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ORGANIC CHEMISTRY REVISION DPP-01

ORGANIC CHEMISTRY REVISION DPP-01

DPP Syllabus : IUPAC Nomenclature, Structural & Stereo Isomerism, GOC-I & II

1. The alkane that yields two isomeric monobromo derivatives is

(1) Neopentane (2) Ethane (3) Pentane (4) Propane

2. The compounds that will give an isomer of 2, 2-dimethyl butane on catalytic hydrogenation is
H
(1) CH3CH=C–CH3 (2) CH3CH=CHCH3 (3) CH3C=CHCH2CH3 (4) CH3C = C–CH3
CH3 CH3 CH3
3. Which of the following will not give positive test with CHCl3 / KOH ?
(1) CH3–CH2–NH–CH3 (2) CH3–CH2–CH2–NH2

CH3
|
(3) (4) CH3  CH  NH2

4. Match the compounds of column-I with the reagent of column-II, which can distinguish between the
compounds of column-I.
Column-I Column-II

(P) , (1) Tollen’s reagent

,
(Q) (2) Lucas reagent

(R) (3) Neutral FeCl3

,
Codes :
P Q R
(1) 3 2 1
(2) 1 2 3
(3) 2 1 3
(4) 1 3 2

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ORGANIC CHEMISTRY REVISION DPP-01

5. In the following sequence of reactions, the alkene affords the compound ‘B’
O HO
CH3CH=CHCH3 
3
 A 
2
 B, The compound B is :
Zn
(1) CH3COCH3 (2) CH3CH2COCH3 (3) CH3CHO (4) CH3CH2CHO
6. Full name of DDT is
(1) 1, 1, 1-trichloro-2, 2-bis(p-chlorophenyl) ethane
(2) 1, 1-dichloro-2, 2-diphenyl trimethylethane
(3) 1, 1-dichloro-2, 2-diphenyl trichloroethane
(4) None of these
7. IUPAC name of given organic compound is –
H CH3
H
H Br

H
(1) 3–bromo-2-methyl propene (2) 2–methyl-2-bromo propene
(3) Bromo methyl pro-1-ene (4) 2–methylene-3-bromopropene
CH3
8. Compound on reductive ozonolysis yields -
(1) 6-oxoheptanal (2) 6-oxoheptanoic acid
(3) 6-hydroxyheptanal (4) 3-hydroxypentanal
9. How many aliphatic carbonyl compounds are possible having the molecular formula C 5H10O ?
(1) 4 (2) 5 (3) 6 (4) 7
10. o-Cresol & benzyl alcohol are :
(1) Functional isomer (2) Position isomer (3) Chain isomer (4) Metamers
11. Which of the following compounds will not show geometrical isomerism ?
(1) Azomethane (2) 1-Bromo-2-chloroethene
(3) 1-Phenylpropene (4) 2-Methyl-2-butene
12. The number of geometrical isomers of CH3CH=CH–CH=CH–CH=CHCl is -
(1) 2 (2) 4 (3) 6 (4) 8
13. Maleic acid and fumaric acid are -
(1) position isomers (2) functional isomers
(3) geometrical isomers (4) optical isomers
14. The number of optically active isomers possible for CH3–CH–CH–CH–CH2OH is -
OH OH OH
(1) 2 (2) 4 (3) 6 (4) 8
15. Which of the following pairs of structures represent enantiomers -
OH
COOH CH3 H
(1) HO H and H OH (2) CH3 OH and H COOH

CH3 COOH COOH CH3

COOH OH CH3 OH
(3) H CH3 and CH3 H (4) HOOC OH and HOOC H

OH COOH H CH3

16. The correct IUPAC name of the compound is

H Br

HO H
(1) (2R, 3R)-3-Bromo-2-butanol (2) (2R, 3S)-3-Bromo-2-hydroxybutane
(3) (2R, 3S)-3-Bromo-2-butanol (4) (2S, 3R)-2-Bromo-3-butanol

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ORGANIC CHEMISTRY REVISION DPP-01
17. The correct statements about the compounds a, b and c is/are :
COOCH3 COOH COOH
H OH H OH H OH
H OH H OH OH H
COOH COOCH3 COOCH3
(a) (b) (c)
(1) a and b are identical (2) a and b are diastereomers
(3) a and c are enantiomers (4) a and b are enantiomers

18. The molecular formula of diphenyl methane, CH2 , is C13H12.

How many structural isomers are possible when one of the hydrogen is replaced by chlorine atom ?
 (1) 4  (2) 8   (3) 7  (4) 6
19. The order of stability of the following tautomeric compounds is :
OH O O O OH O
| || || || | ||
CH2= C – CH2 – C – CH3 CH3 – C – CH2 – C –CH3 CH3 – C –– CH – C – CH3

I II III
(1) III > II > I (2) II > I > III (3) II > III > I (4) I > II > III
20. Most acidic compound is :
OH OH OH
OH
NO2
(1) (2) (3) (4)

NO2 COOH
21. 1, 2-dimethyl cyclohexane has
(1) 2 geometrical isomers and no optical isomers
(2) 2 optical isomers and no geometrical isomers
(3) 3 stereoisomers
(4) four stereoisomers
22. The IUPAC name of HOCH2CH=C(CH3)2
(1) 2-Methyl-2-buten-4-ol (2) 3-Methyl-2-buten-1-ol
(3) 2-Methyl-2-buten-1-ol (4) 3-Methyl-2-butanol
23. Which has the highest pKb value ? (Where R = Ethyl)
(1) R3C–NH2 (2) R2NH (3) RNH2 (4) NH3
24. Lucas reagent reacts fastest with :
(1) butanol-1 (2) butanol-2 (3) 2-methyl-propanol-2 (4) 2-methyl-propanol-1
25. Which of the following reagent is used to distinguish phenol and benzoic acid ?
(1) Aqueous NaOH (2) Tollen's reagent (3) Molisch reagent (4) Neutral FeCl3
26. Among the following which is least acidic ?
(1) p-Nitrophenol (2) p-Chlorophenol (3) Phenol (4) o-Cresol
27. Which one of the following compound is most acidic ?
O OH
(1) ClCH2–CH2OH (2) (3) (4) CHCH

28. Given are cyclohexanol (I), acetic acid (II), 2, 4, 6-trinitrophenol (III) and phenol (IV). In these the order
of decreasing acidic character will be:
(1) III > II > IV > I (2) II > III > I > IV (3) II > III > IV > I (4) III > IV > II > I
29. Structure of 4-Bromomethyl-2-chlorohexane will be ?
Br Cl Br Cl
(1) (2) (3) (4) Br
Cl Br Cl

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ORGANIC CHEMISTRY REVISION DPP-01
30. Which of the following common name is wrong with respect to given structure ?
(1) CH3–CH–CH3 Isopropyl amine (2) CH3–CH–CH2–Cl Isobutyl chloride

NH2 CH3
CH3
(3) CH3–C–CH2–Br Isopentyl bromide (4) (CH3)3C–OH t-Butyl alcohol

CH3

31. How many ethers are possible with molecular formula C5H12O ?
(1) 3 (2) 4 (3) 5 (4) 6
32. Number of total resonating structures of cyclopentadienyl anion is :
(1) 2 (2) 3 (3) 4 (4) 5
33. Which of the following groups shows –M effect when attached with benzene ring ?
O O
(1) –O–C–CH3 (2) –NH–CH3 (3) –C–OCH3 (4) –OCH3
34. Among given species, which one is the most stable ?


(1)  (2)  (3) (4)

35. Which of the followings are aromatic ?



N 
(a) (b) (c) 2– (d)
N
 
(1) a & d (2) b & c (3) c & d (4) a & c
36. Which is the most stable carbanion ?
(1) n-Propyl carbanion (2) Benzyl carbanion
(3) Ethyl carbanion (4) Triphenyl methyl carbanion
37. Decreasing order of electron density in benzene ring in given compounds is :
O
O–C–CH3 HO–C=O NH2 H–C=O

P Q R S
(1) P > Q > R > S (2) R > Q > P > S (3) R > P > Q > S (4) P > R > Q > S
38. Which of the following molecule has highest pKa value in aqueous solution ?
COOH COOH
COOH COOH
CH3
(1) (2) (3) (4)
CH3
OCH3

39. Which of the following species is not stabilised by hyperconjugation ?

(1) Ph–CH–CH3 (2)

(3) (4) CH3 – CH = CH – C2H5

40. Which is/are less acidic than formic acid ?

(i) Ph–OH (ii) Ph–COOH (iii) CH3–SO3H (iv) H2CO3
(1) i & ii (2) i & iv (3) i, ii & iv (4) All

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ORGANIC CHEMISTRY REVISION DPP-01
41. In which molecule C–N bond length is maximum ?

(1) (2) (3) (4)

42. Which of the following molecules will not show geometrical isomerism ?
CH3
CH3
Br CH3
(1) (2) (3) (4)
 Cl H3C

CH3

43. NH NH N

A B O C
Least basic among the given compounds is
(1) A (2) B
(3) C (4) All of them have same basic strength
44. Which of the following ketones results in only one oxime formed after the reaction with NH 2OH ?
O O O
(1) (2) (3) (4)
CH3 C2H5 Ph CH3 CH3 CH3
O
45. Tautomerism is not observed in
(1) Formaldehyde (2) Acetyl acetone (3) Acetophenone (4) Cyclohexanone
46. Which compound has maximum enol content in aqueous solution ?
O O O O
O O
(1) (2) (3) H (4) Ph Ph

47. Which of the following compound is aromatic?

O 
O N
O
(1) (2) (3) (4)

48. Which compound on reaction with ammonia give NH4Cl ?


(1) CH3Cl (2) CH3NH3Cl (3) Ph  NH3Cl (4) PhCl

49. Which of the following molecule is chiral ?

Cl
Cl Me
Cl H
(1) (2) (3) (4) C=C
H Br H Br
Me Cl
Br
50. Which can show stereoisomerism ?
(1) Pent-2-yne (2) 3-Ethyl hex-2-ene (3) 3-Chloro pentane (4) 1-Chlorocyclohex-1-ene
51. How many geometrical isomers are possible for, Ph–CH=CH–CH=CH–Ph?
(1) 2 (2) 3 (3) 4 (4) 5
52. Geometrical isomerism is not found in :
(1) 2-Pentene (2) 1,2-Diphenylethene
(3) 1-Chloro-1-butene (4) 1,1,2-Trichlorocyclobutane

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ORGANIC CHEMISTRY REVISION DPP-01
53. D/L configuration of the following compound is :
CH2OH
HO H
H OH
CH=O
(1) 2D, 3D (2) 2L, 3L (3) 2D, 3L (4) 2L, 3D
54. Which of the following compound gives CO2 gas with NaHCO3 ?
(1) Phenol (2) Aspirin (3) Benzyl alcohol (4) o-Cresol
55. Which is correct for the properties of geometrical isomers ?
(1) Ph–CH=CH–Ph Stability (Cis > Trans)
(2) Cyclodecene Stability (Cis > Trans)
(3) Br–CH=CH–Br Boiling point (Trans > Cis)
(4) CH3–CH=CH–Cl Boiling point (Cis > Trans)
O
56. CH2=CH–CH=CH–CH3  3  Products.
Zn, H O 2

Which product is not obtained in the above reaction ?

(1) CH2=O (2) CH3–CH=O (3) OHC–CHO (4) CH3–COOH
57. Acetaldehyde and benzaldehyde can be differenitated by :
(a) Fehling test (b) Iodoform test (c) Tollen’s reagent (d) 2,4-DNP test
(1) a & b (2) a & c (3) b & c (4) c & d
58. Which of the following species does not exert the mesomeric effect?

(1) C6H5NH2 (2) C6H5NH3 (3) C6H5OH (4) C6H5Cl

59. Which of the following has maximum pKb value?

(1) p-toluidine (2) o-toluidine (3) Benzylamine (4) m-toluidine
60. Which of the following alkyl halide shows optical activity?
(1) Tertiary butylchloride (2) Isobutylchloride
(3) Secondary butylchloride (4) Neopentylchloride

Integer Type Questions

61. How many carbon atoms are present in parent chain (main chain) of the following compound ?

62. How many position isomers of dibromonaphthalene is possible if each ring of naphthalene has one
halogen?
63. How many molecules given below are more basic than aniline ?
NH NH

H2N C NH 2 CH3 C NH 2 CH3 CH2 NH2 NH3

I II III IV
NH 2
O
O
CH3
CH 3 S NH 2 CH3 N H
CH 3 C NH 2

O CH3
V VI VII VIII

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ORGANIC CHEMISTRY REVISION DPP-01
64. How many Geometrical isomers are possible for given compound ?
CH3

65. How many of the following compound will give positive test with ammonical silver nitrate ?
(I) Ethyne (II) Formic acid (III) Formaldehyde (IV) Benzaldehyde
(V) Fructose (VI) Acetal (VII) Sucrose (VIII) Maltose

66. Cocaine is hallucinogen used widely. How many chiral carbons does it have.

67. How many of the following compounds can exhibit tautomerism ?

O O
COCH3
(a) (b) (c) (d)

O
CH3 O
–

(e) Ph – CH2 – C – CH3 (f) CH – C – C – H (g) H – C – Ph (h) CH3—CH—CHO

3
–

O CH3 O Ph

68. The number of possible enantiomeric pairs of the given compound is :

OH

OH

CH2
69. Write the total number of given carbocations which are more stable than benzyl carbocation

CH CH

 2
2 CH

2

 O
(i) (ii) (iii) (iv)

OMe

CH2
 

(v) (vi) (vii) (viii)
NO2

70. How many isomeric alcohols (including stereoisomers) of molecular formula C5H12O give blue colour in
victor maeyer test finally?


71. How many resonating structures of are possible (including given structure ) :

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ORGANIC CHEMISTRY REVISION DPP-01
72. Number of products obtained on ozonolysis of 1, 3-dimethyl benzene is:

73. In how many of the following cases benzene ring is attached to a group that shows both –I as well as
–M effect ?
O
||
NO2 NH2 OH

||
O
O O
||
O SO3H C–OH
O
O
|| O
O
74. Consider the following compounds :

How many species are aromatic.

75. How many acids (given below) react with NaHCO3 and liberate CO2

CCl3–COOH CH3–CCH CCl3–CH2–OH

ORGANIC CHEMISTRY REVISION DPP-01

ANSWER KEY
1. (4) 2. (4) 3. (1) 4. (4) 5. (3) 6. (1) 7. (1)
8. (1) 9. (4) 10. (1) 11. (4) 12. (4) 13. (3) 14. (4)
15. (2) 16. (3) 17. (4) 18. (1) 19. (1) 20. (4) 21. (3)
22. (2) 23. (4) 24. (3) 25. (4) 26. (4) 27. (2) 28. (1)
29. (2) 30. (3) 31. (4) 32. (4) 33. (3) 34. (1) 35. (3)
36. (4) 37. (3) 38. (3) 39. (1) 40. (3) 41. (4) 42. (3)
43. (2) 44. (4) 45. (1) 46. (4) 47. (3) 48. (3) 49. (3)
50. (2) 51. (2) 52. (4) 53. (4) 54. (2) 55. (2) 56. (4)
57. (1) 58. (2) 59. (2) 60. (3) 61. (6) 62. (6) 63. (5)
64. (4) 65. (6) 66. (4) 67. (5) 68. (4) 69. (4) 70. (5)
71. (6) 72. (2) 73. (5) 74. (4) 75. (5)

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