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( R ) -2-Iodobutane is treated with Nal ...

` ( R )` -2-Iodobutane is treated with Nal in acetone and allowed to stand for a long time The product eventually fromed is .

A

(R ) -2- lodobutane

B

S-2- lodobutane

C

`(+-) -2-` lodobutane

D

2-Butane

Text Solution

AI Generated Solution

The correct Answer is:
To solve the question regarding the treatment of (R)-2-Iodobutane with sodium iodide (Nal) in acetone, we will analyze the reaction step by step. ### Step 1: Identify the Reactants The reactant is (R)-2-Iodobutane. This compound is a chiral molecule, meaning it has a specific configuration (R) at the chiral center. **Hint:** Remember that chiral centers have four different substituents attached to them, leading to optical activity. ### Step 2: Understand the Reaction Conditions The reaction takes place in acetone, which is a polar aprotic solvent. Sodium iodide (Nal) is used, where iodide ion (I-) acts as a good nucleophile. **Hint:** Polar aprotic solvents favor SN2 reactions because they do not solvate the nucleophile strongly, allowing it to be more reactive. ### Step 3: Mechanism of the Reaction In an SN2 reaction, the nucleophile (I-) attacks the carbon atom bonded to the leaving group (iodine in this case). Since (R)-2-Iodobutane is chiral, the attack will lead to the inversion of configuration at the carbon center. **Hint:** In SN2 reactions, the nucleophile attacks from the opposite side of the leaving group, resulting in inversion of stereochemistry. ### Step 4: Formation of Products The attack by iodide ion (I-) on (R)-2-Iodobutane will lead to the formation of (S)-2-Butanol. However, because the reaction can occur repeatedly, there can be multiple attacks leading to both (R)- and (S)-2-Butanol being formed. **Hint:** Consider that repeated SN2 reactions can lead to a mixture of products due to the possibility of multiple attacks. ### Step 5: Resulting Product Mixture The final product will be a racemic mixture of (R)-2-Butanol and (S)-2-Butanol, which is represented as ±2-Butanol. A racemic mixture contains equal amounts of both enantiomers, making it optically inactive. **Hint:** A racemic mixture is formed when both enantiomers are present in equal amounts, leading to no net optical activity. ### Conclusion The product eventually formed from the reaction of (R)-2-Iodobutane with sodium iodide in acetone is **±2-Butanol**. ### Final Answer The answer to the question is **±2-Butanol**.
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