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Ask iit jee aieee pet cbse icse state board community Community Discussion Question: Electrophylic Aromatic Substitution 2:
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sahilgupta_iit (355)

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Single Answer Question: Which of the following gives phthalic anhydride on reaction with conc. H2SO4 in the presence of Hg?
(a) Napthalene         (b) Phenol           (c) p-xylene          (d) m-xylene
 
guys first of all tell me what is phthalic anhydride  and  what happens in the reaction with conc. sulphuric acid in presence of Hg...
 
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LAMPARD (1142)

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I think it oxidises...but i am not sure...and if it oxidises,then i think the answer will be a...naphthalene

MaNuTd RoXxXx..MaNuTd 2 WiN PrEmIeR LeAgUe ThIs SeAsOn ToO AlOnG WiTh ChAmPiOnS LeAgUe.....HaiL RoNaLdO ...HaiL LaMpArD...
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elastiboysai (2327)

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Chemical StructurePthalic anhydride
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sahilgupta_iit (355)

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naphthalene is correct... but how naphthalene on oxidation produce the above compound?
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eistien (343)

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yeah its napthalene i hope you remember the use of HgSO4 /H2SO4 in the preparation of aldehydes and ketones from alkynes and alkenes this is a similar way for napthalene but i would prefer to use V2O5 for the above preparation !!!! is my answer correct???elasti boy's stucture explains it!!!
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eistien (343)

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hello reply!!!!
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sahilgupta_iit (355)

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I am in +1. I haven't done the chemistry of aldehyde and ketone
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eistien (343)

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hey you know the mechanism of action of HgSO4 /H2SO4 no similar mechanistic approach one ring gets cleaved!!!
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computer001 (1847)

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napthalene surely..
edit:
u can tell from structur itself

Nitwit Blubber Odment Tweak
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eistien (343)

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oh ok then take this note terminal alkenes aon treatment with HgSO4/H2SO4 a strong oxidising agent gives rise to formation of C=O group leading to aldehyde formation otherwise it gives a ketone when in the middle sometimes it may even give rise to a ether so here's it the two bond in the second ring of napthalene cleave to give rise to two C=O groups with a -O- linkage forming pthalic anhydride is it ok???
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sahilgupta_iit (355)

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but in structure of naphthalene given by elastiboysai, there are only four carbons in the second ring.
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sahilgupta_iit (355)

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i mean in which there is oxygen
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eistien (343)

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hey there are only two carbons in the second ring and the other one is oxygen the other carbons which you think are lost from the napthalene are as by product in the form of CO2!!!! now understood!!!???? thats also oxidation no!!! remember HgSO4 is a very good oxidising agent!!!!
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eistien (343)

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hello sahil???
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sahilgupta_iit (355)

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done
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