Aromatics...

THIS QUESTON IS STRICTLY FOR PRITISH SINCE HE THREATENED TO SHOOT ME IF I DO NOT GIVE HIM AN ORGANIC QUESTION AND I AM AFRAID OF THAT :P

A soln. of 0.01 mole tert-butyl peroxide in excess ethylbenzene was irradiated with ultraviolet light for several hours. Gas chromatographic analysis of the product showed presence of neary 0.02 moles of tert-butyl alcohol. Evaporaton of the alcohol and the unreacted ethyl benzene left a solid residue which was separated by chromatography into just 2 products: A(1 g) and B(1 g). A and B each had the empirical formula C8H9 and mol. wt. 210; each was inert towards cold dilute KMnO4 and toward Br2/CCl4.

When isopropyl benzene was substituted for ethyl benzene in the above reaction, exactly similar results were obtained, except a single product C(2.2 g) was obtained instead of A and B. C had empirical formula of C9H11, mol. wt. 238. and was inert towards cold dilute KMnO4 and toward Br2/CCl4.

What is the most likely structure of A, B and C, and what is most likely mechanism by which they are formed....[1][1]

5 Answers

13
Avik ·

Chal lag jaa kaam pe, Pritish ;)

Aisa lagta hai, sb Qn ko direct Chemistry laboratory se utha ke laaya hai :D

1
hacker ·

abey kya fark padta hai jab woh khud ORGANIC CHEMISTRY se question pooch raha hai!

39
Pritish Chakraborty ·

Irradiation by light and a peroxide(rather hydroperoxide) suggest a radical mechanism to me.
That it is irradiated by light also suggests that usual catalysis is not required and light is performing that function.

But if it formed exactly twice tert-butyl alcohol than the original amount of peroxide, it has to be di-tert-butyl peroxide...

Confirm and let's see. And something of interest, though I'm not sure how it applies here -:

23
qwerty ·

T can plant the bomb either at A or B , lekin pritish is such a ct who always carries a defusal kit with him(even if the map is dima lolzzzz , and hamesha organic ke Qs ko defuse karke hi rehta hai
lolzzzzzzzzzzzzzzzzzzzz

49
Subhomoy Bakshi ·

thread unsloved yet!!!

answer in this format::

A:

B:

C:

i thnk i should have named this googly from ATGS 14 or something !! LOL!! :P

Your Answer

Close [X]