Skip to main content
Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space
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
Tutti i libri di testoMullins 1st EditionCh. 6 - Stereoisomerism: Arrangement of Atoms in SpaceProblema 50a
Capitolo 5, Problema 50a

Assign the absolute stereochemistry for each of the following molecules drawn in their Fischer projection.
(a)

Guida verificata passo dopo passo
1
Step 1: Identify the chiral center in the molecule. In the given Fischer projection, the central carbon atom is the chiral center as it is bonded to four different groups: Br, Cl, H, and CH₃.
Step 2: Assign priorities to the substituents based on the Cahn-Ingold-Prelog priority rules. The priority is determined by atomic number: Br (atomic number 35) > Cl (atomic number 17) > CH₃ (carbon, atomic number 6) > H (atomic number 1).
Step 3: Orient the molecule so that the lowest priority group (H) is pointing away from you. In a Fischer projection, horizontal bonds represent groups coming out of the plane, and vertical bonds represent groups going into the plane. Here, H is on the horizontal line, so it is coming out of the plane.
Step 4: Determine the order of the remaining substituents (Br, Cl, CH₃) in terms of priority. Trace the path from the highest priority (Br) to the second (Cl) to the third (CH₃).
Step 5: Assign the stereochemistry based on the direction of the path traced. If the path is clockwise, the configuration is R. If the path is counterclockwise, the configuration is S. Since H is coming out of the plane, the configuration determined must be reversed.

Risposta video verificata per un problema simile:

Questa soluzione video è stata consigliata dai nostri tutor come utile per risolvere questo problema.

Concetti chiave

Ecco i concetti essenziali che devi comprendere per rispondere correttamente alla domanda.

Fischer Projections

Fischer projections are a two-dimensional representation of three-dimensional organic molecules, particularly useful for depicting stereochemistry in carbohydrates and amino acids. In these projections, vertical lines represent bonds that extend away from the viewer, while horizontal lines represent bonds that come towards the viewer. Understanding how to interpret Fischer projections is crucial for assigning stereochemistry accurately.
Video consigliato:
09:56
Monosaccharides - Drawing Fischer Projections

Absolute Stereochemistry

Absolute stereochemistry refers to the spatial arrangement of atoms in a molecule and is designated using the R/S system. This system is based on the Cahn-Ingold-Prelog priority rules, which assign priorities to substituents attached to a chiral center. By determining the configuration of these substituents, one can classify the stereocenter as either R (rectus) or S (sinister), which is essential for understanding the molecule's 3D structure.
Video consigliato:
Percorso guidato
1:38
Polymer Stereochemistry Concept 1

Chirality

Chirality is a property of a molecule that has non-superimposable mirror images, often due to the presence of chiral centers, typically carbon atoms bonded to four different substituents. This characteristic is fundamental in organic chemistry as it influences the behavior of molecules in biological systems, including their interactions and reactivity. Recognizing chirality is essential for accurately assigning absolute stereochemistry in molecules.
Video consigliato:
05:10
What is chirality?
Pratica correlata
Domanda del libro di testo

Assign the absolute stereochemistry for each of the following molecules drawn in their Fischer projection.

(d)

714
views
Domanda del libro di testo

Define the relationship between each set of two molecules as chain isomers, positional isomers, functional group isomers, enantiomers, diastereomers, conformational isomers, or identical

(f)

968
views
Domanda del libro di testo

Define the relationship between each set of two molecules as chain isomers, positional isomers, functional group isomers, enantiomers, diastereomers, conformational isomers, or identical

(e)

1128
views
Domanda del libro di testo

Assign the absolute stereochemistry for each of the following molecules.

(e)

1318
views
Domanda del libro di testo

Define the relationship between each set of two molecules as chain isomers, positional isomers, functional group isomers, enantiomers, diastereomers, conformational isomers, or identical

(h)

817
views
Domanda del libro di testo

Assign the absolute stereochemistry for each of the following molecules.

(f)

1172
views