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Topic: Structure Eludication  (Read 3680 times)

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Offline specialk08

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Structure Eludication
« on: November 30, 2011, 08:01:15 PM »
Consider the information given below and identify the structure of the unknown
compound  A, with a molecular formula of C8H14.  Compound  A reacts with Br2/CCl4. 
Upon reaction with excess H2/Ni 1-ethyl-2-methylcyclopentane is produced. Subjecting
A to ozonolysis, the product shown below is produced as the  major organic product. 
Draw the correct structure of compound  A, and provide a brief and clear explanation
relating the data provide with the structure selected.

That's all I was given, where it says "the product shown below is produced as the major organic product" we weren't given anything.. I was wondering if anyone could determine what that is, so I can proceed with the question properly?

Offline Vidya

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Re: Structure Eludication
« Reply #1 on: November 30, 2011, 08:31:25 PM »

calculate the Degrees of unsaturation in the compound.From one of the product it is clear that compound has one ring and rest of the degrees of unsaturations are due to double or triple bonds.This compound has only two degrees of unsaturation .One is due to ring and other one is due to a double bond.Now your job left is to take out the position of the double bond from the ozonolysis products.Now the basic skeleton
is  1-ethyl-2-methylcyclopentane  with one double bond which you can easily predict from ozonolysis product.

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