November 25, 2024, 01:28:53 AM
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Topic: What happens when two 6 membered rings that are fused together by a double is re  (Read 1608 times)

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Offline lrhyner

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I was given this question in class, but I am not sure how to go about it

I am not sure what the structure is called but two hexane rings are side by side with a double bond on the side connecting them. The ring on the right has a double bonded CH2 on the second carbon. I counted from top to the right. This structure is then reacted with O3/Me2S. B

Based on my understanding wouldn't the structure have a ring break or will the structure fuse to form one ring?I know with ozone that usually keytones or aldehydes are formed, but I am not sure in this case.

Offline discodermolide

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I think the following reaction all take place.
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Offline orgopete

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It will break the ring creating a new and larger ring. No ring reformation with the reagents listed.

Dimethylsulfide reduces the peroxides created in the ozonization. Hydrolysis of an ozonide will formally produce two carbonyl groups and hydrogen peroxide. The hydrogen peroxide can react with carbonyl groups. Dimethylsulfide reacts with an ozonide or peroxides to produce dimethylsulfoxide and water.
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