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Ask iit jee aieee pet cbse icse state board community Community Discussion Question: URGENT!!!!!!!-SOLVE IF U CAN -ADDITN REACTNS-RTS ASSURED
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entropy (23)

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TELL ME, IF VINYL GP IS ATTACHED TO BENZENE RING,WHR WILL THE   ELECTRONS FLOW.................TOWARDS BENZENE RING i.e TO   C   ATOM ADJ TO BENZENE RING  (SINCE IT IS ELECTRON WITHDRAWING GP)   OR TO THE OTHER   C   ATOM.(DUE TO MARKONIKOFF'S RULE)


 


I THOUGHT  THE 1ST 2 B RIGHT ,BUT ARIHANT  SAYS THE OTHER.          PLEEEEEEEEEEZ REPLY SOON

    
tarinbansal (3903)

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vinyl group attached to benzene ring???


PLZ clarify which case R U talking abt?


1 or 2?



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entropy (23)

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I M TALKING ABT 2 CASE,. ALSO TELL ME HOW TO DRAW STRUCTR
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spideyunlimited (3912)

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tarin 1 is wrong since C is getting 5 bonds

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tarinbansal (3903)

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Ooops.
LOL...
Thanks spidey for correcting me. :)

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entropy (23)

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ARE SOM1 ANS MY Q.ITS URGENT!!!!!!!!!!!!! I M TOTALLY FLUSTERED

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tarinbansal (3903)

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I donno what do u mean by shifting of pi-bond.


Markonikov's rule is used in addition reactions and I have shown an example of addition reaction with H-Br in the figure.


And the intermediate should be the one shown in the figure.


And I neither trust nor follow arihant, so it may be possible that my answer differs from that of arihant's.



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spideyunlimited (3912)

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Since the left side Carbon is somewhat more stabilized due to the aromatic attachment, the pi electrons are a bit closer to the further C.

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pramod6990 (955)

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will shift towards the other carbon....coz benzly carbocation is acuired by doing so and it is very stable....


"Logic is the systematic way of reaching the wrong conclusion with confidence" lol.....
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tarinbansal (3903)

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If U follow the Markonikov's rule that - the acid proton bonds to that carbon atom of alkene that already holds more no. of H atoms.


Then plz stop following this rule.


Markonikov's rule(extended)-In an electrophilic addition to an alkene, the electrophile adds in such a way as to generate the most stable intermediate.


This is the correct and extended Markonikov's rule. Use this and U wud always get ur answers right.


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entropy (23)

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WAT I WAS THINKING
SEE, BENZENE RING IS ELECRON WITHDRAWING.THEH THE PI ELECTRS SHUD FLOW TO LEFT C ATOM
WHY THEY R SHIFTING TO THE OTHER C ATOM , NOW IF TO RIGHT SIDE C ATM 2 CH3 -ELEC RELEASING GPS R ATTACHED STILL THE MOVEMENT OF ELECTRN WILL B SAME
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tarinbansal (3903)

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Arre I have shown U the mechanism.

The pi bonds dont move anywhere. They polarize the H-Br bond to a large extent and extract H+ from H-Br which adds to the double bond in such a way as to generate the most stable intermediate(Markonikov's extended rule).

Still any doubt?

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entropy (23)

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I THOUGHT FIRST THE PI ELECTRN SHIFT ,FORMS ANION , H+ ATTACKS ,THEN REARRANGEMENT OF CATION TAKES PLACE TO ACQUIRE MAX STABLITY.WAS I WRONG?????????/
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entropy (23)

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ACTUALLY THEY HAV MNTIONED BENZYLIC RAD IS MORE STABLE
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