Question

A compound with the formula C6H12O gives a negative Tollens' reagent test and a positive iodoform test. It

produces semicarbazone effect and can be reduced to n-hexane with Clemmensen reduction. Identify the compound.
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Answer 1

Answer:

A compound with the formula C6H12O gives a negative Tollens' reagent test and a positive iodoform test. It

produces semicarbazone effect and can be reduced to n-hexane with Clemmensen reduction. Identify the compound.

Answer 2

Identify the compound.

Explanation:

The given compound is Hexan-2-one

Formation of semi carbazone justifies the presence of carbonyl group. It can be either an aldehyde or a ketone.  

The compound is reduced to n-hexane with Clemmensen Reduction. This indicates the presence of ketone group.

The compound gives a negative Tollens test indicating the absence of  aldehyde group.

Positive iodoform test indicate the presence of methyl ketonic group.

The compound will be:

$CH_{3}CH_{2}CH_{2}CH_{2}COCH_{3}$

Hexan-2-one on reaction with Zinc amalgam in the presence of hydrochloric acid produces n-hexane.

$CH_{3}CH_{2}CH_{2}CH_{2}COCH_{3} --^{Zn-Hg/HCl}-->C_{6}H_{14}$