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FINAL TOUCH
REVISION
OF
ORGANIC CHEMISTRY
FOR JEE ADVANCED
BY
NAVNEET JETHWANI
GRIGNARD REAGENT
OXIDATION
REDUCTION
ETOOSINDIA
INDIA’S NO. 1 ONLINE COACHING
Plot No. 38, Near Union Bank of India, Rajeev Gandhi Nagar,
Kota, Rajasthan – 324005 Mob. : 9214233303
ETOOSINDIA F.T.R. BY N.J. SIR
Single Choice Exercise
1. What is the major product of the following reaction ?
O
CH3MgI H3O
Et2O
CH3 OH
(A) (B)
CH2 OH CH2 CH3
O
CH3 OH
(C) (D)
CH3
CH3
CH3
C OCH3
PhMgBr
2. O (1 equivalent)
(P). Product (P) is :
CH2 COCH3
O
CH3 CH3O
C Ph C Ph
(A) (B)
O
CH2 COCH3 CH2 COCH3

O O
CH3 CH3
C Ph C OCH3
(C) (D)
O O
CH2 COCH3 CH2 C Ph

CH3
O O
Plot No. 38, Near Union Bank of India, Rajeev Gandhi Nagar, Page # 2
3. Reaction- 1 ;
SH O SH OH
CH3
HO C Cl C
CH3
1. x CH3MgBr

2. H 3O OH
CH3
C Cl C
CH3
O OH
Reaction- 2 ;
O OH
C O Et CH3 C CH3
1. y CH3MgBr

2. H3O
CH2 Cl
What is the ratio of (x/y) in above problem ?

(a) 1.5 (b) 2 (c) 2.5 (d) 3
4. In which of the following reaction 2° alcohol is obtained as a product ?
(1). CH3MgBr (1). MgCl

(A) (2). H 2O (B) O
(2). H2O
(1). CH3MgBr
(C) (D) Both (a) and (b)
(2). H2O
5. In which the following reactions product formed is same ?
(A) MeMgX (B) MgX

P P
(C) +
MgBr P
(a) (i) and (ii) (b) (ii) and (iii) (c) (i) and (iii) (d) (i), (ii) and (iii)
6. Which of the following reaction sequences would be the best for synthesis of 2-pentanone ?
O

CH3MgI H 3O
(A) CH3 CH2 CH2 C H Et 2O
CH2 CH2 CH3MgI H3O


(B) CH3 CH O Et2O
CH3MgI H3O 
(C) CH3 CH2 CH2 C N Et 2O
O

CH3MgI H3O
(D) CH3 CH2 CH2 C H Et 2O
OH
CO2CH3 C(CH3)2
7. x CH 3MgI ; Dimethyl phthalate
+
H
CO2CH3 C(CH3)2
OH
Number of mole (x) of Grignard reagent consumed in the above reaction is :
(A) 2 (B) 3 (C) 4 (D) 5
O (1) CH 3MgBr
(excess)
8. Et O C O Et (A), Product (A) is :
(2) H 3O
O O OH
(A) CH 3 C O Et (B) CH3 C CH3 (C) CH3 C CH3 (D) CH3 CH2 CH3
CH3
O O +
9. PhMgBr + H (A), Product (A) is :
excess
O OH OH O
(A) Ph C Ph (B) Ph C Ph (C) Ph C (D) Ph C O
Ph Ph
O
14
(i) PhMgBr
10. CH3 C O H (A)  (B)
(gas) (ii) H 3O
O
14
NaH CO3 (i) PhMgBr
CH3 S O H (C)  (D)
(gas) (ii) H3O
O
Product (B) and (D) in the above reaction are :
O O O O
(A) Ph C O H , Ph S O H (B) Ph C O H , Ph S O H
14
O
O O O O
(C) Ph C O H , Ph C O H (D) Ph C OH , Ph S O H
14 14 14
11. CH3MgBr NH4Cl Products.

diethyl ether H2O
CH3
comment on optical activity of the products. They are :
(A) racemix mixture (B) diastereomers
(C) meso forms (D) optically inactive due to absence of chiral centre
OH H OH H
Ph Ph
MeO2C N N
tBu (1) xPhMgBr HO tBu
12. (2) H 3O

HO HO
Number of equivalents of Grignard reagent (x) used in reaction (1) is :
(A) 3 equivalent (B) 4 equivalent (C) 5 equivalent (D) 6 equivalent
OH
Br CH Ph
13. (1) Mg : ether
(2) Ph–CHO
3 
(3) H O
N N
H H
The given product can not be obtained in the above reaction, Identify the correct product obtained .
(A) (B)
N CH Ph N
H OH CH Ph
OH
OH O
CH Ph CH Ph
(C) (D)
N N
O
Me H
MeMgBr
14. Product of the reaction is :
Ph
H
Me Me
Me H Me H
(A) (B)
HO H H OH
Ph Ph
(C) Both (a) and (b) (D) None of these
(i) MeMgI H+
15 (A) (B) Major
(ii) NH4Cl 
CH2
(A) (B)
(C) (D)
(i) THF
16.  MgBrCH 2 CH 2 CH 2 CH 2 MgBr (ii) H 3O+
product; product of the reaction is :
O O
O
(A) HO   CH 2 3  C CH 2  CH 2  CH3 (B)
HO (CH2)3 OH
(C) HO (D)
CH CH2 CH3
HO CH2 CH2 CH3
OH
O OH
C Cl C CH3
(i) x CH3MgBr CH3
17. +
(ii) H
C Cl C
OH
Me
O Me
Number of moles of CH3MgBr consumed in above reaction is :
(A) 2 (B) 4 (C) 6 (D) 8
18. End product of the given reaction is :
Cl
Mg 1. CH2O
Et 2O
(A) (B)
2. H3O
OH
OH
(A) (B)
OH
(C) (D)
19. Which of the following reaction sequences would be the best for synthesis of t-butyl alcohol ?
O
Et 2O H 3O CO2 H 3O
(A) CH3CH2MgBr + CH2 CH2 (B) CH3CH2CH2MgBr Et2O
O O

(C) CH3MgBr + CH3 C CH3 Et2O H 3O (D) CH3CH2MgBr + CH3 Et2O H 3O
C H
20. What is the major product of the following reaction ?

H 3O
CH3 C N Et 2O
H
N
(A) CH3–CH2–NH–CH3 (B) CH3 C CH3
O O
(C) CH3 C CH3 (D) CH3 CH2 C OH

21. CH 3CO 2 Et   CH 2 5  MgBr 2 
(2) H 
 C7 H14 O ; compound (A) will be :
( A)
OH
OH
OH O
(A) (B) (C) CH3 C (CH2)4 CH3 (D)
O
(1) excess CH3–Li
22. PhMgBr  CH 3  CN 
H O
(A) Ph C O H (2) H 3O
(A)
3
Same product (A) will form in both reactions . A is :

OH
(A) Ph C CH3 (B) Ph CHO
CH3
O
(C) Ph C CH3 (D) Ph CH2 CO2H
23. What is the product (B) of the following reaction sequence ?

Br
Mg
Et2O
A
O
(1) Et2O
B
A+ CH3 (2) H 3O

OH
OH CH3
(A) (B)
CH3
O OH
CH3
CH3
(C) (D)
OH
OH
CH2 OH
CH OH + CH3MgBr xCH4
24. (Excess)
CH2 SH
What is the value of x in the above reaction ?
(A) 1 (B) 2 (C) 3 (D) 4
25. 0.40 g of an organic compound (A), (M. F. - C5H8O) reacts with x mole of CH3 MgBr to liberate 224 mL of a gas at
STP. With excess of H2, (A) given pentan -1-ol. The correct structure of (A) is :
(A) CH3– C C –CH2–CH2–OH (B) CH 3  CH 2 – C C –CH2–OH
(C) H– C C CH 2  CH 2  CH 2  OH (D) H– C C –CH2– CH CH3
OH
O
Br2 Mg CH3 C CH3 H

+
26. CH3  CH  CH 2 h Dry ether 

(X)
(low conc.) NH4Cl (major)
End product (X) of the above reaction is :

CH2
(A) CH 2  CH  CH 2  C CH3 (B) H 2 C  CH  CH  C CH3

OH CH3
(C) H 2 C  CH  CH 2  C CH3 (D) H 2 C  CH  CH 2  CH  CH2 OH
CH3 CH3
27. In the given reaction
[X] will be :
(A) (B) (C) (D)
28. Which will give silver mirror test with Tollens reagent :
(A) C6H5CHO (B) CH3–CHO (C) HCOOH (D) All of these
29. ; A is :
(A) (B)
(C) (D)
30. Major product is :
COOH
(A) (B) (C) (D)
31. Which of the following can be oxidised by MnO2 :
(A) (B)
(C) (D)
32. A ; A is :
COOH OH
(A) (B)
O O
(C) (D)
O
O O
33. Phthalic Anhydride : A is :
Me Me
(A) (B)
Me
Me
Me
(C) (D)
Me
Me
SH
HS H2/Ni
34. O
The end product of the reaction are :
(A) SH and SH (B) S CH2 CH2 SH
S SH
(C) and H2O (D) and HS
S
CH2
35. H2,Pd
CH3
Products of the above reaction will be :
(A) Racemic mixture (B) Diasteromers
(C) Meso (D) Structural isomer
D
NH2-NH 2
36. H 2O 2
Product :
(A) ` (B) H
D
H
(C) H (D) Both (B) and (C)

H
D
H3C D
H2/Ni
C C
37.
D CH3
Product of above reaction will be :
(A) Racemic mixture ` (B) Diastereomers
(C) Meso (D) Constitutional isomers
O O
38. C C
Which reagent will be used for the above conversion ?

(A) Na/Liq. NH3 (B) H2, Pd–CaCO3
(C) Li, Ph–NH2 (D) H2, Pt
COOH
Li
39. Liq. NH 3
Major product :
COOH COOH COOH CH2OH
(A) (B) (C) (D)
OCH3
Na, Liq, NH3

40. Major product :
OCH3 OCH3
(A) (B)
OCH3
(C) (D) None of these
41. If the following compound is treated with Pd in excess of H2 gas, how many stereoisomers of the product will be
obtained ?
(A) 1 (B) 2 (C) 3 (D) 4
O O
NaBH4
42. Product
O Cl
O
The product is :
(A) HO OH (B) CH3–CH3–OH
OH
O
OH O
O
(C) HO OH (D)
O OH
OH
AgCN H2, Ni
43. Br A B
The final product (B) is :
NH2
(A) (B) N
H
H
(C) N (D) NH2
44. In organic layer test, CS2 or CCl4 is added to Lassaigne’s extract and then Cl2 water or KMnO4 is added. This test is
used to distinguish between
(A) Br and I (B) Cl and Br
(C) Cl and I (D) Cl , Br and I
45. Which alkyne gives 3-ethylhexane on catalytic hydrogenation ?
(A) (B) (C) (D) All of these

7
46. Number of moles CrO3 required to oxidise completely 9 moles of 2-heptanol to the corresponding ketone ?
(A) 5 (B) 6 (C) 4 (D) None
47. In compound A(C30H60O) following tests are observed negatively, A can be
Br2/H2O
-Ve
Tollen's reagent
C30 H60 O -Ve
(A) Na metal -Ve
(A) An unsaturated ether (B) An epoxide (C) A cycloalkanol (D) Can’t predict
48. A set of reagents (1 to 7) are successively reacted with the following compound
O O
HO
OH
OH
CH
1. NaHCO3 2. 2,4, DNP 3. Na metal 4. AgNO3 + NH4OH 5. Fehling’s solution

6. Cu2Cl2 + NH4OH 7. Br2/H2O
The reagent which give positive test with the given compound are :
(A) 1, 2, 3, 4, 5 (B) 3, 4, 5, 6, 7 (C) 1, 2, 3, 4, 7 (D) 1, 2, 3, 4, 6, 7
49. Give the correct order of initials T or F for following statements. Use T if statement is true and F if it is false.
X (molecular formula, C7H6O2) is an aromatic white solid which liberates colourless. odourless gas on reacting with
S1 : Only three of the five functional isomers of X (including ‘X’ itself) will give positive 2, 4-DNP test.
S2 : The liberated colourless, odourless gas will containing radioactive 14C.
14
S3 : Except ‘X’, no other functional isomer will liberate colourless odourless gas with NaH C O3 .
S4 : The DU of higher homolog of ‘X’ will be four.

(A) TTTF (B) FTTF (C) FTTT (D) TTFF
50. The reaction among following produces meso-compound
Me H Me H
(A) KMnO4 /OH /H 2O(cold)

  (B) KMnO4 /OH /H 2O(cold)
 
Me H H Et
Me H Me H
KMnO 4 /OH /H 2O(cold)

(C) KMnO4 /OH /H 2O(cold)
  (D)  
Et H H Me
Multiple Choice Exercise

1. Silver mirror test with Tollens reagents is given by :
(A) C6H5CHO (B) Ph–NH–OH
(C) C 6H5 CH2 C CH2OH (D) CH3CHO
2. Fehling solution gives red precipitate with :

(A) Aromatic aldehyde (B) Aliphatic aldehyde
(C) Ketones (D)
3. Which of the following compound will give positive Tollens test
(A) CH3CHO (B)
(C) (D)
4. Which will give the Tollen test.
(A) (B)
CH2OH
O OH
O
HO H
(C) R C CH2 (D) H
H HO
H OH
OH H
O
5. CH3 C can be obtained as one of the product in reaction -
OH
O – O
(i) I2/OH CH3CO3H
(A) CH3 C + (B) CH3 C
CH3 (ii) H H
O
CH3CO3H O3
(C) C (D) CH3 CH CH2
H2O
H
6. Following conversion can be carried out by using sequence
O O
CH3 CH2 C CH3 CH2 C
OH H
(A) (i) SOCl2 (ii) H2, Pd/ BaSO4 (B) (i) R’–OH/H+ (ii) DI-BAL H
(C) (i) Ca(OH)2 (ii) (HCOO)2 Ca/Dry distillation (D) (i) LiAlH4 (ii) Cu/300°C
7. With reference the scheme given, which of the given statement(s) about T, U, V & W is/ are correct
O
C
O LiAlH4 excess
T U W
(CH3CO)2O
+
 CrO3/H
V
(1) “T” is soluble in hot aq NaOH (2) “U” is optically active
(3) Molecular formula of W is C10H18O4 (4) V gives effervescence with aq NaHCO3
8. Compound ‘X’ (C8H8) rapidly decolourises cold aqueous KMnO4 solution. It reacts with Br2/CCl4 to yield C8H8Br8.
The structure of ‘X’ cannot be
(A) (B) (C) (D)
9. Which of the following halides does not form G.R. when treated with magnesium in the presence of ether ?
(A) Br (B) HO
H Br
(C) O2N Br (D) HOOC Br
10. Hexan-3-one can be obtained by the reaction of EtMgBr and

(A) Butanamide (B) Propanamide (C) Butane nitrile (D) Propane nitrile
11. Consider the following reactions :
(A) COOH B and  (C)

COOH
(I) (II) (III) (IV)
Which of the following group(s) of reagents is/are used in the above conversion ?
(A) (A)  Acidic KMnO4 , (B)  Ca(OH)2 , (C)  Zn-Hg/HCl
(B) (A)  O3/Ph3P, (B)  Ba(OH)2 , (C)  LAH/ether

(C) (A)  O3/H2O , (B)  Sr(OH)2 , (C)  NH 2 NH 2 O H
(D) (A)  O3/Ag2O, (B)  Ba(OH)2 , (C)  HI + Red P
12. Select the correct Baeyer-Villiger oxidation reaction :
(A) H2SO4
  Caprolactone
O
Me Me O Ph
(B) Me PhCO3H
Ph   Me
Me Me O
O O
Me Me
PhCO 3H Ph
(C) Me Ph 
 Me O
Me Me
O O
PhCO3 H Ph
(D) Ph H  
H O
13. Select the correct group(s) of reagent(s) used in the following conversions:
Me COOH
Me Me
II
Reagent
 ,  
I
Me COOH
NO2 NO2
Me COOH Me COOH
Cl Cl OH OH
III , IV
 
(A) I  dil. HNO3 , II  Na2Cr2O7/H2SO4, III  KMnO4/NaOH, IV  PbO4/OH–, H3O

(B) I  dil. HNO3 , II  KMnO4/H, III  KMnO4/NaOH, IV  TsCl + acidic KMnO4 + H2O
(C) I  KMnO4/NaOH, II  Na2Cr2O7/H, III  KMnO4/OH–, IV  dil. HNO3
(D) I  CrO3/MeCOOH, II  KMnO4/OH–, III  KMnO4/H, IV  dil. HNO3
14. Which of the following reactions is/are correct ?
(A) Me Me 
3CrO
 Me COOH + HOOC Me
CH COOH
3
(Jones reagent)
H2CrO4 MnO2
+
Me OH No
Aq. acetone reaction
(B) H
Me OH
SeO 2/CH 3COOH

(C) Me CH CH C CH3 CH2 CH CH C CHO
O OH O
NO2 NH2
NO2
HOOC
Oxid. Sn + HCl
B A B A B
(D)
HOOC COOH
Acidic
A KMnO4
[O]
COOH
15. Which of the following reaction(s) is/are wrong ?
Me COOH COOH
Me
Br COOH
Br 1.Mg/ether
1.Mg/ether
  

2.CO2 /H3O
(A) 2.H O (B)
3
 3.KMnO4 /H
3.KMnO4 /H 4.
Me CHO Me
CHO
1.CrO2Cl2 /CCl4
  1.CrO3  (MeCO )2 O
 
(C) 2.H2 O (D) 2.H O/OH 
2
16. Which of the following reactions is/are correct ?
SH (i) BF3
(A) O+ + C2H6 + NiS
SH (ii) Raney Ni + H2
SH
(i) BF 3
(B) CHO + Me + C3H8 + NiS
(ii) Raney Ni + H2
SH
O
O NO2
(C) Ph NO2 
PhCO H /H O 
 Ph
3 3
O O
(D) Ph Me   Ph O Me
HCO3 H/ H 3O
17. Which of the following methods can be used to prepare propanic acid ?
Me
Me (i )Ca (OI) 2
 
(A) (ii)H O 
3
O
High pressure
(B) CH 2  CH 2  CO  H 2O 
570 670K

(Steam)
(C) Reaction of EtMgBr with dry ice followed by the acidification with dil. HCl.
(D) Sodium ethoxide is heated with CO under pressure followed by the acidification with dil. HCl.
18. Which of the following compounds reacts with NaCNBH3 ?
(A) Me – CH = NH (B) Me2C=N–Me (C) CH2OH (D) PhNO2

19. Acetonitrile (MeN C) on reaction with Cl2 with DMSO gives methyl isocyanate (MeN=C=O). Isocyanides can
also be oxidised to alkyl isocyanates with :
(A) HgO (B) Hg2O (C) Ag2O (D) O3
Misc. Exercise
Subjective Type Questions

H /KMnO4
1. (i) (ii) CH3 CH CH2
H/KMnO4 H/KMnO4
(iii) (iv)
 
H /KMnO4 H /KMnO4
(v) (vi)
H/KMnO4 H/KMnO4,
(vii) (viii)
CO2-
 
H /KMnO 4 H /KMnO 4
(ix)  (x) 

H /KMnO4
(xi)

H /KMnO 4
(xii) C10H10  HOOC C C C COOH
C COOH
2. A to F alkenes with minimum possible carbon.

H/KMnO4
(i) A MeCOOH as the only product
H/KMnO4
(ii) B O as the only product
H/KMnO4
(iii) C MeCH2COOH as the only organic product
H/KMnO4
(iv) D
O

H /KMnO4
(v) E HOOC–C–C–C– C C –C–C–C–COOH
O
H/KMnO4
(vi) F Acetone + Ethanoic acid
3. (i) Me CH CH CH3
(ii)
(iii) Me  CH 2  CH  CH  CH 2  CH 3
(iv)
(v) ,
(vi)
1%alkaline
A
KMnO 4
4. (i) (ii) mCPBA
+
m-CPBA/H3 O
B
Me Me
mCPBA mCPBA
(iii) (iv) C C 
Hydrolysis

hydrolysis
H H
Me
Me H Me H 1
mCPBA Ag2O or 2Ag + 2 O2
(v) C C hydrolysis (vi) C C
H Me H Ph
OH
–
KMnO4/OH , KMnO4,H 
5. (i) CH2–CH2–CH2– OH ? (ii) CH3 CH CH2 CH3 or K 2Cr2O7,H 
?
+
K2Cr2O7/H ,
or conc.HNO3, +
or conc. KMnO4/H ,
PCC
6. (i) CH 2  CH   CH 2 3  CH 2  OH CH 2Cl 2
PCC
(ii) C6 H 5  CH  CH  CH 2  OH CH 2Cl 2
OH
PCC
(iii) CH3 CH CH2 CH2 CH2 OH CH2Cl2
(A)
OH
(iv) PCC
CH 2Cl2
CH2OH
OH
MnO2 MnO2
(v) CH 2  CH  CH 2  OH  ? (vi) CH3O CH CH2 CH2 OH Acetone
CH3O
CH3 OH
MnO2 MnO2
(vii) CH C CH C CH2 OH Acetone
? (viii) C6H5 CH CH3 CCl4 ?
HlO4 HlO4
7. (i) Me CH CH2 OH (ii) Me2C CH Et
OH OH OH
OH
HlO4
(iii) HlO4 (iv) HO CH2 CH2 CH CH2 OH
OH
OH
HlO4 HlO4
(v) CH2 CH CH2 CH3 (vi) CH2 CH CH CH3
OH OH OH OH OH
HlO4 HlO4
(vii) CH2 CH CH CH2 (viii) Me C CH Me
OH OH OH OH O OH
HlO4
(IX) Me C C Me
O O
8. How many alkene on catalytic reduction give normal butane as product.
H 2 /Pt H 2 /Pt
(i) (A)   n-butane (ii) (B)   Iso-pentane
H 2 /Pt H 2 /Pt
(iii) (C)   Neo-pentane (iv) (D)   Cyclopentane
H2
(v) (E)
Pt
9. (a) Identify the product ?
lH 4 lH 4
LiA LiA
NaBH 4 NaBH 4
(i)  Me CHO DIB (ii)  Me2CO DIB
A A L-
L- H
H
lH 4 lH 4
LiA LiA
NaBH 4 NaBH 4
(iii)  Me COCl DIB (iv)  Me COOEt DIB
A L- A
H L-
H
(b) Identify the product ?

NaBH 4 LiAlH 4 NaBH 4 LiAlH 4
(v)  Me–COOH   (vi)  Me–COOMe  
NaBH 4 LiAlH 4 NaBH LiAlH
(vii)  Me–CONH2   (viii) 
4
Me–CONH –Me 
4

NaBH 4 NaBH 4 LiAlH4
(ix)  LiAlH 4
Me–CONMe2   (x)  CH3  CH  CH 2  
10. Give product in following reactions.
NaBH 4 LiAlH 4 NaBH 4 LiAlH4

(i)  O   (ii)  H N O  
NaBH 4 NaBH 4 LiAlH 4

(iii)  O 
4
 LiAlH (iv)   
N N
H
NaBH 4 LiAlH NaBH 4 LiAlH 4

(v)  O 
4
 (vi)  O  
O O
NaBH 4 LiAlH 4 NaBH LiAlH4

(vii)  Me CO N   (viii) 
4
CH 2  CH  CHO  
NaBH 4 LiAlH 4 NaBH 4 LiAlH4

(ix)  Ph  CH  CH  COOH   (x)   
O
O
O
Red P + HI
(a) H (b) Red P + HI
(excess)
OH
CHO
COCH3
(c) Red P + HI
(excess)
HO CH2OH
CHO
NaBH 4 LAH
(i)   
O
COOEt
O
O
(i) LiAlH4
LAH NaOI
(ii) D 2O
(ii) C OEt 
 (A)   (B) (iii)
(iii) LiAlH4
(iv) H2O
Zn(Hg) NBS alc. HCl

O C CH3 HCl
(A) (B) (C) (D)
KOH R2O2
13. (a)
O
O
Zn(Hg)
(b) Zn(Hg) (c) Ph C CH3 HCl
HCl ,
O O
(i) H2NNH2
(d) Zn(Hg) (e) (ii) KOH, heat
HCl , H2O
N2H4
O O KOH, heat
(excess)
Zn(Hg)
(f) HCl
(excess)
O
14. Among the following, the total number of compound which does not give Lassaigne’s test for nitrogen.
NH2
(i) (ii) H 2 N  CH 2  COOH (iii) NH 2  NH 2 (iv) Ph  N  N  Ph
O O
(v) NH2OH (vi) NH2 C NH2 (vii) Ph NH C Ph (viii) Ph – NO2
(ix) CH3CHO (x) CH3CN (xi) N
15. Amongst the following compounds the total number of compounds which gives coloured test with both Ceric
Ammonium Nitrate (CAN) and neutral FeCl3 solution.
(i) Phenol (ii) Benzyl Alcohol (iii) Benzaldehyde (iv) Aniline
(v) CH2OH (vi) (vii)

HOH2C
CH2OH
(viii) PhCH2CH(OH) CH3 (ix) Urea (x) Thiourea
Comprehension
Paragraph for Q.16 to Q.17
Type of Addition
(a) Syn Addition (b) Anti Addition
(a) Syn Addition :- Addition of 2-groups from same side of double bond is known as Syn addition and various
products formed during reaction are
(I) Syn Addition at cis Alkene
A H A
R R
A H R
Syn addition A H A
H of A - A H A
H R
R
R
Meso
(II) Syn Addition at trans alkene
A R A
H R
A Up side R H
A A H
H Syn addition
H H A
R R
R
Threo
Optical active
R H R
H R H A
down side A
A H
Syn addition
A
R
Threo
(b) Anti Addition : Addition of 2 groups from opposite side at double bond is known as anti addition
(i) Anti addition at trans alkene
R H
R R
H A A A H
A A Anti addition
of A - A A H
H
R H
R R
Meso
(ii) Anti addition at cis alkene
R H
R R
H A H A
A
A A A H
R
R H
R
H Threo
A R
R H A H
R H H A
A R
Threo
1% Alkaline
16. Maleic acid 
cold KMNO4
 product
COOH
COOH
COOH
HO H OH
(A) (B)
HOOC H
H OH
H OH
OH
H COOH
OH COOH
(C) OH (D) HOOC
H COOH
OH
(1)mCPBA
17. Fumeric acid 
(2)H3 O
 product
COOH COOH
COOH
COOH
HO HO H
(A) (B) H OH (C) (D) Both (A) & (C) are correct
H OH H OH
H OH COOH
H COOH
Match The Column

18. Match the column I and II. (Matrix)
Column - I Column - II
Reactant Product
O
(A) PhMgBr  Cl  C O  Et 

H (P) Ph–CH2–OH
(excess)
(B) PhMgBr  H  C O  Et 

H (Q) Ph CH2 Ph
(excess)
OH
O OH
(C) PhMgBr  H  C  H 
H
(R) Ph C Ph
(excess)
Ph
O OH
(D) PhMgBr  CH 3  C O  Et 
H
(S) Ph C Ph
(excess )
CH3
19. Match the column I and II. (Matrix)
Reactant Moles of PhMgBr used
O
(A) PhMgBr  Et  O  C O  Et 

H
3°alcohol (P) 1
O
(B) PhMgBr  HO  CH 2  C CH3 

H
3°alcohol (Q) 2
O
(C) PhMgBr  CH3  C CH3 

H
3°alcohol (R) 3
O
HO C Cl
(D) PhMgBr  
H
3°alcohol (S) 4
HO
20. Column - I Column - II
(Reaction) (Reagents)
H3C CH3
(A) H3C – C  C – CH3  C C (P) NaNH2/
H H
H3C H
(B) H3C – C  C – CH3  C C (Q) Alc KOH/
H CH3
(C) H3C – C  C – CH3  CH3 – CH2 – C  CH (R) H2Pd/BaSO4

(D) H3C – CH2C  CH  CH3 – C  C – CH3 (S) Na in liquid NH3
(T) Product can evolve CH4 with CH3MgBr
21. Match the column

(Component of mixture) (Reagent)
(A) Crystalline Na2CO3 + (P) Fehling solution
Sodium citrate + CuSO4 (aq. sol.)
(B) CuSO4 + Rochelle Salt + NaOH(Aq. sol.) (Q) Nesseler’s Reagent
(C) 10%  - naphthol in alcohol (R) Bennedict’s Reagent
(D) HgCl + KI + KOH (aq. sol.) (S) Molisch’s Reagent

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FINAL TOUCH

Single Choice Exercise

1. What is the major product of the following reaction ?

CH2 OH CH2 CH3

CH2 COCH3 CH2 COCH3

CH2 COCH3 CH2 C Ph

What is the ratio of (x/y) in above problem ?

4. In which of the following reaction 2° alcohol is obtained as a product ?

(1). CH3MgBr (1). MgCl

5. In which the following reactions product formed is same ?

(A) MeMgX (B) MgX

CH2 CH2 CH3MgI H3O

(B) CH3 CH O Et2O

11. CH3MgBr NH4Cl Products.

20. What is the major product of the following reaction ?

(C) CH3 C CH3 (D) CH3 CH2 C OH

(A) (B) (C) CH3 C (CH2)4 CH3 (D)

Same product (A) will form in both reactions . A is :

23. What is the product (B) of the following reaction sequence ?

Br2 Mg CH3 C CH3 H

26. CH3  CH  CH 2 h Dry ether 

End product (X) of the above reaction is :

(A) CH 2  CH  CH 2  C CH3 (B) H 2 C  CH  CH  C CH3

(A) (B) (C) (D)

30. Major product is :

(A) (B) (C) (D)

31. Which of the following can be oxidised by MnO2 :

33. Phthalic Anhydride : A is :

The end product of the reaction are :

(A) SH and SH (B) S CH2 CH2 SH

(C) H (D) Both (B) and (C)

Which reagent will be used for the above conversion ?

COOH COOH COOH CH2OH

(A) (B) (C) (D)

Na, Liq, NH3

(C) (D) None of these

(A) 1 (B) 2 (C) 3 (D) 4

(A) HO OH (B) CH3–CH3–OH

The final product (B) is :

(A) (B) (C) (D) All of these

47. In compound A(C30H60O) following tests are observed negatively, A can be

1. NaHCO3 2. 2,4, DNP 3. Na metal 4. AgNO3 + NH4OH 5. Fehling’s solution

S4 : The DU of higher homolog of ‘X’ will be four.

(A) KMnO4 /OH /H 2O(cold)

KMnO 4 /OH /H 2O(cold)

Multiple Choice Exercise

2. Fehling solution gives red precipitate with :

3. Which of the following compound will give positive Tollens test

(A) CH3CHO (B)

4. Which will give the Tollen test.

6. Following conversion can be carried out by using sequence

(A) (B) (C) (D)

(C) O2N Br (D) HOOC Br

10. Hexan-3-one can be obtained by the reaction of EtMgBr and

(A) COOH B and  (C)

(D) (A)  O3/Ag2O, (B)  Ba(OH)2 , (C)  HI + Red P

12. Select the correct Baeyer-Villiger oxidation reaction :

(A) I  dil. HNO3 , II  Na2Cr2O7/H2SO4, III  KMnO4/NaOH, IV  PbO4/OH–, H3O

SeO 2/CH 3COOH

15. Which of the following reaction(s) is/are wrong ?

16. Which of the following reactions is/are correct ?

(A) Me – CH = NH (B) Me2C=N–Me (C) CH2OH (D) PhNO2

2. A to F alkenes with minimum possible carbon.