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Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
All textbooksMullins 1st EditionCh. 10 - Alkynes: Electrophilic Addition and Redox ReactionsProblem 11b
Chapter 9, Problem 11b

Draw the structures that correspond to the following names.
(b) (3Z,8S)-8-ethyl-3-methylundec-3-en-6-yne

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Step 1: Break down the name systematically. The name '(3Z,8S)-8-ethyl-3-methylundec-3-en-6-yne' provides information about the structure. 'Undec' indicates the parent chain has 11 carbon atoms. '3-en' specifies a double bond at carbon 3, and '6-yne' specifies a triple bond at carbon 6.
Step 2: Analyze the stereochemistry. The '(3Z)' indicates the double bond at carbon 3 has the Z configuration (the higher priority groups are on the same side). The '(8S)' specifies the stereochemistry at carbon 8, which is in the S configuration.
Step 3: Add substituents to the parent chain. The '8-ethyl' means there is an ethyl group (-CH₂CH₃) attached to carbon 8, and '3-methyl' means there is a methyl group (-CH₃) attached to carbon 3.
Step 4: Place the double and triple bonds. Draw the 11-carbon chain, then add a double bond between carbons 3 and 4, ensuring the Z configuration. Next, add a triple bond between carbons 6 and 7.
Step 5: Confirm the stereochemistry and substituent placement. Verify that the ethyl group at carbon 8 is in the S configuration and the methyl group at carbon 3 is correctly positioned. Ensure the double bond at carbon 3 has the Z configuration.

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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 (3Z,8S) notation indicates specific stereochemical configurations at certain carbon centers, which are crucial for accurately drawing the structure.
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Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In this compound, the presence of an alkene (double bond) and an alkyne (triple bond) indicates the need to recognize these functional groups to understand the reactivity and properties of the molecule.
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IUPAC Nomenclature

IUPAC nomenclature is a systematic method of naming organic chemical compounds. The name provided includes information about the carbon chain length, branching, and the position of double and triple bonds, which is essential for constructing the correct molecular structure. Understanding this nomenclature is key to translating the name into a visual representation.
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