[IntheNameofScience]

Okay, so I read up that one could do a simple free radical substation of alkanes using either Cl2 or Br2. So I figured I would do this with some butane since it is easy to get my hands on. For my chlorine supply I theorized standard bleach would suffice. I did some research and found that Cl2 and butane should react to form 1-chlorobutane and 2-chlorobutane. Both which are poorly soluble in water and are liquid at standard temperature. So after measuring out about 210ml of bleach, and allowing to heat up to about 30-35C I bubbled in the butane. After about ten minutes of doing so and no visible reaction I came up with an idea to get it going. I mixed about 10ml of acetone with equal parts HCl (31.45%). I then added this to the bleach to capture the Cl2 gas that was released from the reaction between NaClO and HCl. Sure enough the acetone captured a decent amount of Cl2 gas. After all the HCl reacted and enough Cl2 gas dissolved in the acetone I proceeded to re-bubble the butane. I started to notice more bubbles appearing in solution. After a couple minutes of doing this a reaction took off. The bleach turned cloudy almost instantly and the bleach raised temperature to about 45C. After I let it sit for about a day all the cloudiness cleared and a darkish colored precipitate was seen at the bottom. I do realize that acetone does react with bleach to form chloroform and phosgene. Thank you for reading through all of that, and any hypothesis would be incredibly helpful because I'm clueless and technically not even an undergraduate in chemistry. (I'm a senior in high school who just really loves chemistry.)

[hypervalent_iodine]

a friendly suggestion: I very strongly recommend you stop doing these sorts of experiments if you don't know what you're doing (and you don't seem to). Wait until you've actually learnt some chemistry and can properly assess risks of your experiments, and can employ proper controls to minimise them.

[IntheNameofScience]

@ hypervalent_iodine: I will admit to this. Half the time I do often go off a whim. However, I do at times have a good idea of what would come out of a reaction. If I did have proper equipment I would have just directly reacted Chlorine gas a Butane. However, I don't have the right kind of equipment to handle Chlorine safely (I had to save up a couple months worth of my paychecks to afford the most basic of lab equipment). I should also mention I did this with very little control for a reason. I wanted to see if I could just make a homogenous mixture to see if bleach would suffice for a Chlorine source. Looking back now instead of being impulsive, I should have just slowly heated the bleach for more controlled results. I would also like to point out that if I didn't know chemistry all to well I probably wouldn't even know what a free radical substation is and the mechanics behind it. Thank you for your input and have a nice day.

[hypervalent_iodine]

I can't help but think that if you did know chemistry, you would have known that bleach plus butane wasn't going to do anything in the way of radical chlorination. Or that acetone plus bleach is not a good idea.

[LookAroundYou]

It is a bad idea to simply mix chemicals at random.

[sekio]

Free radical addition of halogens to butane generally doesn't happen at room temperature/pressure, it needs some pretty extreme reaction conditions to proceed to completion. In fact, hydrocarbons like butane, pentane, hexane etc are often used as solvents for reactions simply due to their rather unreactive nature. It's very hard to get them to react with anything at room temperature.

Also, chlorine bleach is not a good source of molecular chlorine. It's sodium hypochlorite solution - NaOCl and not just dissolved Cl2.

I also second everyone elses' advice to not mix chemicals without having some idea of what to expect. You don't want to be making chloroacetone or phosgene; they're chemical weapons and are strong irritants to any mucous membrane.

[sekio]

I'll second what everyone else is saying: free radical chlorination is not something you can, or should, go about doing in a bucket in your backyard. Most of the time it's conducted in high-pressure reactors as a gas phase reaction, and it's certainly not a common lab reaction.

Even if you mixed butane and chlorine gas in a sealed flask they wouldn't react at room temperature in the absence of any sort of energy to get the reaction going (light, heat etc). So doing it in a bucket of bleach water probably won't work either.