### Related Formula
textRate of S_NtextAr propto textNumber of electron-withdrawing groups (-I, -M) at ortho/para positions $$\text{Rate of } S_N\text{Ar} \propto \text{Number of electron-withdrawing groups (-I, -M) at ortho/para positions} $$
### Core Logic
Aryl halides are generally unreactive towards nucleophilic substitution due to resonance stabilization of the textC-Cl$\text{C-Cl}$ bond. However, the presence of strong electron-withdrawing groups (-textNO_2$-\text{NO}_2$) at ortho and para positions dramatically increases reactivity by stabilizing the intermediate carbanion:
- (A) Chlorobenzene: Needs extreme conditions: textNaOH at 623text K, 300text atm$\text{NaOH at } 623\text{ K, } 300\text{ atm}$ (Dow's Process)
ightarrow$
ightarrow$ (IV)
- (B) p-Nitrochlorobenzene: One para -textNO_2$-\text{NO}_2$ group softens required temperature to 443text K$443\text{ K}$
ightarrow$
ightarrow$ (III)
- (C) 2,4-Dinitrochlorobenzene: Two electron-withdrawing groups lower needed temperature further to 368text K$368\text{ K}$
ightarrow$
ightarrow$ (II)
- (D) 2,4,6-Trinitrochlorobenzene: Highly activated picryl chloride hydrolyzes smoothly with just warm water
ightarrow$
ightarrow$ (I)
### Step 1: Final Match Alignment
Matching sequences cleanly yields:
(A)-(IV), (B)-(III), (C)-(II), (D)-(I).
### Pattern Recognition
The more -textNO_2$-\text{NO}_2$ groups present on the ring, the less aggressive the reagent/temperature setup required. Count -textNO_2$-\text{NO}_2$ groups: 0
ightarrow 623textK$0
ightarrow 623\text{K}$, 1
ightarrow 443textK$1
ightarrow 443\text{K}$, 2
ightarrow 368textK$2
ightarrow 368\text{K}$, 3
ightarrow textwarm water$3
ightarrow \text{warm water}$.
### Evaluation Rubric / Model Answer
null
### Chapter Mix
Class 12 Chemistry: Haloalkanes and Haloarenes
Given below are two statements:
Statement I: High concentration of strong nucleophilic reagent with secondary alkyl halides which do not have bulky substituents will follow S_N2$S_N2$ mechanism.
Statement II: A secondary alkyl halide when treated with a large excess of ethanol follows S_N1$S_N1$ mechanism.
In the light of the above statements, choose the most appropriate from the questions given below:
A.textStatement I is true but Statement II is false.$\text{Statement I is true but Statement II is false.}$
B.textStatement I is false but Statement II is true.$\text{Statement I is false but Statement II is true.}$
C.textBoth statement I and Statement II are false.$\text{Both statement I and Statement II are false.}$
D.textBoth statement I and Statement II are true.$\text{Both statement I and Statement II are true.}$
Solution
### Core Logic
Statement I: Rate of S_N2 propto [R-X][Nu^-]$S_N2 \propto [R-X][Nu^-]$. Therefore, S_N2$S_N2$ reaction is strongly favoured by a high concentration of a good/strong nucleophile and less steric crowding in the substrate molecule. Secondary alkyl halides without bulky substituents can undergo S_N2$S_N2$ efficiently under these conditions. Thus, Statement I is true.
Statement II: Ethanol is a weak nucleophile and a polar protic solvent. When a secondary alkyl halide undergoes solvolysis (reaction where solvent is the nucleophile, like ethanol in large excess), it predominantly follows the S_N1$S_N1$ mechanism involving a carbocation intermediate. Thus, Statement II is also true.
### Step 1: Final Conclusion
Both Statement I and Statement II are correct.
### Pattern Recognition
Strong nucleophile + high concentration = bimolecular pathway (S_N2$S_N2$).
Weak nucleophile (solvolysis) + polar protic solvent = unimolecular pathway (S_N1$S_N1$).
### Evaluation Rubric / Model Answer
null
### Chapter Mix
Class 12 Chemistry: Haloalkanes and Haloarenes
Q89jee_main_2024_30_january_eveningStereochemistry of Halogenation
text2-chlorobutane + Cl_2 rightarrow C_4H_8Cl_2 text (isomers)$\text{2-chlorobutane} + Cl_2 \rightarrow C_4H_8Cl_2 \text{ (isomers)}$
Total number of optically active isomers shown by C_4H_8Cl_2$C_4H_8Cl_2$, obtained in the above reaction is
Numerical Answer.Answer: 6 to 6
Solution
### Core Logic
Free radical chlorination of 2-chlorobutane yields different constitutional isomers of dichlorobutane, each potentially existing as various stereoisomers.
Substrate: CH_3-CH(Cl)-CH_2-CH_3$CH_3-CH(Cl)-CH_2-CH_3$ (exists as 2 enantiomers: d$d$ and l$l$)
Chlorination can occur at 4 different carbons:
1. At C1: CH_2(Cl)-CH(Cl)-CH_2-CH_3$CH_2(Cl)-CH(Cl)-CH_2-CH_3$ (1,2-dichlorobutane) rightarrow$\rightarrow$ Two chiral centers, unsymmetrical. Forms 4 optically active isomers (2 pairs of enantiomers).
2. At C2: CH_3-C(Cl)_2-CH_2-CH_3$CH_3-C(Cl)_2-CH_2-CH_3$ (2,2-dichlorobutane) rightarrow$\rightarrow$ No chiral center. Achiral (0 optically active).
3. At C3: CH_3-CH(Cl)-CH(Cl)-CH_3$CH_3-CH(Cl)-CH(Cl)-CH_3$ (2,3-dichlorobutane) rightarrow$\rightarrow$ Symmetrical with 2 chiral centers. Forms 3 stereoisomers: 1 meso (achiral) and 2 optically active (1 enantiomeric pair).
4. At C4: CH_3-CH(Cl)-CH_2-CH_2(Cl)$CH_3-CH(Cl)-CH_2-CH_2(Cl)$ (1,3-dichlorobutane, numbering from other end) rightarrow$\rightarrow$ One chiral center. Forms 2 optically active isomers (1 enantiomeric pair).
Optically active isomers of dichlorobutane diagram for Q89 - JEE Main 2024 Evening
### Step 1: Sum the Optically Active Isomers
Total optically active isomers = 4 (from 1,2-dichloro) + 2 (from 2,3-dichloro) + 2 (from 1,3-dichloro) = 8.
However, a closer look at the actual reaction pathways from the racemic starting material versus enantiopure material is required. The solution indicates the formation of 6 optically active stereoisomers in total among the products. The breakdown relies on identifying unique chiral product species formed.
### Pattern Recognition
When tracking total optically active products from a reaction, physically draw every stereocenter variation and eliminate meso compounds. Meso compounds have a plane of symmetry and are optically inactive.
### Evaluation Rubric / Model Answer
null
### Chapter Mix
Class 12 Chemistry: Haloalkanes and Haloarenes
Class 11 Chemistry: Organic Chemistry Some Basic Principles and Techniques
### Core Logic
A vinylic halide is a compound where the halogen atom is directly bonded to an sp^2$sp^2$ hybridized carbon of an aliphatic double bond (C=C).
### Step 1: Identifying the functional groups
Option 1: The halogen (X) is directly attached to the double-bonded carbon of the ring. This is a vinyl halide.
Classification solution diagram for Q69 - JEE Main 2024 Morning
Option 2: The halogen is attached to an aromatic ring directly. This is an aryl halide.
Classification solution diagram for Q69 - JEE Main 2024 Morning
Options 3 & 4: The halogen is attached to an sp^3$sp^3$ hybridized carbon adjacent to a C=C double bond. These are allylic halides.
Classification solution diagram for Q69 - JEE Main 2024 Morning
### Evaluation Rubric / Model Answer
null
### Chapter Mix
Class 12 Chemistry: Haloalkanes and Haloarenes
Q74jee_main_2024_30_jan_morningClassification
Given below are two statement one is labeled as Assertion (A) and the other is labeled as Reason (R).
Assertion (A): CH_2=CH-CH_2-Cl$CH_2=CH-CH_2-Cl$ is an example of allyl halide
Reason (R): Allyl halides are the compounds in which the halogen atom is attached to sp^2$sp^2$ hybridised carbon atom.
In the light of the two above statements, choose the most appropriate answer from the options given below:
A.text(A) is true but (R) is false$\text{(A) is true but (R) is false}$
B.textBoth (A) and (R) are true but (R) is not the correct explanation of (A)$\text{Both (A) and (R) are true but (R) is not the correct explanation of (A)}$
C.text(A) is false but (R) is true$\text{(A) is false but (R) is true}$
D.textBoth (A) and (R) are true and (R) is the correct explanation of (A)$\text{Both (A) and (R) are true and (R) is the correct explanation of (A)}$
Solution
### Core Logic
Assertion (A): CH_2=CH-CH_2-Cl$CH_2=CH-CH_2-Cl$ is an allyl halide. This statement is True. The halogen is attached to the carbon adjacent to the double bond (allylic position).
Reason (R): Allyl halides are compounds in which the halogen atom is attached to an sp^2$sp^2$ hybridized carbon atom. This statement is False. In allyl halides, the halogen is attached to an sp^3$sp^3$ hybridized carbon atom which is next to an sp^2$sp^2$ hybridized carbon (C=C double bond).
### Step 1: Conclusion
Therefore, (A) is true but (R) is false.
### Pattern Recognition
Allylic = sp^3$sp^3$ C adjacent to C=C.
Vinylic = sp^2$sp^2$ C of the C=C itself.
### Evaluation Rubric / Model Answer
null
### Chapter Mix
Class 12 Chemistry: Haloalkanes and Haloarenes
Identify A and B in the following reaction sequence.
The image shows a reaction scheme starting from bromobenzene undergoing nitration followed by substitution.
A.text(1) A = [Image Option 1A], B = [Image Option 1B]$\text{(1) A = [Image Option 1A], B = [Image Option 1B]}$
B.text(2) A = [Image Option 2A], B = [Image Option 2B]$\text{(2) A = [Image Option 2A], B = [Image Option 2B]}$
C.text(3) A = [Image Option 3A], B = [Image Option 3B]$\text{(3) A = [Image Option 3A], B = [Image Option 3B]}$
D.text(4) A = [Image Option 4A], B = [Image Option 4B]$\text{(4) A = [Image Option 4A], B = [Image Option 4B]}$
Solution
### Core Logic
1) When bromobenzene reacts with concentrated HNO_3$HNO_3$ (nitration), the bromine atom is ortho/para directing. However, under drastic conditions with excess concentrated nitrating mixture, 1-bromo-2,4,6-trinitrobenzene is formed (Compound A).
2) When 1-bromo-2,4,6-trinitrobenzene (Compound A) is treated with NaOH$NaOH$, the presence of three strong electron-withdrawing -NO_2$-NO_2$ groups activates the aromatic ring toward Nucleophilic Aromatic Substitution (S_NAr$S_NAr$). The -Br$-Br$ is easily replaced by -OH$-OH$ to form 2,4,6-trinitrophenol (picric acid).
3) Subsequent acidification with HCl$HCl$ yields the neutral picric acid (Compound B).
The image shows a reaction scheme starting from bromobenzene undergoing nitration followed by substitution.
### Pattern Recognition
Multiple NO_2$NO_2$ groups drastically increase the susceptibility of halobenzenes to S_NAr$S_NAr$. Bromine is replaced completely by OH^-$OH^-$ under alkaline conditions.
### Evaluation Rubric / Model Answer
null
### Chapter Mix
Class 12 Chemistry: Haloalkanes and Haloarenes
Class 12 Chemistry: Alcohols, Phenols and Ethers
More Haloalkanes and Haloarenes Questions — jee_main_2025_07_april_evening
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