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Haloalkanes and Haloarenes question

2021 · 18 Mar · Shift 1 · Q3
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Haloalkanes and Haloarenes question

2021 · 18 Mar · Shift 1 · Q3

JEE MainChemistryHaloalkanes and HaloarenesMCQ+4 / −1
Reaction of Grignard reagent, C2H5MgBrC_2H_5MgBrC2​H5​MgBr with C8H8OC_8H_8OC8​H8​O followed by hydrolysis gives compound "A" which reacts instantly with Lucas reagent to give compound B, C10H13ClC_{10}H_{13}ClC10​H13​Cl. The Compound B is :
  1. A
    JEE Main 2021 (Online) 18th March Morning Shift Chemistry - Haloalkanes and Haloarenes Question 95 English Option 1
  2. B
    JEE Main 2021 (Online) 18th March Morning Shift Chemistry - Haloalkanes and Haloarenes Question 95 English Option 2
  3. C
    JEE Main 2021 (Online) 18th March Morning Shift Chemistry - Haloalkanes and Haloarenes Question 95 English Option 3
  4. D
    JEE Main 2021 (Online) 18th March Morning Shift Chemistry - Haloalkanes and Haloarenes Question 95 English Option 4
View written solutionFree

Correct answer: C

  1. Identify the carbonyl compound from the formula C8H8OC_8H_8OC8​H8​O

    A Grignard reagent C2H5MgBrC_2H_5MgBrC2​H5​MgBr adds an ethyl group to a carbonyl compound.

    The product after hydrolysis is said to react instantly with Lucas reagent, which means the alcohol formed is a tertiary alcohol.

    Therefore, the starting compound C8H8OC_8H_8OC8​H8​O must be a ketone (since Grignard addition to a ketone gives a tertiary alcohol).

    A ketone with formula C8H8OC_8H_8OC8​H8​O is acetophenone: C6H5COCH3C_6H_5COCH_3C6​H5​COCH3​

  2. Reaction with ethylmagnesium bromide

    Acetophenone reacts with C2H5MgBrC_2H_5MgBrC2​H5​MgBr as: C6H5COCH3+C2H5MgBr→C6H5C(OMgBr)(CH3)(C2H5)C_6H_5COCH_3 + C_2H_5MgBr \rightarrow C_6H_5C(OMgBr)(CH_3)(C_2H_5)C6​H5​COCH3​+C2​H5​MgBr→C6​H5​C(OMgBr)(CH3​)(C2​H5​)

    On hydrolysis: C6H5C(OH)(CH3)(C2H5)C_6H_5C(OH)(CH_3)(C_2H_5)C6​H5​C(OH)(CH3​)(C2​H5​)

    So compound AAA is a tertiary alcohol, namely: 2-phenyl-2-butanol\text{2-phenyl-2-butanol}2-phenyl-2-butanol

  3. Reaction with Lucas reagent

    Lucas reagent converts tertiary alcohols immediately to alkyl chlorides: C6H5C(OH)(CH3)(C2H5)→ZnCl2conc. HClC6H5C(Cl)(CH3)(C2H5)C_6H_5C(OH)(CH_3)(C_2H_5) \xrightarrow[\text{ZnCl}_2]{\text{conc. HCl}} C_6H_5C(Cl)(CH_3)(C_2H_5)C6​H5​C(OH)(CH3​)(C2​H5​)conc. HClZnCl2​​C6​H5​C(Cl)(CH3​)(C2​H5​)

    Thus compound BBB is: C6H5C(Cl)(CH3)(C2H5)C_6H_5C(Cl)(CH_3)(C_2H_5)C6​H5​C(Cl)(CH3​)(C2​H5​)

  4. Check molecular formula

    Phenyl group: C6H5C_6H_5C6​H5​

    Other groups attached to central carbon: CH3CH_3CH3​ and C2H5C_2H_5C2​H5​

    Total: C=6+1+2+1(central carbon)=10C = 6+1+2+1(central\ carbon)=10C=6+1+2+1(central carbon)=10 H=5+3+5=13H = 5+3+5=13H=5+3+5=13 and one Cl.

    So formula is: C10H13ClC_{10}H_{13}ClC10​H13​Cl

    This matches the given formula.

  5. Conclusion

    Compound BBB is: C6H5C(Cl)(CH3)(C2H5)\boxed{C_6H_5C(Cl)(CH_3)(C_2H_5)}C6​H5​C(Cl)(CH3​)(C2​H5​)​

    This corresponds to option C.

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