Quantrex Quantrex AcademyJEE · NEET · NDA PYQs with solutions Open app
JEE Main 20266 AprilMorning Shift
Exam
JEE Main
Year
2026
Date
6 April
Shift
Morning Shift
Subject
Chemistry
Chapter
Hydrocarbons

JEE Main 2026 · 6 April · Morning Shift · Chemistry · Hydrocarbons

Given below are two statements: Statement I: 3 -phenylpropene...

Given below are two statements:

Statement I: 33-phenylpropene reacts with HBr and gives secondary alkyl bromide having a chiral carbon atom as the major product.

Statement II: Aryl chlorides and aryl cyanides can be prepared by Sandmeyer reaction as well as Gattermann reaction.

In the light of the above statements, choose the correct answer from the options given below

Options

  1. ABoth Statement I and Statement II are true
  2. BBoth Statement I and Statement II are false
  3. CStatement I is true but Statement II is false
  4. DStatement I is false but Statement II is true

Correct answer

C. Statement I is true but Statement II is false

Step-by-step solution

Statement I:
When 33-phenylpropene reacts with HBrHBr, protonation of the alkene occurs to form a secondary carbocation.

C6H5−CH2−CH=CH2+H+→C6H5−CH2−CH+−CH3C_6H_5-CH_2-CH=CH_2 + H^+ \rightarrow C_6H_5-CH_2-CH^+-CH_3

This secondary carbocation undergoes a 1,21,2-hydride shift to form a more stable, resonance-stabilized benzylic carbocation.

C6H5−CH2−CH+−CH3→C6H5−CH+−CH2−CH3C_6H_5-CH_2-CH^+-CH_3 \rightarrow C_6H_5-CH^+-CH_2-CH_3

The bromide ion then attacks this benzylic carbocation to form the major product, 11-bromo-11-phenylpropane.

C6H5−CH+−CH2−CH3+Br−→C6H5−CH(Br)−CH2−CH3C_6H_5-CH^+-CH_2-CH_3 + Br^- \rightarrow C_6H_5-CH(Br)-CH_2-CH_3

The carbon atom bonded to the bromine is attached to four different groups: a phenyl group (−C6H5-C_6H_5), an ethyl group (−CH2CH3-CH_2CH_3), a hydrogen atom (−H-H), and a bromine atom (−Br-Br). Thus, it is a chiral carbon. The product is a secondary alkyl bromide. Therefore, Statement I is true.

Statement II:
The Sandmeyer reaction involves treating a diazonium salt with Cu(I)Cu(I) salts (CuClCuCl, CuBrCuBr, CuCNCuCN) to prepare aryl chlorides, aryl bromides, and aryl cyanides, respectively.

The Gattermann reaction involves treating a diazonium salt with copper powder (CuCu) and halogen acids (HClHCl, HBrHBr) to prepare aryl chlorides and aryl bromides. Aryl cyanides are not prepared using the Gattermann reaction. Therefore, Statement II is false.

Conclusion: Statement I is true but Statement II is false.

Answer: Statement I is true but Statement II is false
Practice Hydrocarbons on Quantrex Academy →

More from Hydrocarbons

In the following reaction sequence, Q , R , S and T are the major products. The correct… JEE Advanced 2026Treatment of buta-1,3-diyne with NaNH_2 ( 2 equivalents), followed by reaction with… JEE Advanced 2026The List-II contains products obtained from the reaction of compounds in List-I with O_3… JEE Advanced 2026Natural rubber on complete ozonolysis ( O_3 /Zn- H_2O ) gives compound X as the major… JEE Advanced 2026An optically active alkyl bromide C _4 H _9 Br, reacts with ethanolic KOH to form major… JEE Main 2026An alkane (Y) requires 8 moles of oxygen for complete combustion and on chlorination with… JEE Main 2026R_f value for 2 -methylpropene in a solvent system (Ethyl acetate + ether) is 0.42 . 2… JEE Main 2026Given below are two statements: Statement I: Methane can be prepared by decarboxylation… JEE Main 2026 Full Hydrocarbons list All JEE Main PYQs