Given below are two statements : Statement-I: The conversion proceeds well in the less polar medium. mathrmCH_3-mathrmCH_2-mathrmCH_2-mathrmCH_2-mathrmCl xrightarrowmathrmHO^- mathrmCH_3-mathrmCH_2-mathrmCH_2-mathrmCH_2-mathrmOH + mathrmCl^- Statement-II: The conversion proceeds well in the more polar medium. mathrmCH_3-mathrmCH_2-mathrmCH_2-mathrmCH_2-mathrmCl xrightarrowmathrmR_3mathrmN [mathrmCH_3-mathrmCH_2-mathrmCH_2-mathrmCH_2-mathrmNR_3]^+mathrmCl^-

Solution & Explanation

### Core Logic Analyzing the solvent effects on reaction kinetics: - In Statement-I, the reaction involves an anionic nucleophile (OH^-), creating a highly localized charge density on the reactant side. The resulting transition state disperses this negative charge over a larger volume, lowering its charge density. Highly polar solvents strongly solvate the reactant ion, increasing the activation energy barrier. Consequently, less polar solvents accelerate this process.
SN2 pathway charge density solvent dynamics part 1
SN2 pathway charge density solvent dynamics part 1
- In Statement-II, the reaction begins with neutral precursors (R_3N and alkyl chloride). The resulting transition state develops partial charges (delta+ and delta-) as the new bond forms, increasing its charge density relative to the reactants. Polar solvents stabilize this charged transition state, lowering the activation energy barrier. Thus, highly polar media accelerate this substitution pathway.
SN2 pathway charge density solvent dynamics part 1
SN2 pathway charge density solvent dynamics part 1
### Pattern Recognition If the transition state concentrates charge relative to the reactants, polar solvents accelerate the reaction. If the transition state disperses charge, less polar solvents are favored. ### Evaluation Rubric / Model Answer null ### Chapter Mix Class 12 Chemistry: Haloalkanes and Haloarenes

Reference Study Guides

More Haloalkanes and Haloarenes Previous-Year Questions — Page 5

Q63 jee_main_2024_30_january_evening Nucleophilic Substitution Reactions
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 mechanism. Statement II: A secondary alkyl halide when treated with a large excess of ethanol follows 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.
  • B. textStatement I is false but Statement II is true.
  • C. textBoth statement I and Statement II are false.
  • D. textBoth statement I and Statement II are true.

Solution

### Core Logic Statement I: Rate of S_N2 propto [R-X][Nu^-]. Therefore, 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 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 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). Weak nucleophile (solvolysis) + polar protic solvent = unimolecular pathway (S_N1). ### Evaluation Rubric / Model Answer null ### Chapter Mix Class 12 Chemistry: Haloalkanes and Haloarenes
Q89 jee_main_2024_30_january_evening Stereochemistry of Halogenation
text2-chlorobutane + Cl_2 rightarrow C_4H_8Cl_2 text (isomers) Total number of optically active isomers shown by 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 (exists as 2 enantiomers: d and l) Chlorination can occur at 4 different carbons: 1. At C1: CH_2(Cl)-CH(Cl)-CH_2-CH_3 (1,2-dichlorobutane) 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 (2,2-dichlorobutane) rightarrow No chiral center. Achiral (0 optically active). 3. At C3: CH_3-CH(Cl)-CH(Cl)-CH_3 (2,3-dichlorobutane) 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) (1,3-dichlorobutane, numbering from other end) rightarrow One chiral center. Forms 2 optically active isomers (1 enantiomeric pair).
Optically active isomers of dichlorobutane diagram for Q89 - JEE Main 2024 Evening
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
Q69 jee_main_2024_30_jan_morning Classification
Example of vinylic halide is
  • A.
  • B.
  • C.
  • D.

Solution

### Core Logic A vinylic halide is a compound where the halogen atom is directly bonded to an 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
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
Classification solution diagram for Q69 - JEE Main 2024 Morning
Options 3 & 4: The halogen is attached to an sp^3 hybridized carbon adjacent to a C=C double bond. These are allylic halides.
Classification solution diagram for Q69 - JEE Main 2024 Morning
Classification solution diagram for Q69 - JEE Main 2024 Morning
### Evaluation Rubric / Model Answer null ### Chapter Mix Class 12 Chemistry: Haloalkanes and Haloarenes
Q74 jee_main_2024_30_jan_morning Classification
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 is an example of allyl halide Reason (R): Allyl halides are the compounds in which the halogen atom is attached to 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
  • B. textBoth (A) and (R) are true but (R) is not the correct explanation of (A)
  • C. text(A) is false but (R) is true
  • D. textBoth (A) and (R) are true and (R) is the correct explanation of (A)

Solution

### Core Logic Assertion (A): 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 hybridized carbon atom. This statement is False. In allyl halides, the halogen is attached to an sp^3 hybridized carbon atom which is next to an sp^2 hybridized carbon (C=C double bond). ### Step 1: Conclusion Therefore, (A) is true but (R) is false. ### Pattern Recognition Allylic = sp^3 C adjacent to C=C. Vinylic = sp^2 C of the C=C itself. ### Evaluation Rubric / Model Answer null ### Chapter Mix Class 12 Chemistry: Haloalkanes and Haloarenes
Q63 jee_main_2024_31_jan_evening Nucleophilic Aromatic Substitution
Identify A and B in the following reaction sequence.
Nucleophilic Aromatic Substitution diagram for Q63 - JEE Main 2024 Evening
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]
  • B. text(2) A = [Image Option 2A], B = [Image Option 2B]
  • C. text(3) A = [Image Option 3A], B = [Image Option 3B]
  • D. text(4) A = [Image Option 4A], B = [Image Option 4B]

Solution

### Core Logic 1) When bromobenzene reacts with concentrated 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, the presence of three strong electron-withdrawing -NO_2 groups activates the aromatic ring toward Nucleophilic Aromatic Substitution (S_NAr). The -Br is easily replaced by -OH to form 2,4,6-trinitrophenol (picric acid). 3) Subsequent acidification with HCl yields the neutral picric acid (Compound B).
Nucleophilic Aromatic Substitution diagram for Q63 - JEE Main 2024 Evening
The image shows a reaction scheme starting from bromobenzene undergoing nitration followed by substitution.
### Pattern Recognition Multiple NO_2 groups drastically increase the susceptibility of halobenzenes to S_NAr. Bromine is replaced completely by OH^- under alkaline conditions. ### Evaluation Rubric / Model Answer null ### Chapter Mix Class 12 Chemistry: Haloalkanes and Haloarenes Class 12 Chemistry: Alcohols, Phenols and Ethers

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