Q13 / 150 · MHT CET 2009 · Chemistry

A dihaloalkane ' $X$, having formula $\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{Cl}_{2}$, on hydrolysis gives a compound, that can reduce Tollen's reagent. The compound $X^{\prime}$ is

  • A
    1,2 -dichloropropane
  • Correct answer
    B
    1 , 1 -dichloropropane
  • C
    1,3 -dichloropropane
  • D
    2, 2-dichloropropane

Solution

Since, the obtained compound reduces Tollen's reagent, it must be an aldehyde. Thus, it is obvious that both the $-\mathrm{Cl}$ atoms are present at $\mathrm{C}_{1} . \quad$ Hence, $\quad$ the $\quad$ compound $\quad{X}^{\prime}$ is 1, 1-dichloropropane and the reactions are as follows Figure

Hence, the correct answer is option: 'B'.

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