Classification & Nomenclature of OC - Problem Solving - JEE Sheet PDF

JEE MAIN & ADVANCED
ORGANIC CHEMISTRY
Problem Solving Sheet
Chapter Name
Classification and Nomenclature of Organic Compounds
ETOOS EDUCATION PVT. LTD.

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Organic Chemistry | Problem Solving Sheet

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

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
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

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

. 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)

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

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)

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

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

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

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


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

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

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.

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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JEE MAIN & ADVANCED

Problem Solving Sheet

ETOOS EDUCATION PVT. LTD.

Classification and Nomenclature of Organic Compounds

(B) CH3 – CH – CH – CH 3 (Q) 3°

(C) CH3–CH2–CH2–CH2–CH3 (R) 4°

(D) CH3 –CH–CH2–CH3 (S) 1°

2. Statement 1 : Urea is an organic compound.

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

(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 -

JEE | NEET | CBSE | Foundation (www.etoosindia.com) 1

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

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

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

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

12. Match the column

(B) CH2 = CH – CH3 (Q) 2° Carbon

(C) (R) 3° Carbon

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

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

15. Which of the following is a Heterocyclic compound.

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16. Which of the following is homologue of CH3NHCH2CH2CH3

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

21. Calculate index of Hydrogen deficiency is

(a) (b) COOH

23. Match the column

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

(C) (R) Even number of 2° Carbon

(D) (S) Even number of 3° Carbon

24. Statement 1 : Phenol is a heterocyclic compound.

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. In which compound 1°C : 2ºC : 3°C (carbon) = 1 : 1 : 1.?

. 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 :

28. All the members of homologous series have same :

(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 -

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

34. Match the column

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35. The correct IUPAC name of the compound is :

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

36. IUPAC name of the compound

CH3 – CH2 – CH – CH2 – CH – CH2CH2CH3

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

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

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

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

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41. In following compound

. In which compound 1°C : 2ºC : 3°C (carbon) = 1 : 1 : 1.?

. The compound having only primary hydrogens is :

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