See image — Isomerism and Stereochemistry Chemistry Question
Question
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💡 Solution & Explanation
# IUPAC Naming of the Amino Acid Derivative **Step 1: Identify the parent chain** The main backbone contains 4 carbons in a chain with two carboxylic acid groups at positions 1 and 4: $$\text{COOH-C-C-C-COOH}$$ This gives the parent name: **butane-1,4-dioic acid** **Step 2: Locate and number the stereogenic centers** Starting from the carboxylic acid end (position 1): - Position 2: Has $-H$, $-NH_2$, $-COOH$, and $-CH(CONH_2)$ groups - Position 3: Has $-H$, $-CONH_2$, $-COOH$, and $-CH(NH_2)$ groups **Step 3: Assign stereochemistry using CIP rules** For position 2 ($R/S$ priority): - Group 1: $-COOH$ (highest priority) - Group 2: $-CH(CONH_2)COOH$ (carbon attached to C,C,N) - Group 3: $-NH_2$ - Group 4: $-H$ Tracing 1→2→3 gives **R configuration** at position 2. For position 3: Similarly analyzing priorities gives **R configuration** at position 3. **Step 4: Name substituents in alphabetical order** - Amino group at position 2 - Carbamoyl group ($-CONH_2$) at position 3 Alphabetically: **amino** comes before **carbamoyl** **Answer: (D) 2R, 3R-2-amino-3-carbamoyl butane-1,4-dioic acid** Both stereocenters have R configuration, and substituents are listed in correct alphabetical order.