Question

for the substituted cyclohexane compound shown, identify the atoms that are cis to the hydroxyl (oh) substituent.

Explanation:

In cyclohexane chair conformations, substituents are cis if they are on the same face (both axial-up/equatorial-up or axial-down/equatorial-down) of the ring. The hydroxyl (OH) group is on an equatorial (up-facing) position.

• H (A): Axial down (opposite face, trans)
• CH₃ (E): Axial up (same face, cis)
• Cl (D): Equatorial down (opposite face, trans)
• F (C): Axial up (same face, cis)
• H (B): Equatorial down (opposite face, trans)
• H (F): Equatorial up (same face, cis)
• Br (H): Axial down (opposite face, trans)
• H (I): Equatorial down (opposite face, trans)
• Cl (K): Axial up (same face, cis)
• H (J): Equatorial up (same face, cis)
• F (G): Axial down (opposite face, trans)

Atoms on the same face as OH are cis to it.

Answer:

E (CH₃), C (F), F (H), K (Cl), J (H)