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The addition of Br2 to ( E)-but-2-ene gi...

The addition of `Br_2` to ( E)-but-2-ene gives

A

(R,R)-2-3-dibromobutane

B

(S,R)-2-3-dibromobutane

C

(R,S)-2-3-dibromobutane

D

A mixture of (R,R) and (S,S) 2,3 dibromobutane

Text Solution

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The correct Answer is:
To solve the problem of the addition of \( \text{Br}_2 \) to (E)-but-2-ene, we will follow these steps: ### Step 1: Identify the structure of (E)-but-2-ene (E)-but-2-ene has the following structure: \[ \text{CH}_3 - \text{C}=\text{C} - \text{CH}_3 \] In the (E) configuration, the two methyl groups (CH₃) are on opposite sides of the double bond. ### Step 2: Understand the addition reaction When \( \text{Br}_2 \) is added to an alkene, it undergoes an electrophilic addition reaction. The double bond acts as a nucleophile and attacks a bromine molecule, leading to the formation of a cyclic bromonium ion intermediate. ### Step 3: Draw the bromonium ion intermediate Upon the addition of \( \text{Br}_2 \), the double bond attacks one of the bromine atoms, forming a cyclic bromonium ion. The bromonium ion has a three-membered ring structure where one bromine atom is positively charged and is bonded to both carbons of the former double bond. ### Step 4: Nucleophilic attack by bromide ion The bromide ion (Br⁻), which is generated from the dissociation of \( \text{Br}_2 \), can now attack the more substituted carbon of the bromonium ion. This attack occurs from the opposite side of the bromonium ion due to steric hindrance, leading to anti-addition. ### Step 5: Determine the products The product of this reaction will be 2,3-dibromobutane. Since (E)-but-2-ene is symmetrical, the addition of bromine will yield two stereoisomers: 1. (2R,3S)-2,3-dibromobutane 2. (2S,3R)-2,3-dibromobutane However, these two stereoisomers are actually meso compounds because they are superimposable on their mirror images. ### Step 6: Conclusion The final product of the addition of \( \text{Br}_2 \) to (E)-but-2-ene is meso-2,3-dibromobutane, which can be represented as: \[ \text{meso-2,3-dibromobutane} \] ### Final Answer The addition of \( \text{Br}_2 \) to (E)-but-2-ene gives meso-2,3-dibromobutane. ---
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