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Ch. 8 - Alkenes I: Properties and Electrophilic Additions
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
Chapter 7, Problem 60c

Given the name, draw the structure of the following compounds.
(c) (3S,6Z)-8-ethyl-3-iododeca-1,5-diene

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Step 1: Break down the name of the compound systematically. The name '(3S,6Z)-8-ethyl-3-iododeca-1,5-diene' provides stereochemical information, substituents, and the main chain structure. The main chain is 'deca,' indicating a 10-carbon chain. The '1,5-diene' indicates double bonds at positions 1 and 5.
Step 2: Identify the substituents and their positions. The substituents are '8-ethyl' (an ethyl group at carbon 8) and '3-iodo' (an iodine atom at carbon 3). These need to be added to the main chain at the specified positions.
Step 3: Incorporate stereochemistry. The '(3S)' indicates that the configuration at carbon 3 is 'S' (using the Cahn-Ingold-Prelog priority rules). The '(6Z)' indicates that the double bond at position 6 has the 'Z' configuration, meaning the higher-priority groups on either side of the double bond are on the same side.
Step 4: Draw the main chain with the double bonds. Start by sketching a 10-carbon chain with double bonds at positions 1 and 5. Ensure the double bond at position 5 has the 'Z' configuration.
Step 5: Add the substituents and stereochemistry. Place the ethyl group at carbon 8 and the iodine atom at carbon 3. Adjust the stereochemistry at carbon 3 to match the 'S' configuration. Verify that all bonds, substituents, and stereochemical configurations are correctly 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 properties and reactions. In the given compound, the '3S' notation indicates the specific three-dimensional configuration of the chiral center at carbon 3, which is crucial for accurately drawing the structure.
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Geometric Isomerism

Geometric isomerism refers to the different spatial arrangements of atoms in a molecule that can occur due to restricted rotation around double bonds. The '6Z' in the compound's name indicates that the substituents on the double bond at carbon 6 are on the same side, which is essential for determining the correct structure of the diene.
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IUPAC Nomenclature

IUPAC nomenclature is a systematic method for naming organic chemical compounds. The name '(3S,6Z)-8-ethyl-3-iododeca-1,5-diene' provides information about the compound's structure, including the position of substituents (ethyl and iodine), the type of bonds (double bonds), and the overall carbon chain length, which is vital for constructing the correct molecular structure.
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