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How many isomers of C(5)H(11)Br show ste...

How many isomers of `C_(5)H_(11)Br` show stereochemical inversion when it undergoes `SN^(2)` reaction?

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To determine how many isomers of \(C_5H_{11}Br\) show stereochemical inversion when undergoing an \(S_N2\) reaction, we need to follow these steps: ### Step 1: Identify the molecular formula and possible structures The molecular formula \(C_5H_{11}Br\) indicates that we are dealing with bromopentane. We need to identify all possible structural isomers of this compound. ### Step 2: Draw the structural isomers 1. **Straight-chain isomers**: - **1-bromopentane**: \(CH_3(CH_2)_3CH_2Br\) - **2-bromopentane**: \(CH_3CH(CH_2)CH_2Br\) - **3-bromopentane**: \(CH_3CH_2CH(CH_2)Br\) 2. **Branched-chain isomers**: - **2-bromobutane**: \(CH_3CH(CH_3)CH_2Br\) - **3-bromobutane**: \(CH_3CH_2CH(CH_3)Br\) - **1-bromo-2-methylbutane**: \(CH_3CH(CH_3)CH_2CH_2Br\) - **2-bromo-2-methylbutane**: \(C(CH_3)_3Br\) ### Step 3: Identify chiral centers For stereochemical inversion to occur during an \(S_N2\) reaction, the carbon atom bonded to the bromine must be a chiral center. A chiral center is a carbon atom that is attached to four different substituents. - **1-bromopentane**: No chiral center. - **2-bromopentane**: Chiral center (attached to \(CH_3\), \(CH_2Br\), \(H\), and \(CH_2CH_3\)). - **3-bromopentane**: No chiral center. - **2-bromobutane**: Chiral center (attached to \(CH_3\), \(CH_3\), \(H\), and \(CH_2Br\)). - **3-bromobutane**: Chiral center (attached to \(CH_3\), \(CH_2Br\), \(H\), and \(CH_2CH_3\)). - **1-bromo-2-methylbutane**: Chiral center (attached to \(CH_3\), \(CH_2Br\), \(H\), and \(CH(CH_3)\)). - **2-bromo-2-methylbutane**: No chiral center. ### Step 4: Count the isomers with chiral centers From our analysis, the following isomers have chiral centers: - **2-bromopentane** - **2-bromobutane** - **3-bromobutane** - **1-bromo-2-methylbutane** ### Conclusion The total number of isomers of \(C_5H_{11}Br\) that show stereochemical inversion during an \(S_N2\) reaction is **four**.
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Knowledge Check

  • How many meso isomers of C_4H_8Cl_2 will be ?

    A
    0
    B
    1
    C
    2
    D
    3
  • The organic chloro compound, which shows complete stereochemical inversion during a S_(N^2) reaction is

    A
    `(C_2 H_5 )_2 CHCl`
    B
    `(CH_3 )_3 C Cl`
    C
    `(CH_3)_2 CHCl`
    D
    `CH_3 Cl`
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