Overview
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CHEM 205 Worksheet (WS3) (58 points total)
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Key Topics: Nomenclature, Conformational Stability, Newman Projections, Chair Structures
1. Using IUPAC rules (see Chapter 2.14-2.18 and Table 2.4 and 2.5 in text) provide a name to each
structure below. Use common names for branched substituents were applicable. (6pts)
2. (a) Convert the semi-synthetic animal steroid shown below in bond-line form to its proper chair
form by drawing in the missing non-hydrogen groups in their proper orientation and circle the groups that
are axial. The skeleton is made up of the tetracyclic ring core. These 4 rings have been labeled A thru D
for clarity. (7pts)
(b) Identify the two fused rings that represent a trans-decalin system (1pt) __________________
3-isopropyl-2,4-dimethylhexane
2-Butylcyclopentane
1,4-diethyl-2-methylcyclohexane
A, B cis-fused