Most stable product of the following reaction is:
The Correct Option is B
Solution and Explanation
The given reaction involves a two-step process where an alcohol reacts to form a more stable product. Let's analyze the reaction step-by-step:
- The reaction starts with the treatment of an alcohol with \(\text{TsCl (p-toluenesulfonyl chloride)}\) in pyridine. This step results in the formation of a tosylate ester, converting the -OH group into a better leaving group without changing the configuration at the chiral center.
- In the second step, the resulting tosylate compound is treated with \(\text{NaCN in DMF (dimethylformamide)}\). This is a nucleophilic substitution reaction where the CN- ion, a good nucleophile, attacks the tosylate. The configuration is inverted due to the backside attack, as per the SN2 mechanism.
- The final product is a nitrile, formed after the substitution of the tosyl group with the cyanide ion. Considering the stereochemistry, the product configuration is inverted relative to the starting alcohol due to the SN2 reaction.
The most stable product from this reaction sequence is represented by the following image:
Conclusion: The correct and most stable product results from the nucleophilic substitution where the cyanide ion replaces the tosyl group. The stereochemistry of the final product will be opposite to that of the initial substrate due to the SN2 mechanism. Therefore, the correct answer corresponds to the structure shown in the image above.
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Concepts Used:
Preparation of Haloarenes
- Preparation by Electrophilic Substitution Reaction: Electrophilic Substitution helps in the preparation of Haloarenes like aryl bromides and aryl chlorides by using the halogens such as chlorine and bromine in the presence of Lewis Acid. But for this reaction to be fruitful, it is compulsory that the reaction takes place in the presence of Lewis Acid and must be carried out in dark.
- Preparation by Sandmeyer’s Reaction: In this case, in order to form diazonium salt in the presence of cold mineral water, the primary aromatic amine has to react with sodium nitrate. Here, the reaction of sodium nitrate with HX will prepare HNO2 at a temperature of 273-278 K.
Read More: Haloalkanes and Haloarenes