Challenge 1: Converting a staggered Newman projection to a wedge-and-dash structure

Question:

Translate the following Newman projection into a wedge-and-dash structure

Step 1: Decide the viewing angle

Before we dive in, we need to decide which angle we’re looking at the Newman projection from—left or right. This will determine how we position the substituents in our bond-line structure.

For this challenge, we’ll view the Newman projection from the right side. (Don’t worry—we’ll explore the left side in the next challenge.)

Step 2: Draw a carbon-carbon bond

In a Newman projection, you’re viewing the molecule by looking straight down a bond connecting two carbons—one in the front and one in the back.

To start, draw a single line to represent the bond between these two carbons.

To keep track of things, we’ll color the front carbon (and its substituents) and the back carbon (and its substituents). This color-coding helps us visualize which groups belong to which carbon.

Think of this bond as the backbone for the wedge-and-dash structure you’re about to create.

Step 3: Place the front carbon’s substituents

Now, let’s focus on the front carbon.

Take a look at the three groups attached to this carbon. In this example:

• A methyl group (CH₃) is pointing straight up.
• A bromine atom is pointing towards you.
• A fluorine atom is pointing away from you.

To draw these groups in a wedge-and-dash structure:

• Groups pointing up or down are in the plane of the page, so draw them as straight lines.
• Groups pointing towards you are drawn as wedges.
• Groups pointing away from you are drawn as dashes.

Step 4: Place the back carbon’s substituents

Finally, let’s focus on the back carbon. 

Just like before, look at the three groups attached to it. In this case:

• A ethyl group (CH₂CH₃) is pointing straight down.
• An OH group is pointing towards you.
• A methyl group (CH₃) is pointing away from you.

Using the same rules:

• Groups pointing up or down are drawn as straight lines.
• Groups pointing towards you are drawn as wedges.
• Groups pointing away from you are drawn as dashes.

Review your structure

Take a moment to compare your wedge-and-dash structure with the original Newman projection.

• Do the positions of the substituents match? Yes
• Are the wedges, dashes, and straight lines placed correctly? Yes

If everything checks out, congratulations—you’ve successfully converted a staggered Newman projection into a wedge-and-dash structure! 🎉