Gestrinone is a synthetic steroid hormone that is marketed as a treatment for endometriosis. What is the index of hydrogen deficiency (IHD)–or degree of unsaturation–for gestrinone?

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Correct Answer: B. 10
Recall that the degrees of unsaturation corresponds to the sum of pi bonds and/or rings present in a molecule. Each ring and each pi bond contributes one degree of unsaturation; triple bonds, possessing one sigma and two pi bonds, contribute two degrees of unsaturation. Gestrinone has four rings (4), three alkenes (3), one carbonyl (1) and one alkyne (2). Thus IHD = 4 + 3 + 1 + 2 = 10
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