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Which alkyl halide from the following pa...

Which alkyl halide from the following pairs would you expect to react more rapidly by an `S_(N)2` mechanism? Explain your answer.
(i) `CH_(3)CH_(2)CH_(2)CH_(2)Br` or `CH_(3)CH_(2)underset(Br)underset(|)CHCH_(3)` (ii) `CH_(3)CH_(2)underset(Br)underset(|)CHCH_(3)` or `H_(2)C-underset(CH_(3))underset(|)overset(CH_(3))overset(|)C-Br`

Text Solution

AI Generated Solution

To determine which alkyl halide from the given pairs would react more rapidly by an `S_N2` mechanism, we need to analyze the structure of each alkyl halide and consider the steric hindrance around the carbon atom that is bonded to the halogen. The `S_N2` mechanism is favored by less sterically hindered (primary) alkyl halides, as the nucleophile can approach and attack the carbon more easily. ### Step-by-Step Solution: **(i)** Compare `CH₃CH₂CH₂CH₂Br` (1-bromobutane) and `CH₃CH₂Br` (2-bromobutane). 1. **Identify the type of carbon attached to the halogen:** - In `CH₃CH₂CH₂CH₂Br`, the bromine is attached to a primary carbon (the terminal carbon). ...
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Which alkyl halide from the following pairs would you expect to react more rapidly by an SN_2 mechanism? Explain your answer. (i) CH_(3)CH_(2)CH_(2)CH_(2)Br or CH_(3)CH_(2)underset(Br)underset(|)C HCH_(3) , (ii) CH_(3)CH_(2)underset(Br)underset(|)CHCH_(3) or H_(3)C-underset(CH_(3))underset(|) overset(CH_(3))overset(|)C-Br (iii) CH_(3)underset(CH_(3))underset(|)CHCH_(2)CH_(2)Br or CH_(3)CH_(2)underset(CH_(3))underset(|)CHCH_(2)Br

Which alkyl halide from the following pairs would you expect to react more rapidly by S_(N)2 mechanism? Explain your answer. (i) CH_(3)CH_(2)CH_(2)CH_(2)Br or CH_(3)CH_(2)-underset(Br)underset(|)(C)H-CH_(3) (ii) CH_(3)CH_(2)-underset(Br)underset(|)(C)H-CH_(3) or H_(3)C-underset(CH_(3))underset(|)overset(CH_(3))overset(|)(C)-Br (iii) CH_(3)-underset(CH_(3))underset(|)(C)H-CH_(2)CH_(2)Br or CH_(3)CH_(2)-underset(CH_(3))underset(|)(C)H-CH_(2)Br

Knowledge Check

  • CH_(3)-Br+NaO-underset(CH_(3))underset(|)overset(CH_(3))overset(|)C-CH_(3)to ?

    A
    `CH_(3)-O-underset(CH_(3))underset(|)overset(CH_(3))overset(|)C-CH_(3)`
    B
    `CH_(3)-underset(CH_(3))underset(|)overset(CH_(2))overset(||)(C)`
    C
    `CH_(2)=CH_(2)`
    D
    `CH_(3)-O-underset(CH_(3))underset(|)(CH)-CH_(3)`
  • IUPAC name of CH_(2)=CH-CH(CH_(3)CH_(2))underset(Br)underset(|)C=CH_(2) is

    A
    4-Bromo-3-ethyl-1, 4-pentadiene
    B
    2-Bromo-3-ethyl-1, 4-pentadiene
    C
    2-Bromo-3-ethyl-1, 5-pentadiene
    D
    None of these
  • IUPAC name of CH_(2)=CH-CH(CH_(3)CH_(2))underset(Br)underset(|)C=CH_(2) is

    A
    4-Bromo-3-ethyl-1,4-pentadiene
    B
    2-Bromo-3-ethyl-1,4-pentadiene
    C
    2-Bromo-3-ethyl-1,5-pentadiene
    D
    None of the above
  • Similar Questions

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    Which alkyl halide from the following pairs would you expect to react more rapidly by S_(N)2 mechanism ? Explain your answer. CH_(3)CH_(2)CH_(2)CH_(2) " or " CH_(3)CH_(2) - underset(Br)underset(|)CH - CH_(3) (ii) CH_(3)CH_(2)underset(Br)underset(|)CHCH_(3)" or " H_(3)C - underset(CH_(3))underset(|)overset(CH_(3))overset(|)C-Br (iii) CH_(3)underset(CH_(3))underset(|)CHCH_(2)CH_(2) Br " or " CH_(3)CH_(2)underset(CH_(3))underset(|)CHCH_(2)Br

    CH_(3)underset(Br)underset(|)CHCH_(2)COOCH_(3)

    CH_(3)underset(Br)underset(|)CH-overset(CH_(3))overset(|)underset(OH)underset(|)(C)-C-O-CH_(3)

    IUPAC name of CH_(2)=CH-CH (CH_(3)CH_(2))underset(Br)underset(|)(C)=CH_(2) is :

    The reaction CH_(2)=CH-CH_(3)+HBrrarrCH_(3)underset(Br)underset(|)CHCH_(3) is