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Author Topic: Bicyclic compounds: tricyclo [2.2.1.0] heptane + chlorine in UV light  (Read 792 times)

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jongokkim

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tricyclo [2.2.1.0] heptane with chlorine in UV light results in formation of a dichloro product with ring opening.

a) what is the product? Name it & explain its formation with a scheme of reactions (mechanism not required)

b) when the dichloro product was subjected to an E1 reaction, two alkenes were formed. What are they? Show in detail, the mechanism for the formation of these E1 products.  ???
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Borek

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Re: Bicyclic compounds: tricyclo [2.2.1.0] heptane + chlorine in UV light
« Reply #1 on: December 05, 2012, 01:26:11 AM »

You have to show your attempts at solving the question to receive help. This is a forum policy.

Please read forum rules.
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orgopete

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Re: Bicyclic compounds: tricyclo [2.2.1.0] heptane + chlorine in UV light
« Reply #2 on: December 05, 2012, 01:53:09 AM »

If I understand the question correctly, then I'd like to suggest that cyclopropanes can sometimes react as though they were a double bond with ring opening. If that were to happen here, what would be the product?
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jongokkim

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Re: Bicyclic compounds: tricyclo [2.2.1.0] heptane + chlorine in UV light
« Reply #3 on: December 05, 2012, 08:13:28 PM »

ok my attempt at solving this is
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fledarmus

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Re: Bicyclic compounds: tricyclo [2.2.1.0] heptane + chlorine in UV light
« Reply #4 on: December 07, 2012, 02:47:57 AM »

First you need to get your starting material right - that doesn't appear to be a tricyclic compound you are starting with.
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orgopete

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Re: Bicyclic compounds: tricyclo [2.2.1.0] heptane + chlorine in UV light
« Reply #5 on: December 07, 2012, 05:49:22 AM »

The starting material should look like a cyclopropane with two cyclobutane rings annealated to the same bond of the cyclopropane. Hint, that is the bond that breaks in the chlorination. Hint #2, Bredt's Law was probably discussed in class.
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