CBSE 2025, Set 1

Question

Draw the structure of the major monohalo product for each of the following reactions:

![Q26A reaction schemes](https://www.edvaya.com/images/chemistry/cbse/2025/set1/q26a-question-monohalo-reactions.webp)

(a) 4-chloro-1-ethylbenzene + Br$_2$, Heat $\rightarrow$ ?

(b) 1-methylcyclohexene + HBr $\rightarrow$ ?

(c) 4-(hydroxymethyl)phenol + HCl, Heat $\rightarrow$ ?

Edvaya · Accepted Answer

The correct answer is Subjective. ![Q26A answer — major monohalo products](https://www.edvaya.com/images/chemistry/cbse/2025/set1/q26a-answer-monohalo-products.webp) **(a) Free radical bromination (Br$_2$, heat):** Occurs at the **benzylic position** ($\alpha$-C of –CH$_2$CH$_3$) as the benzylic radical is resonance-stabilised by the ring. **Product:** 1-(1-bromoethyl)-4-chlorobenzene **(b) Addition of HBr to 1-methylcyclohexene (Markovnikov's rule):** H$^+$ adds to C2 (less substituted); Br$^-$ adds to C1 (forms stable tertiary carbocation). **Product:** 1-bromo-1-methylcyclohexane **(c) 4-(Hydroxymethyl)phenol + HCl, Heat:** The aliphatic **–CH$_2$OH** undergoes nucleophilic substitution to give **–CH$_2$Cl**. The phenolic –OH is unaffected under these mild acidic conditions. **Product:** 4-(chloromethyl)phenol

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Chemistry > Organic Chemistry > Haloalkanes And Haloarenes

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