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Ch. 25 - Amines: Structure, Reactions, and Synthesis
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
Chapter 24, Problem 8c

Given the following names, draw the structure of the molecule.
c. (S)-2-methyloctan-4-amine

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1
Step 1: Identify the parent chain. The name '2-methyloctan-4-amine' indicates that the parent chain is 'octane,' which consists of 8 carbon atoms in a straight chain.
Step 2: Locate the substituents. The '2-methyl' group indicates a methyl (-CH₃) substituent attached to the second carbon of the octane chain. The '4-amine' indicates an amino (-NH₂) group attached to the fourth carbon.
Step 3: Assign stereochemistry. The '(S)' configuration specifies the absolute stereochemistry at the chiral center. The chiral center is located at the fourth carbon (where the amino group is attached). Use the Cahn-Ingold-Prelog priority rules to assign the (S) configuration.
Step 4: Draw the structure. Begin by sketching the octane chain, then add the methyl group at carbon 2 and the amino group at carbon 4. Ensure the stereochemistry at carbon 4 matches the (S) configuration by arranging the substituents in 3D space appropriately.
Step 5: Double-check the structure. Verify that the molecule adheres to the IUPAC name, including the correct placement of substituents, the correct number of carbons in the chain, and the proper stereochemistry.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Stereochemistry

Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the context of (S)-2-methyloctan-4-amine, the 'S' designation indicates that the molecule has a specific three-dimensional configuration at the chiral center, which is crucial for understanding its properties and reactivity.
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Chirality

Chirality refers to the geometric property of a molecule that makes it non-superimposable on its mirror image, much like left and right hands. In (S)-2-methyloctan-4-amine, the presence of a chiral center at the second carbon atom means that the molecule can exist in two enantiomeric forms, which can have different biological activities and interactions.
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IUPAC Nomenclature

IUPAC nomenclature is a systematic method for naming organic chemical compounds. The name (S)-2-methyloctan-4-amine indicates the structure of the molecule, where 'octan' refers to an eight-carbon chain, '2-methyl' indicates a methyl group on the second carbon, and '4-amine' signifies an amine functional group on the fourth carbon, guiding the drawing of the correct molecular structure.
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