chem- reaction mechanism..

CH3- CH2 -CH= CH2 + CH3-OH + (H+) -------> CH3-CH2 -CH(OCH3)-CH3

which is the electrophile in the first step ?

12 Answers

3
msp ·

it is the H+ ion

1
skygirl ·

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

3
msp ·

if u know the mechanism please post

3
msp ·

i thought that charged electrophiles r more reactive than that of the uncharged one

33
Abhishek Priyam ·

But H+ will first attack lone pairs of oxygen naa??

so H+ can't be

_______________________________________________________

(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

11
Anirudh Narayanan ·

What's tukkabaji?

33
Abhishek Priyam ·

Guess work

1
gagar.iitk ·

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)

1
abhijeetkumar kumar ·

i think carbonium ion would be attacked again by lone pairs od oxygen thereby removing H+!

so h+ is the answer

1
skygirl ·

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.

1
voldy ·

good one sky.

1
greatvishal swami ·

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

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