Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids

Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition

Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Non è quello che usi tu?Cambia libro di testo

Mullins 1st Edition

Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids

Problema 7c

Capitolo 26, Problema 7c

Draw Fischer projections of the following molecules.
(c)

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Step 1: Understand the structure provided. The molecule has an amine group (NH₂) attached to a chiral carbon, along with a phenyl group (Ph) and a methyl group (CH₃). The dashed wedge indicates that the NH₂ group is oriented away from the viewer.

Step 2: Recall the rules for drawing Fischer projections. In a Fischer projection, the horizontal lines represent bonds coming out of the plane (towards the viewer), and the vertical lines represent bonds going into the plane (away from the viewer). The chiral carbon is at the intersection of the lines.

Step 3: Assign priorities to the substituents based on the Cahn-Ingold-Prelog rules. The NH₂ group has the highest priority, followed by the phenyl group (Ph), the methyl group (CH₃), and finally the hydrogen atom.

Step 4: Orient the molecule so that the lowest priority group (hydrogen) is on the vertical line pointing away from the viewer. This ensures the correct stereochemistry is represented in the Fischer projection.

Step 5: Draw the Fischer projection. Place the NH₂ group and the phenyl group on the horizontal lines (coming out of the plane), and the methyl group and hydrogen on the vertical lines (going into the plane). Ensure the stereochemistry matches the original molecule.

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Fischer Projections

Fischer projections are a two-dimensional representation of three-dimensional organic molecules, particularly useful for depicting stereochemistry. In these diagrams, vertical lines represent bonds that project behind the plane of the page, while horizontal lines represent bonds that project out towards the viewer. This format is especially common for carbohydrates and amino acids, allowing for easy visualization of chiral centers and their configurations.

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Monosaccharides - Drawing Fischer Projections

Chirality and Stereocenters

Chirality refers to the property of a molecule that makes it non-superimposable on its mirror image, often due to the presence of one or more stereocenters. A stereocenter is typically a carbon atom bonded to four different substituents, leading to two possible configurations (R and S). Understanding chirality is crucial for accurately drawing Fischer projections, as it determines the spatial arrangement of the substituents around the stereocenter.

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Determining Chirality using Stereocenter

Configuration Notation (R/S)

The R/S notation is a system used to specify the absolute configuration of chiral centers in molecules. To assign R (rectus) or S (sinister) configuration, one must prioritize the substituents attached to the stereocenter based on atomic number, with higher atomic numbers receiving higher priority. This systematic approach is essential for accurately representing the stereochemistry in Fischer projections and understanding the molecule's reactivity and interactions.

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R and S Naming- Step 4

Pratica correlata

Domanda del libro di testo

In this attempt to convert the line angle drawing of d-erythrose (shown) to the Fischer projection (shown), by viewing it from a certain direction (shown), a mistake was made. What was the mistake?

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Domanda del libro di testo

Convert each line-angle drawing, using appropriate bond rotations, into a correct Fischer projection.

(a)

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Domanda del libro di testo

Draw Fischer projections of the following molecules.

(a)

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