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gokul07 (0)

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convert toluene to o-bromotoluene without using direct bromination

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aman23iit (191)

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hi friend its simple see first step is mono nitration at ortho position then reduction of -NO2 group by LiAlH4 then treatment with NaNO2/HCl which convert it into dissonium salt and finally treatment with CuBr and you will get the desired product
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DON007 (1463)

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hey aman if u will use NO2+ THEN THE PARA will also be formed.............
 
so the major concern is to make 100% ortho...........
for this ..............para should be blocked..............ok.........
 
now.............
C6H5CH3 +   ( CH3)3Br  --->  (CH3)3--C6H5- CH3
[ NOTE : HERE ORTHO WILL NOT BE FORMED BECAUSE........
             due to stearic hindrance..........only para will be formed]
now use NO2+ REAGENT............NO2  WILL HAVE NO OPTION BUT JUST ...IT WILL ATTACH TO ORTHO.............
NOW..............REDUCE IT BY Sn/HCl.............to NH2............
USE NaNO2 / HCl  AND  then CuBr................
the desired product will be obtained.................
thanku...........

BELIEVE IN URSELF.....BECAUSE I BELIEVE IN U..............
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madhusudan.chavan (1302)

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Sulphonation of toluene will give mainly p-toluenesulphonic acid. Bromination of this will introduce bromine w.r.t. methyl group. Desulphonation with HCl at 423k under pressure will give the desired o-bromotoluene.
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