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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Steenrod on October 19, 2012, 02:26:11 AM

Title: Ozönolysis
Post by: Steenrod on October 19, 2012, 02:26:11 AM

What are the products formed by reductive ozonolysis of penta-1,3-diene?It seems the two double bonds are confusing me.Thanks.

Title: Re: Ozönolysis
Post by: discodermolide on October 19, 2012, 02:34:41 AM

Complete reductive ozonolysis should give methanol, ethanol and ethylene diol.

Title: Re: Ozönolysis
Post by: Steenrod on October 19, 2012, 03:37:48 AM

Can you please explain how you arrived at the answer?

Title: Re: Ozönolysis
Post by: discodermolide on October 19, 2012, 03:39:48 AM

What does ozonolysis do to a double bond, and what does the reductive work-up do?

Title: Re: Ozönolysis
Post by: Hunter2 on October 19, 2012, 03:49:23 AM

Quote

ethylene diol

Do you mean ethane-1,2-diol or ethylene glycol?

Title: Re: Ozönolysis
Post by: discodermolide on October 19, 2012, 04:07:09 AM

The first one.

Title: Re: Ozönolysis
Post by: discodermolide on October 19, 2012, 04:51:07 AM

@Steenrod
Have a read at this page:
http://www.ch.ic.ac.uk/local/organic/18.html (http://www.ch.ic.ac.uk/local/organic/18.html)

Title: Re: Ozönolysis
Post by: Hunter2 on October 19, 2012, 04:55:12 AM

Both are the same, only ethylene diol is not known.

If existing, it would be HOCH=CHOH, what converts to OHC-CHO Ethane-dial (Glyoxale).

Title: Re: Ozönolysis
Post by: discodermolide on October 19, 2012, 06:50:35 AM

It is a reductive ozonoylsis, that means the aldehydes and ketones produced are reduced to the corresponding alcohols.

Title: Re: Ozönolysis
Post by: Hunter2 on October 19, 2012, 06:56:20 AM

Thats correct, but I was talking about the name ethylene diole. Not about the ozonolysis.

Title: Re: Ozönolysis
Post by: discodermolide on October 19, 2012, 06:57:35 AM

Sorry, I was not clear what you meant.

Title: Re: Ozönolysis
Post by: orgopete on October 19, 2012, 06:28:55 PM

I would have suggested different products. I always thought that ozonolysis had and oxidative (H+, H2O2) or reductive (Me2S or Zn, HOAc) work up. If that were the reductive work up, then aldehydes would be the products, formaldehyde, glyoxal, and acetaldehyde.

Title: Re: Ozönolysis
Post by: discodermolide on October 19, 2012, 09:14:26 PM

If that's the case here then I agree with your suggested products.