Twisting stereoisomers with rings to determine R/S
Rotating structures is a recipe for disaster because errors in transcription will invariable occur. Use the best chirality tool you have---your hands. Leave the structure where it is! Use either hand to make a "thumbs up" gesture. Point your thumb in the direction of the lowest priority group. The remaining fingers should point in the direction of the highest to next to lowest priority group (OH>C2H5 >CH3). If not, you are using the wrong hand. Left hand = S. Right hand = R. Try to rotate structures 1-3 and see how it compares with the "hand method". Structures 1-3 are of the S-configuration. Cyclopentene 4 is Jon's structure with substituents. It is of the R-configuration (=CH>CH2>CH3), a conclusion reached without redrawing the structure.