Organic Class - 3

Grand Marathon
Organic Class - 3
29 . COOH
ph 0h
Pas Alas
A
1
.
What is D- U of A ?
Me
Pas
to
acylium
ion
+0
4¥
E = 3
Ph
Ph
'
b Alds 21
He C)
the
(1)
Ph
(4) (4) DU =
? 14
1
Me
30 NHZ
c,
Nice
.
NHS aN0z
(a) ale UCI 0°C

,
5034
5034
5034
EWG
Ars,v2 = SNZA.se
+ +
olé : N=N G- N=N
↓
•
an electrophile EWG
stronger
•
weak C-Ii -
M )
Nice -
ONE
04
AOH
5034
(d- Napthol) N
ON
CUZCOOU
÷
H2O
* lsoj Not
N Ht
acidification
÷
↳ 03h
◦
(b) %
~ LiA1H¢Cex) ~
ether
0 1-
OH
Noz
NHZ
Find in 1
(a) no .
of Tl bands (P) .
=
(b) Find no .
of moles of Methane obtained if

P reacts with excess of MeMgBr = 3
# 8-1
Base
Br
BV + HA + Mg
-
Meng → Men
"
A
↓
methane
Selected Questions for Workbook -
Class -
3- Organic
±
1 : resonance if
-1 _
𝓚𝓲𝓷𝓮𝓶𝓪𝓽𝓲𝓬𝓼
↳ Br A
-ÉÉcn=cuz +0
cuz
cn-cnz-H.L T
=
cnz
-
•
anhydrous
(
-
Br a
good ]
Nu
𝓜𝓸𝓽𝓲𝓸𝓷 HBV SNZ
𝓘𝓷 ↓
2𝓓 cry
_ÉE+u cuz -
BV
% cuz + ◦ = en
cuz
- -
+9 halide
(a) dehyde )
cuz -0 = ch -
cuz
(alkyl )
p Etaddis
"
cuz-0 ch
.
-
→
-
ρꪖᧁꫀ ꪀꪮ
'
; m addn
Qᵁᴬᴰᴿᴬᵀᴵᶜ Br
ℙ𝕒𝕘𝕖 ℕ𝕠 ᴱQᵁᴬᵀᴵᴼᴺˢ
P𝕷𝖎𝖌𝖍𝖙
͎ er͎ m i᭙ꪮ᥅ᛕ
͎ o͎ 𝙲𝚘𝚗𝚒𝚌
͎ t͎ ᴬᴺᴰ
͎ ͎ u-t͎ a
𝕽𝖊𝖋𝖑𝖊𝖈𝖙𝖎𝖔𝖓 ͎ ͎Cꪖꪀᦔ ͎ bC̲
͎n͎ ͎&ᴵᴺᴱQᵁᴬᵀᴵᴼᴺˢ
͎ o&͎m ꫀꪀꫀ᥅ᧁꪗ
𝚂𝚎𝚌𝚝𝚒𝚘𝚗𝚜
𝕽𝖊𝖋𝖗𝖆𝖈𝖙𝖎𝖔𝖓͎ ̲rt͎ ̲c̲
͎in͎ ia i͎ o͎ l͎n̲e͎ ̲
-
Vinylic
a
Cannizzaro 7
§
NO
_
0h ,
𝓚𝓲𝓷𝓮𝓶𝓪𝓽𝓲𝓬𝓼Cb c- n
Chloroform reaction
- -
no d-H
with does not Cannizzaro Rxn

An aldehyde X H show
-
𝓜𝓸𝓽𝓲𝓸𝓷
.
Why ?
𝓘𝓷
2𝓓 on
enolises → -
Aldol condensation
An
•
aldehyde with vinyls 'o (B) a -4 →

Cannizzaro
↓
yes ! !
Rxn
formation
.
Show No end .
ρꪖᧁꫀ ꪀꪮ Qᵁᴬᴰᴿᴬᵀᴵᶜ ᴱQᵁᴬᵀᴵᴼᴺˢ

ℙ𝕒𝕘𝕖 ℕ𝕠 P𝕷𝖎𝖌𝖍𝖙
͎ t͎ ᴬᴺᴰ
͎ ͎ u-t͎ a
• •
• •
✓ -
m
"
5 -
M
+H
° O
-
M
in
Ei) -
c- on = -
c=o : -
Ifm :
deactivating Gop
in ' director
𝓜𝓸𝓽𝓲𝓸𝓷 Ciii
, FGÑ=o : + M :
o/ p
𝓘𝓷
2𝓓
Cri ) -
Ñ=Nu ,
: + m :
Otp
: m
-
director
ρꪖᧁꫀ ꪀꪮ .
Qᵁᴬᴰᴿᴬᵀᴵᶜ
͎ t͎ ᴬᴺᴰ
͎ ͎ u-t͎ a
͎ o&͎m
͎in͎ ia
ꫀꪀꫀ᥅ᧁꪗ
𝚂𝚎𝚌𝚝𝚒𝚘𝚗𝚜 i͎ o͎ l͎n̲e͎ ̲
Ph CHO / RCHO Rzco
/
⑤
•
•
Ph NH
2
Ph OH
¥67
-
•
☒
•
Me zco
CUZ •
Ph come
𝓘𝓷
2𝓓
ρꪖᧁꫀ ꪀꪮ .Qᵁᴬᴰᴿᴬᵀᴵᶜ
͎ t͎ ᴬᴺᴰ
͎ ͎ u-t͎ a
͎ o&͎m
͎in͎ ia
ꫀꪀꫀ᥅ᧁꪗ
- - -
𝓘𝓷
2𝓓
͎ t͎ ᴬᴺᴰ
͎ ͎ u-t͎ a
͎ o&͎m
͎in͎ ia
ꫀꪀꫀ᥅ᧁꪗ
Fries Rearrangement
More = 5
× ×
bromo
✗
• .
Nu addn
- - elimn
Fries Rearrangement
OH OH
°"
60°C)
-1%-93
°
Ctlzcoq Along come
𝓜𝓸𝓽𝓲𝓸𝓷 T > 120%

Py
𝓘𝓷 cocnj
"
Phenyl
4193
acetate
2𝓓% " "
? visualise FC Acylation : but
Aids
cnzc
-=É :
Acylium
↳ 1- Acid
1. Base
phenol do not like FC Reactions
.
.
Aniline
ꪀꪮ
ρꪖᧁꫀ
& AIKO Qᵁᴬᴰᴿᴬᵀᴵᶜ
ℙ𝕒𝕘𝕖 ℕ𝕠
benzene ᴱQᵁᴬᵀᴵᴼᴺˢ
͎ t͎ ᴬᴺᴰ
͎ ͎ u-t͎ a
② .
*
£⑥5 ✗
&bd&
✓ SNZ
inve&Fn
•
BE E- 2 ③ Ctlbh 'D
(1)
•
(2)
Etaddn
bridgehead EL
SNI ←
80 Lucas -1*60 { 2B$ (6)
on
𝓜𝓸𝓽𝓲𝓸𝓷 1. Ht
𝓘𝓷
2.
-420
2𝓓
ti
allylic Ct
-
Ht
͎ t͎ ᴬᴺᴰ
͎ ͎ u-t͎ a
͎ o&͎m
͎in͎ ia
ꫀꪀꫀ᥅ᧁꪗ
15 Cl
↑"
MezG0- NaOH Ht
.
✗ A B
/
Me] COH 02,1-302
" 6- Tatm
B
↓ heindred
sterically bulky base
↓
-
produces Hoffmann 's
product as
Major
-
abstracts less
sterically
hindered
(1%13)
h
𝓘𝓷 p
-
2𝓓
(Tantomerises)
Kolbe's
o -
salicylic Acid .
Rxn
-
COOH
͎ er͎ m
OH
i᭙ꪮ᥅ᛕ
͎ t͎ ᴬᴺᴰ
͎ ͎ u-t͎ a
͎ o&͎m
͎in͎ ia
ꫀꪀꫀ᥅ᧁꪗ i͎ o͎ l͎n̲e͎ ̲
alk cold dit
.
KMn0q
Br
-
/
𝓚𝓲𝓷𝓮𝓶𝓪𝓽𝓲𝓬𝓼 -
37
NaBr/42504=-4138
𝓜𝓸𝓽𝓲𝓸𝓷 Br
Br Br
𝓘𝓷 HBR
2𝓓 ex . -1¥ -
C- H2O) I 3° H Shift
Ho
-
,
30
HO
-
+
6h -4
͎ t͎ ᴬᴺᴰ
͎ ͎ u-t͎ a
͎ o&͎m
͎in͎ ia
ꫀꪀꫀ᥅ᧁꪗ
(0/10)
°" °"
OH
HCN / net 8h OH
𝓜𝓸𝓽𝓲𝓸𝓷 µ -1
𝓘𝓷 420 1-
2𝓓 duo I
Gattermann Aldehyde
- £004 cnzott
Syn
Cannizzaro Rxn (Y) ( x)
?
͎ t͎ ᴬᴺᴰ
͎ ͎ u-t͎ a
͎ o&͎m
͎in͎ ia
ꫀꪀꫀ᥅ᧁꪗ
H N°3
/ 42504
E
+1402
𝓜𝓸𝓽𝓲𝓸𝓷 Cl G' ome
𝓘𝓷
+
NO 2 Me5N+a - NO 2
2𝓓
ARSNZ
Cl Cl
=
SN2Ar
͎ t͎ ᴬᴺᴰ
͎ ͎ u-t͎ a
͎ o&͎m
͎in͎ ia
ꫀꪀꫀ᥅ᧁꪗ
J
benzylic : ≤N2
- +
ArsN2 .
☆SAng NU
✓
𝓘𝓷
2𝓓
͎ t͎ ᴬᴺᴰ
͎ ͎ u-t͎ a
͎ o&͎m
͎in͎ ia
ꫀꪀꫀ᥅ᧁꪗ
𝓘𝓷
2𝓓
-
͎ t͎ ᴬᴺᴰ
͎ ͎ u-t͎ a
͎ o&͎m
͎in͎ ia
ꫀꪀꫀ᥅ᧁꪗ
①
%
OH
✓
CUzCUO✓ '
o
'
+
cuo
-
Hz
Gattermann
Fc acylation
- Koch
✗ → cy✓
CM-3
,
✗
𝓚𝓲𝓷𝓮𝓶𝓪𝓽𝓲𝓬𝓼 EMO
Fries Ream
anhydride
✓
Forms aldehyde✓ it does not oxidise
-
CHO
𝓜𝓸𝓽𝓲𝓸𝓷 Cros/
420=-42004
𝓘𝓷
COOH
2𝓓 ,
on
Oxidise Reno - RCOOH
͎ t͎ ᴬᴺᴰ
͎ ͎ u-t͎ a
͎ o&͎m
͎in͎ ia
ꫀꪀꫀ᥅ᧁꪗ
?⃝
Clemmensen 's reduces aldehydes &
-Ég-
-
ketones to satdhydso -
ai
Zn
Hg
-
H
HCl I
,
4
H
𝓘𝓷
2𝓓 ÷
͎ t͎ ᴬᴺᴰ
͎ ͎ u-t͎ a
͎ o&͎m
͎in͎ ia
ꫀꪀꫀ᥅ᧁꪗ
org cornpd is
carbonyl conn
.pd .
0 . e is an
aldehyde
𝓘𝓷
Totten's)
2𝓓 920 (
Photo ✓ Agt, + PHCOE
Cuz
✗
Fehring
son
.
.
ρꪖᧁꫀ ꪀꪮ Qᵁᴬᴰᴿᴬᵀᴵᶜ
͎ t͎ ᴬᴺᴰ
͎ ͎ u-t͎ a
REOOR
↓ 430-1
1200011
𝓜𝓸𝓽𝓲𝓸𝓷 on
𝓘𝓷 aldol Conan : ✗ : has carbonyl group
2𝓓 Ht EI :
dehydration × : OH
group
-
:
•
• Phcno +
cuz
- % -
✗
cuz
-
COOEE
P"
¥ ¥5 Ph -
ch =L -
coots
,
COCH
}
.
d- h : acidic
ρꪖᧁꫀ ꪀꪮ Qᵁᴬᴰᴿᴬᵀᴵᶜ
͎ t͎ ᴬᴺᴰ
͎ ͎ u-t͎ a
Phcno +
cuz
% Enz COOEE
P"
¥5 Ph
#-) cook
↓
- - -
-
•
Loca ,
d- n : acidic hydrolysis
of ester
-420 C- H2O)
Modified form of
aldol condensation
Pg ↓
a
i
Ph
-cn=qÉÉÉi .
Etc:*
c- C'
13
⇐
ph-cn-n.CH -
C -
cuz
-
coz
p
Benzol acetone keto acid
p -
NUz.NHz
𝓘𝓷 Wolf -
Kishinev Rendn
Kou
2𝓓
(glycol )
Ph cn=cn
=o →
Yours
Ching
-
-
͎ t͎ ᴬᴺᴰ
͎ ͎ u-t͎ a
͎ o&͎m
͎in͎ ia
ꫀꪀꫀ᥅ᧁꪗ
RNHZ RN
1- !l2
H R
.
C : C C -
pH = 4-5 Neutral
𝓚𝓲𝓷𝓮𝓶𝓪𝓽𝓲𝓬𝓼 .
imine
↓
n -1 Protonated
carbonyl group
÷
•
pit < 4 : RNH
,
will be
protonated = R -
NEG :
nucleophilic
𝓘𝓷 nature is lost
2𝓓
PH > 5 : carbonyl group is NOT

protonated ,
is that case
all neutral
nucleophiles can't attack carbonyl compd .
͎ t͎ ᴬᴺᴰ
͎ ͎ u-t͎ a
͎ o&͎m
͎in͎ ia
ꫀꪀꫀ᥅ᧁꪗ
""" '" a " ' H+
9ᵗʰ H+
A(C4Hg0z) B Cuzco on
↑
an ester sole product
alcohol .
(? ) NaOH Cfz
/
𝓘𝓷 Chloroform
formation
2𝓓
reagent
"
B:
CH3¥H -
or
cuzcn
-
Chs
ethyl alcohol
isopropyl alcohols
,
͎ t͎ ᴬᴺᴰ
͎ ͎ u-t͎ a
͎ o&͎m
͎in͎ ia
ꫀꪀꫀ᥅ᧁꪗ
A R P T S
+ : side product
↳
if it has an
eg organic flavour
↓
R-MGB.si t -
É -
O -
R! it becomes
tmp .
R ; Ph
n ; cyclo
𝓜𝓸𝓽𝓲𝓸𝓷 O
.
É
'
sole
Mg product
_
𝓘𝓷 R - -
+
top
/
.
2𝓓 ED
( R-gt-R-mg-F.ie/--sr-c-r+
RMgBr
0-7%132 Nu -
addn Mg( b) Br
◦
% +
R' OH
.
or 1
ρꪖᧁꫀ ꪀꪮ QᵁᴬᴰᴿᴬᵀᴵᶜhᴱQᵁᴬᵀᴵᴼᴺˢ
ℙ𝕒𝕘𝕖 ℕ𝕠 -1
͎ er͎ m
͎ ͎ u-t͎ a i᭙ꪮ᥅ᛕ
͎ t͎ ᴬᴺᴰ
𝕽𝖊𝖋𝖑𝖊𝖈𝖙𝖎𝖔𝖓 ͎ ͎Cꪖꪀᦔ 𝚂𝚎𝚌𝚝𝚒𝚘𝚗𝚜
͎ o&͎m C̲ i ̲r ̲c̲l ̲e̲
͎ bꫀꪀꫀ᥅ᧁꪗ
͎in͎ a
͎ t͎ i͎ o͎ ͎n͎
𝕽𝖊𝖋𝖗𝖆𝖈𝖙𝖎𝖔𝖓
'
R
ca-s-qnmg-t.cn
±
] I
+
¥452
Ester :
n -
§ -0 -
en -
en
Me "^9 "
H § M⇐
.
}
- -
En
,
MEM.gi-ss.mg/F- - Ch }
Me -
f- MgBr
Cn -
Me
𝓘𝓷 You }
2𝓓
cuz -4h -
on (B)
ℙ𝕒𝕘𝕖 ℕ𝕠
cuz
ᴱQᵁᴬᵀᴵᴼᴺˢ
͎ t͎ ᴬᴺᴰ
͎ ͎ u-t͎ a
͎ o&͎m
͎in͎ ia
ꫀꪀꫀ᥅ᧁꪗ i͎ o͎ l͎n̲e͎ ̲
Vidyamandir Classes
¥0888800833
Marathon 1 Organic Chemistry Chemistry
1.
2.
3.
4.
5.
6.
7.
VMC | Marathon 1 1 Organic Chemistry

Vidyamandir Classes
8.
9.
10.
11.
12. How many of the following groups if substituted at o- and / p-positions of chlorobenzene, increase its reactivity towards
nucleophilic substitution (ArSN2) ?
 CN,  CH 3  NH(CH 3 ),  COOH,  NO 2 ,  OCH3 ,  SO3 H
13.
14.

Vidyamandir Classes
15.
16.
17.
18.
19.
20.

Vidyamandir Classes
21.
22.
23.
24.

Vidyamandir Classes
25.
26.
27.
28.
29.
30.

Vidyamandir Classes
31.
32.
33.
34.
35.

Vidyamandir Classes
35.
37.
38.
39.
40

Vidyamandir Classes
Answers to Marathon 1 | Organic Chemistry
1 2 3 4 5 6 7 8 9 10
3 B C B B D C D 5 5
11 12 13 14 15 16 17 18 19 20
A 4 D 2 B 2 D A C A
21 22 23 24 25 26 27 28 29 30
A B 4 B C D 6 4 B B
31 32 33 34 35 36 37 38 39 40
A C C B C B B C A A

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Organic Class - 3

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Organic Class - 3

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Grand Marathon

(a) ale UCI 0°C

olé : N=N G- N=N

of moles of Methane obtained if

with does not Cannizzaro Rxn

aldehyde with vinyls 'o (B) a -4 →

ρꪖᧁꫀ ꪀꪮ Qᵁᴬᴰᴿᴬᵀᴵᶜ ᴱQᵁᴬᵀᴵᴼᴺˢ

Ctlzcoq Along come

𝓜𝓸𝓽𝓲𝓸𝓷 T > 120%

Oxidise Reno - RCOOH

PH > 5 : carbonyl group is NOT

VMC | Marathon 1 1 Organic Chemistry

VMC | Marathon 1 2 Organic Chemistry

VMC | Marathon 1 3 Organic Chemistry

VMC | Marathon 1 4 Organic Chemistry

VMC | Marathon 1 5 Organic Chemistry

VMC | Marathon 1 6 Organic Chemistry

VMC | Marathon 1 7 Organic Chemistry

Answers to Marathon 1 | Organic Chemistry

VMC | Marathon 1 8 Organic Chemistry

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