Question 31.19 - Organic Chemistry

Question

Convert the ball-and-stick model of androsterone to (a) a skeletal structure using wedges and dashed wedges around all stereogenic centers; and (b) a three-dimensional representation using chair cyclohexane rings.

Step-by-Step Solution

Answer

Answer

(a)

(b)

Step-by-Step Solution Step 1: Androsterone

Androsterone is a natural organic compound with a chemical formula ${\mathbf{C}}_{\mathbf{19}}{\mathbf{H}}_{\mathbf{30}}{\mathbf{O}}_{\mathbf{2}}$. It contains four cyclic rings (three 6-membered and one 5-membered), one OH group, and one C-O double bond.

At the 17^th position, the carbonyl group is present.

Step 2: A skeletal structure of androsterone

(a) The skeletal structure of androsterone is drawn as:

Skeletal structure of androsterone

Step 3: A three-dimensional representation of androsterone using chair cyclohexane rings

(b) The chair cyclohexane rings of androsterone are shown as:

Chair conformation of androsterone