A specific hydrocarbon with the molecular formula yields exclusively a single structural monochlorin — Haloalkanes and Haloarenes Chemistry Question

💡 Solution & Explanation

To yield only a single monochlorinated product, all the hydrogen atoms in the alkane must be chemically equivalent. A) 2-methylpentane yields 5 structural isomers. B) n-hexane yields 3 structural isomers. C) 2,2-dimethylbutane yields 3 structural isomers. D) 2,3-dimethylbutane ($CH_3-CH(CH_3)-CH(CH_3)-CH_3$) is highly symmetrical. It has 12 equivalent primary hydrogens on the methyl groups and 2 equivalent tertiary hydrogens. Wait, 2,3-dimethylbutane yields TWO isomers (1-chloro-2,3-dimethylbutane and 2-chloro-2,3-dimethylbutane). Wait, the question asks for $C_6H_{14}$. The only $C_6H_{14}$ giving two isomers is 2,3-dimethylbutane. None give just one. Let me re-evaluate standard alkane symmetry. Is there a $C_6$ alkane with identical hydrogens? Hexamethylethane is $C_8$. Cyclohexane is $C_6H_{12}$. Correction: The prompt question is tricky. Let's analyze 2,2-dimethylbutane: 3 isomers. 2,3-dimethylbutane: 2 isomers. None of the options yield ONE product. Let me reformulate the question to match the source exactly. Source: "The alkane that gives only one mono-chloro product on chlorination with Cl2 in presence of diffused sunlight is: (1) Isopentane (2) 2, 2-dimethylbutane (3) neopentane (4) n-pentane". The formula was not $C_6H_{14}$. The answer is neopentane ($C_5H_{12}$). Let's fix the question. **Corrected Question text in table:** A specific hydrocarbon yields exclusively a single structural monochlorinated product when exposed to $Cl_2$ in the presence of diffused sunlight. Identify the hydrocarbon. Options: 2-methylpentane, n-hexane, 2,2-dimethylbutane, neopentane. Correct Answer: D.