JEE MAIN & ADVANCED

ORGANIC CHEMISTRY

Problem Solving Sheet

Chapter Name
Classification and Nomenclature of Organic Compounds

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 Organic Chemistry | Problem Solving Sheet

Classification and Nomenclature of Organic Compounds

1. Match the compounds with Type of carbon (which are chemically different).
Column-I Column-II
(Compound) (Types of Carbon)

CH3 CH3
(A) H3C – C –– C – CH3 (P) 2°
CH3 CH3

(B) CH3 – CH – CH – CH 3 (Q) 3°

CH3 CH3

(C) CH3–CH2–CH2–CH2–CH3 (R) 4°

(D) CH3 –CH–CH2–CH3 (S) 1°

CH3

2. Statement 1 : Urea is an organic compound.

Statement 2 : It can be synthesized only by living organism.

(A) Statement-1 is true, statement-2 is true and statement-2 is correct explanation for statement-1.

(B) Statement-1 is true, statement-2 is true and statement-2 is NOT the correct explanation for statement-1.

(C) Statement-1 is true, statement-2 is false.

(D) Statement-1 is false, statement-2 is true.

3. Number of 1°, 2°, 3° and 4° C present in compound are respectively

(A) 7, 4, 5 and 1 (B) 7, 3, 4 and 1 (C) 7, 3, 5 and 1 (D) 7, 4, 4 and 1

4. Total number of s and p-bonds present in benzene is:

(A) 5p and 10 s (B) 3p and 10 s (C) 3p and 12 s (D) 5p and 14 s

5. Compound which is not heterocyclic -

O
(A) (B) (C) (D)
N O S

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 Classification and Nomenclature of Organic Compounds
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Paragraph for Q. 6 to 7
O
N–H NH2
N
(I) (II) (III) (IV)

6. Heterocyclic compound is –
(A) I & II (B) II & III (C) III & IV (D) I, II, III & IV
7. Compound which is not amine –
(A) I (B) II (C) III (D) IV
CH3
CH 2–CH2–CH2–CH2–Cl
8.
N
CH3 O H
CH2

(a) Find out the total number of 1° hydrgoen.

(b) Find out the total number of 2° hydrogen

(c) Find out the total number of 3° hydrogen

(d) Find out the total number of 1° carbon.
(e) Find out the total number of 2° carbon.
(f) Find out the total number of 3° carbon.
(g) Find out the total number of 4° carbon.
(h) Find out the total numbe of type of functional groups.
9. Classify the following alcohols as primary, secondary, or tertiary:
(a) (CH3)3CCH2OH (b) CH3CH(OH)CH(CH3)2
(c) (CH3)2C(OH)CH2CH3

OH
(d) (e) OH

10. Classify the following amines as primary, secondary, or tertiary:

(a) CH3NHCH(CH3)2 (b) CH3CH2CH(CH3)CH2NH2
(c) (CH3CH2)3N (d) (C6H5)2CHCH2NHCH3

(e) HN (f) N

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11. Compound having both 2º alcohol & 2º carbon only .

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

12. Match the column

Column-I Column II

CH3
(A) CH3–CH2–N (P) 1° Carbon
H

(B) CH2 = CH – CH3 (Q) 2° Carbon

(C) (R) 3° Carbon

OH
(D) (S) 4° Carbon

13. Statement 1 : If number of p bonds in the compound is 3 then its degree of unsaturation must be 3
Because
Statement 2 : For one p bond degree of unsaturation is equal to 1
(A) Statement-1 is true, statement-2 is true and statement-2 is correct explanation for statement-1.
(B) S ement-1 is true, statement-2 is true and statement-2 is NOT the correct explanation for
statement-1.
(C) Statement-1 is true, statement-2 is false.
(D) Statement-1 is false, statement-2 is true.

14. Which of the following is/are heterocyclic compound(s)

(A) (B) (C) (D) X1

OH O
H 2N Å

15. Which of the following is a Heterocyclic compound.

O
H3C N
HOOC NO2 (B)
(A) OH (C) (D) N

OH
OH

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16. Which of the following is homologue of CH3NHCH2CH2CH3

(A) CH 3CH2NHCH2CH3 (B) CH3CH2CH2NH2
(C) CH3 – CH – NH2 (D) CH3CH2NHCH3
CH3
17. Isooctane contains
(A) five (1° –C), one (2° –C), two(3° –C) atoms
(B) four (1° –C), two (2° –C), one (3° –C) and one (4° –C)
atoms
(C) four (1° –C), two (2° –C) and one (3° –C) atoms
(D) five (1° –C), one (2° –C), one (3° –C) and one (4° –C) atoms

18.

I II III

Select the correct statement about, I, II & III compounds.

(A) I is having four 2° & four 3° carbons
(B) II is having three 1°, six 2°, three 3° & two 4° carbons
(C) III is having three 1°, three 2° & three 3° carbons
(D) All are homocyclic compounds

OH
19.
NH2 NH 2
Cl
NH
Cl

(a) Find out the total number of 1° hydrogen. (b) Find out the total number of 2° hydrogen
(c) Find out the total number of 3° hydrogen (d) Find out the total number of 1° carbon.
(e) Find out the total number of 2° carbon. (f) Find out the total number of 3° carbon.
(g) Find out the total number of 4° carbon. (h) Find out the total number of type functional groups.
OCH3
20. N

N CH2
CH2 CH2 – NH 2
N
Cl – C – Cl
H
(a) Find and total number of 1° Hydrogen. (b) Find and total number of 2° Hydrogen.
(c) Find and total number of 3° Hydrogen. (d) Find and total number of 1° Carbon.(f)
(e) Find and total number of 2° Carbon Find and total number of 3° Carbon
(g) Find and total number of 4° Carbon
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 Classification and Nomenclature of Organic Compounds
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21. Calculate index of Hydrogen deficiency is

CHO
Ph

(a) (b) COOH

CN
22. Compound having only three different functional group is :
O
(A) O (B) O
O O O
O
O O O
(C) O (D) HO
O O

23. Match the column

Column I Column II
(General formula)

(A) (P) Index of hydrogen deficiency is odd

CO2H
(B) (Q) Index of hydrogen deficiency is Even

(C) (R) Even number of 2° Carbon

(D) (S) Even number of 3° Carbon

24. Statement 1 : Phenol is a heterocyclic compound.

Statement 2 : In heterocyclic compound different atoms like O, N, S etc. are present in the ring.
(A) Statement-1 is true, statement-2 is true and statement-2 is correct explanation for statement-1.
(B) Statement-1 is true, statement-2 is true and statement-2 is NOT the correct explanation for
statement-1.
(C) Statement-1 is true, statement-2 is false.
(D) Statement-1 is false, statement-2 is true.

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 Classification and Nomenclature of Organic Compounds
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. In which compound 1°C : 2ºC : 3°C (carbon) = 1 : 1 : 1.?

CH2–CH3
CH3
(A) (B)
H2 C CH2–CH3
H3C CH3
CH3

CH3
CH3
(C) (D)
CH3

. The compound having only primary hydrogens is :

(A) Isobutene (B) 2,3-Dimethyl-1-butene

(C) Cyclohexane (D) Propane

. C6H14 has two tertiary carbons. Its IUPAC name is :

(A) n-hexane (B) 2-methylpentane
(C) 3-methylpentane (D) 2,3-dimethylbutane

28. All the members of homologous series have same :

(A) molecular mass
(B) functional group
(C) empirical formula
(D) general molecular formula
29. Neohexane contains :
(A) Four 1° carbon atoms and two 2° hydrogen
(B) Twelve 1° hydrogen but no 3° carbon
(C) Two 2° carbon and one 4° carbon

(D) One 4° carbon and two 3° hydrogen

30. The correct structure/s of 2,3,4-Trimethylhexane is/are :

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

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31. DOU of the following compound -

CN

Ph
CN

(A) 11 (B) 13 (C) 15 (D) 17

32. Calculate molecular weight of the lowest alkane containing a sequence of 1°, 2°, 3° and 4° carbon atoms.
33. Compound having molecular formula CnH2n–4O3 can have functional group.
(A) 3-Aldehyde group
(B) 1-Carboxylic acid & 2-Aldehyde
(C) 1-Carboxylic acid anhydride & 1-alcohol
(D) 1-Carboxylic acid & 1-alcohol

34. Match the column

Column I Column II
(Compound) (Double bond equivalent)
CH3
C–N S
O N
(A) O (P) 4
COOH
(penicillin)

(B) (Q) 5

(Hexahelicene)

(C) (R) 7
(Prismane)
O
C OH
C
C OH
(D) (S) 19
O
(Ninhydrin)

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35. The correct IUPAC name of the compound is :

CH3
CH3 –CH2–CH2–CH–CH–C(C2H5)3
CH(CH3)2

(A) 3,3-Diethyl-4-methyl 5-(1-methyl ethyl) octane

(B) 6,6-Diethyl-4-methyl-5-isopropyloctane
(C) 6,6-Diethyl-3-methyl 5-(1-methylethyl) octane
(D) 6,6-Diethyl-4-isopropyl-5-methyloctane

36. IUPAC name of the compound

CH3 – CH2 – CH – CH2 – CH – CH2CH2CH3

CH3 CH – CH3
CH3
(A) 4-Isopropyl-6-methyloctane
(B) 3-Methyl-5-(1-methylethyl) octane
(C) 3-Methyl-5-isopropyloctane
(D) 6-Methyl-4-(1-methylethyl) octane

37. The IUPAC name of the crotonaldehyde is: (CH3–CH = CH–CHO) is -

(A) 2-Propenal (B) Propenal (C) 2-Butenal (D) Butenals

38. Which of the following compound has wrong IUPAC name?

(A) CH3 – CH2 – CH2 – COOCH2CH3 (B) CH3 – CH – CH2 – CHO

CH3
Ethyl butanoate 3-Methylbutanol

(C) CH3 – CH – CH – CH 3 (D) CH3 – CH – C – CH2 – CH3

OH CH3 CH3 O
2-Methyl-3-butanol 2-Methyl-3-pentanone

39. C5H12 has a symmetrical structure with one quaternary carbon. Its IUPAC name is :
(A) n-pentane (B) 2-methylbutane (C) 2,2-dimethylpropane (D) 3-methylbutane

40. Which of the following compound has all four type (1°,2°,3°, 4°) of carbon atoms :

(A) 2,3,4-Trimethylpentane (B) 2,2,3-Trimethylpentane

(C) neo-pentane (D) none of the three

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41. In following compound

CH3 CH3
CH3 –CH2–C–—CH–CH–CH2–CH3
CH3 CH3
The correct lowest set of locant is :
(A) 3,3,4,5 (B) 3,4,5,5 (C) 4,5,3,3 (D) 5,5,4,3
42. The IUPAC name of
CH3 – C = C — CH – CH2 – C º CH
Cl CH3 C2H5
(A) 2-Chloro-4-ethyl-3-methyl-6-heptyn-2 ene
(B) 2-Chloro-4-ethyl-3-methyl-2-heptyn-6 yne
(C) 6-Chloro-4-ethyl-5-methyl-1-heptyn-5 ene
(D) 6-Chloro-4-ethyl-5-methyl-5-hepten-1 yne

H C4H9

43 IUPAC name of CH 3– C — C — CH 2– CH 3 is:

CH3 CH3
(A) 3,4,4- Trimethylheptane (B) 4-Ethyl-3,4-dimethyl octane
(C) 2-Butyl-2-methyl-3-ethylbutane (D) None of these

44. Match the column:

Column I Column II
(Compounds) (Property)

(A) (P) Homocyclic compound

N

(B) (Q) Homocyclic hydrocarbon

NH2
(C) (R) Heterocyclic

(D) (S) Even number of p-bond

(T) Odd number of s-bond

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45. Statement 1 : 3-Bromo-4-ethyl pentanoyl bromide is not the correct IUPAC name
Statement 2 : Selection of carbon chain in 3-Bromo-4-ethyl pentanoyl bromide is not according to
IUPAC rule.
(A) Statement-1 is true, statement-2 is true and statement-2 is correct explanation for statement-1.
(B) Statement-1 is true, statement-2 is true and statement-2 is NOT the correct explanation for
statement-1.
(C) Statement-1 is true, statement-2 is false.
(D) Statement-1 is false, statement-2 is true.
CH2 – CH3

46. CH3 – CH2 – CH2 – CH2 – CH – CH – CH2 – CH2 – CH2 – CH3

CH3 – C – CH3
CH 3

(A) 5-(1, 1-Dimethyl Ethyl)-6-Ethyl decane

(B) 5-Ethyl-6-(1, 1-Dimethyl Ethyl) decane
(C) 6-Ethyl-5-(1, 1-Dimethyl Ethyl) decane
(D) 6-(1, 1-Dimethyl Ethyl)-5 Ethyl decane

47. IUPAC name of CH3 – CH = CH – C º CH is:

(A) 2-Penten-4-yne (B) 1-Pentyn-3-ene (C) 3-Penten-1-yne (D) None of these

48. The incorrect IUPAC name is:

CH3
(A) CH3 – C – CH (B) CH3 – CH – CH – CH3
O CH3 CH3 CH2 – CH3
2-Methyl-3-butanone 2,3-Dimethylpentane

CH3
(C) CH3 – C º C – CH (D) CH3 – CH – CH – CH3
CH3
Cl Br
4-Methyl-2-pentyne 3-Chloro-2-bromobutane

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49. Find out the correct statement(s) about given molecule.

CH3 – C º C – CH = CH – CH = CH 2

(A) All the carbons in given molecule are not in same plane
(B) IUPAC name is hepta-1,3-dien-5-yne
(C) It has 4 sp2 hybrid carbons, 2 sp hybrid carbons and 1 sp3 hybrid carbon
(D) All the carbons in given molecule are in same plane
50. IUPAC name of given organic compound:
(CH3)2C(CH2CH3)CH2CH(Cl)CH3 is:
(A) 5-Chloro-3,3-dimethylhexane (B) 5-Chloro-2-ethyl-2-methylpentane
(C) 2-Chloro-4-ethyl-4-methylpentane (D) 2-Chloro-4,4-dimethylhexane
51. Number of functional groups and double bond equivalent are respectively.
CN

COOMe
H2N
O COOH

CHO
(A) 6, 1 (B) 6, 5 (C) 6, 6 (D) 6, 7

52. IUPAC name of N–CHO is

D
(A) N-deutero-N-formylcyclohexanamine
(B) N-cyclohexylamino-N-deuteromethanal
(C) N-cyclohexyl-N-deuteromethanamide
(D) N-deutero cyclohexanaminal

53 Provide the IUPAC name of following compounds :

CH3
H3C–CH
(a) (b) CH3–(CH2)2–CH–CH–CH2–CH2–CH3
CH2–CH2–CH3
CH3
H3C–CH C2H5
(c) CH3–CH2–CH2–CH–CH—C—CH2–CH 3 (d) (e)
CH3 C2H5

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54. Match the column

Column I Column II
(Compound) (Number of carbons in selected carbon
chain for IUPAC nomenclature)

OH
(A) CH2 – CH – CH2 – COOH (P) 4
CH
CH2

CH3 – CH2

(B) CH3 – CH – CH2 – C = CH2 (Q) 5

CH2
CH3

CHO
(C) CH3 – CH2 – CH – CH2 – CH2 – CH2 – COOH (R) 6

(D) CH3 – CH2 – CH2 – CH – COOH (S) 7

CH2
COOH

55. The DBE in bezoic acid is :

(A) 3 (B) 4 (C) 5 (D) 6
56. IUPAC name for compound

is :

(A) 3-Ethyl hexa-1,5-diene

(B) 3-Propenyl penta-1,4-diene

(C) 4-Ethyl hexa-1,5-diene

(D) None of these

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Paragraph for Question 57 and 58

Observe following compound and answer questions given below :

OH(d)
O
OH(c)
O O
(e)
HO
O
N
N
Me
OH H
(a) (b)

57. Total number of different types of functional groups in this compound are
(A) 5 (B) 6 (C) 7 (D) 8
58. Degree of unsaturation of this compound is
(A) 8 (B) 9 (C) 10 (D) 11
59. Compounds Property
C5H12 (A) All hydrogens are identical & 1°.
C8H18 (B) All hydrogens are identical & 1°.
C5H10 (C) All hydrogens are identical & 2°.
C6H12 (D) All hydrogens are identical & 2°.
A,B,C,D are respectively :

(A) ; ; C ; (B) C ; ; ; C

(C) ; C C ; ; (D) C ; C C ; ;

60. Write correct IUPAC names of following compounds

(i) 2-Ethyl-5-hexyne (ii) 1-amino-3-isopropylpentan-1-one
(iii) 1-methyl-2-vinyl cyclohex-1(6)-ene

61. Find the total number of sigma bond(s) in naphthalene

Fill your answer as sum of digits (excluding decimal places) till you get the single digit answer.
62. How many functional groups are presents.
CN

COOMe
H2N
O COOH

CHO

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CH3 CH3
63. CH3–CH 2–CH–CH–C–CH 3 compound (M)
CH3 CH3
(a) No. of 1° carbon atoms in compound (M) is X
(b) No. of 2° carbon atoms in compound (M) is Y
(c) No. of 3° carbon atoms in compound (M) is Z
Write answer of part (a), (b) & (c) in the same order and present the three digit number XYZ as your
answer. for example : If all these answers are 9 (X = 9, Y = 9, Z =9 ) then fill 999.

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ANSWER KEY
1. (A)®R,S ; (B)®Q,S ; (C)®P,S ; (D)®P,Q,S 2. C 3. C 4. C
5. C 6. A 7. C 8. (a) 12, (b) 16, (c) 1, (d) 5, (e) 9, (f) 1, (g) 1, (h) 3
9. (a) 1°, (b) 2°, (c) 3°, (d) 3°, (e) 2° 10. (a) 2°, (b) 1°, (c) 3°, (d) 2°, (e) 2°, (f) 3° 11. A
12. (A) P; (B) P,Q; (C) P,Q,R,S; (D) Q,R 13. D 14. D 15. B 16. D
17. D 18. ABCD 19. (a) 13, (b) 13, (c) 3, (d) 5, (e) 9, (f) 3, (g) 0, (h) 4
20. (a) 9, (b) 4, (c) 0, (d) 5, (e) 6, (f) 1, (g) 0 21. (a) 5, (b) 12 22. BD
23. (A) P,R,S (B) P ; (C) -Q,S (D) Q,R,S, 24. D 25. A 26. A 27. D
28. B,D 29. A,B 30. ABCD 31. B 32. 114 33. AD
34. (A) Q; (B) S; (C) P; (D) R 35. A 36. B 37. C 38. B,C 39. C
40. B 41. A 42. D 43. D
44. (A)-R,T ; (B)-P,Q,S,T ; (C)-S,T , (D) - Q, 45. A 46. A 47. C 48. A,D
49. ABCD 50. D 51. C 52. C
53. (a) 2,2,7-trimethyl-4-(1-methylpropyl)xonane (b)4-(1-methyl ethyl)-5-propyl octane (c) 3,3-di
ethyl-1-5-(1-methyl ethyl) octane (d) 5-ethyl-2,5-dimethyl octane (e) 5-(2,2-dimethyl propyl) nona-2,
4-diene
54. (A)-Q ; (B)-R ; (C)-S ; (D)-P 55. C 56. A 57. B 58. C 59. D
60. (i) 5-Methyl hept-1-yne (ii) 3-Ethyl-4-methylpentanamide (iii)1-Methyl-6-vinylcyclohexene
61. 19 62. 6 63. 612

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