PREVIOUS YEAR

PROBLEM SOLVING
IIT JEE MAIN + ADVANCED
ORGANIC CHEMISTRY

BY
NAVNEET JETHWANI

IUPAC
&
NOMENCLATURE

ETOOSINDIA
INDIA’S NO. 1 ONLINE COACHING

Plot No. 38, Near Union Bank of India, Rajeev Gandhi Nagar,
Kota, Rajasthan – 324005 Mob. : 9214233303
ETOOSINDIA N.J. SIR
INDIA’S NO. 1 ONLINE COACHING

JEE MAIN
1. Carbon is sp hybridised in – [AIEEE -2002]
(1) CH3CH = CH2 (2) CH3CH2–NH2 (3) CH3CONH2 (4) CH3CH2CN
Ans. (4)
2. Which of the following compound has wrong IUPAC name ? [AIEEE -2002]
(1) CH3CH2– CH2COO–CH2CH3 (Ethyl butanoate)
(2) CH3 CH CH2 CHO (3-Methylbutanal)
CH3

(3) CH3 CH CH CH3 (2-Methyl-3-butanol)

OH CH3

(4) CH 3 CH C CH 2 CH 3 (2-Methyl-3-pentanone)
CH 3 O
Ans. (3)

3. The IUPAC name of CH3COCH(CH3)2 is [AIEEE -2003]

(1) isopropyl methyl ketone (2) 2-methyl-3-butanone
(3) 4-methylisopropyl ketone (4) 3-methyl-2-butanone
Ans. (4)

4. The general formula of CnH2nO2 could be for open chain [AIEEE -2003]
(1) diketones (2) carboxylic acids (3) diols (4) dialdehydes
Ans. (2)

5. Which one of the following does not have sp2 hybridised carbon? [AIEEE -2004]
(1) Acetone (2) Acetic acid (3) Acetonitrile (4) Acetamide
Ans. (3)

6. The IUPAC name of the compound is [AIEEE -2004]

HO
(1) 1, 1-dimethyl-3-cyclohexanol (2) 1, 1-dimethyl-3-hydroxy cyclohexane
(3) 3, 3-dimethyl-1-cyclohexanol (4) 3, 3-dimethyl-1-hydroxy cyclohexane
Ans. (3)

7. The IUPAC name of the compound is [AIEEE -2006]

Cl

Br
(1) 6-bromo-2chlorocyclohexene (2) 3-bromo-1-chlorocyclohexene
(3) 1-bromo-3-chlorocyclohexene (4) 2-bromo-6-chlorocyclohex-1-en
Ans. (2)

Plot No. 38, Near Union Bank of India, Rajeev Gandhi Nagar, Page # 2
Kota, Rajasthan – 324005 Mob. : 9214233303
 ETOOSINDIA N.J. SIR
INDIA’S NO. 1 ONLINE COACHING

8. The IUPAC name of is [AIEEE -2007]

(1) 1, 1-diethyl-2, 2-dimethylpentane (2) 4, 4-dimethyl-5, 5-diethylpentane

(3) 5, 5-diethyl-4, 4-dimethylpentane (4) 3-ethyl-4, 4-dimethylpentane
Ans. (4)
9. The correct decreasing order of priority for the functional groups of organic compounds in the IUPAC system of
nomenclature is [AIEEE -2008]
(1) –COOH, –SO3H, –CONH2, –CHO (2) –SO3H, –COOH, –CONH2, –CHO
(3) –CHO, –COOH, –SO3H, –CONH2 (4) –CONH2, –CHO, –SO3H, –COOH
Ans. (1)

10. The IUPAC name of neopentane is : [AIEEE -2009]

(1) 2-methylpropane (2) 2, 2-dimethylbutane (3) 2-methylbutane (4) 2, 2-dimethylpropane
Ans. (4)
O

11. The IUPAC name of compound H2C CH CH3 is :- [JEE Main -2012 (Online)]
(1) 1, 2-Epoxy propane (2) Propylene oxide
(3) 1, 2-Oxo propane (4) 1, 2-Propoxide
Ans. (1)
12. The IUPAC name of the following compounds is : [JEE Main -2012(Online)]

(1) (Z) – 5– hepten – 3 – yne (2) (Z) – 2– hepten – 4 – yne

(3) (E) – 5– hepten – 3 – yne (4) (E) – 2– hepten – 4 – yne
Ans. (4)
13. Aspirin is known as : [JEE Main -2012]
(1) Acetyl salicyclic acid (2) Phenyl salicylate
(3) Acetyl salicylate (4) Methyl salicylic acid
Ans. (1)
14. The hydrocarbon with seven carbon atoms containing a neopentyl and a vinyl group is: [JEE Main (Online) -2016]
(1) 2, 2-dimethyl-4-pentene (2) Isopropyl -2-butene
(3) 4, 4-dimethylpentene (4) 2,2-dimethyl-3-pentene
Ans. (3)

15. The IUPAC name of the following compound is : [JEE Main (Online) -2017]

(1) 2– Ethyl -1, 1-dimethylcyclohexane (2) 1, 1-Dimethyl 1-2 -ethylcyclohexane

(3) 2, 2-Dimethyl-1-1 -ethylcyclohexane (4) 1– Ethyl -2, 2-dimethylcyclohexane
Ans. (1)

Plot No. 38, Near Union Bank of India, Rajeev Gandhi Nagar, Page # 3
Kota, Rajasthan – 324005 Mob. : 9214233303
 ETOOSINDIA N.J. SIR
INDIA’S NO. 1 ONLINE COACHING

JEE ADVANCED
Subjective Type Questions

1. Write the IUPAC name of CH3CH2CH=CH – COOH – [IIT-1986]

Ans. 2-pentene -1-oic acid and or 2-pentenoic acid

2. Write the IUPAC name of the following : [IIT - 1990]

Me
Me Me
(a) Me = Methyl group
Me Me

CH3
(b) H 3C N CH CH 2CH 3
CH 3 C2H5
Ans. (a) 5, 6-diethyl-3-methyl-dec-4-ene (b) N,N,3-trimethyl-3-pentanamine

3. Write the IUPAC name of succinic acid is [IIT 1994]

Ans. Butan-1,4-dioic Acid

4. Write IUPAC name of the following [IIT-2002]

CH2CHO

OH

Ans. 2-(4-Hydroxyphenyl) ethanal

5. Write IUPAC name of the following [IIT - 2004]

COOH

NH2
Ans. 3-Aminobenzoic acid

6. Write IUPAC name of the following [IIT-2005]

SO3H

CH3

Ans. 4-Methylbenzensulphonic acid

Plot No. 38, Near Union Bank of India, Rajeev Gandhi Nagar, Page # 4
Kota, Rajasthan – 324005 Mob. : 9214233303
 ETOOSINDIA N.J. SIR
INDIA’S NO. 1 ONLINE COACHING

Objective Type Questions

7. The IUPAC name of the compound having the formula is [IIT-1984]
CH3
H3C C CH CH2
CH3
(A) 3, 3, 3-trimethyl-1-propene (B) 1, 1, 1-trimethyl-2-propene
(C) 3, 3-dimethyl-1-butene (D) 2, 2-dimethyl-3-butene
Ans. (C)
8. The IUPAC name of the compound, CH2 = CH – CH(CH3)2 is – [IIT-1988]
(A) 1, 1-Dimethylprop-2-ene (B) 3-Methylbut-1-ene
(C) 2-Vinylpropane (D) 1-Isopropylethylene
Ans. (B)

9. The number of sigma and pi-bonds in 1-butene- 3-yne are [IIT - 1989]
(A) 5 sigma and 5 pi (B) 7 sigma and 3 pi (C) 8 sigma and 2 pi (D) 6 sigma and 4 pi
Ans. (D)

10. The correct IUPAC name of the compound is : [IIT-1990]

CH3
CH3 CH2C=CH CHCH2CH3
CH3CH2 CH CH2CH2CH2CH3
(A) 5, 6-diethyl-8-methyl dec -6-ene (B) 5, 6-diethyl-3-methyl dec -4-ene
(C) 6-butyl-5-ethyl-3-methyl oct-4-ene (D) 2, 4, 5-triethyl-3-ene
Ans. (B)

11. The IUPAC name of – [IIT-1991]

OHCCH=CH CH CH=CH2
is –
CH2CH2CH 2CH3
(A) 5-Vinyloct-3-en-1-al (B) 4-Butylhexa-2, 5-dien-1-al
(C) 5-Vinyloct-5-en-8-al (D) 3-Butylhexa-1, 4-dien-8-al

Ans. (B)

12. Choose the correct IUPAC name for CH3 CH CHO is – [IIT-1993]
CH2 CH3
(A) Butan-2-aldehyde (B) 2-Methylbutanal
(C) 3-Methyl iso butyraldehyde (D) 2-Ethylpropanal
Ans. (B)

Plot No. 38, Near Union Bank of India, Rajeev Gandhi Nagar, Page # 5
Kota, Rajasthan – 324005 Mob. : 9214233303
 ETOOSINDIA N.J. SIR
INDIA’S NO. 1 ONLINE COACHING

O
13. IUPAC name of C6H5 C Cl [IIT-2006]
(A) Benzoylchloride (B) Benzenecarbonylchloride
(C) Chlorophenyl ketone (D) Phenylchloroketone
Ans. (B)

14. The IUPAC name of the following compound is : [IIT-2009]

OH

CN
Br
(A) 4-Bromo-3-cyanophenol (B) 2-Bromo-5-hydroxybenzonitrile
(C) 2-Cyano-4-hydroxybromobenzene (D) 6-Bromo-3-hydroxybenzonitrile
Ans. (B)

Multiple Choice Question

15. A compound with molecular formula C8H14, contains 12 secondary and two tertiary H atoms. The compound is –
[IIT-1993]

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

Ans. (B, C, D)

16. The correct combination of names for isomeric alcohols with molecular formula C4H10O is/are [IIT-2014]
(A) Tert-butanol and 2-methylpropan-2-ol (B) Tert-butanol and 1, 1-dimethylrthan-1-ol
(C) n-Butanol and butan-1-ol (D) Isobutyl alcohol and 2-methylpropan-1-ol
Ans. (A, D)
17. The IUPAC name(s) of the following compound is(are) : [JEE Advanced-2017]

H3C Cl

(A) 4-methylchlorobenzene (B) 4-chlorotoluene

(C) 1-chloro-4-methylbenzene (D) 1-methyl-1-4-methylbenzene
Ans. (B,C)

Plot No. 38, Near Union Bank of India, Rajeev Gandhi Nagar, Page # 6
Kota, Rajasthan – 324005 Mob. : 9214233303