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Question

An organic compound 'A', C8H6 on reacting with dil H2SO4 and HgSO4 gives a compound 'B' which can also be obtained from reaction of benzene with acid chloride in the presence of anh. AlCl3. Compound 'B' when reacted with iodine and aq. NaOH yields 'C' and a yellow compound 'D' . Identify A to D with proper justification.

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Solution

Given that the compound B can also obtained by reaction between benzene with acid chloride in presence of anhy. AlCl3.
The reaction can be given as follow:
C6H6Benzene+CH3COClanhy.AlCl3−−−−−−C6H5O||CCH3acetophenone(B)
Also, compound B is also obtained by reaction of compound A with H2SO4 and HgSO4.
This reaction is hydration of alkyne which give aldehyde and ketones on rearrangement.
Thus the compound A must be alkyne.
Looking at product B, it can be concluded that the compound A will be C6H5CCH which is 1phenyl ethyne
Now, the compound B is acetophenone i.e. a methyl ketone. Thus it can react with I2+NaOH to undergo Haloform reaction to give sodium benzoate(C) and yellow coloured Iodoform(D)
C6H5O||CCH3BI2+NaOH−−−−−C6H5O||CONaC+CHI3D

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