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Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
Chapter 18, Problem 10e

Provide a molecular structure that corresponds to the given name.
(e) (R)-N,N-diethyl 5-cyclohexyl-3-methoxypentanamide

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1
Identify the main functional group in the compound name, which is 'pentanamide'. This indicates the presence of a five-carbon chain with an amide group (\( \text{CONH}_2 \)).
Determine the substituents on the main chain. The name specifies '3-methoxy', meaning a methoxy group (\( \text{OCH}_3 \)) is attached to the third carbon of the pentanamide chain.
Locate the '5-cyclohexyl' group, which indicates a cyclohexyl group (a six-carbon ring) is attached to the fifth carbon of the pentanamide chain.
Consider the 'N,N-diethyl' prefix, which means two ethyl groups (\( \text{C}_2\text{H}_5 \)) are attached to the nitrogen atom of the amide group.
Ensure the stereochemistry is correct by assigning the (R) configuration at the chiral center. This involves prioritizing the groups attached to the chiral center according to the Cahn-Ingold-Prelog rules and arranging them to determine the (R) configuration.

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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 involves identifying the longest carbon chain, functional groups, and substituents, and arranging them according to specific rules. Understanding this system is crucial for interpreting and constructing molecular structures from chemical names.
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The different parts of an IUPAC name

Stereochemistry

Stereochemistry involves the study of the spatial arrangement of atoms in molecules. The '(R)' designation in the compound name indicates the configuration of the chiral center, which affects the molecule's 3D structure and properties. Recognizing stereochemistry is essential for accurately depicting the molecular structure.
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Functional Groups

Functional groups are specific groups of atoms within molecules that determine the chemical properties and reactions of those molecules. In the given compound, groups like 'N,N-diethyl', 'methoxy', and 'pentanamide' define the molecule's reactivity and interactions. Identifying these groups helps in constructing the correct molecular structure.
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