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2. FACTORS:
1. Nature of substrate structure
2. Nature of the solvent
3. Nature of the Nucleophile
4. Nature of the leaving group

3.  In nucleophilic substitution, the atoms of the
attacking nucleophile which gets bonded to the
substrate is called attacking atom
 As the electrons of the attacking atom undergo
coordination hence the most effective
nucleophile would be that which can easily
donate electrons for coordination

4.  BASE NUCLEOPHILE
 Basicity refers Nucleophilicity refers
to coordination with to coordination with
H+ Carbon.

5.  BASE NUCLEOPHILE
 Basicity is a thermo- Nucleophilicity is a
-dynamic property and kinetic property,. i.e it
Depends on the Ka of is a measure of reaction
The equilibrium. Rate
Where B- base combine with
proton of acid.
All nucleophile are basic, though basicity and nucleophiicity
are not always synonymous.

7.  SN2 reaction is nucleophile induced reaction
substrate nucleophile product leaving group
Reaction rate is directly proportional to nucleophile
concentration which appears in the rate law.

8.  following are the Factors on which
nucleophilicity depends
1. The electronegativity of the donor atom
2. The size and polarizibility of the donor atom
3. The density of the electrons on donor atom
4. The nature of the solvent used
5. The size of the nucleophile as a whole

9. Nucleophilicity order along a period runs parallel
with basicity
Explanation:
Strong nucleophile which easily donate electrons so
So as we go along the period from left to right
Electronegativity increases nucleus strongly attract the e- so it
will not be easy to donate electrons nucleophilicity
Basicity:
Strong base which easily donate electrons so along the period
Electronagativity increases so difficult to donate electrons so basicity
So the order will be same i.e

10. strong acid which easily donate H+
So along the period from left to right
The electronegativity the nucleus strongly attracts the e-
Even the atom of F will attract the e- of H-atom as well..so it iis
easy to donate H+ so acidity increases along the period
so, CH4<NH3<H2O<HF
After removal of H+ conjugate bases will form as
acid conjugate base
Acid strong conjugate base so F- will be the weakest base
So basicity decreases along the period

11.  Order of nucleophilicity along the group is just
opposite to the basicity
 Explanation:
 strong nucleophile which easily donate e-
 As we go down the group the size atom polarizibility hold of
nucleus on e- so easily donate e- so nucleophilicity down the
group so the order will be :F-<Cl-<Br-<I-
 BASICITY:
 Strong acid which easily donate H+
 Down the group Size of atom increases so bond length increases
between HI as compared to HF
 Bond between HI is weaker than HF so easily donate H+
 So acidity HF<HCl<HBr<HI

13.  Acidity order STRONG ACID
 HF<HCl<HBr<HI
 Basicity order weaker conjugate base
 F->Cl->Br->I-
 Nucleophilicity order: strong nucleophile
 F-<Cl-<Br-<I-
 Basicity down the group
 Nucleophilicity down the group
 hence proved ”the order of nucleophilicity is just
opposite to the order of Basicity”

14.  A Nucleophile which have more than one
donor atom is called ambient nucleophile
 For example: CN-,SCN-,NO2 etc
 An ambient nucleophile is often
characterized by the presence of
1. soft donor atom (less electronegative and
more polarizable).
2. hard donor atoms( more electronegative
and less polarizable).

15.  In CN- C is soft nucleophile and N is hard
 In first exampleC of CH3-Br is soft electrophile so it
combines with C (soft nucleophilic atom) of CN.Via SN2
 In 2nd example due to presence of Ag, Br leaves out
rapidly and formAgBr .so in this case the C of CH3
become hard electrophilic site so it combines with
N(hard nucleophilic atom).Via SN1

16.  With same donor atom,nucleophilicity is proportional to the
electron density on the donor atom.
 For example: CH3COO- is less basic and weaker nucleophile
than CH3O-.
 Reason:
 Because of less charge density on oxygen atom due to
resonance.

17.  PhO- is weaker than CH3O- though it is better nucleophile
than CH3COO-.
 Reason:
negative charge is resonance stabilized so electrons are
not easily available

18.  A Charged nucleophile is always stronger
than the correspondiing neutral one
 Reason:
because of the more concentrated
electrons.
For example:
CH3O->CH3OH
In CH3O- electrons are more concentrated so
stronger nucleophile.

19.  Nucleophilicity is enhanced by the presence of
unshared pair of electrons adjacent to the donor
atom.
 Reason:
 The ground state of the nucleophile is destabilized
by the repulsion of the adjacent electron pairs and
makes it more reactive towards SN2
 It is also called α-effect.

20.  In polar aprotic solvent like DMF,DMSO
 The cationic part of the nucleophilic reagent is solvated strongly
so the nucleophile is free and hence its nucleopohilicity is
proportional to the concentration of negative charge on the
donor atom.
 In case of polar aprotic solvent( hydrogen absent)
nucleophilicity of F- is much greater than that of I- due to more
conc. Electrons because of its small size. So the order of
nucleophilicity in polar aprotic solvent is
 F- >Cl- >Br- >I-

21.  In polar protic solvent the order will be reverse
 Reason:
 In polar protic solvent H+ is present it will react
with nucleophile as F- is more electronegative and
smaller in size so H+ will strongly bind with F
and form HF.
 While I- is larger in size so H+ will bind but bond
will be weaker so it will be easily broken down.
So electrons are available. So I- will be strong
nucleophile.
 Order will be
 F- <Cl-<Br-< I-