$\underset{\text{symmetrical Ketone}}{(A)}\,$ $\xrightarrow{LiAlH_{4}}(B)$ $\xrightarrow[\Delta ]{H^{\oplus }}\text{Diastereomers}$
Reactant $(A)$ is

  • A
    $CH_{3}-C(=O)-CH_{3}$
  • B
    $CH_{3}-C(=O)-CH_{2}-CH_{3}$
  • C
    $CH_{3}-CH_{2}-C(=O)-CH_{2}-CH_{3}$
  • D
    $CH_{3}-CH_{2}-CH_{2}-CH=O$

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Clemmensen's reduction will convert cyclohexanone into

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