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An unsaturated hydrocarbon 'A' adds two ...

An unsaturated hydrocarbon 'A' adds two molecules of `H_(2)` and on reductive ozonolysis gives butane-1, 4-dial, ethanal and propanone. Give the structure of 'A' , write its IUPAC name and explain the reactions involved.

Text Solution

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(i)Since the hydrocarbon (A) adds two molecules of `H_2` , therefore, (A) is either an alkadiene or an alkyne.
(ii)On reductive ozonolysis 'A', gives three fragements , one of which is a dialdehyde. Therefore , the molecule has undergone cleavage at two unsaturated sites. In other words, hydrocarbon 'A' has two double bonds, i.e., A is an alkadiene and not an alkyne.
(iii) Place the three fragements of reductive cleavage side by side in such a way that the dialdehyde is placed in the middle while the other two products on either side of the dialdehyde. Thus, we have,

Now , remove the oxygen atoms, and connect the remaining three fragments by double bonds, the structure of the alkadiene (A) is

Step 3.To explain reactions involved in the question .
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