1)An aldehyde (A) (C11H8O), dosen't undergo self aldol condensation, & gives Benzaldehyde & 2moles of (B) on Ozonolysis.
One mole (B) on oxidation with Silver ion gives a dibasic acid (C), one mole of which liberates 2 mole CO2 at STP upon the action of 1 mole nascent Oxygen.
Identify the unknowns.
2) C6H5-COO-C6H5 ----Mononitration Product ?
3) 
---(Br2/Fe ; 1eq.)--> ?
4) Liquid(A) reacted with hot aqueous Na2CO3 sol.n giving a mixture of 2 salts (B) & (C).
The mixture on acidification with H2SO4 & distillation produces the liquid (A) again.
Identify A,B,C & explain the steps involved.
391)Aldehyde A has no alpha hydrogen for sure if it doesn't undergo aldol...
but don't alkenes give ozonolysis?
3) mein I think Br will attach to the right most benzene ring para to the nitrogen...
4)Aldol and retro aldol reactions? just a guess.
131) Okay got ur point, yes noa lpha hydrogens... but do alkynes also give ozonolysis with cleavage ?
3) U're right.
4) Zyaada mat socho. (waise, when i saw the sol.n it was tomfoolery, not a very clear Qn though.)
39http://en.wikipedia.org/wiki/Ozonolysis#Ozonolysis_of_alkynes
I mean...how can aldehydes undergo ozonolysis??
B being oxidized by silver means it responds to Tollen's reagent.
C would be a dicarboxylic acid.
Also in 2), ester group has -I effect. Meta position nitration?
13Where is the aldehyde undergoing ozonolysis...? The double/triple bonds will be there fr tht & the -CHO will be intact & will become a part of (B). [1]
131) Yeah, tht way (C) comes out 2b Oxalic Acid.
2) Kaun se -Phenyl mein, the one attached with -O or the one with -C=O ?
131) Yeah avinav, i got the same. (Ans nahi hai mere paas iska)
2)Govind's rite, Are v considering the 2nd ring (-O waali) to be activated by the lp(s) of oxygen ??
13Ok see the solution given fr Q4)....
R-C(=O)-O-C(=O)-R' ---(Hot aq. Na2CO3)---> R-C(=O)-ONa (B) + R'-C(=O)-ONa (C).
(C) + H2SO4 ----> R-COOH + R'COOH. (Acids)
---(Distill.)----> R-C(=O)-O-C(=O)-R'.
Aisa toh sapney mein bhi nahi socha tha maine...[3]
(IIT MAy 1997 Qn!)
