Ozonolysis and other Orgo stuff!

[drteeth]

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Yo Kids,

So I have some more ochem questions that need answers. Ive asked Poc about 10milllllllion questions regarding orgo so I figured I would give a him a bit of a break 😀 and drill you guys on a few additional questions...

Regarding Ozonolysis, Kaplan shows that if you have a terminal alkYNE added with O3, CCl4, and
H20 you would get 2 Carboxylic products.

1). Is it true that this would not occur on a terminal alkyne if you added the O3 with Zn?

2). If the alkYNE was internal added with O3 CCl4 would you still get the COOH products or only aldehydes?

3). Would you get COOH products if you had the O3 + CCl4 added to a terminal alkENE? What about these reactants on an internal alkENE?

4). Would there ever be a situation in which O3 + Zn could result in COOH - ever?

Thanks for the help guys!!🙂

 

[TheWiredNerv]

1. I'm not quite sure. I'd assume you'd generate some type of anhydride,with the terminal carbonyl being an aldehyde.

2. You need water to produce the COOH groups so you'll get an acid anhydride. Remember acid anhydride + water gives you two carboxylic acids.

3. No COOH products from ozonolysis of alkenes. Terminal will yield two aldehydes or an aldehyde and a ketoen depending on the substitution. Internal will again yield either ketones or aldehydes depending on how the alkene is substituted.
4. You need water to produce COOH with ozone.
Hope this helps.