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Flow Chart - 241111 - 101342 - Removed

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0% found this document useful (0 votes)
16 views40 pages

Flow Chart - 241111 - 101342 - Removed

Uploaded by

mansiharshit725
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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Road map

Cl2/hv Alc. Br2 NaNH2 Red hot Br2


CH3−CH3 A B C D E F
KOH CCl4 ∆ Fe-tube Fe
HNO3 + H2SO4

NH2OH 1) MeMgBr KCN


K + J I + H G
dil. 2) H3O
H2SO4
NaNO2
+
dil. H3O HCl
R L M + N
H2SO4

H3O+
NaOH Sn/
O P
Sn/ NaNO2 H3PO2 CaO HCl
S + T T’ T’’ E
HCl HCl ∆ NaNO
0 - 5°C HCl 2
SOCl2 Q
CH2N2 Moist H3PO2 / ∆
U V X E
Ag2O
soda lime H3O+
CH3−CH3 Y

Road map
Cl2/hv Cl Alc. Br2 Br NaNH2 Red hot Br2 Br
CH3−CH3 N2
KOH CCl4 ∆ Fe-tube Fe
HNO3 + H2SO4

O2N O CN Br
OH NH OH || KCN
1) MeMgBr
••

C=N + C=N
2

dil. O2N 2) H3O+


••

CH3 OH CH3
H2SO4 NO2 NO2
COOH NaNO2
dil. H3O+ HCl
CH3−C−NH− NO2 O2N −C−NHCH3 + CH3NH2 CH3 OH
H2SO4 ||
O
NO2 NO2 NH2
H3O+ ⊕
NH2 NO2 N2 NaOH Sn/
O
|| Sn/ NaNO2 H3PO2 CaO HCl
CH3 − C − OH + HCl HCl ∆ ⊕ ⊝
N2 Cl NaNO
⊕ 0 - 5°C HCl 2
O O N2
SOCl2
|| CH N
2 2 || ⊕ Moist H3PO2 / ∆
CH3−C−Cl CH3−C−CH2−N≡N Ag O CH3−CH=C=O
2
soda lime H3O+
CH3−CH3 CH3−CH2−COO
H
Road map

Br2/hv aq. NaOH conc. Br2 NaNH2


A B C D E
H2SO4 CCl4 (Excess)
NBS
1eq.

conc. Zn-Hg alc.


J I HCl
H G F
H2SO4 O KOH
1) MeMgBr anhy
O
2) H3O+ AlCl3
O

conc. 1) O3 LiAlH4
K L M N
H3PO4/∆ 2) Zn/H2O
SOCl2/Py

aq. Cl2/hv Pd-C Na


S NaOH
R Q P O
excess ∆ DE

Road map

Br OH Br
Br2/hv aq. NaOH conc. Br2 Br NaNH2
H2SO4 CCl4 (Excess)
NBS
1eq.
O
conc. Zn-Hg alc.
H2SO4 HCl O KOH S
1) MeMgBr O HO O HO O anhy
O
2) H3O+ AlCl3
O

conc. 1) O3 LiAlH4
H3PO4/∆
O OH
2) Zn/H2O O OH SOCl /Py
OH 2

aq. Cl2/hv Pd-C Na


NaOH excess ∆ DE Cl
Cl
COOH CCl3
Road map

Br aq. NaOH conc. cold KMnO4 HIO4


A B C D
H2SO4

I2/NaOH
CH2OH
+ H+
H3O LiAlH4 CH2OH CH3I
H G F E

H+
O3 H3O+ H+
I J Zn/H2O
K L

Road map

Br aq. NaOH OH conc. cold KMnO4 HIO4


H2SO4 OH O
OH O
I2/NaOH
CH2OH
OH O H+ O O
+
H3O LiAlH4 CH2OH CH3I ⊝
OCH3 OCH3 O
O O
O O O O

•• ••
OH
••

O OH + O O3 O O H O+ OH
•• H+
H 3
+ HCOOH
∆ Zn/H2O O
O O

O OH
O +
H
Road map

HNO3 Fe/HCl NaNO2 + HCl CuCN


A B C D
H2SO4 0-5°C KCN

Na/EtOH

CH3CHO NBS NaNH2


H G F E
OH−/∆ + HCl

LiAlH4

conc. m-CPBA H3O+ H+/∆


I J K L M
H2SO4

PCl5 NaBH4
O N

Road map
⊕ ⊝
N2 Cl
HNO3 NO2 Fe/HCl NH2 NaNO2 + HCl CuCN CN
H2SO4 0-5°C KCN

Na/EtOH

CH=CH−CHO CH3CHO CH=O NBS CH2OH NaNH2 CH2NH2


OH−/∆ + HCl

LiAlH4
O OH
conc. m-CPBA H3O+ H+/∆
OH 2SO4
H HO O
Dinacol

PCl5 NaBH4
Cl OH
Road map

HNO3 Sn/HCl Ac2O Cl2/Fe


A B C
H2SO4

NaNO2 + Br2/H2O H3O+


G F E D
HCl
0 - 5°C

HO− −NH2
H
Ph = 4-5

HO− −NH2
I
Ph = 9-10

H2O NaOH NBS



J K L
Ph Br

Road map
O
||
HNO3 NO2 Sn/HCl NH2 Ac2O NH2−C−CH3 Cl2/Fe
H2SO4
⊕ ⊝ O
N2 Cl NH2 ||
Br NO2 NaNO2 + Br NO2 Br2/H2O NH2 H3O+ NH−C−CH3
HCl
Cl Cl
0 - 5°C
Cl Cl
Br NH2
HO− −NH2
Cl N=N
Ph = 4-5
Br OH Br OH
HO− −NH2
Cl N=N
Ph = 9-10 Br-CH
OH Br NH2 O Ph O
H2O O2 Br NaOH O2 Br NBS O2 Br

Ph Br
Cl Cl Cl
Road map

O
|| H2O2/OH⊝ NH2NH2 PCC
A B C
NaOH DCM
rt

O O
|| || H ⊝
H2O2/OH⊝ NH2NH2 ⊝
O O O
NaOH

A Woak up H⊕
R
DCC
DCM
OH
O
C B

Road map
MeO OMe B.R H3O+
A B
(Birch Reduction)
H
MeO OMe H3O HO + OH O O O O

A B

OMe
Na/Liq.NH3 C7H15Br HCl (Aq)
COOH A B C

OMe OMe OH O

COO
⊝ HCl (Aq)
COOH || COOH
H COO
C7H15 Br C7H15 C7H15 C7H15
H ⊝:

H
O OH O O
|| C7H15 || C=O
C7H15 ∆
C7H15
Road map
Na2S
OMe
Na/Liq.NH3 O3 NaBH4
A B
1 Eq
LiAlH4
Me

Me Me
OMe
Na/Liq.NH3 OMe O3
1 Eq O
B.R H3C H3C
O H
OMe OMe

NaBH4
LiAlH4 Na2S

O
OH || OMe COOMe

Me CHO Me
OH Me OH

Road map
OH Br2
?

NGP •
+ CCl3
Br Br •
O O + CCl3
••

+
H
CCl3
Br
O CCl4 +

+ CCl4 A CCl3
Ph−C−O−O−C−Ph
|| ||
O O •
+ CCl3
-2CO2↑ Cl
Ph−C−O−O−C−Ph Ph•
|| ||
O O

Ph• + Cl−CCl3 PhCl + •CCl3


Road map
O
Hg (OAc)2 Na[BH (OAc)3]
A B
AcOH CH2Cl2

O O O O
Hg (OAc)2 OAc Na[BH (OAc)3]
AcOH H III
+ OAc
Hg OAc
Hg

OAc OAc
A
O O


Na[BH (OAc)3]
H III III H H III III H

OAc OAc

Road map

Hg(OAc)2 Na[BH(OAc)3] Pd−C/H2


A B C
N−C−OBr OMe LiAlH4
| ||
H O

N2
O O 1) hv/Aq.THF
?
2) ∆
OH
O
N2 O C
•• C
O O hv O O Wolf Rearrangement O H2O O

O OH

Road map

CHCl3/KOH
N A and B
| II) H3O+
H

Me (i) Base Rdi


+ O= + A B
Me (ii) H /∆

Ph−C−CH3 (i) LDA


|| (ii) Ph−CH=CH−Ph
CH2 +
(iii) H

Road map
OH OH

Me

⊝ ⊕
O−H O H O−SPh
••
BuLi Ph−S−Cl LDA
−S−Ph −S−Ph Me−I
||
O EWG

O

OH O−SPh O
2,3 ||
P(OMe)3
sigma
−S−Ph
Me MeOH Me Me

OR
Cl
NaOR Cl C=O
C−Ph ? O

X || Ph
O OR
X Ph X
Road map
COOEt
KOH H+ PCl5 LiAlH4 H+/∆
A B C D E
EtOOC COOEt

CH3
| K2Cr2O7, H2SO4 SOCl2 (CH3)3NH LiAlH4
CH3−C−CH2−CH2−O A B C D
H2O, Heat 2 Mole H2O
|
CH3 H

CH2−COOH
EtOH NaH NaOH SOCl2
A B C D
H+ Me−I H+ AlCl3

Cl2/AlCl3 Fe, HCl Br2/FeBr3 NaOH H2SO4, NaNO2


A B C D E F
NaOH H2O
NO2
H3PO2
G
H2O

Road map

CH3
Br2 Sn/HCl NaNO2 + HCl H3PO2 KMnO4
A B C D ⊝
E
Fe OH
NO2

NO2

Benzene
NO2
OCH3
Road map
Me O
Me OH
i) Excess Li
⊕ A
ii) H ,H2O

HO What is the
Oestrone function of ‘A’ HO
Ethynylestradiol

CN O CN
NC NC ||
BuLi ZnBr2 Ph−C−Cl
Br THF Li THF
100°C
A ZnBr O=C
Ph
B C
Cl Cl

(i) C Cl
Br Li || Cl
N BuLi N O

N N (ii) H3O+ N Cl
OH
A N
B

Road map

MeO S dithioacetal
S
O CF3CO2H ,
OHC S S
O
MeO A
O H O (solvent)
CHCl
2 3
Ordinary O
dioxolane 0°C
Acetal
To complex number of σ and π bond.
Low temperature
A

OH OH
NaBr Na/Hg
Br
R CO H CO2H
2

OH HNO2 OH OH
HgO
H2N HO HO
S CO2H S CO2H CHO
+ Isoserine A D + glyceraldehyde
Road map

O H2N CO2H
MeO i) KCN, NH4Cl MeO

ii) HCl H2O i) Ac2O ii)Na ⊝
MeO MeO O
Racemic A.A

A B
AcHN O O
AcHN
MeO O MeO O CH2

MeO MeO
KOH, EtOH, H2O KOH, EtOH, H2O
AcHN CO2H H2N CO2H AcHN CO2H
MeO MeO
MeO
H2N CO2H
MeO MeO
MeO MeO
20% NaOH 5 enantiomer
MeO 20% NaOH

Road map
O
O
O−S−Cl O ⊝
SO3
S ⊕
Bu4N CH3−CO2 O
H OH N H O +
+ Pyridine Sn2Rxn O H
O DMF

O R

O Ph3P CH3 H
O
+ + N CO2Et
EtO2−CN=N EtO2C N
R OH HO Ph CO2Et R O Ph H
A

H−NH3

H O Ph H O Ph H OH Ph PPh H OH Ph
NaN3 3

NH4Cl H2O
Ph H Ph H Ph H Ph H
H2O EtOH ⊝ N3 NH2
⊝ ⊕ ⊝
N=N=N
N=N=N ⊕
Road map

Me O Me O Me O
OH OMs
N MsCl, Et3N N DBU
N

O N O N O N
Me Me Me

OH O
i) HCl, H2O H O
OEt
ii) Et3N, Et2O
Cl O
E,C,B
Lactonize
in Acid

O ⊝

:NEt3 O
C H
H O H O

Cl Cl

Road map

O OLi Me SiCl OSiMe3 Br2


O
R LDA R 3 R R Br

A B C

O O O O O O
S (NH4)2CO3 S KMnO4 S HCl
Cl NH2 NH2
Me Me CO2H
A B O O
S
NH

Saccharin O
C
Road map
OH OH OH OH
X2 X X NH OH X X Hot. P O X X H3O+
2 2 5
D

O H O C H HON C H N≡C
A B C

H
NaNO2 ON NH2SH H2N Ac2O N

OH HCl OH H2O OH OH
C=O

A B C
H
N NMe2
i) conc. HCl C Cl
NMe2
ii) NaOH O O NaOEt

Road map


H2N NaNO2 HCl N2 H2O
NMe2 H2O 5°C NMe2
O O heat

E F
HO
NMe2
O

Ac2O Pyridine

O
C
NMe2
O O
Road map
Ph Ph
O O O OH ⊕
N NaBH4 N H2 Pd/CH
MeO MeO
O
HO Ph HO Ph
A OMe

OH OH H O OH H
N LiAlH4 N
MeO
HO OMe HO OMe
C B

H H2N LiNEt2
nBu C nBu N n−Bu

THF − 60°C N
O Cat H
H B H
R2 N−Li
A O
O i)
Br O
n−Bu O
ii) H+, H2O
O

Road map

O O
EtO2C CO2Et CO2Et CO2Et
Excess EtO EtO
+ H
NaOEt ⊝
Br Br Br Et Br
A

COOH EtO2C CO2Et


NaOH
HCl heat

⊝ ⊝
O O NaH O O O O
H
OMe OMe OMe
Bu-Li
BuLi

Br H
O O H+ OH O O O

OMe OMe OMe


Road map
Br
O OSiMe3 OLi Br O O
Me2CoLi Me2Li Br KH
Me3SiCl Me THF THF
Me
Me

OMe
CN MeO H2/Pd/C MeO
Triton B OMe OMe
OMe [Ph CH NMe⊕ OH⊝ CN CO2Et CO2Et
2 3
CO2Et NH2
]
MeO MeO
OMe Alkylation OMe Spontaneous
N And Red H N Cyclization
O
Pr H

Road map

BOC BOC
N N
H2/Pd/C

BOC
SO2Ar A SO2Ar N OMe
N
OMe BuLi OMe
Br N Li N SO2Ar
B C

O O O O O O
+
MeMgI H mcPBA

O
H OH H H O H
Road map

Road map Set 3

Question

H3O+ Fe tube Cl/AlCl3 O2/∆


CaC2 1 2 3
Red hot

i) Cl2/NaOH dil. H2SO4


CH3COOH + 7 6 + 5 4
ii) H+
Ketone
7 + NaOH
i) CO2+NaOH
+
H ii) H+
9 8
O
||
CH3CCl
11 10
H (major)
PhO
MeOH
12
13
Road map Set 3

Answer

−O−OH
1 CH≡CH 2 3 4


OH O OH
O
−CHO −CHO
5 6 7 CHCl3 8 9

OH OCOCH3 OH OH
−COOH −COOH −COOPh −COOMe
10 11 12 13

Road map Set 3

Question

Br2/hv alc. KOH Br2 NaNH2


1 2 3 4
CCl4 excess
NBS
NH4NS HNO3 HNO3 alc. KOH
8 7 6 5
H2SO4 H2SO4

Ac2O HNO3 H3O+ NaNO2/HCl


9 10 11 12 13
H2SO4 0-5°C

KNO2 NaNO2/HCl Na2S H3PO2/∆


17 16 15 14
CuNO2 0-5°C
Road map Set 3

Answer

Br Br NO2
Br
1 2 3 4 5 6 7

Br

NO2 NH2 NHCOCH3 NHCOCH3 NH2

8 9 10 11 12
NO2 NO2 NO2 NO2 NO2
NO2 NO2
⊕ ⊝
N2 Cl

13 14 15 16 17
NO2 NO2 NO2 NO2 NO2
⊕ ⊝
NO2 NO2 NH2 N2 Cl NO2

Road map Set 3

Question

OH NaOCl Ag Fe tube AlCl3 Br2/ Fe


CH3COONa + 1 2 3 4
powder Red hot CH3COCl

OH
Me2CHLi PCC NH4Cl CH2=O Mg ether OH
11 10 9 8 7 6 5
THC ether dry H+

NH4Cl PCC PhMgBr NH4Cl H3O+ NaH


12 13 14 15 16 17

NH4Cl PhMgBr m-CPBA Al2O3 NaBH4 PhCH2Br


23 22 ether
21 20 19 18

Road map Set 3

Answer

O O O O
1 CHCl3 2 CH≡CH 3 4 5 6
Br Br

O O O O O O O O
7 8 9 10
⊕ ⊝
BrMg MgBr OH2C HOH2C HC
O

O O O O O O O O
11 12 13 14

⊝ ⊕ ⊝ ⊕
O Li OH O Ph O MgBr

Road map Set 3

Answer

O O O O O OH
15 16 17 18 19

⊝ ⊕

Ph OH Ph OH Ph O Na Ph O-CH2Ph Ph OCH2Ph

⊝ ⊕

O O MgBr OH
20 21 22 23
Ph Ph
Ph OCH2Ph Ph OCH2Ph Ph OCH2Ph Ph OCH2Ph
Road map Set 3

Question OH− AB
Z AA MeMgCl

Br2
M Me2CuLi
CCl4 Aq. KOH AC

D2 / Ni
N G H I J K L
Na liq.
NH3 Pd Excess O3/H2O 2Br2/CCl4 HgSO4
OsO4
O BaSO4/H2 HCl Dil H2SO4
NaNH2 (1Eq)
C
MeI
mepha MeI HgSO4
P A B
H3O+ D
Dil H2SO4
Dry NaNH2 (1Eq)
Q HC≡CH B(Sia)3H
Ag2O E
H2O2/OH−
NaOCl
HOBr O X Ni/H2
R Ag/
+ Y F
Heat

Road map Set 3

Question
HC≡CH
Conc. KMnO4 F

Gas Cl2/hv

Lime AD
PhOH OH− EtMgCl H3O+
water
Na/Dry ether Alc. KOH
S T U
AE AF

Ac2O LAH

V W
Road map Set 3
OH
Answer O OH− O
∆ MeMgCl
Me
Br2
H Br O
H Br Me2CuLi
CCl4 Aq. KOH
Me
Me Br Br
D2 / Ni Cl Cl O
(±) H D
D D Me−COOH Br Br
Me Na liq.
Me NH3 Pd Excess O3/H2O 2Br2/CCl4 HgSO4
OsO4
(±) H OH HCl
BaSO4/H2 Dil H2SO4
HO H
NaNH2 (1Eq)
Me Me−C≡C−Me
Me MeI
H OH mepha MeI HgSO4 O

(±) H OH H3O+ HC≡C Me−C≡CH
Dil H2SO4
Me
O Dry NaNH2 (1Eq)
B(Sia)3H
O O
(±) HC≡CH
Ag2O
H2O2/OH− C−H
Me NaOCl ⊝
HOBr O MeCOO + Ni/H2
(±) H OH Ag/
H Br CHCl3 Heat
Me

Road map Set 3

Answer
HC≡CH
Conc. KMnO4

CO2 Cl2/hv

Lime
Cl
PhOH OH− EtMgCl H3O+
water
Na/Dry ether Alc. KOH
OH EtCOOH Milk
COOH [CaCO3]

Ac2O LAH

OAc OH
COOH
Road map 9 May

Question

Cl2/hv alc.KOH HOCl RhO2/∆ NaNH2


1 2 3 4 5

(CH3CO)2 O H⊕ NaOH Conc. alco.KoH NBS


11 10 9 8 7 6
fusion H2SO4

HNO3+H2SO4 H3O⊕ Sn/HCl NaNO2+HCl H3PO2/Δ


Conc.
12 13 14 15 16 17
H2SO4 0 - 5oC
O
||
NaBH4 CH3NH2 Cl-C-CH2-Cl H⊕ NaOH (s)
22 21 20 19 18
POCl3 fusion

Road map 9 May

Answer

Cl OH
Cl Cl
1 2 3 4 5 6
Br

O
SO3H O−Na+ OH O−C−CH3
7 8 9 10 11

O
12 O 13 OH 14 OH 15 OH

O2N O2N O2N SO3H H2N SO3H


Road map 9 May

Answer

⊝ ⊕
16 OH 17 OH 18 O Na 19 OH
⊝ ⊕ ⊝ ⊕
ClN2 SO3H SO3H O Na OH

O O OH
HO HO Cl HO
20 NH2 21 22 NH2
HO HO HO
Adrenaline

Road map 9 May

Question

Li Cu2Br2 Me - I Cl2/hv alco.


CH3−CH2−Cl 1 2 3 4 5
KOH

H2O/H⊕ i. EtONa NaOet MeOH K2Cr2O7 I. a-BBN


11 10 9 8 7 H2SO4
6
ii. etOH H⊕ II. H2O2/OH-
Cu2CH2Br

Δ LDA PhCH2Br
12 13 14
THF
Road map 9 May

Answer

− + Cl
1 CH3CH2Li 2 (CH3CH2)CuLi 3 CH3−CH2−CH3 4

5 6 OH 7 OH 8 OMe
O O

O O O
9 OMe 10 11 OH
OEt
O O O

O O O
12 13 14

Ph

Road map 9 May

Question

An organic compound (A) When treated with alcohol (B) forms an ester (C)
along with acid (D) ester (C) on hydrolysis gives acid (D) and alcohol (B) which
give positive test with I2/OH⊝ (B) on oxidation gives acid (D) which on heating
with calcium hydroxide gives (E) having molecular formula C3H6O. (E) doesn’t
give Tollen’s test but forms oxime (F) containing 19.17% N. Two moles of ester
(C) when treated with EtONa gives β-keto ester (G) along with alcohol (B). (G)
on hydrolysis gives a β. Keto acid (H) which on decarboxylation gives (E). (G)
forms (I) with alkyl halide (J) in presence of EtONa. (I) on hydrolysis gives (k)
which on decarboxylation gives 4-methylpentan-2-one. Find the structures
from (A) to (J)
Road map 9 May

Answer

A O O B C O D O E O
O OH O OH

O O O O O O
F N−OH G H I
O OH O

O O
X
J K
OH

Road map 9 May

Question Identify optically active compounds

1 2 3 4

5 6 7 8

9 10 11 12

13 14 15 16
Road map 9 May

Question

17 18

19 20

21 22 23

24 25 26 27 28

Road map 9 May

Question

29 30 31 32 33 34

35 36 37 38 39

40 41 42 43 44

45 46 47 48 49 50
Road map 9 May

Answer

Optically active compounds


4, 7, 8 , 10, 12, 14, 15, 22, 23, 24, 25, 27, 28, 30, 34, 36, 37, 38, 39, 41, 43, 44, 45,
46, 48, 49, 50, 59, 62, 63, 64, 65, 66, 67, 69, 73.

Road map 12th May

Question

Cl Cl
Cl aq. NaOH -H2O MeMgBr NH4Cl
Cl 1 2 3 4

Cl Cl

H2CrO4 HIO4 Cold. dil Conc.


9 8 7 6 5
KMnO4 ∆ H2SO4

Ca(OH)2 I. Mg - Mg H⊕
10 11 12
Δ II. H2O
Road map 9 May

Answer

Cl Cl Cl OH
Cl aq. NaOH Cl -H2O
Cl OH
Cl Cl Cl Cl
1

⊝ ⊕
Cl OH Cl OMgQ Cl O
Cl Cl Cl
NH4Cl MeMgBr
Me
Cl Cl Cl Cl Cl Cl
4 3 2

Cl Cl
Cl Cl
Conc. Cold. dil
H2SO4 ∆ KMnO4
Cl Cl Cl Cl
5 6

Road map 9 May

Answer
Cl O Cl OH
Cl Cl
H2CrO4 O HIO4

Cl Cl Cl Cl OH
8 7

Cl O Cl
Cl Ca(OH)2
Cl
OH I. Mg - Mg
O
OH Δ II. H2O
Cl Cl O Cl Cl
9 10

Cl
Cl Cl
Cl
H⊕ Cl Cl Cl Cl

Cl Cl Cl Cl Cl Cl
Cl Cl HO OH
O
11
12
Road map 9 May

Question

Alkene (A) on ozonolysis gives acetone and an aldehyde. The aldehyde is easily
oxidised to acid (B). When is treated with bromine in presence of P. it yields
compound (C) which on hydrolysis gives a hydroxy acid (D) This acid can also be
obtained from acetone by reaction with HCN followed by hydrolysis. An isomeric
form (E) of acid (D) loses its optical activity on strong heating yielding (F) Which
reacts with KMnO4. (F) m reaction with SOCl2 forms (G) which on reaction with a
nitrogenous base (H) with molecular formula C2H7N gives (I). (H) forms a product
(J) With benzene sulphonyl chloride which is insoluble in alkali. Compound (E) on
oxidation with dil. H2CrO4 gives an unstable compound (k) which decarboxylate
readily to give (L) which is isomer of acetone. (L) on heating with dilute NaOH
gives (M) which does not give positive iodoform test. While acetone on heating
with dil NaOH gives (N). (N) on treating with NaOI solution gives iodoform along
with an acid (O) which on carboxylation gives (P). (P) on reaction with isobutanol
in presence of acid catalyst followed by H2N gives (Q) Which has acetone
number 100. Assign the structures from (A) to (Q)

Road map 9 May

Answer

CH3 O
| || CH3
A CH3−C=CH−CH−CH3 E CH3−CH−CH2−OH I CH2=C−C−N
| | | CH3
CH3 COOH CH3

B CH3−CH−COOH F F−CH2=C−COOH J C6H5SO2NMe2


| |
CH3 CH3
CH3 O
| ||
C CH3−C−COOH G CH2=C−C−Cl K O=HC−CH−COOH
| | |
Br CH3 CH3
CH3
|
D CH3−C−COOH H (CH3)2NH L CH3−CH2−CH=O
|
OH
Road map 9 May

Answer

CH3
|
M CH3−CH2−CH=C-CH=C Q CH3−CH−CH2−C−CH3
| | |
CH3 CH3 CH3
O
||
N CH3−CH=CH−C−CH3
|
CH3

O CH3−C=C−COONa
|
CH3

P CH3−CH=CH
|
CH3

Road map 19 May

Question

Cl2/hv Na Br2/hv alco.KOH 2CO + 2H2


CH4 1 2 3 4 5
Dry ether Co(HCO)4

HNO3+H2SO4 Fe-tube Ag Cl2+NaOH


9 8 7 6 + HCOONa
red-hot Powder


Sn/HCl NaNO2+HCl KCN H3O CH3CH2OH
10 11 12 13 14
o
0-5 C CuCN H⊕
OMe
COCH3

Tautomerism MeO OMe


H⊕/HCl
17 16 15
-H2O
-3MeCl (Major enol)
Road map 9 May

Answer

1 CH3-Cl 2 CH3-CH3 3 CH3-CH2-Br 4 CH2=CH2 5 CH3CHO 6 CHCl3


⊕ ⊝
NO2 NH2 N2 Cl CN

7 CH ≡ CH 8 9 10 11 12

COOH COOCH2CH3 O O
OMe || OMe ||
13 14 15 C 16 C
CH2 CH
MeO OMe C=O MeO OMe C
HO
OH O
||
17
chrysin
HO O

Road map

Question
Mg(1 eqv.) CH2=CH2/Δ Br2/CCl4 NaNH2
CH2−CH=CH−CH2 1 2 3 4
ether Δ
| |
I I

Δ I. O3 Li/liq.NH3 alc.KOH NBS


9 8 7 6 5
II. H2O

SOCl2 Me2Cd Mg-Hg H2SO4 NaOI


10 11 12 13 14 + 15
H2O

I. CH2N2 SOCl2
18 17
II. Ag2O(moist)
III. H2O
Fe-tube Ag Powder
6 16 Δ
Red hot
Road map 9 May

Answer

Br Br
1 2 3 4 5 6
Br

O
||
7 8 CH2(COOH)2 9 CH3COOH 10 CH3COCl 11

O O
12 13 14 15 CHI3 16 CH≡CH
OH
HO OH

O
17 18 || OH
Cl O

Road map 9 May

Question

An organic compound (A) gave a foul smelling product when treated with
CHCl3/alc.KOH. 0.435 g of A is treated with NaNO2/HCl and liberates 112 ml of a
colourless, odourless gas at STP, along with a compound (B), (B) gives lucas test
within 5 to 10 minutes and on oxidation gives (C) which forms a yellow
compound (D) along with an acid salt (E) on treating with sodium hypoiodite
solution (E) on acidification gives an acid (F) which is isomer of an acid (G). The
acids (F) and (G) both can be obtained when a hydrocarbon (H), molecular
formula (C5H8) is treated with NaNH2 followed by n-propyl iodide followed by
oxidation with strong oxidising agent. Assign the structures of A to (H).
Road map 9 May

Answer

NH2 OH
A B C
O
⊝ ⊕
O Na OH
D CHI3 E F
O O

O
G H CH3−CH−C≡CH
OH |
CH3

Road map 25 May

Question

Cl2/hv KCN (2 moles) H3O⊕ EtOH/H⊕ EtONa+


CH4 1 2 3 4 5
dichlorination 2Et-I

P2O5/Δ Δ H3O⊕ NaOEt +


10 9 8 7
Br-CH2-COOEt O
||
Veronal H2N C - NH2
6
(Tranquiliser) H⊕

Zn.Hg/HCl SOCl2 anhy AlCl3 NH2-NH2/OH-


11 12 13 14 15
Any. AlCl3

PhN⊕2/dil NaOH I. O2 Mg Br2/Fe Pd-C/Δ


20 19 18 17 16
II. H3O+ Dry
Red-orange dye. ether
Road map 25 May

Answer
O O
Cl NH
1 CH2 6 10 O
Cl O NH O
veronal O
CN O
2 CH2 COOEt
CH
CN 11
7 COOEt
COOH CH2−COOEt HO
O
3 CH2
COOH COOH
CH 12
COOEt 8 COOH
HO
4 CH2 CH2−COOEt O
COOEt

CH2−COOH 13
Et COOEt
5 CH2 9
Cl
Et COOEt CH2−COOH O

Road map 25 May

Answer

Br OH

14 17 20
O MgBr N
N
15 18

OH

16 19
Road map 25 May

Question

An organic compound (A) (mol. formula C8H14O) forms an oxime and gives
positive haloform test. (A) on ozonolysis followed by Zn/H2O gives (B) and (C)
(mol. formula C5H8O2). (B) does not give Tollen’s test but forms oxime (D)
containing 19.17% nitrogen. (B) on heating with dilute alkali gives (E) which on
treating with sodium hypochlorite solution gives chloroform along with salt (F).
(F) on decarboxylation followed by treating with concentrated H2SO4 gives a
dimer of decarboxylation product of (F). Compound (C) forms a dioxime and on
treating with I2/NaOH, gives iodoform and acid salt (G) which on acidification
gives a dibasic acid (H). (H) on heating forms (I) while an isomeric form of (H) on
heating gives a monobasic acid (J) having molecular mass 74. Assign structures
of A to (J) with the reactions involved.

Road map 25 May

Answer
O
CH2 − C
A CH3 - C = CH-CH2-CH2-C-CH3 E CH3-C=CH-C-CH3 I O
| || | || CH2 − C
CH3 O CH3 CH3 O
B CH3 - C = O F CH3-C=CH-C-O- Na+ Isomeric form of H ➝
| | || COOH
CH3 CH3 O CH3-CH
COOH

C OCH - CH2 - CH2 -C - CH3 G CH2 - COONa J CH3 - CH3COOH


|| |
CH3
CH2 - COONa

D CH3 - C = N - OH H CH2 - COOH


| |
CH3 CH2 - COOH
Road map 25 May

Question

A dibasic acid (A) on heating gives a monobasic acid (B) having molecular mass
60. Ethyl ester (A’) of (A) when treated with benzyl chloride in presence of
sodium ethoxide gives (C) which on acid hydrolysis followed by decarboxylation
gives (D). Which (E) on hydrolysis followed by heating gives a monobasic acid
(E). (D) on dibromination in presence of sunlight followed by aq. KOH gives
compound (F) which forms two isomeric products with NH2OH. (B) on treating
with Br2 in presence of red phosphorous followed by treating with KCN gives (G)
which on acid hydrolysis gives (A). (B) on heating at high temperature gives (H)
which further on treating with (B) gives (I). (I) reacts with benzene in presence of
anhydrous AlCl3 to give (F) which on reduction with Zn- Hg/HCl gives (D).
𝛼-halogenated ethyl ester of (B) on treating with (F) in presence of zinc gives a
product which on treating with water gives (J). Assign structures from (A) to (J)
and give the reactions involved.

Road map 25 May

Answer

A CH2(COOH)2 E C6H5-CH2-CH2-COO I (CH3CO)2O


H

B CH3COOH F C6H5 - C - CH3 CH3


|| |
O J C6H5−C−CH2−COOEt
|
A’ CH2(COOEt)2 OH
G CH2 - COOH
|
CN

C C6H5CH2CH(COOEt)2
H CH2 = C = O

D C6H5CH2 - CH3
Road map 25 May

Question

Cl2/hv Na Br2/hv Mg
CH4 1 2 3 4
DE ether

Br2/KOH NH4 SOCl2 1. CO2


8 Δ
7 6 5 2. NH4Cl

Cu/300oC dil. NaOH/Δ 1. PhMgBr Al (t-BuO)3,


9 10 11 12
2. NH4Cl CH3COCH3

H⊕/Δ H⊕ 1. PhMgBr + CuBr


15 14 13 2. NH4Cl

Road map 9 May

Answer

1 -CH3-Cl 2 CH3-CH3 3 CH3-CH2Br

4 CH3-CH2-MgBr 5 CH3-CH2-COOH 6 CH3CH2-COCl

7 CH3-CH2-CONH2 8 CH3-CH2-NH2 9 CH3-CH=O

OH OH
| ||
10 CH3-CH=CH-CH=O 11 CH3-CH=CH-CH-Ph 12 CH3-CH=CH-C-Ph

O CH3 CH3
||
13 CH3-CH-CH2-C-Ph 14 15
|
Ph HO Ph Ph
Road map 25 May

Question

An organic compound (A) (C18H20O) on reductive ozonolysis gives (B) (C10H12O)


and (C) (C8H8O2). (B) gives iodoform test also produces oxime (D) (C10H13ON) on
treatment with NH2OH. (D) reacts with PCl5 to give (E) which on hydrolysis gives
(F) C8H11N along with a monobasic acid (G) having molecular mass 60. (F) on
treating with NaNO2 + HCl gives (H) which on oxidation gives a dibasic acid (I). (I)
on heating gives anhydride (J), (J) on heating with liquid NH3 gives (K). (K) on
treating with KOH followed by treating with a compound (L) and hydrolysis gives
(I) and alanine (lowest molecular mass optically active a-amino acid). (J) on
reaction with benzene + anhydrous AlCl3 followed by Zn-Hg/HCl followed by
conc. H2SO4 followed by NH2NH/OH− followed by Pd-c and heat gives
anthracene. Also, (J) on hydrolysis followed by treating with PCl5 followed by
Rossenmund’s reduction gives (M). (M) on reaction with hydrazine gives a
cyclised compound (N). Compound (C) on mild oxidation gives (O) which gives
effervessence with NaHCO3. (O) on treatment with HI produces p-hydroxy
benzoic acid and CH3−I. Give structures from (A) to (O) with reactions involved.

Road map 25 May

Answer CH3 O
CH3−C−NH−CH2
CH2−C=CH
E J O
A
H3C
CH3 O
OCH3 CH2−NH2 O
CH3 F
K NH
CH2−C=O CH3
B O
CH3 G CH3COOH Br−CH−COOH
L
CHO
CH2−OH CH3
C H CHO
CH3 M
OCH3 CH3 CHO
CH2−C=N−OH COOH CH N
D I N
CH3 COOH CH N
Road map 25 May

Question

An organic compound (A) gives Lucas test within test 5 to 10 minutes. 0.051 g of
(A) when treated with MeMgI gives 11.2 ml of methane at STP. (A) on dehydration
gives (B) which on ozonolysis gives two isomeric compounds (C) and (D). (D)
gives positive Tollens test but not iodoform test while (C) gives positive iodoform
test but not Tollens test. (D) on oxidation gives (E). The silver salt of (E) contains
59.6% silver. (C) on heating with dilute NaOH gives (F) which on treating with
sodium hypoiodite solution gives yellow compound along with sodium salt of
acid (G). (G) on decarboxylation gives (H) which on treating with sodium
hypoiodite solution gives yellow compound along with sodium salt of acid (G).
(G) on decarboxylation gives (H) which on treating with t-Bu-Cl/AlCl3 followed by
H2/Ni gives (I). (I) on monochlorination gives four mono-chloro structural isomers.
(C) on treating with Mg-Hg followed by hydrolysis gives (J). (J) on periodic
oxidation gives back (C) , and (J) on treating with dil H2SO4 undergoes a
rearrangement to give (K). (K) forms oxime but doesn’t give Fehling’s test. Assign
structures from (A) to (K).

Road map 25 May

Answer
CH3 CH3
| |
A CH3-CH2-CH - CH-CH3 F CH3-C=CH-C-CH3 J CH3- C - C - CH3
| | | | | |
OH CH3 CH3 O OH OH
O CH3
|| |
B CH3-CH2-CH = C-CH3 G CH3-C=CH-C-ONa K CH3- C - C - CH3
| | ||
CH3 CH3 O

C CH3-C=O H CH3-C=CH2
| |
CH3 CH3
CH3
|
D CH3-CH2-CH=O I CH3-CH-CH2-C-CH3
| |
CH3 CH3

E CH3-CH2-COOH

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