39
Pritish Chakraborty
·2010-03-26 22:29:47
Q1. A would be Ph-CO-COCl and B would be Ph-CH2-COCl...? not sure about B. Damned Clemmensen reduction.
Q2. A would be formed by intramolecular EAS. It would be a benzene ring with a cyclohexanone ring. B would be benzene and cyclohexane fused(Wolff Kishner reduction). Dunno C..
1
Tapas Gandhi
·2010-03-26 22:41:45
@pritish how can B be wolff kishner theres only HYDRAZINE nothin else?
Se might oxidise B!
39
Pritish Chakraborty
·2010-03-26 22:49:38
Well..I assumed he forgot to mention it lols.
1
Ankur
·2010-03-26 23:31:14
@Pritish: Right.. I forgot to mention KOH/glycol.. :D .. well.. for Q2, you are right till B but the hurdle was C only. C is napthalene.
for Q1: no.. it's not right.
1
Ankur
·2010-03-26 23:58:02
@anyone: Can anyone justify role of Se in Q2?
@Pritish: IN Q1 : it is , I guess you saw it wrong.
39
Pritish Chakraborty
·2010-03-27 00:05:05
I didn't see it wrong Ankur...COCl-COCl mein ek Cl toh AlCl3 le lega...C+(=O)-COCl attacks benzene ring then!
1
Ankur
·2010-03-27 00:07:50
k.. let's assume that there are 2eq. of AlCl3 [because they didn't mention that, but answer depicts action of AlCl3 twice.].. now go on..
1
raghu
·2010-03-27 00:37:11
Selenium is used for aromatization .eg-cyclohexane+Se+heat gives benzene .Dont know the mechanism but sure of its function.
39
Pritish Chakraborty
·2010-03-27 00:38:54
Nice raghu! We didn't know that one.
1
Ankur
·2010-03-27 03:16:02
@Raghu: all right... is there 'no' function of Se on aliphatic hydrocarbon?
39
Pritish Chakraborty
·2010-03-27 03:18:27
Ankur...then will a four membered diketone(fused with napthalene) form? [In the COCl question]
1
Ankur
·2010-04-07 03:19:23
Answer for 1.. you are almost right.. sorry for late reply
1
rickde
·2010-04-07 03:24:02
q2)
ankur...u see in second step another ring will form attached to the benzene already present....Se will aromatize it to give napthalene.........