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Forum Index -> Organic Chemistry like the article? email it to a friend.  
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prakhar_galaxy (501)

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Sir
this ques i am not getting it at all.Means how can it occur
So
Plzz explain it with the mechanism
Thanx
[Thumb - Locus ques 2.JPG]

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lokeshsardana (675)

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yeah! this is an exceptional case.............

in this case , instead of forming viccinal dihalide , cyclic sulphite is formed........

this is due to fact that both OH groups are close to each other, which is quickly attacked by SOCl2 molecule and 2 molecules of HCl are removed forming stable sulphit ring..........now as this ring is quit stable and due to absence of one more halogen atom(because both Cl are removed by 2 OH groups) further breaking into SO2 and alkyl halides .....does not takes place............and so final product is sulphite ring of given diol......

satisfied!!!!!!!

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lokeshsardana (675)

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however if we use PCl instead of SOCl2 ...........the final product will be viccinal dihalide..........

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There are only two ways to live your life. One is as though nothing is a miracle. The other is as though everything is a miracle.
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lokeshsardana (675)

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sorry dude............didn't see the heading that it was 4 madhusudan sir...........

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tarinbansal (3637)

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How do we know all the exceptions in organic chem?

Should we learn all the exceptions of organic? That will be too bulky.

The quality of a person's life is in direct proportion to their commitment to excellence, regardless of their chosen field of endeavor.

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lokeshsardana (675)

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no.................not all...............this one is imp..........and is found in each book under topic of diols...........

my future signature:
LOKESH SARDANA,
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There are only two ways to live your life. One is as though nothing is a miracle. The other is as though everything is a miracle.
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madhusudan.chavan (777)

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HO¾CH2¾CH2¾CH2¾OH + O=S(¾Cl)¾Cl ®

H¾O+¾CH2¾CH2¾CH2¾OH
ï - HCl
O-¾S(¾Cl)¾Cl ®


CH2¾CH2¾CH2
ï ï
O¾S(=O) OH
ï
Cl ®


CH2¾CH2¾CH2
ï ï
O¾S(=O)¾O+¾H
ï -HCl
Cl ®

CH2¾CH2¾CH2
ï ï
O¾S(=O)¾O

As explained in the earlier mechanism for formation of corresponding chloride the intermediate is formed by the reaction of thionyl chloride instead of being attacked by Cl- by SN2, the lone pair of electron on second OH attacks the sulphur atom to form the intermediate as shown above which loses the HCl to give six membered ring.This is the possible mechanism for the formation of the product shown by you.
Thank you for correcting me. Initially it appears to be a simple reaction of thionyl chloride and alcoholic OH. If the reaction is with only one mole of thionyl chloride there 3-chloro ?1-propanol should be formed along with the above mentioned product. The % of each product will depend on the reaction condition. I have my own doubt about the stability of the cyclic product as sulphur is attached to three more electronegative atoms.
The problems posted by you are really challenging , keep it up; do share such problems with me.




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madhusudan.chavan (777)

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HO¾CH2¾CH2¾CH2¾OH  + O=S(¾Cl)¾Cl ®
 
H¾O+¾CH2¾CH2¾CH2¾OH
        ï                                              - HCl
O-¾S(¾Cl)¾Cl                            ®
 
 
CH2¾CH2¾CH2
ï                              ï
O¾S(=O)     OH
        ï
        Cl                                         ®
 
 
CH2¾CH2¾CH2
ï                        ï
O¾S(=O)¾O+¾H
        ï                                        -HCl
        Cl                                        ®
 
CH2¾CH2¾CH2
ï                     ï
O¾S(=O)¾O
 
As explained in the earlier mechanism for formation of corresponding chloride the intermediate is formed by the reaction of thionyl chloride instead of being attacked by Cl- by SN2, the lone pair of electron on second OH attacks the sulphur atom to form the intermediate as shown above which loses the HCl to give six membered ring.This is the possible mechanism for the formation of the product shown by you.
Thank you for correcting me. Initially it appears to be a simple reaction of thionyl chloride and alcoholic OH. If the reaction is with only one mole of thionyl chloride there 3-chloro ?1-propanol should be formed along with the above mentioned product. The % of each product will depend on the reaction condition. I have my own doubt about the stability of the cyclic product as sulphur is attached to three more electronegative atoms.
The problems posted by you are really challenging , keep it up; do share such problems with me.
 
 
 
 
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prakhar_galaxy (501)

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Thanx sir for ur answer
i will keep asking my queries
bye

PLZ DONT RATE ME FOR MY ANSWERS,IF U WANT TO COMPLIMENT ME THEN JUST HELP ANY OTHER IN FUTURE AS I AM DOING IT NOW

FILL THE UNFORGIVING MINUTE WITH 60 SECONDS THEN THE LIFE WILL BE YOURS

The woods are lovely, dark &deep
But I have promises to keep
And miles to go before I sleep
And miles to go before I sleep
-Robert Frost
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