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Which of the following will be the major...

Which of the following will be the major product when 3 - phenylpropene reacts with HBr?

A

`C_(6)H_(5)CH_(2)CHBrCH_(3)`

B

`C_(6)H_(5)CHBrCHCH_(2)`

C

`C_(6)H_(5)CH_(2)CH_(2)CH_(2)Br`

D

`C_(6)H_(5)CHBrCH_(2)CH_(3)`

Text Solution

AI Generated Solution

The correct Answer is:
To determine the major product when 3-phenylpropene reacts with HBr, we can follow these steps: ### Step 1: Identify the Structure of 3-Phenylpropene 3-Phenylpropene has a phenyl group (C6H5) attached to a propene chain. The structure can be represented as follows: ``` C6H5 | H2C=C-CH2-CH3 ``` ### Step 2: Understand the Reaction with HBr When 3-phenylpropene reacts with HBr, the alkene (C=C) will undergo electrophilic addition. The double bond will react with HBr, where H+ will add to one carbon and Br- will add to the other carbon. ### Step 3: Determine Possible Carbocation Formation When HBr adds to the double bond, two possible carbocations can form: 1. If H+ adds to the terminal carbon (CH2), a primary carbocation is formed. 2. If H+ adds to the carbon adjacent to the phenyl group, a secondary carbocation is formed. The secondary carbocation is more stable due to the resonance stabilization provided by the phenyl group. ### Step 4: Identify the More Stable Carbocation The more stable carbocation will be formed when H+ adds to the carbon adjacent to the phenyl group. This results in a secondary carbocation: ``` C6H5 | H2C-CH+-CH3 ``` ### Step 5: Carbocation Rearrangement The secondary carbocation can undergo rearrangement. The positive charge can shift to the carbon adjacent to the phenyl group, which is stabilized by resonance from the phenyl ring. ### Step 6: Nucleophilic Attack by Br- Once the more stable carbocation is formed, the Br- ion will attack the positively charged carbon, leading to the final product. ### Step 7: Write the Final Product The final product of the reaction will be: ``` C6H5-CHBr-CH2-CH3 ``` This can be represented as: - C6H5CHBrCH2CH3 ### Conclusion The major product when 3-phenylpropene reacts with HBr is **C6H5CHBrCH2CH3**.
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