consider 3 reactions
hydrolysis of EtSCH2CH2Cl , EtNCH2CH2Cl , EtOCH2CH2Cl
Arrange them in increasing order oh reactivity, where N , O , S act as neighbouring group......
1no . sky go through Sykes . it has it. even though not fully I think . this should do a whole lot of good , I think .and it's not extra. it's one of the needed concepts.
http://en.wikipedia.org/wiki/Neighbouring_group_participation. this should be good enough :)
1DUN BOTHER TO KNOW!
IT IS NOT IN THE SYLLABUS!
LEAST INTERESTED TO KNOW EXTRA THINGS IN CHEM ...
SORRY :(
1@ sky
i told about it in 1 of the posts above
its strange dat u dont know it!!!!
1i dunno wat is that anchimeric assistance... may be same as intramolecular substituition..
1wat intramolecular substitution???!!!!
its anchimeric asistance which means SN2 twice
@shrinath
if u are talking about ease of donating elec to form 3 member ring then u r right
bt then larger size of S willalways afct rate of SN2
1yes me wrong...
its intramolecular substiturtion...
wat srinath told is correct...
1the ans is 1>2>3 . Nitrogen is a better donor than O .right?????
then b/w O and S . S is better. fine????? . then b/w N and S . S is obvious as it has two lone pairs ans also it's e.n is less. .
1ok no comments :P
i have weird knowledge in chem..
wont debate on a topic on which i am leeeaaast confident :P
1but is anythng wrong in my view
& anyways i never easily consider the given ans as correct
13>2>1
for 3&2 its obvious as 2p-2p orbitals hav gud overlap
thnk more if ans is correct
1how come S has no lone pair
sky r u getting the word neburing gp???? apply anchimeric assistance
lone pairs of S,O,N will first force Cl- out by SN2 by making a 3 member cyclic ring
then again attaking nucleophile will substitute through SN2 mechanism
S being bigger in size will inhibit SN2 a bit hence i gave 3>2>1 as ans
1the H2O molecule(nucleophile) will attack at the most electrophilic site...
now compare which is more electrophilic site...
S has no lone pairs... so most electrophilic center..
O is very electronegative but has lone pairs...
N is less electrophilic than O and also has lone pairs...
(O has two lone pairs n N has only one but O is far more electronegative than N...)
i thnk this is a correct way to think.. if some chem expert assures me...
correct me, if wrong..
1explanation .go through Peter Sykes.
It's the ability of the atom to donate electrons , that matters not by inductive effect , I feel .
again for mechanism and better understanding . go to Peter Sykes.
1@sankar where r u applying in ductive effect
in 3&2 or all 3
1wrong dude.......... i know that 1st reacts 104 times faster than 3rd. but i have confusion with second.... check your ans....
