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Alcohols Phenols and Ethers question

2023 · 13 Apr · Shift 1 · Q8
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Alcohols Phenols and Ethers question

2023 · 13 Apr · Shift 1 · Q8

JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
2-Methyl propyl bromide reacts with C2H5O−\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{O}^{-}C2​H5​O− and gives 'A' whereas on reaction with C2H5OH\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OH}C2​H5​OH it gives 'B'. The mechanism followed in these reactions and the products 'A' and 'B' respectively are :
  1. A
    SN1,A=\mathrm{S}_{N} 1, A=SN​1,A= tert-butyl ethyl ether; SN2,B=\mathrm{S}_{N} 2, B=SN​2,B= iso-butyl ethyl ether
  2. B
    SN1, A=\mathrm{S}_{\mathrm{N}} 1, \mathrm{~A}=SN​1, A= tert-butyl ethyl ether; SN1, B=\mathrm{S}_{\mathrm{N}} 1, \mathrm{~B}=SN​1, B= 2-butyl ethyl ether
  3. C
    SN2, A=\mathrm{S}_{\mathrm{N}} 2, \mathrm{~A}=SN​2, A= iso-butyl ethyl ether; SN1, B=\mathrm{S}_{\mathrm{N}} 1, \mathrm{~B}=SN​1, B= tert-butyl ethyl ether
  4. D
    SN2, A=\mathrm{S}_{\mathrm{N}} 2, \mathrm{~A}=SN​2, A= 2-butyl ethyl ether; SN2, B=\mathrm{S}_{\mathrm{N}} 2, \mathrm{~B}=SN​2, B= iso-butyl ethyl ether
View written solutionFree

Correct answer: C

  1. Identify the substrate

    2-Methyl propyl bromide means isobutyl bromide: CH3−CH(CH3)−CH2Br\mathrm{CH_3-CH(CH_3)-CH_2Br}CH3​−CH(CH3​)−CH2​Br

    This is a primary alkyl bromide.

  2. Reaction with C2H5O−\mathrm{C_2H_5O^-}C2​H5​O−

    Ethoxide ion is a strong nucleophile. With a primary alkyl halide, the reaction proceeds mainly by SN2\mathrm{S_N2}SN​2 mechanism.

    So substitution occurs at the carbon bearing bromine: CH3−CH(CH3)−CH2Br+C2H5O−→CH3−CH(CH3)−CH2OC2H5\mathrm{CH_3-CH(CH_3)-CH_2Br + C_2H_5O^- \rightarrow CH_3-CH(CH_3)-CH_2OC_2H_5}CH3​−CH(CH3​)−CH2​Br+C2​H5​O−→CH3​−CH(CH3​)−CH2​OC2​H5​

    The product is isobutyl ethyl ether.

    Hence,

    • Mechanism for formation of AAA: SN2\mathrm{S_N2}SN​2
    • A=A =A= iso-butyl ethyl ether
  3. Reaction with C2H5OH\mathrm{C_2H_5OH}C2​H5​OH

    Ethanol is a weak nucleophile and a polar protic solvent. In such conditions, ionization is favored. The initially formed primary carbocation is unstable: CH3−CH(CH3)−CH2+\mathrm{CH_3-CH(CH_3)-CH_2^+}CH3​−CH(CH3​)−CH2+​

    It undergoes 1,2-hydride shift to form the more stable tert-butyl carbocation: (CH3)3C+\mathrm{(CH_3)_3C^+}(CH3​)3​C+

    Then ethanol attacks this carbocation: (CH3)3C++C2H5OH→(CH3)3C−OC2H5\mathrm{(CH_3)_3C^+ + C_2H_5OH \rightarrow (CH_3)_3C-OC_2H_5}(CH3​)3​C++C2​H5​OH→(CH3​)3​C−OC2​H5​

    So the reaction proceeds through SN1\mathrm{S_N1}SN​1 with rearrangement, giving tert-butyl ethyl ether.

    Hence,

    • Mechanism for formation of BBB: SN1\mathrm{S_N1}SN​1
    • B=B =B= tert-butyl ethyl ether
  4. Match with options

    We found:

    • AAA: SN2\mathrm{S_N2}SN​2, iso-butyl ethyl ether
    • BBB: SN1\mathrm{S_N1}SN​1, tert-butyl ethyl ether

    This matches Option C.

  5. Comparison with stored answer

    Stored correct answer = C

    Our derived answer = C

    Therefore, they agree.

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