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JEE Advanced Previous Year Questions 
(2021-2023): General Organic Chemistry 
2023 
Single Correct Type 
JEE Advanced 2023 Paper 1 Online 
Q1. Match the reactions in List-I with the features of their products in List-II and choose the 
correct option. 
 
 
 
Page 2


JEE Advanced Previous Year Questions 
(2021-2023): General Organic Chemistry 
2023 
Single Correct Type 
JEE Advanced 2023 Paper 1 Online 
Q1. Match the reactions in List-I with the features of their products in List-II and choose the 
correct option. 
 
 
 
?? . ?? ? ?? ; ?? ? ?? ; ?? ? ?? ; ?? ? ?? 
B. ?? ? ?? ; ?? ? ?? ; ?? ? ?? ; ?? ? ?? 
C.  ?? ? ?? ; ?? ? ?? ; ?? ? ?? ; ?? ? ?? 
D. ?? ? ?? ; ?? ? ?? ; ?? ? ?? ; ?? ? ?? 
Ans: (B) 
 
 
 
 
Page 3


JEE Advanced Previous Year Questions 
(2021-2023): General Organic Chemistry 
2023 
Single Correct Type 
JEE Advanced 2023 Paper 1 Online 
Q1. Match the reactions in List-I with the features of their products in List-II and choose the 
correct option. 
 
 
 
?? . ?? ? ?? ; ?? ? ?? ; ?? ? ?? ; ?? ? ?? 
B. ?? ? ?? ; ?? ? ?? ; ?? ? ?? ; ?? ? ?? 
C.  ?? ? ?? ; ?? ? ?? ; ?? ? ?? ; ?? ? ?? 
D. ?? ? ?? ; ?? ? ?? ; ?? ? ?? ; ?? ? ?? 
Ans: (B) 
 
 
 
 
2021 
Numerical Type 
JEE Advanced 2021 Paper 1 Online 
Q1. The maximum number of possible isomers (including stereoisomers) which may be formed 
on mono-bromination of 1-methylcyclohex-1-ene using ????
?? and ???? light is 
Ans: 13 
Monobromination of 1-methyl cyclohex-1-ene in presence of UV-light gives following products ( 1 
achiral and 6 optically active (*) compounds). So, total 13 products are formed ( 1 + 6 + 6 
enantiomers) 
 
Radicals formed are 
Page 4


JEE Advanced Previous Year Questions 
(2021-2023): General Organic Chemistry 
2023 
Single Correct Type 
JEE Advanced 2023 Paper 1 Online 
Q1. Match the reactions in List-I with the features of their products in List-II and choose the 
correct option. 
 
 
 
?? . ?? ? ?? ; ?? ? ?? ; ?? ? ?? ; ?? ? ?? 
B. ?? ? ?? ; ?? ? ?? ; ?? ? ?? ; ?? ? ?? 
C.  ?? ? ?? ; ?? ? ?? ; ?? ? ?? ; ?? ? ?? 
D. ?? ? ?? ; ?? ? ?? ; ?? ? ?? ; ?? ? ?? 
Ans: (B) 
 
 
 
 
2021 
Numerical Type 
JEE Advanced 2021 Paper 1 Online 
Q1. The maximum number of possible isomers (including stereoisomers) which may be formed 
on mono-bromination of 1-methylcyclohex-1-ene using ????
?? and ???? light is 
Ans: 13 
Monobromination of 1-methyl cyclohex-1-ene in presence of UV-light gives following products ( 1 
achiral and 6 optically active (*) compounds). So, total 13 products are formed ( 1 + 6 + 6 
enantiomers) 
 
Radicals formed are 
 
JEE Advanced 2021 Paper 2 Online 
Q2. The amount of energy required to break a bond is same as the amount of energy released 
when the same bond is formed. In gaseous state, the energy required for homolytic cleavage of 
a bond is called Bond Dissociation Energy (BDE) or Bond Strength. BDE is affected by s-
character of the bond and the stability of the radicals formed. Shorter bonds are typically 
stronger bonds. BDEs for some bonds are given below : 
 
Correct match of the ?? - ?? bonds (shown in bold) in Column ?? with their BDE in Column ?? is 
Column J 
Molecule 
 
Column K 
BDE (kcal mol  
-?? ) 
 
(P) ?? - ?? ?? (????
?? )
?? (i) 132 
(Q) ?? - ????
?? ???? (ii) 110 
(R) ?? - ???? = ????
?? (iii) 95 
(S) ?? - ?? = ???? (iv) 88 
Page 5


JEE Advanced Previous Year Questions 
(2021-2023): General Organic Chemistry 
2023 
Single Correct Type 
JEE Advanced 2023 Paper 1 Online 
Q1. Match the reactions in List-I with the features of their products in List-II and choose the 
correct option. 
 
 
 
?? . ?? ? ?? ; ?? ? ?? ; ?? ? ?? ; ?? ? ?? 
B. ?? ? ?? ; ?? ? ?? ; ?? ? ?? ; ?? ? ?? 
C.  ?? ? ?? ; ?? ? ?? ; ?? ? ?? ; ?? ? ?? 
D. ?? ? ?? ; ?? ? ?? ; ?? ? ?? ; ?? ? ?? 
Ans: (B) 
 
 
 
 
2021 
Numerical Type 
JEE Advanced 2021 Paper 1 Online 
Q1. The maximum number of possible isomers (including stereoisomers) which may be formed 
on mono-bromination of 1-methylcyclohex-1-ene using ????
?? and ???? light is 
Ans: 13 
Monobromination of 1-methyl cyclohex-1-ene in presence of UV-light gives following products ( 1 
achiral and 6 optically active (*) compounds). So, total 13 products are formed ( 1 + 6 + 6 
enantiomers) 
 
Radicals formed are 
 
JEE Advanced 2021 Paper 2 Online 
Q2. The amount of energy required to break a bond is same as the amount of energy released 
when the same bond is formed. In gaseous state, the energy required for homolytic cleavage of 
a bond is called Bond Dissociation Energy (BDE) or Bond Strength. BDE is affected by s-
character of the bond and the stability of the radicals formed. Shorter bonds are typically 
stronger bonds. BDEs for some bonds are given below : 
 
Correct match of the ?? - ?? bonds (shown in bold) in Column ?? with their BDE in Column ?? is 
Column J 
Molecule 
 
Column K 
BDE (kcal mol  
-?? ) 
 
(P) ?? - ?? ?? (????
?? )
?? (i) 132 
(Q) ?? - ????
?? ???? (ii) 110 
(R) ?? - ???? = ????
?? (iii) 95 
(S) ?? - ?? = ???? (iv) 88 
A. P - iii, Q - iv, R - ii, S - i 
B. P - i, Q - ii, R - iii, S - iv 
C. P - iii, Q - ii, R - i, S - iv 
D. P - ii, Q - i, R - iv, S – ii 
Ans: (A) 
A more stable radical means lesser the bond dissociation energy. 
Radicals formed are 
 
Radical formed from Q(PhCH
2
- H) is most stable due to resonance. 
Stability of free radical decreases with increase in % s-character. 
P radical ? sp
3
? % s-character 25% 
R radical ? sp
2
? % s-character 33% 
S radical ? sp ? % s-character 50% 
Thus, order of stability of free radical is 
Q > P > R > S 
Order of bond dissociation energy is 
?? > ?? > ?? > ?? 
JEE Advanced 2021 Paper 2 Online 
Q3.The amount of energy required to break a bond is same as the amount of energy released 
when the same bond is formed. In gaseous state, the energy required for homolytic cleavage of 
a bond is called Bond Dissociation Energy (BDE) or Bond Strength. BDE is affected by s-
character of the bond and the stability of the radicals formed. Shorter bonds are typically 
stronger bonds. BDEs for some bonds are given below : 
 
???? - ???? (?? ) ? ????
(?? )
·
+ ????
(?? )
·
?? ?? °
= ???????????? ?????? -?? 
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