Session 1,Nucleophile vs Base-1,

2021
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 Session -1
General Organic Chemistry
Nucleophile vs Base
 Solvent

Polar Solvent Non Polar Solvent

Non Polar Solvent

● Benzene

● CCl4

● Cyclohexane

● Petrol

● Organic solvent

● Toluene
 Polar Solvent

Polar Protic Solvent Polar Aprotic Solvent

Polar Protic Solvent

● H2 O

● Alcohol

● RCOOH

● R-NH2
Polar Aprotic Solvent

● Ethere (CH3-O-CH3)

● Acetone (CH3-CO-CH3)

● Dimethyl sulphoxide (CH3-SO-CH3)

● Dimethyl formamide ((CH3)2N-CHO)

● Dimethylacetamide ((CH3)2N-COCH3)
 Note:

PPS favours SN1 mechanism

PAS favours SN2 mechanism

 Reagents

● Electrophiles (E+)

● Nucleophiles (Nu-)
● Electrophiles (E+)

● Electron deficient

● +ve charged and neutral atom as well

● e- pairs acceptors (L.A)

● Electrophiles (E+)

● Examples:

Charged species Neutral species

● SO3
● H+
● :CH2
● R+
● :CHR
● Cl+
● :CR2
● Br+
● :CHX
● I+
● :CX2
● NO+
● AlCl3
● NO2+
● BF3
● ZnCl2
 ● Electrophiles (E+)

● Examples:

Charged species +ve charged species but not E+

● Pt+ ● H3 O +
● Ag+ ● NH4+
● Hg+2
● Na+
● K+
● Nucleophiles (Nu-)

● Electron rich species

● They donate e- pairs to e- deficient centres (except H+)

● e- pairs donors (L.B)

● Nucleophiles (Nu-)

Nucleophile not only donate electron pair to electron deficient

species but also form bond with the centre.
Bases

Species which donate electron pair to H+ are called as base

All nucleophile may be bases, but all bases are not nucleophile.
For organic chemistry,

Nu- are C⊕ or Cδ⊕ seeking species.

Nucleophilicity

It means the attacking speed of nucleophile.

● Nucleophile is a kinetically controlled specie.

● But basicity is thermodynamically controlled process.

Steric hindrance in Nucleophile

If the nucleophile is bulky, the bond formation is difficult.

But there is not any issues in case of a base. It accepts H + which is

very small specie and so it doesn’t matter if the base is bulky or not.
Factors of nucleophilicity:

1. Electron density: If electron density increases, strength of

nucleophile increases.

Examples:
OH- > H2O
SH- > H2S
NH2- > NH3
Factors of nucleophilicity:

2. Electronegativity:
Electronegativity of that atom which is behaving like a nucleophile
increases, nucleophilicity decreases.

Examples:
CH3- > NH2- > OH- > F-
Factors of nucleophilicity:

3. Size:
If size of a nucleophile increases, polarisation increases, and hence
nucleophilicity increases.
Polarisation:
It is a phenomenon due to which e- pair comes at the centre from
the anion.
For organic chemistry,

Now C⊕ or Cδ⊕ will have same polarising power but the polarizability
of nucleophile can vary.

Bigger the size of nucleophile, more will be the polarizability and

more will be the tendency to form covalent bonds.
In periodic table, the strength of nucleophile increases down the
group whereas its strength decreases across any period.
But in the case of bases, In periodic table, the strength of bases
decreases down the group and its strength across any period also
decreases.
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