Q. An organic compound A, C6H10O3 is an ester. A reacts with NaOH and I2 to give CHI3 and a salt which is hydrolysed in acidic medium to give B. On de-carboxylation, B gives an organic compound C.
Then:
the organic compound A may be:
a) C2H5COCOOC2H5
b) CH3COCH3COOCH2CH3
c) CH3COCOOCH(CH3)2
d) CH3COCH2CH2COOCH3
The organic compound B and C are:
a) (CH2)2(COOH)2 ; CH3CH2COOH
b) (COOH)2 ; HCOOH
c) CH2(COOH)2 ; CH3COOH
d) CH2(COOH)2 ; CH3CH2COOH
Please give me your answer as soon as possible...
is the ans d and c resp.
Well for the 1st ques. I also got (d). But r u sure on treatment with NaOH/I2 the option d) will give CH2(COOH)2. Shouldn't it give (CH2)2(COOH)2 and hence CH3CH2COOH i.e. option (a).
Bcouz i dunno the correct answer, I would like u to give me the steps by which u got option (c) correct.
Bcouz i dunno the correct answer, I would like u to give me the steps by which u got option (c) correct.
Hi Ankul,
When i first read the qn i also got the same answer as u have! but on giving it a further thought i cudnt get a reason why the ans cant be b and c respectively! cud u pls post ur comments! it wil b nice of u if u wil post the correct solns after u get them!thanking u! kvs
Well Karthik... What's even wrong with c and b resp. 
Karthik u didn't further gave any suggestion... well how r u getting b and c correct??
Hi ankul,
the qn was so confusing that i thought i wud ask my chemistry teacher, but as he was not available for the past 3 days i cud not giv any confirmatory answer!!! so sorry for the delay frnd!!! but as far as my b and c options are concerned it is based on the fact that when b undergoes holoform it forms (COOH)-COOCH2CH3 which on further rn wid the OH part of NaOH which is a condition of haloform it forms the first part of the option C! this on decarboxylation once wil giv the second part of C! but as u said the ans cud be C and B also ! but if this was a single option qn i wud hav chosen D and A for the dicarboxylic acid formed in option D is the weakest when compared to the dicarboxylic acids formed in options B and C! so it wil undergo the easiest decarboxylation to form option A!! what say dude???? kvs
Hi Kvs,
I have received the answers of my test. The answer to these 2 ques. is given as (b) and (c). So i think u were right earlier. Since the soln. isn't given so i can't justify the answer... Any comments???
I have received the answers of my test. The answer to these 2 ques. is given as (b) and (c). So i think u were right earlier. Since the soln. isn't given so i can't justify the answer... Any comments???