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Translate the wedge‐and‐hashed structure to its Fischer projection

A) Rotate the structure 180 degrees
B) Rotate the structure 90 degrees clockwise
C) Swap the groups on the wedge and hashed lines
D) Swap the horizontal and vertical lines

User Schmalzy
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Final answer:

To translate a wedge-and-hashed structure to a Fischer projection, bonds towards the viewer are drawn horizontally and away from the viewer vertically in the projection. The lowest priority group is brought to a vertical line for stereochemical assignment. A 90-degree clockwise rotation of the Fischer projection is used to convert it to a Haworth projection.

Step-by-step explanation:

To translate a wedge-and-hashed structure to its Fischer projection, the correct sequence of actions should include viewing the central atom such that the bonds extending towards the viewer (wedges) are placed horizontally and the bonds extending away from the viewer (hashed lines) are drawn vertically. In Fischer projections, the horizontal lines represent bonds coming forward, towards the viewer, and the vertical lines represent bonds going backward.

When dealing with chirality and stereochemistry, orienting the lowest priority group (usually labeled #4) correctly is crucial for assigning the R or S configuration. If the lowest priority group is on a hashed wedge, it should be swapped with the group on the opposite side to bring it onto a vertical line in the Fischer projection. Then, an arrow is drawn from the highest priority group (#1) through the second (#2) and third (#3) highest priorities. If two groups are swapped during this process, the final chirality assignment should be reversed compared to the direction of the arrow (counterclockwise becomes R and clockwise becomes S).

In cyclic conformation transformations, such as converting a Fisher projection to a Haworth projection, a 90-degree clockwise rotation to the Fisher projection may be applied first, followed by adjustments to ensure the cyclic structure reflects the correct orientation of substituents as per the Haworth convention.

User Mouseroot
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