Question 46

Given below are two statements : Statement (I) : $$S_N2$$ reactions are 'stereospecific', indicating that they result in the formation of only one stereo-isomer as the product. Statement (II) : $$S_N1$$ reactions generally result in formation of product as racemic mixtures. In the light of the above statements, choose the correct answer from the options given below :

We need to evaluate both statements about nucleophilic substitution reactions.

Statement (I): $$S_N2$$ reactions are 'stereospecific', indicating that they result in the formation of only one stereo-isomer as the product.

In $$S_N2$$ reactions, the nucleophile attacks from the back side of the carbon bearing the leaving group (backside attack). This results in a Walden inversion, producing a single stereoisomer with inverted configuration. Hence, $$S_N2$$ reactions are indeed stereospecific. Statement I is true.

Statement (II): $$S_N1$$ reactions generally result in formation of product as racemic mixtures.

In $$S_N1$$ reactions, the rate-determining step involves the formation of a planar carbocation intermediate. The nucleophile can attack this planar carbocation from either side with nearly equal probability, leading to a mixture of both R and S configurations — a racemic mixture. Statement II is true.

Since both statements are true, the correct answer is Option 4: Both Statement I and Statement II are true.

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