See image — GOC and Organic Chemistry Basics Chemistry Question

💡 Solution & Explanation

**Analysis of C-Br Bond Ionization** To determine ease of ionization (C-Br bond cleavage), consider what stabilizes the resulting carbocation. **Structure Assessment:** - **I.** $R-O-CH_2-Br$ → Cleavage gives $R-O-CH_2^+$ (carbocation stabilized by oxygen's lone pair via resonance) - **II.** $R-CH_2-CH_2-Br$ → Cleavage gives $R-CH_2-CH_2^+$ (primary carbocation, no stabilization) - **III.** $R-N(CH_3)-CH_2-Br$ → Cleavage gives $R-N(CH_3)-CH_2^+$ (carbocation stabilized by nitrogen's lone pair via resonance) **Stability Order:** Both oxygen and nitrogen can stabilize adjacent carbocations through lone-pair donation. Nitrogen is more polarizable and a better electron donor than oxygen, making the carbocation in **III** more stable than in **I**. The primary carbocation in **II** is least stable. $$\text{Carbocation stability: III} > \text{I} > \text{II}$$ Since more stable carbocations form more readily: $$\text{Ease of ionization: III} > \text{I} > \text{II}$$ **Answer: (B) III > I > II**