Draw the structure that corresponds to the name provided. (c) (2E,4S,6Z)-octa-2,6-dien-4-ol
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Step 1: Break down the name systematically. The name '(2E,4S,6Z)-octa-2,6-dien-4-ol' provides information about the molecule's structure, including the number of carbons, the presence of double bonds, stereochemistry, and functional groups. 'Octa' indicates an 8-carbon chain, 'dien' specifies two double bonds, and 'ol' indicates the presence of an alcohol group (-OH).
Step 2: Identify the positions of the double bonds and their stereochemistry. The '2E' and '6Z' indicate the configuration of the double bonds at carbons 2 and 6, respectively. 'E' (entgegen) means the substituents on the double bond are on opposite sides, while 'Z' (zusammen) means they are on the same side. Use this information to correctly orient the double bonds.
Step 3: Determine the stereochemistry at carbon 4. The '4S' indicates the stereochemistry at the chiral center on carbon 4. Assign priorities to the substituents around carbon 4 based on the Cahn-Ingold-Prelog rules and ensure the configuration matches the 'S' (sinister) designation.
Step 4: Place the functional group. The '-ol' suffix specifies an alcohol group (-OH) attached to carbon 4. Ensure the hydroxyl group is correctly positioned on the chiral center while maintaining the '4S' stereochemistry.
Step 5: Assemble the structure. Combine all the information: an 8-carbon chain, double bonds at positions 2 and 6 with 'E' and 'Z' configurations, respectively, and an alcohol group at carbon 4 with 'S' stereochemistry. Draw the structure ensuring all bonds, stereochemistry, and functional groups are accurately represented.
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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 given compound, the stereochemical descriptors (E/Z and S) indicate the specific configurations of the double bonds and chiral centers, respectively. Understanding these configurations is crucial for accurately drawing the molecular structure.
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the name provided, 'ol' indicates the presence of a hydroxyl (-OH) group, which defines the compound as an alcohol. Recognizing functional groups helps in predicting the reactivity and properties of the compound.
Nomenclature in organic chemistry refers to the systematic naming of chemical compounds based on their structure and functional groups. The name '(c) (2E,4S,6Z)-octa-2,6-dien-4-ol' provides information about the carbon chain length, the position of double bonds, stereochemistry, and the presence of the alcohol functional group. Mastery of nomenclature is essential for translating names into structural representations.