1-Class Test-T To AJ (Without Answer) - Metamorphosis

ORGANIC CHEMISTRY
XIII (ALL)
A TO Z METAMORPHOSIS
QUESTIONS & SOLUTIONS
VIBRANT ACADEMY (India) Private Limited

Believe In Excellence
B-41, Road No.2, Indraprastha Industrial Area, Kota-324005 (Raj.)
Tel. : 06377791915, (0744) 2778899, Fax : (0744) 2423405
Email: admin@vibrantacademy.com Website : www.vibrantacademy.com
Website : dlp.vibrantacademy.com
VIBRANT ACADEMY ORGANIC CHEMISTRY
Class Test-T
(India) Private Limited Target IIT ADVANCE-2020
(XIII-GOOGOL) TIME : 30 MIN.
H3O
Z Y
O H2/Pd–C
O—C  HCN K'
Q. * * –
CH3–CH CH–CH OH
3 X X' –
C—O  OH LiAlH4
J B K K''
O dil.H2SO4 CrO 
O 4
3 Stereoisomers dil. HgSO4 H 3 HI
2O
H2/Ni
W A K'''
Cold KMnO4
Silver, 
AgNO3 NaOH O3, Zn HBr tBuO K HBr
U T + S R C D E
NH4 OH I2 H2O CCl4 tBuOH R2O2 /h
Ca ,
O
+2
Se, 

– N K
V'
OD
V L KMnO4/OH H L'
D2O
(Solvent) O
Prolonged Cl2, h
treatment
F
M
–
(i) aq. KOH (ii) P.C.C. OH/H2O
Conc.KOH G + Salt H
O P  N
Conc.H2SO4
Ph – C – O – CH2 Ph + AcO CHCl3 + KOH
 N'
Ester Ac2O, 
O (prolonged Trans geometry
treatment) (Major) I
NaOH/CaO/ Pungent smell
CH = O O3, Zn
Q
CH = O
Vibrant Academy (I) Pvt. Ltd. "B-41" Road No.2, IPIA, Kota (Raj.) Ph. 06377791915 (www.vibrantacademy.com) [2]
Class Test-U
Q. Compound A have molecular formula C2H4O2 gives effervercence with NaHCO3
Ca(OH)2 NaBH4 Dehydration (i) H+ O2, hv H3O+

(A) (B) (C) (D) (E) (F) (G) (i) Cl2, –OH
 (ii) Benzene (I) + CHCl3
+ (H) (ii) Hydrolysis
SOCl2
Fehling
Br2, P Hydrolysis solution O3 N2H4, –OH (i) –OH Cd(CH3)2
(R) (Q) (P) (O) + (N) (M) (L) (K) (J)
HVZ reaction Zn, H2O (ii) 
O
C
– +
O
C C
OH
O O
OH
C
NaOH O NH2
(S) (T) + CO2 + H2O + (U)
+ Ninhydrine H
O
– + O oxidation [O]
ONa
– +
ONa
(V)
O
CHO P2O5
O
CH3–C–O Na
– + , O O
H2, Pd
(X) (W)
PCl5 Perkins reaction
O
(Y)
AlCl3
(Z)
Class Test-V
Q. Cu/523K
(A)
100 atm
CH4 PCC
Mo2O3
(B)
+ –
Ph3–P–CH2
Zn conc. H2SO4
(D) (C)
H2O cold dil.KMnO4
O
(E) O
– +
O LiAlH4 H2O Cu NaOH Cl2, OH Workup H ,H2 O CrO3  NaBH4
F G H  J K L M N O P Q
dry HCl (gas) 573K anhydride
+
CHCl3
H H SOCl2
O O
Dry HCl HCHO HCHO (i) DIBAL-H KCN

V U T S R
HCHO OH OH (ii) H2O
(W)
+
H
Ring expansion rearrangement
+
O (i) [Ag(NH3)2] ,OH NaOH, CaO
(X) (Y)
+
(ii) H3O 
(i) B2H6 or LiAlH4/ether
+
(Z)
(ii) H3O
Class Test-W
HCHO(excess)
B + HCOO
Q. OH

H /H2O Cl2/OH
A + CH3–CH2–OH D + HCOO
OH /
Ph–OH
CH2= CH – O – CH2– CH3 C CH3–NH2/OH H
E F
O3/Zn
O
LiAlH4
G + H – C – O – CH2 – CH3 H + CH3 –CH2 – OH
HBr
Conc.
Ph–CHO Br2/h H3PO4
Li CuI CH3–CH2–I aq.KOH
+ P Q R S T U V
OH
N.B.S
Alc. KOH
Cu 300ºC foolowed by
HCOO + I (Cyclization) NaNH2
Z Y X HBr W
P.C.C.
NaNO2/HCl
NH2–OH/H SOCl2 Br2/OH (0–5ºC) H3PO2
J K L M N O
Class Test-X
CH3–CH2–CH2–Cl
Q. + AlCl3 O2/h CCl4/KOH (CH3CO2)O
A B C D
H O/H
2 +
CH3–C–CH3
O
O
CH3–C–Cl Zn–Hg N.B.S Alc. KOH H2O2
E F G H I
AlCl3 Conc.HCl h
O O3/Zn
SOCl2 H2/Pd–C (CH3–C—2 O )

M L K J +H–C–H
O
O
AlCl3 CH3–C—O
Zn–Hg/
N conc.HCl O
Conc. N2O5/ Cl2/AlCl3
H2SO4 a b
NaOH Fusion Zn dust NaNO2/HCl dil. HNO3

P Q R S T
H2O/H
Conc.H2SO4
+
Conc.HNO3
 NaNO2/HCl (NH4)+2S
NaOH H2O/H CuCN
Z Y X W V U
CaO (0–5)ºC
Class Test-Y
Q.
Cl2/light KOH(alc) Br2/CCl4 NaNH2 (i) BH3 K2Cr2O7/H SOCl2 H2

(A) (B) (C) (D) –
(E) (F) (G) (H)
2-mol (ii) H2O2/ OH  Pd-BaSO4
O
Ni/H2
(i) –
N K
+
+–
(NaOH+ CaO) KOH(alc) Red P/Cl2 H+/H2O KCN TsCl dil.HNO2 O PCl5
(R) (Q) (P) (O) (N) (M) (L) (K) (J) (I)
 excess + 
(ii) H /H2O
Br2/H2O
+ + + +
CH3–O H /CH3–OH H /H2O H / KMnO4/H Red P/Cl2 NH3 
(S) (T) (U) (V) (W) (X) (Y) (Z) (Z')
(excess)
Class Test-Z
Q. (i) CH3–I
+– + –
AgNO2 H2/Pd–C (i) moist Ag2O Ag/; air PCl5 KCN H/H2O NaOH; HI
(A) (B) (C) (D) (E) (F) (G) (H) (I)
Cl   (2-mol) electrolysis
CH3–COO–Na+
KMnO4/H+ H+/ 1% dil t-BuO– H-Br Ag H–Br  Br–Cl 
(T) (S) (R) (Q) (P) (O) (N) (M) (L) (K) (J)
KMnO4  (2-mol) (2-mol)
NaNH2
Red P/Cl2
KOH(alc) H+/H2O  P.C.C OH–/

(U) (V) (W) (X) (Y) (Z)
excess NaOH
+ CaO
Class Test-AA
Q. Moles of gaseous hydrocarbon released in last step.

H /A O3/Zn (i)C2H5MgBr Cu/ Cold H

2 + NaOH 
H
(B) (C) (D) (F) + (E) (G) (H) () (J)
(TCP product only) H2O (ii)H3O

573K KMnO4  
OH
NaOH
+
O3/Zn (i)Alc KOH/ Cl2 E elimination Cl2 + h CaO
(R) (Q) (P) (O) 2 (N) + (L) (K)
(ii)NaNH2/ CCl4 (Minor) (Major) (Monochlorination)
Fe Na Dry ether
red hot tube
(M)
n Na
/Z (S) /Li
O O
3 q.
H2 NH
excess
(T) Ni/H2 3
O3/Zn NaOH + 2
(U) (X) (Y) NaOH + CaO (Z)
H2O  
+ (W)
(V)
Class Test-AB
Cl Na Cr2O3 Fe
Q. (B) (C) (D)
dry ether + Al2O3/ C Cl2/dark
ex l /h
ce v
2
O3 ss
H3O OH AlCl3 (E)
(K) (J) (I) Zn/H2O C–Cl Lindane
conc.
(F) O
LAH Zn
/Hg
(G) HCl
H (L) Ho
tA
D lka
KM line
(H) nO
4 / NaOH + Cao
O3/Zn H2O (M) (N) + gas

O
(i) CH3–C–O Na
H O O O
Red hot
C C (i) CH3–C–O–C–CH3/ PCl5 Alc/KOH
C OH tube
(U) + (V) (X) (Y) (Z)
H NaNH2/
(W)
(trans+cis)
Se/ (S) Zn/Hg SOCl2 O3

(T) (R) (Q) (P) + (O)
+HCl AlCl3/ V2O5/500ºC
Class Test-AC
Q.
Cl2 aq. Na CH3–CH2–I
CH4 (A) (B) (C) (D)
h KOH –½H2
KCN NaNO2 + H–Cl Conc. H–I
(O) (K) P + I2
(F) (E)

H3 O +
2H2/Ni CHCl3/KOH
KNO2 AgNO2 (G)
(Q)
(P) (L)
HNO2
(i) RedP + Cl2 (ii) H2 O /H2O LiAlH4
(H) Ph–MgBr
(E) (M)
(R)
Cl2/AlCl3 Cl2 /h
NaNO2 + HCl
(I) 
(N) KMnO4/OH/
(J)
(S)
(Z) DIABAL–H
Ag2 O/ (T)

 AC2O/  
(i) HCHO/OH/ CH3–CO2Na
(X) + (W) 
(ii) H3O /
(ii) H 
(Q) + (Y)
O

CH3 –C–CH3/OH
(V) (U)
Zn(Hg)/H–Cl
Class Test-AD
Q. H2O EtOH
(A) (B)
CH3OH
(C) NaOH (D)
NH3 (E) KOBr (F)
Ph–NH2 (G) Br2 (H)

FeBr3
CH3COOH PhCH=O
(I) (J)
Py CH3COONa
C6H6 KOI (L)
(K)
O AlCl3
CH3 – C – Cl H2
(M) dil.KOH (N)
Pd-BaSO4 
LiAlH4
(O) PCC (P)
CH3MgCl (Q) Mg–Hg (R)

H2O
2PhMgBr Conc.
(S) (T)
H2SO4
DiBAl–H (U) Tollen (V)
Ni/H2 PCl5
(W) (X)
(C2H5)2CuLi
(Y) Br2 (Z)
H
Class Test-AE
Q. HCl (A) Alc.KOH (B)
R2O2
HBr Aq.KOH
(C) (C)
R2O2
O3
(E) Conc.KOH (F)
Zn 
HBO (G) PCC (H)
OMDM (I) KOH (J)

I2
Cl2
(K) alc.NaNH2 (L)
3 mole
Br2
H2O (M) CH3MgBr (N)
1 mole
Ph – CH = CH2
Ni (O) Hot (P)
H2 KMnO4
dil.H2SO4 Conc.H2SO4
(Q) (R)
HBr Na/DE
(S) (T)
CCl4
O
H (U) (V)
CH2=O
dil.KMnO4
(W) HIO4 (X)
Polymer O3
(Y) (Z)
Zn
Class Test-AF
Q.
conc.H2SO4 cold dil.H2SO4 2/NaOH H+ NH3 Br2/KOH CH3– AgOH/
OH (A) (B) (C) (D) + (E) (G) (H) () (J)
 KMnO4    (excess)
6Ag/
L(Minor) K(Major)
O3/H2O
[NaNO2 + HCl] NH3/ V2O5/300°C Fe/

(R) (Q) (N) (M) (F)
0°–5°C (T) + Gas
NaOH, CH3OH
CHCl3/OH
CuCN/HCN
OCH3 (O) + (P)
Positional
isomer
(i) (CH3)2CuLi,THF 
(S) (X) (W) (V) (U)
(ii) aq. NH4Cl
Colourfull
Dyes
LAH H3O+
(Y) (Z)
Class Test-AG
Q. Cl
Alc.KOH OsO4 HIO4 NaOH  NH2–NH2 O3 SBH

(A) (B) (C) (D) (E) (F) (G)
 H+   H2O, Zn
OH
NBS h Al(OEt)3/AlCl3 (H)
PCC
(i) Mg/Dry ether P + Br2
(ii) CO2 (Q) (L) (Excess)
(N)
(iii) H+  18
Na Dry ether (i) OH H2O H+ ()
(T) (ii) H
(R) (M)
(O) excess
SOCl2/Py, Se  KCN

(J)
(U) (S) (P)
H3O
CH3MgBr(1eq.)
(K)
(V)
per acid
(X)  (Y)  (Z)
Cl2 + Ca(OH)2
(W)
[Anaesthatic]
Class Test-AH
Q.
COOH
K2Cr2O7  NH3 E NaOH+CaO/ NaNO2+HCl
o–xylene (B) (C) (D) (F) (G)
H2SO4 
(A) NH2
H2O/
dil OH/ DIBAL-H (Q) + (P) H2O H2SO4 NH2–OH CH3COCl NaOH
CH3–CH=CH–CHO (R) (O) (N) (M) (L) (H)
H AlCl3 C2H5Cl
(S) + Na
O Excess (E-isomer) Major
/ I2/KOH Br2+
H ) 2] HI H2O Br2 + CS2
3 )2
[Ag(N a(OH (V) + (V')
(i) (ii)
C
 (W) + Et–I
(I) (J) + (K)
(T)
(X)
Mg, Hg
Mg
(U) (Z)
H , (Y), H3O
(Y) (Z')
Class Test-AI
MCPBA,
O
||
Q. C–O–OH
BH3 CrO3 Ph3P = CH2 Cl PhCH2OH,Na

Cyclohexene (B) (C) (D) (E) (F)
H2O2 Pyridine O
M
(A) D
BO
M
H
(G) (H)
Structural isomers

H /

Se/ (I) O3 dil OH/
(J) K + L + M
(Major) Zn/H2O
hot NaOH + CaO/ CH3–CH=CH2

(N) (O) (P) (Q)
KMnO4 H
H
AL– (T) CHC
O2, h
lB l3 + K
OH

H , H2O
D
(Major) [O]
(V) (R) + (S) (X)
H
CO2 + KO Oxidation
(W)
(U) I2 /KOH
(V) + (Y)
(Major) (W) + CHI3 (Y)
(W)/
(Z)
Class Test-AJ
Q. Br2, h Br2 1. CH3I, CH3CH2Br KOH

Br–CH–CH–Br (D) (C) (B) (A) NH
| | 2. Ag2O H2O, O–H Gabriel
Br Br 3.  Phthalimide
O
(E)
2NaNH2
O3, 
CH3CH2C C2, h KOC(CH3)3 Zn /H2O
(F) Red hot (G) (H) (T) (U) (V) + (W) + (X)
Fe AC3 Mol.Wt. : 30
CH3Cl, OH
AlCl3 Acidic work up
(Y + Z)
(I)
hot KMnO4
(J) O
||
SOCl2 B2H6/THF, H3C S—C
H2, Pd, ||
BaSO4 PPh3CH2 H2O2/OH O NaCN
(K) (L) (M) (N) (O) (P)
N(CH3)2
|
NaNO2 LiAH4
(S) (R) (Q)
HC

1-Class Test-T To AJ (Without Answer) - Metamorphosis

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1-Class Test-T To AJ (Without Answer) - Metamorphosis

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ORGANIC CHEMISTRY

VIBRANT ACADEMY (India) Private Limited

Ca(OH)2 NaBH4 Dehydration (i) H+ O2, hv H3O+

Dry HCl HCHO HCHO (i) DIBAL-H KCN

SOCl2 H2/Pd–C (CH3–C—2 O )

NaOH Fusion Zn dust NaNO2/HCl dil. HNO3

Cl2/light KOH(alc) Br2/CCl4 NaNH2 (i) BH3 K2Cr2O7/H SOCl2 H2

KOH(alc) H+/H2O  P.C.C OH–/

Se/ (S) Zn/Hg SOCl2 O3

Ag2 O/ (T)

NH3 (E) KOBr (F)

Ph–NH2 (G) Br2 (H)

CH3MgCl (Q) Mg–Hg (R)

OMDM (I) KOH (J)

[NaNO2 + HCl] NH3/ V2O5/300°C Fe/

OCH3 (O) + (P)

Alc.KOH OsO4 HIO4 NaOH  NH2–NH2 O3 SBH

BH3 CrO3 Ph3P = CH2 Cl PhCH2OH,Na

hot NaOH + CaO/ CH3–CH=CH2

Q. Br2, h Br2 1. CH3I, CH3CH2Br KOH

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