Answer them out! Tell the steps and reasons too!

Just answer all these organic's question and tag reason with it as well.
Q1: Napthalene + ( COCl-COCl ) ------(AlCl3)--> A ---(Zn(Hg)/HCl)--> B.

Q2: ---> A ----( NH2-NH2 ) B --- (Se + heat ) ----> C

13 Answers

39
Pritish Chakraborty ·

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 ·

@pritish how can B be wolff kishner theres only HYDRAZINE nothin else?

Se might oxidise B!

39
Pritish Chakraborty ·

Well..I assumed he forgot to mention it lols.

1
Ankur ·

@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 ·

@anyone: Can anyone justify role of Se in Q2?
@Pritish: IN Q1 : it is , I guess you saw it wrong.

39
Pritish Chakraborty ·

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 ·

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 ·

Selenium is used for aromatization .eg-cyclohexane+Se+heat gives benzene .Dont know the mechanism but sure of its function.

39
Pritish Chakraborty ·

Nice raghu! We didn't know that one.

1
Ankur ·

@Raghu: all right... is there 'no' function of Se on aliphatic hydrocarbon?

39
Pritish Chakraborty ·

Ankur...then will a four membered diketone(fused with napthalene) form? [In the COCl question]

1
Ankur ·

Answer for 1.. you are almost right.. sorry for late reply

1
rickde ·

q2)

ankur...u see in second step another ring will form attached to the benzene already present....Se will aromatize it to give napthalene.........

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