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An aldehyde (A) (C(11)H(8)O), which does...

An aldehyde (A) `(C_(11)H_(8)O)`, which does not undergo self aldol condensation, gives benzaldehyde and 2 mol of (B) on ozonolysis. Compound (B) on oxidation with silver ion gives oxalic acid. Identify the compounds (A) and (B).

Text Solution

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(i) As the compound 'A' `(C_(11)H_(8)O)` gives benzaldehyde as one of the products on ozonolysis, it must have a benzene nucleus or phenyl group `(C_(6)H_(5))`. The formula of the side chain is `(C_(11)H_(8)O - C_(6)H_(5)) = C_(5)H_(3)O`
(ii) Since the compound 'A' is an aldehyde therefore, the side chain may be written as `C_(4)H_(2)CHO`. Thus, the compound 'A' may be expressed as : `C_(6)H_(5)(C_(4)H_(2)CHO)`
(iii) As one mole of 'A' on ozonolysis gives two moles of 'B'. This mean that the size chain must have two unsaturated bonds and one of them must be a triple bond.
(iv) As the compound 'A' does not undergo Aldol condensation, there should no `alpha`-hydrogen atom. Keeping in view the above observations, the formula of the compound 'A' is `C_(6)H_(5)-CH=CH-C-=C-CHO`. The sequence of the reactions involved is as follows :
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