Contents
Preface v
Acknowledgements vi
About the Authors vii
Chapter 1 General Organic Chemistry 1.1–1.78
Chapter 2 Isomerism 2.1–2.80
ST
Chapter 3 Hydrocarbons 3.1–3.60
Chapter 4 Alkyl Halides, Alcohols and Ethers 4.1–4.68
Chapter 5 Carbonyl Compounds and Acid Derivatives 5.1–5.68
O
Chapter 6 ESR Amines and Phenols 6.1–6.70
IC
Chapter 7 Biomolecules 7.1–7.36
Chapter 8 Organic Reaction Mechanisms and Reagents 8.1–8.76
Chapter 9 Practical Organic Chemistry 9.1–9.12
Chapter 10 Nomenclature 10.1–10.20
, About the Authors
Akshay Choudhary, a renowned faculty of organic chemistry, teaches IIT-JEE
aspirants, assisting them to achieve their goal. Many students have been success-
ful under his guidance and achieved top ranks in the IIT–JEE exam. The author is
a postgraduate in chemistry as well as Junior Research Fellow from NCL, Pune.
His has keen interest in the subject and strives to present it to students in a lucid
style to help them ace the exams effortlessly.
Mandakini Choudhary, specializes in reaction mechanisms and intermediates. She is a dedi-
cated teacher with four years’ experience and is popular among students for her zeal to help
ST
them with their board examinations.
O
IC
, General Organic
CHAPTER
1 Chemistry
Question Bank
ST
LEVEL 1
O
Arrange the items in Questions 1–38 in DECREASING ORDER (i.e., greatest, most etc.
IC
first) with respect to the indicated property.
Use the following code to indicate your answers.
1. The acidity of the protons H in each of the following is
O O
(i) (ii) H C
C 3 C
H3C H O CH3
O O
(iii) H C CH3
3 C C
O
O CH2
(a) i > ii > iii (b) ii > iii > i (c) i > iii > ii (d) iii > i > ii
2. Rate of reaction of HNO3/H2SO4 with each of the following is
(i) OCH3 (ii) CN (iii) CH3
(a) i > ii > iii (b) ii > iii > i (c) i > iii > ii (d) iii > i > ii
, 1.2 chapter one
3. Reactivity towards hydrolysis using aqueous acid of the following is
CH3
H3C CH3 H3C Cl
(i) C (ii) H3C N (iii) C
C CH3
O O
O
(a) i > ii > iii (b) iii > ii > i (c) i > iii > ii (d) iii > i > ii
4. Reactivity of the following towards reaction with LiAlH4 is
O O
H3C Cl
(i) (ii) C (iii) OCH3
O
(a) ii > i > iii (b) ii > iii > i (c) i > iii > ii (d) iii > i> ii
5. The relative yield of the following alkenyl bromides from the reaction of 1,3-butadiene
with HBr (dark, N2 atmosphere) at –15ºC is
(i) (ii) (iii)
Br
ST
Br Br
(a) i > ii > iii (b) ii > iii > i (c) i > iii > ii (d) iii > i > ii
6. The amount of conjugate addition obtained in the reaction of the following with 3-butenone
is
(i) CH3Li (ii) CH3MgBr (iii) CH3O2C– CH–CO2CH3
O
(a) i > ii > iii (b) ii > iii > i (c) i > iii > ii (d) iii > i > ii
7. The relative reactivity towards Br2 in CHCl3 of the following is
IC
(i) CH2=CH–CO2CH3 (ii) CH2=CH–CH3 (iii) CH2=CH–O–CH3
(a) i > ii > iii (b) iii > ii > i (c) i > iii > ii (d) iii > i > ii
8. The % of the para product produced in the reaction of Br2/FeBr3 with each of the following
is
CH3 NO2 C(CH3)3
(i) (ii) (iii)
(a) i > ii > iii (b) ii > iii > i (c) i > iii > ii (d) iii > i > ii
9. The number of enolizable protons in each of the following is
O
O
O
(i) (ii) O (iii)
H C CH3
(a) i > ii > iii (b) ii > iii > i (c) i > iii > ii (d) iii > i > ii
Preface v
Acknowledgements vi
About the Authors vii
Chapter 1 General Organic Chemistry 1.1–1.78
Chapter 2 Isomerism 2.1–2.80
ST
Chapter 3 Hydrocarbons 3.1–3.60
Chapter 4 Alkyl Halides, Alcohols and Ethers 4.1–4.68
Chapter 5 Carbonyl Compounds and Acid Derivatives 5.1–5.68
O
Chapter 6 ESR Amines and Phenols 6.1–6.70
IC
Chapter 7 Biomolecules 7.1–7.36
Chapter 8 Organic Reaction Mechanisms and Reagents 8.1–8.76
Chapter 9 Practical Organic Chemistry 9.1–9.12
Chapter 10 Nomenclature 10.1–10.20
, About the Authors
Akshay Choudhary, a renowned faculty of organic chemistry, teaches IIT-JEE
aspirants, assisting them to achieve their goal. Many students have been success-
ful under his guidance and achieved top ranks in the IIT–JEE exam. The author is
a postgraduate in chemistry as well as Junior Research Fellow from NCL, Pune.
His has keen interest in the subject and strives to present it to students in a lucid
style to help them ace the exams effortlessly.
Mandakini Choudhary, specializes in reaction mechanisms and intermediates. She is a dedi-
cated teacher with four years’ experience and is popular among students for her zeal to help
ST
them with their board examinations.
O
IC
, General Organic
CHAPTER
1 Chemistry
Question Bank
ST
LEVEL 1
O
Arrange the items in Questions 1–38 in DECREASING ORDER (i.e., greatest, most etc.
IC
first) with respect to the indicated property.
Use the following code to indicate your answers.
1. The acidity of the protons H in each of the following is
O O
(i) (ii) H C
C 3 C
H3C H O CH3
O O
(iii) H C CH3
3 C C
O
O CH2
(a) i > ii > iii (b) ii > iii > i (c) i > iii > ii (d) iii > i > ii
2. Rate of reaction of HNO3/H2SO4 with each of the following is
(i) OCH3 (ii) CN (iii) CH3
(a) i > ii > iii (b) ii > iii > i (c) i > iii > ii (d) iii > i > ii
, 1.2 chapter one
3. Reactivity towards hydrolysis using aqueous acid of the following is
CH3
H3C CH3 H3C Cl
(i) C (ii) H3C N (iii) C
C CH3
O O
O
(a) i > ii > iii (b) iii > ii > i (c) i > iii > ii (d) iii > i > ii
4. Reactivity of the following towards reaction with LiAlH4 is
O O
H3C Cl
(i) (ii) C (iii) OCH3
O
(a) ii > i > iii (b) ii > iii > i (c) i > iii > ii (d) iii > i> ii
5. The relative yield of the following alkenyl bromides from the reaction of 1,3-butadiene
with HBr (dark, N2 atmosphere) at –15ºC is
(i) (ii) (iii)
Br
ST
Br Br
(a) i > ii > iii (b) ii > iii > i (c) i > iii > ii (d) iii > i > ii
6. The amount of conjugate addition obtained in the reaction of the following with 3-butenone
is
(i) CH3Li (ii) CH3MgBr (iii) CH3O2C– CH–CO2CH3
O
(a) i > ii > iii (b) ii > iii > i (c) i > iii > ii (d) iii > i > ii
7. The relative reactivity towards Br2 in CHCl3 of the following is
IC
(i) CH2=CH–CO2CH3 (ii) CH2=CH–CH3 (iii) CH2=CH–O–CH3
(a) i > ii > iii (b) iii > ii > i (c) i > iii > ii (d) iii > i > ii
8. The % of the para product produced in the reaction of Br2/FeBr3 with each of the following
is
CH3 NO2 C(CH3)3
(i) (ii) (iii)
(a) i > ii > iii (b) ii > iii > i (c) i > iii > ii (d) iii > i > ii
9. The number of enolizable protons in each of the following is
O
O
O
(i) (ii) O (iii)
H C CH3
(a) i > ii > iii (b) ii > iii > i (c) i > iii > ii (d) iii > i > ii
