While I was doing problems on reduction of aldehydes and ketones, I encountered this particular questionenter image description here

Here, I know that Clemensen reduction reduces the ketone group to $-CH_2-$ group. But, the answer key has given the option (c). I also know that the mechanism for this reduction is still shaky for the senior high school kid. But, how to deal with substitution like these as in case of this question

enter image description here

In this question option (a) is the answer though this is wolf kishner reduction.

Any suggestions how to solve these reactions?

  • $\begingroup$ Pardon me if I don't know any particular fact about it as I am reading and practicing myself on this. Reading from David Klein's organic chemistry book. But, practising from M. S. Chouhan's Problem on oRganic chemistry chemistry. $\endgroup$ – jayant98 Jan 19 '19 at 18:16
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    $\begingroup$ Under the conditions quoted I'm surprised you don't get hydrazine displacing Cl in a SNAR $\endgroup$ – Waylander Jan 19 '19 at 19:19