IUPAC and NomenclaturemediumSUBJECTIVE

See imageIUPAC and Nomenclature Chemistry Question

Question

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Answer: 3-BROMO-N-(2-BROMOETHYL)-4-CHLOROPENTANAMIDE

💡 Solution & Explanation

Step 1: Identify the parent chain. The compound contains an amide group (C=O connected to NH), so the parent chain is named as an alkanamide. Counting the carbons in the longest chain that includes the carbonyl carbon: C1(=O)-C2H2-C3H(Br)-C4H(Cl)-C5H3 (methyl). This gives a 5-carbon chain: pentanamide. Step 2: Identify substituents on the main chain. At C3, there is a bromine substituent. At C4, there is a chlorine substituent. The chain terminates with a methyl group at C5, confirming pentanamide. Step 3: Number the chain. In amide nomenclature, C1 is the carbonyl carbon. Moving along the chain: C1 (carbonyl), C2 (CH2), C3 (CHBr), C4 (CHCl), C5 (CH3). So bromine is at C3 and chlorine is at C4. Step 4: Identify the substituent on nitrogen. The NH is connected to CH2CH2Br, which is a 2-bromoethyl group. This is denoted with the prefix N-(2-bromoethyl). Step 5: Assemble the name. Combining all parts: the parent chain is pentanamide, with bromo at C3, chloro at C4, and N-(2-bromoethyl) substituent. Alphabetical order of substituents: bromo, chloro. Full name: 3-bromo-N-(2-bromoethyl)-4-chloropentanamide. Therefore, the correct answer is 3-bromo-N-(2-bromoethyl)-4-chloropentanamide.

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