alkyl halides

we all know that when reacted with alkyl halide
KCN forms cyanide
AgCN forms isocyanide
and
KNO2 forms alkyl nitrite
AgNO2 forms nitroalkane
the difference is 'cos CN and ONO are ambident nucleophiles
Can anyone pls tell me the mechanism of these reactions and
what is the role of K and Ag ??????

11 Answers

39
Dr.House ·

it is explained based on SHAB- soft and hard acid base theory.

it says that soft prefers soft and hard prefers hard ( let it be base or acid)

1
rickde ·

PLEASE EXPLAIN MORE
wats SHAB and where can i know more about it????
pls help.

11
mona100 ·

plz explain what are hard and soft bases
what is its basis to decide which one is hard and which one is soft?

11
Mani Pal Singh ·

http://en.wikipedia.org/wiki/HSAB_theory

1
rickde ·

how does it explain the above reactions

1
vector ·

i dunno about hard n soft bases
we were told tht φ value of ag is mmuchh more than potassium so kcn is ionic n thus k+cn_ n thus c is donating site while in agcen more covalent character so n l be d donating site ther

1
kamalendu ghosh ·

richa s reason is NCERT s but hard soft acid base is more accurate and apt

1
rickde ·

still i dont get the funda??
how does SHAB explain that once K makes N get attached to the alkyl and in the other case it attaches C???

11
Gone.. ·

1
RAY ·

hard base is highly electronegitive like F O N ......n soft bases r large in size n less electronegitive..like Br..I.....soft bases act as nucleophile.....
n hard bases act as base....

hard acid is small in size n has electropositivity..like H+∂+

wheres large cations are soft acids......

1
RAY ·

hard base ie potasium..will attac the hard centre ie N will react....
while AG is a soft base so C which is a soft centre generally will react here..

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