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Three-Dimensional Representations

Assigning Priorities

Determining Stereochemical Relationships

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Three-Dimensional Representations: Cyclic Wedge-Dash Notation

Wedge-Dash Notation is also commonly used for cyclic systems. As with straight chains, cyclic Wedge-Dash Notation has two bonds drawn in the plane of the page (sticks), one bond drawn coming toward you, out of the page and above the ring (wedged), and one bond drawn going away from you, behind the page and below the ring (dashed). It is important to note that groups with the same orientation (both wedged or both dashed) are cis to one another, and groups with opposite orientations (one wedged and one dashed) are trans to one another.

In the structure above, the methyl group is behind the page. Since there must be four bonds to each carbon, and two sticks and one dash have already been drawn in, the remaining hydrogen must be wedged.

A similar analysis can be done for the carbons with the alcohol and the bromine. What is the orientation of the remaining hydrogens on these carbons?

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