism**. ---

To analyze the given reaction and determine the mechanism it follows, we will break down the steps involved in the reaction and the characteristics of the mechanisms. ### Step-by-Step Solution: 1. **Identify the Reaction Components:** The reaction involves a haloalkane (C6H5C(CH3)Br) and water (H2O) as reactants, producing an alcohol (C6H5C(CH3)OH) and HBr as products. 2. **Understand the Mechanism:** ...
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NCERT FINGERTIPS ENGLISH-HALOALKANES AND HALOARENES-Chemical reactions
  1. Consider the following bromides: The correct order of S(N^1) reac...

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  2. Which of the following statement regarding S(N)1 reaction shown by alk...

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  3. Consider the following reaction: C6H5-underset(H)underset(|)overset(...

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  4. Which one of the following chlorohydrocarbons readily undergoes solvol...

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  5. Which of the following is the most reactive towards nucleophilic subst...

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  6. S(N^1) reaction is fastest in

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  7. Which of the following alkyl halides is hydrolysed by S(N^(1)) mechani...

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  8. Which of the following will give enantiomeric pair on reaction with wa...

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  9. Which of the following is most reactive towards aqueous NaOH?

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  10. In the following pairs of halogen compounds, which compounds undergoes...

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  11. Which of the following haloalkanes reacts with aqueous KOH most easily...

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  12. Which alkyl halide exhibits complete racemisation in S(N^1) reaction?

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  13. The order of reactivity of various alkyl halides towards nucleophilic ...

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  14. Alkyl halides are formed when thionyl chloride and are refluxed in pr...

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  15. 2-Bromo-3,3- dimethylbutane on reaction with aqueous KOH yields X as t...

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  16. Among the isomers of C5H11Cl, the one which is chiral is (i) 2,2-Dim...

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  17. Ethylene dichloride and ethylidene chloride are isomeric compounds. Th...

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  18. The major product formed in the following reaction is CH3-underset(H...

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  19. Which of the following reactions will give the major and minor product...

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  20. The products (A) and (B) are respectively. (i) CH3-underset(Br)under...

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