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Question

Hydrocarbon (A)(C=87.2%) on hydrogenation forms (B)(C=84.1%). Ozonolysis of (A) forms acetic acid, acetone and pyruvic acid CH3OCCOOH. What are (A) and (B)?

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Solution

Percentage composition shows that (A) and (B) has empirical formula (A)C4H7 and (B)C4H9.
Compound(A)Ozonolysis−−−−−CH3OCOH+CH3OCCH3+CH3OCOCOH
Thus, compound (A) should have eight carbons.
Molecular formula of (A)willbeC_{8}H_{14}andthatof(B)willbeC_{8}H_{18}.Degreeofunsaturationincompound(A) = \dfrac {2n_{1} - n_{2} + 2}{2} = \dfrac {2\times 8 - 14 + 2}{2} = 2Thus,compound(A)shouldhavetwodoublebonds.Onthebasisofozonolysisproductsstructureof(A)$ can be guessed as,
1542997_1719702_ans_589976c7666f457a9357c66fad693ba9.jpg

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