194k views
1 vote
Translate the given conformer from the wedge-dash drawing into its newman projection?

User Jane Wayne
by
7.3k points

1 Answer

5 votes

Final answer:

To translate a wedge-dash drawing into a Newman projection, you look down the bond between two carbon atoms, and represent substituents in regards to their dihedral angles, identifying configurations such as antiperiplanar, gauche, eclipsed, or synperiplanar.

Step-by-step explanation:

To translate a wedge-dash drawing into a Newman projection, imagine yourself looking straight down the bond that connects the two carbon atoms of interest.

The carbon atom that is closer to you will be represented by a dot at the center of the Newman projection, while the carbon atom further away will be represented by a circle. Atomic substituents attached to these carbon atoms will be drawn as lines protruding from the dot or the circle.

In a Newman projection, the angle between substituents on the front and back carbons, known as the dihedral angle, allows us to identify the different conformations: antiperiplanar (anti), gauche, eclipsed, or synperiplanar (cis).

The antiperiplanar configuration has a dihedral angle of 180°, and substituents are staggered directly opposite each other. The gauche configuration has substituents at a 60° angle, and in the eclipsed conformation, substituents are aligned with a 0° angle. The synperiplanar configuration is similar to eclipsed but with substituents on the same side, making a dihedral angle of 120°.

User Nbz
by
7.4k points