Isomerism and StereochemistryhardNUMERICAL

Determine the exact integer number of true chiral (stereogenic) centers present in the highly substiIsomerism and Stereochemistry Chemistry Question

Question

Determine the exact integer number of true chiral (stereogenic) centers present in the highly substituted cyclic molecule: Ethyl 2,2-dibromo-4-ethyl-6-methoxycyclohexanecarboxylate.

Answer: 3

💡 Solution & Explanation

Examining the cyclohexane ring's six carbons: C1 is bonded to $-COOEt$, $-H$, C2, and C6 (four different paths, making it chiral). C2 is bonded to two identical $-Br$ atoms, rendering it achiral. C3 and C5 are bonded to two identical $-H$ atoms (achiral). C4 is bonded to $-Ethyl$, $-H$, C3, and C5 (four different paths, chiral). C6 is bonded to $-OMe$, $-H$, C5, and C1 (four different paths, chiral). The total is exactly 3 chiral centers.

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