JEE 2005 Q

Can sum1 simplify Organic 4 me please[2]

I guessed the answer but dont have a perfect Xplanation

14 Answers

11
Anirudh Narayanan ·

Wat does the rxn b/w an alcohol and a grignard reagent give?? In general, will there be any rxn between a grignard product and grignard reagent???

1
skygirl ·

1
Pavithra Ramamoorthy ·

i think it shld be c)

11
Anirudh Narayanan ·

sky, since R is 30, won't the carbocation be more stable??

1
skygirl ·

is backside attack favourable in 3 degrees ??????

11
Anirudh Narayanan ·

back side attack??? that sounds ominous....

anyway, wat's the answer to my quesion??

1
skygirl ·

pehli baat toh yeh hai.. ki three degree cabocation form hi nahi hoga...

grinard follows SN2 => backside attack which is impossible in 3deg carbocation.

1
Vivek ·

The alcohol contains acidic hydrogen,which will be removed by the grignard reagent,so the product will be benzene

1
skygirl ·

phenol? i think typo.............

1
skygirl ·

yep... :)

1
Optimus Prime ·

grignard reagent with any compound containing active hydrogen (H2O,ROH,NH3 etc)
forms a hydrocarbon

HENCE THE ANSWER IS BENZENE
option B

1
Kalyan Pilla ·

ThanQ frns

I jus completely forgot abt this thread

Yup the answer is B Benzene.

ThnX 4 da Xplanation skygirl

1
Vivek ·

@ sky no need to complicate this as much as you have done,even if R was primary ,only benzene will be formed,nothing related to Sn1 or Sn2 as long as there is an acidic hydrogen

1
voldy ·

basically think of an acid base reaction guys don't think too much.

the grignard always acts as a base . try to find an acidic roton in the molecule then if you've found one put that with R . if not , then think of SN2 or whatever.

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