if u know the mechanism please post
CH3- CH2 -CH= CH2 + CH3-OH + (H+) -------> CH3-CH2 -CH(OCH3)-CH3
which is the electrophile in the first step ?
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12 Answers
yup
srinath also told it is H+ only
actually this question came in some aits n i wrote H+ and they gave it
wrong :(
:P
i thought that charged electrophiles r more reactive than that of the uncharged one
But H+ will first attack lone pairs of oxygen naa??
so H+ can't be
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(and if it was so straight forward they will never have asked it :P)**
** this idea is for tests...and student should use it at their own risk... tukkabaji may be injurious to helath
it must be H+ because as u suggested H+ going on attack on lone pair of oxygen then it that case corbonium ion will generate which is wrong because of two reasons
1-: H+ is more reactive
2-: product will get change
mechanism of rxn started with addition of H+ on π bond sys generating carbonium ion then attack of lone pair of oxygen on carbonium ion then removal of H+ therefore hydrogen is coming from the soln (point to remember in case of isotopic effect here it is secondary effect)
i think carbonium ion would be attacked again by lone pairs od oxygen thereby removing H+!
so h+ is the answer
mechanism :
1) H+ attacks double bond.
2) secondary C+ formed.
3) lone pair of O in CH3OH attacks the carbocation..
4) positive charge on O (so, unstable)
5) H+ leaves.
but still a prob is there
if we r given the product then H+ is the obvious choice but still O is a much better electrophilic centre than the doubly bonded carban so y shudnt it attack CH3OH