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When cis-but-2-ene is treated with Br(2)...

When cis-but-2-ene is treated with `Br_(2)` in `"CCl"_(4)` medium the product formed will be

A

(2R, 3S) dibromobutane

B

(2R, 3R) dibromobutane

C

(2S, 3S) dibromobutane

D

Mixture of (2R, 3R) and (2S, 3S) dibromobutane

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AI Generated Solution

The correct Answer is:
To determine the product formed when cis-but-2-ene is treated with Br₂ in CCl₄, we will follow these steps: ### Step 1: Identify the structure of cis-but-2-ene Cis-but-2-ene has the following structure: ``` CH3 | CH3-C=C-CH2 | H ``` In this structure, both methyl (CH₃) groups are on the same side of the double bond. ### Step 2: Understand the reaction with Br₂ When cis-but-2-ene is treated with bromine (Br₂), the double bond will react with bromine to form a vicinal dibromide. The reaction occurs via an electrophilic addition mechanism. ### Step 3: Formation of the bromonium ion 1. The π bond of the double bond attacks one of the bromine atoms, leading to the formation of a bromonium ion. This intermediate has a positive charge on one of the carbons. 2. The other bromine atom is released as Br⁻. ### Step 4: Nucleophilic attack by Br⁻ 1. The Br⁻ ion will attack the more substituted carbon of the bromonium ion from the opposite side (backside attack), leading to anti-addition. 2. This results in the formation of two stereoisomers due to the possibility of the nucleophile attacking from either side of the bromonium ion. ### Step 5: Draw the products The products formed will be: 1. (2R,3S)-2,3-dibromobutane 2. (2S,3R)-2,3-dibromobutane These two products are enantiomers of each other. ### Final Answer The product formed when cis-but-2-ene is treated with Br₂ in CCl₄ is a mixture of (2R,3S)-2,3-dibromobutane and (2S,3R)-2,3-dibromobutane. ---
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