IUPAC and NomenclaturemediumSUBJECTIVE

See imageIUPAC and Nomenclature Chemistry Question

Question

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Chemistry diagram for: See image
Answer: 3-BROMO-4,5-DICHLORO-N-(2-CHLOROETHYL)HEXANAMIDE

💡 Solution & Explanation

Step 1: Identify the parent chain. The longest carbon chain containing the principal characteristic group (amide C=O) is hexanamide (6 carbons: C1=carbonyl carbon through C6=terminal methyl). Step 2: Number the chain. C1 is the carbonyl carbon of the amide. Going along the chain: C1(C=O)-C2(H2)-C3(HBr)-C4(HCl)-C5(HCl)-C6(H3). Step 3: Identify substituents on the main chain. At C3: bromine (bromo). At C4: chlorine (chloro). At C5: chlorine (chloro). Step 4: Identify the N-substituent. The nitrogen bears a 2-chloroethyl group (-CH2CH2Cl), so the N-substituent is N-(2-chloroethyl). Step 5: Assemble the IUPAC name. Parent chain = hexanamide. Substituents listed alphabetically: bromo (C3), dichloro (C4, C5). Full name: 3-bromo-4,5-dichloro-N-(2-chloroethyl)hexanamide. Step 6: Verify locants. C3-Br, C4-Cl, C5-Cl, C6-CH3 — consistent with hexanamide backbone and the structure drawn. No other naming possibilities arise because the amide group fixes C1 and the chain length is unambiguously 6. Therefore, the correct answer is 3-bromo-4,5-dichloro-N-(2-chloroethyl)hexanamide.

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