[Pranav]

I came across this question recently where I have to determine the products after each step.

After reaction with ammonia, Br gets replaced by NH₂. I have never seen a reaction of ozone with amine so I am unable to proceed further.

Any help is appreciated. Thanks!

[sjb]

I'm not sure it is ozonolysis (could be wrong though). What kind of reagent is ozone?

[discodermolide]

What reacts with ozone? And find out that and you will realise what the ammonia does (it is not a displacement of bromine).

[Pranav]

I'm not sure it is ozonolysis (could be wrong though). What kind of reagent is ozone?

Well, I should have chosen a better title for this thread. I realised it soon after posting the thread.
Ozone is an oxidising agent.

What reacts with ozone? And find out that and you will realise what the ammonia does (it is not a displacement of bromine).

Why it does not replace Br? 
Ozone reacts with alkenes and alkynes. Do you mean that an alkene is formed after reaction with ammonia?

[discodermolide]

Yes, exactly that.

[Pranav]

Yes, exactly that.

Thanks but can you please shed some light on why Br is not replaced by NH₂?

Also, I am unaware of the action of BaO here. I haven't ever used this reagent.

[discodermolide]

You don't say what form the ammonia is in, as a gas, concentrated solution?.
BaO probably destroys the ozonide, although I have never seen that reagent used for this purpose.
So you will end up with the di-aldehyde?

[Pranav]

You don't say what form the ammonia is in, as a gas, concentrated solution?.
BaO probably destroys the ozonide, although I have never seen that reagent used for this purpose.
So you will end up with the di-aldehyde?

The question doesn't mention anything about the state of ammonia.
I am not sure of the answer because I don't have the answer key.

Thanks for the help.

[sjb]

You don't say what form the ammonia is in, as a gas, concentrated solution?.
BaO probably destroys the ozonide, although I have never seen that reagent used for this purpose.
So you will end up with the di-aldehyde?

Ahhh, that wasn't what I was thinking. I was going bromocyclohexane aminocyclohexane  1-aminocyclohex-1-ene (perhaps via the imine, ozone acting as an oxidant), and then losing myself. Could the barium oxide be acting as a dehydrating agent (it's certainly used as a drying agent..?), so forming e.g. adipic anhydride from the diacid, or if you think it's the dial, an aldol condensation?

[discodermolide]

As the ozonide is an oxidising agent I think the BaO decomposes the ozonide by forming BaO₂. This would give the di-aldehyde as the product.

BaO₂ reacts with water to give oxygen and BaO, what a surprise.
http://simple.wikipedia.org/wiki/Barium_peroxide
http://en.wikipedia.org/wiki/Barium_peroxide

[Pranav]

I managed to get the answer key and it says that the final product is cyclohexanol. I don't see how this could form.

[discodermolide]

Neither do I.

[Pranav]

Neither do I.

So di-aldehyde is the answer then?
Also, dialdehyde is not given as an answer in any of the options given with this question.

Can you provide me a link where I can understand the reaction of ammonia in different states? Thanks.

[Dan]

Also, dialdehyde is not given as an answer in any of the options given with this question.

Can you post the options given with the question?

[orgopete]

I don't see how that can be the product from a prior oxidation reaction. If we leave out ammonia and ozone, then cyclohexanol may form to some extent.