Flow Chart - 241111 - 101342 - Removed
Flow Chart - 241111 - 101342 - Removed
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
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
conc. 1) O3 LiAlH4
K L M N
H3PO4/∆ 2) Zn/H2O
SOCl2/Py
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
I2/NaOH
CH2OH
+ H+
H3O LiAlH4 CH2OH CH3I
H G F E
H+
O3 H3O+ H+
I J Zn/H2O
K L
∆
Road map
•• ••
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
Na/EtOH
LiAlH4
PCl5 NaBH4
O N
Road map
⊕ ⊝
N2 Cl
HNO3 NO2 Fe/HCl NH2 NaNO2 + HCl CuCN CN
H2SO4 0-5°C KCN
Na/EtOH
LiAlH4
O OH
conc. m-CPBA H3O+ H+/∆
OH 2SO4
H HO O
Dinacol
PCl5 NaBH4
Cl OH
Road map
HO− −NH2
H
Ph = 4-5
HO− −NH2
I
Ph = 9-10
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
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
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
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
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
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
⊝ ⊝
O O NaH O O O O
H
OMe OMe OMe
Bu-Li
BuLi
Br H
O O H+ OH O O O
⊝
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
Question
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
Question
Answer
Br Br NO2
Br
1 2 3 4 5 6 7
Br
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
Question
OH
Me2CHLi PCC NH4Cl CH2=O Mg ether OH
11 10 9 8 7 6 5
THC ether dry H+
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
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
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
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
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
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
Question
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
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
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
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
Question
Cl Cl
Cl aq. NaOH -H2O MeMgBr NH4Cl
Cl 1 2 3 4
Cl Cl
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
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)
Answer
CH3 O
| || CH3
A CH3−C=CH−CH−CH3 E CH3−CH−CH2−OH I CH2=C−C−N
| | | CH3
CH3 COOH CH3
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
Question
⊕
Sn/HCl NaNO2+HCl KCN H3O CH3CH2OH
10 11 12 13 14
o
0-5 C CuCN H⊕
OMe
COCH3
Answer
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
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
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
Question
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
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.
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
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.
Answer
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
Answer
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
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).
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
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CH3 CH3
CH3
|
D CH3-CH2-CH=O I CH3-CH-CH2-C-CH3
| |
CH3 CH3
E CH3-CH2-COOH