Draw the correct structure from the following IUPAC names: (a) (4R,2Z)-4-methylhex-2-en-1-ol
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Step 1: Begin by identifying the longest carbon chain in the IUPAC name. The name 'hex-2-en-1-ol' indicates a six-carbon chain (hexane) with a double bond at the second carbon (en) and an alcohol group at the first carbon (ol).
Step 2: Draw the six-carbon chain. Number the carbons from 1 to 6, starting from the end closest to the alcohol group. This ensures the alcohol group is on the first carbon.
Step 3: Add the double bond between carbon 2 and carbon 3. The '2Z' configuration indicates that the higher priority groups on each carbon of the double bond are on the same side. Use the Cahn-Ingold-Prelog priority rules to determine the priority of the groups attached to these carbons.
Step 4: Introduce the methyl group at carbon 4. The '4R' configuration specifies the stereochemistry at this carbon. Use the Cahn-Ingold-Prelog priority rules to assign the R configuration, ensuring the groups are arranged in a clockwise manner when viewed from a specific angle.
Step 5: Finally, add the hydroxyl group (-OH) to carbon 1, completing the structure. Double-check the placement of all groups and the stereochemistry to ensure accuracy.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
IUPAC Nomenclature
IUPAC nomenclature is a standardized system for naming chemical compounds. It provides a systematic way to describe the structure of a molecule using specific rules and conventions. Understanding IUPAC names involves recognizing prefixes, suffixes, and locants that indicate the type and position of functional groups and substituents in the molecule.
Stereochemistry involves the study of the spatial arrangement of atoms in molecules. Terms like (4R) and (2Z) in the IUPAC name indicate stereochemical configurations. 'R' and 'S' refer to the absolute configuration of chiral centers, while 'E' and 'Z' describe the geometry of double bonds, crucial for determining the correct 3D structure of the compound.
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the given IUPAC name, 'en' indicates an alkene (double bond), and 'ol' signifies an alcohol group. Recognizing these groups helps in constructing the molecular structure and understanding its chemical behavior.