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As S(N^(2)) reaction at an asymmetric ca...

As `S_(N^(2))` reaction at an asymmetric carbon of a compound always gives:

A

An enantiomer of the substrate

B

A product with opposite optical rotation

C

A mixture of diasteromers

D

A product with 100% inversion

Text Solution

AI Generated Solution

The correct Answer is:
To answer the question regarding what an \( S_N2 \) reaction at an asymmetric carbon of a compound always gives, we will analyze the characteristics of the \( S_N2 \) mechanism step by step. ### Step 1: Understanding \( S_N2 \) Mechanism The \( S_N2 \) (Substitution Nucleophilic Bimolecular) reaction involves a nucleophile attacking the electrophilic carbon atom from the opposite side of the leaving group. This backside attack leads to a transition state where the nucleophile and the leaving group are both partially bonded to the carbon. **Hint:** Remember that in \( S_N2 \) reactions, the nucleophile attacks from the opposite side of the leaving group. ### Step 2: Inversion of Configuration When the nucleophile attacks the asymmetric carbon, it causes the configuration of the carbon to invert. This means that if the original configuration was R (rectus), the product will be S (sinister), or vice versa. This is known as Walden inversion. **Hint:** Focus on how the configuration changes due to the backside attack of the nucleophile. ### Step 3: Formation of a Single Product In \( S_N2 \) reactions, only one product is formed due to the specific nature of the reaction mechanism. This product will have the opposite stereochemistry compared to the starting material. **Hint:** Recall that \( S_N2 \) reactions do not lead to a mixture of products; they produce a single stereoisomer. ### Step 4: Analyzing the Options Now, let's analyze the provided options based on our understanding: 1. **An enantiomer of a substrate is formed** - This is incorrect; while an enantiomer is a type of stereoisomer, the \( S_N2 \) reaction specifically results in inversion. 2. **A product with opposite optical rotation is formed** - This is correct; the product will have an opposite optical rotation due to the inversion. 3. **A mixture of diastereomers is formed** - This is incorrect; \( S_N2 \) does not produce diastereomers. 4. **A product with 100% inversion is formed** - This is also correct; the reaction results in complete inversion of configuration. ### Conclusion Thus, the correct answers are: - A product with opposite optical rotation is formed. - A product with 100% inversion is formed. ### Final Answer The \( S_N2 \) reaction at an asymmetric carbon of a compound always gives a product with opposite optical rotation and a product with 100% inversion.
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