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Ask iit jee aieee pet cbse icse state board community Community Discussion Question: wat is the ans to this???
Forum Index -> Organic Chemistry like the article? email it to a friend.  
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iitjee08aspirant (280)

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http://www.hashminds.com/public/question.do?mode=salone&questionid=221
a good question plz ans

FAILURE IS NOT FALLING IN LIFE BUT NOT RISING AGAIN AFTER FALLING!!!!!!

I LIKE WAVES NOT BECAUSE THEY RISE AND FALL..
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dream (569)

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the answer is C and not D      [edited]

see in the first step, CHCl3 add up to ring as CHCl2-

in second step, one of the -Cl is replaces by -CN

final step, -CN gives acid, and -Cl being a better leaving group gets out and gives place for -OH

the reason is that -OH is a better activating grp as compared to -CH3
so subsn shud take place in acc with -OH group and hence subn will take place at o- group to -OH

the coloured part is edited one
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ashgirl (1429)

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er are u sure its correct???
 
i think the ans shud be C

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iitjee08aspirant (280)

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ya thats wat i was thinkin the orintation shud be decided by OH grp....

FAILURE IS NOT FALLING IN LIFE BUT NOT RISING AGAIN AFTER FALLING!!!!!!

I LIKE WAVES NOT BECAUSE THEY RISE AND FALL..
BUT BECAUSE EVERYTIME THEY FALL THEY RISE AGAIN!!!!!!!



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ashgirl (1429)

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yup.same here
 
CHO shud go to ortho wrt OH

Remember Cedric. Remember, if the time should come when you have to make a choice between what is right and what is easy, remember what happened to a boy who was good, and kind, and brave, because he strayed across the path of Lord Voldemort. Remember Cedric Diggory.


Albus Dumbledore
Goblet of Fire, Chapter 37, Page 724
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tarinbansal (3247)

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Hmm, the answer shud be C.

See, to place an electrophile U need to see a position with MAX electron density.
Now both OH and CH3 hav +R effect but OH shows Mesomeric effect and CH3 shows hyperconjugation.
Now the priority order of the effects is-
 
MESOMERIC > HYPERCONJUGATION > INDUCTIVE

So electron density near OH will be more than that near CH3.

So the CHO will be placed near OH NOT CH3.

EDITED

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