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GOC Short Notes

This document discusses the basicity of nucleophiles. It provides three main points: 1. Nucleophilic basicity is affected by inductive and resonance effects of substituents. Meta-positioned groups do not have any effect. 2. The order of basicity for polar aprotic solvents is F- > Cl- > Br- > I-. Conjugation and cyclic structures increase basicity over linear structures. 3. The priority order of nucleophiles is: amines (RNH2) > alkoxides (RO-) > hydroxides (OH-) > halides (X-) > hydrides (H-). Charged nucleophiles are more

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100% found this document useful (1 vote)
286 views7 pages

GOC Short Notes

This document discusses the basicity of nucleophiles. It provides three main points: 1. Nucleophilic basicity is affected by inductive and resonance effects of substituents. Meta-positioned groups do not have any effect. 2. The order of basicity for polar aprotic solvents is F- > Cl- > Br- > I-. Conjugation and cyclic structures increase basicity over linear structures. 3. The priority order of nucleophiles is: amines (RNH2) > alkoxides (RO-) > hydroxides (OH-) > halides (X-) > hydrides (H-). Charged nucleophiles are more

Uploaded by

redop9op
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
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GOC

I >
Nucleophilic ily Ys Basicity : -

%eEnri-s.tn#....e...wmM
,

jbitd
Not M
5 I✓
-

- .

*
CH} -

CHZ
-

o
-

> CH} -
É -
-

o >

I
→ shows -

NU-tLPX-vechaogexsig.eu#cyyww-
Meta position do not have
any

Ñ or Reso effect .

!
Only inductive

Pootic
_←[ polar
-

F- a- < Bo < I
<
solvent cyclic > Linear > Cross

Polar Aprotic = F- > Ci > Bo


-

> I?
conjugation .

☆ More
Equivalent↑ Acidic
F-
2>
Priority Order Rs Nature
: -

Acuminate • Rules
stability
for
: -
Resonating
Least Stable : -

<++)
Sto
(--
.

near.

3> ORDERS :-.

Neutral Sto
+ M : -

ÉHZ > ÑH > 6 > iitlz > H


① >
Charged ones .

%
0

> CH} > ÑH - -


Ctb > - I -
R
② Octet
complete .

③ More EN
:É § :& I: charge
= -
ve
B
.

> : > : > : >


Less EN + ve
charge
=
.
. .

+I :
ÑH 5
-

Ctb > > > RCOE >


. ..


Butyl
> T > D >H
>
isopropyl > Et > Me
Boeadthˢ)Rule I> At
bridge head carbon
till
ve is not
accepted
-

carbon -8 after 8- Carbon

Étlz
.%É¥sw)
SPZ !
-
M : -
> NO, > CN > Sgt Chalega
COR NHZ

pgfgonant.ge?iO
Effect
> CHO > > COOR >
Max e-
> COJ ②
density .

yfgf.ie?1eatofHydoogen
-
I : - - ÑF }
> - ÑR, > -
ÑH, > No,

1- ✗ IT
Reso bond
> CN > 503177 CHO > COR > COOH

> COOR > Halogens > OCH ,


> OH >
oomaticity ✗ Reso
Energy ✗ Reso .

MHz > ph > %


% 7 IT e-
energy ✗
¥
GOC
I >
Nucleophilic ily Ys Basicity : -

%eEnri-s.tn#....e...wmM
,

jbitd
Not M
5 I✓
-

- .

*
CH} -

CHZ
-

o
-

> CH} -
É -
-

o >

I
→ shows -

NU-tLPX-vechaogexsig.eu#cyyww-
Meta position do not have
any

Ñ or Reso effect .

!
Only inductive

Pootic
_←[ polar
-

F- a- < Bo < I
<
solvent cyclic > Linear > Cross

Polar Aprotic = F- > Ci > Bo


-

> I?
conjugation .

☆ More
Equivalent↑ Acidic
F-
2>
Priority Order Rs Nature
: -

Acuminate • Rules
stability
for
: -
Resonating
Least Stable : -

<++)
Sto
(--
.

near.

3> ORDERS :-.

Neutral Sto
+ M : -

ÉHZ > ÑH > 6 > iitlz > H


① >
Charged ones .

Activators
%
0

> CH} > ÑH - -


Ctb > - I -
R
② Octet
complete .

③ More EN
:É § :& I: charge
= -
ve
B
.

> : > : > : >


Less EN + ve
charge
=
.
. .

+I :
ÑH 5
-

Ctb > > > RCOE >


. ..


Butyl
> T > D >H
>
isopropyl > Et > Me
Boeadthˢ)Rule I> At
bridge head carbon
till
ve is not
accepted
-

carbon -8 after 8- Carbon

Étlz
.%É¥sw)
SPZ !
-
M : -
> NO, > CN > Sgt Chalega
COR NHZ

pgfgonant.ge?iO
Effect
> CHO > > COOR >

Deactivor. Max e-
> COJ ②
density .

yfgf.ie?1eatofHydoogen
-
I : - - ÑF }
> - ÑR, > -
ÑH, > No,

1- ✗ IT
Reso bond
> CN > 503177 CHO > COR > COOH

> COOR > Halogens > OCH ,


> OH >
oomaticity ✗ Reso
Energy ✗ Reso .

MHz > ph > %


% 7 IT e-
energy ✗
¥
Free
!
Stability : -

* ÉB > ÉD, > EH ,


-
UN

>
un

☆ Ctb -
CÑ > CDs -
CHI > CB CFI -

CCEwwdjgd-edisoc.nu#cumu1atedun
_

51-1=3
-

34th -3×1-1 .

1-101-1 : -

*
CÑZ
>
AA .
> AN > AA
g✗H 412.5
Hyperconjugation
.

[H TJ
}R
D
> >
at Dancing
*
F- cik > ph >
Alkane Pi
: o
overlap
-
-

10125
.

✗ 1-1=1 .

Alkene o JT* overlap "°

ktby.e c/cH3Mey=gHW00l d 'scM-oststab1emn#


: - -
.

"
propyl
""
methyl
[ =É+ ,
µ
, -
µ
µ
, nm,
carbocation .

Stability order of carbocation.


Me

Gal
Germinal Cis trans .

F- > D- g- H > D- CHA


Geominal>Toans>Cis.mwwM

Heat of
Hydoog
"
is
energy oeq
to
>
1/1%1 > ph > C+ > phzct
convert ✗ into 1 .
ÉHZ

Stability ↓ Hot, ↑ > ¢+13)sC+ >


/ > +

É
_5tabilityInHXH-eFrecta¥mmwwJ
-
{ Reactivity a

> ✗ Hiiiii > CH}


-
Citi > Étk > I
>
Reactivity of benzene. "
THz Ctiz
✗ "'

É¥
3 me I
¢ me
- time -

☆ .
"

> >
<

✗ 1-1=3 ✗ 1-1=0 I Max


H=2 ✗ 1-1=1 OH
- .
.

+ "" I Min

distn
*
Reactivity H
#
✗ ✗
-

.
.

independ + na .

✓ imp Trick cñz


Fitz
wT5NP j
* "

win un
.
TT
#④
6-
distance

Number ↓ -

Imax -
Imin .

Power .
- I > -
M m -

position
!
only induce .
→sPˢHyb
of is
Stability
: -

game "
.

phci-i-zc-x-II.is#-.mw)
C

I¥_
+ for ✗
< ✗

phsct > phzcti >


phsi > Phai " > Phai .

(43 Ph2CÑ > ph } C- >


phctiz

PCH } ✗ OCH }

>
'

+ Nl ✗ 2 CH

Ina
} "

+1×1×1
.

*
+ I oodeo
#
:
ph
-

"

?¥¥
T "
> ☐ >H .

> > pn

Simp Examples : -

Equivalent
"°_ 5 ÉÉ ph
R" ph
>
-5-12 "

case ping Y
> >

if
-

i
'

doobital ph
c-
ph
.

f- c- < c, Rest
f÷ /
_

,
ÉHZ
ti > ph -

P
µ
World Most
⊖ stable C ?
7 / >
THz IRS .

Anti
IRS .
IRS aromatic .

( ↳ nstét
M
⑧ ReSO
-

Ctlz X C H > ⑦A
- -

§ É
M M N
"
- - -

H - -
EH - -
H > CH} -
CE -
C -
H

> I > 1- Acidic nature of C. Acids.


i
-


to i > COOH
>
{ ¥
H -
coat

£-7 -
_7x ◦◦ ,
Q
% xp cyclic
Reso .

2 > HCOOH > Ph -


COOH > CH COOH

[
-

2>1730
}
.

② ③
Basicity order.
37 I
> µ -
c ≤ E-Ii > CHECK
Aromatic
¥ ↓
SP? Guanidine > R -
Niti , > him,

COOH > Aromatic R É iitk


Hy
" amine > - -

COOH
:

11
ni
I > > R ⇐
-

ÑHz
/- COO 'H
µ \H Guanidine : -
Hani - D= titi
Coote
Matic acid .

Fumaric Acid
Basicity Re÷ ±¥y
.
✗ ✗ ✗ Hz .

- OH % - OH
s>

F Para effect
3
>

G-effe Their is no
repulsion bln
Acid n-bond
+I M
NO,
-

A
}
.

" & NH after LP


=
Ortho effect .
paoa group so

Benzoic
,
donation it becomes stable
H-bond
more

Ortho effect youly


.

in
Pheno .

Phenol
=

not
in ASd
In Para > Ortho

Ortho
Repulsion bln
such that
COOH
COOH
& Amines Amines .

group goes
out of
plane & M does not +
/p>m>a= ⑧

operate Acidity ↑
.
÷
ÑH ,
.

ÑHZ

°°ᵗ%ids>Acids.wwJ u
""
Benzoic > > >
,
3

Basic nature of amine ¥


Reactivity of RX act
stability .


Aliphate 7 Aromatic .

Neet
Reactivity of carbonyl compounds
☆ ↑ R
o

141-13 . R -
ÑHz .
R -
N -
H R -

HY -
R {
E
① ⑤
-
R H -


-


⑦↑ Reactivity ↑
⑦←
.

If .

Gas Phase : -

Acid anhydride > acyl


3° > 2° > 1° > NH}
chloride > Ester > acetone
.

Solvent

¥0
.

"
R R=
Ethyl
CH } Acid
anhydride
=
.
. : -

R -
C

to
27173 > ÑH 273 > I > ÑHz
}

Acyl Chloride : -

r -
É -
o.

-ide
¥aticity. e-density
Acetone
Basicity ✗

%


Estes RCOÑHA
decreates R
:- -
-
OR .
EH .es .

I
SPZ he
-

+ gp2

① ② ③ ④ .

Kb : -
① > @ > ③ > ⊕ .

Ñp2 Benzyne .

I -

Rearrangement of carbocation.

Migratory Aptitude
: -

H > As > R .

1-
Benzyl .

Reaitionwo
P ☆

Substitution Addition

[
Rx? Rxh

[
.

single bond Hook


bond
involve .

• Mao Konikoff Anti Markonikoff


Rule Rule .


ve
part goes re
part goes
"
"
to less H to more ⊕

carbon
containing .

containing carbon .

Br

( Peroxided
EH .es .

I
SPZ he
-

+ gp2

① ② ③ ④ .

Kb : -
① > @ > ③ > ⊕ .

Ñp2 Benzyne .

I -

Migratory Aptitude
: -

H > As > R .

1-
Benzyl .

Reaitionwo
P ☆

Substitution Addition

[
Rx? Rxh

[
.

single bond Hook


bond
involve .

• Mao Konikoff Anti Markonikoff


Rule Rule .


ve
part goes re
part goes
"
"
to less H to more ⊕

carbon
containing .

containing carbon .

Br

( Peroxided

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