Ch. 5 - ChiralityWorksheetSee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins

Solution: Give the IUPAC name, including stereochemistry of the compound below

Problem

Give the IUPAC name, including stereochemistry of the compound below

Solution

We’re being asked to name the given structure using IUPAC nomenclature with the correct stereochemistry.



We can see that this is a chiral molecule because:

– there is no plane of symmetry present

– there is a chiral center present


Recall that the R/S configuration gives us the absolute stereochemistry of chiral centers. It involves:

Step 1: Name the structure without R/S configuration.


Step 2: Determine the priority of groups at the chiral center.

• Priority is determined using atomic mass.

• If the same atom is present, we compare the other atoms it is bonded to.

– Double and triple bonds count twice/thrice.


Step 3: Determine the R/S configuration of the chiral center.

• If the lowest priority is on a dashed line: trace a path from 1 to 3

– If the order is clockwise R (rectus or right)

– If the order is counterclockwise S (sinister or left)


• If the lowest priority is not on a dashed line: swap with the group on a dashed line

– Trace a path from 1 to 3:

– Clockwise R becomes S because of the swap

– Counterclockwise S becomes R because of the swap


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