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Yes, it can.

It is just like the famous iodoform (tri-iodomethane) test, where, instead of iodine, chlorine in aqueous sodium hydroxide is used.

The mechanism and overall reaction are shown below:

1. In the first instance, chlorine oxidises ethanol to the aldehyde ethanal:

2Cl2 + CH3CH2OH gives CH3CHO + 2HCl

2. Next, the three hydrogen atoms in the methyl group is substituted by chlorine atoms:

3Cl2 + CH3CHO gives CCl3CHO + 3HCl

3. Finally, the base (sodium hydroxide, for example) reacts with the intermediate organic compound formed to give chloroform and the methanoate anion:

XOH + CCl3CHO gives CHCl3 + HCOO- + X+

The overall reaction can be represented by:

5Cl2 + CH3CH2OH + XOH gives CHCl3 + HCOO- + X+ + 5HCl

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