Skip to main content
Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination
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. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 87d
Chapter 12, Problem 87d

Draw the correct structure from the following IUPAC names:
(d) (2R,3S)-methoxy-3-methylpentane

Verified step by step guidance
1
Start by identifying the longest carbon chain in the name, which is 'pentane'. This indicates a five-carbon chain.
Locate the substituents on the main chain. The name indicates a 'methoxy' group and a 'methyl' group. The 'methoxy' group is an -OCH₃ group, and the 'methyl' group is a -CH₃ group.
Determine the positions of the substituents. The '3-methyl' indicates a methyl group attached to the third carbon, and 'methoxy' is not numbered, so it is assumed to be on the second carbon.
Consider the stereochemistry indicated by (2R,3S). The 'R' and 'S' configurations refer to the absolute configuration of the chiral centers. Use the Cahn-Ingold-Prelog priority rules to assign the correct stereochemistry to the second and third carbon atoms.
Draw the structure by placing the substituents on the correct carbons and ensuring the stereochemistry is accurately represented. The second carbon should have the 'R' configuration, and the third carbon should have the 'S' configuration.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above.
Was this helpful?

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 numbers that indicate the type and position of functional groups and substituents in the molecule.
Recommended video:
Guided course
03:43
The different parts of an IUPAC name

Stereochemistry

Stereochemistry involves the study of the spatial arrangement of atoms in molecules and its impact on chemical properties. The terms '2R,3S' refer to the configuration of chiral centers in the molecule, where 'R' and 'S' denote the absolute configuration based on the Cahn-Ingold-Prelog priority rules. Correctly identifying these configurations is crucial for drawing the accurate 3D structure.
Recommended video:
1:38
Polymer Stereochemistry Concept 1

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the given compound, 'methoxy' refers to an -OCH3 group, which is an ether functional group. Recognizing and placing functional groups correctly is essential for constructing the molecular structure from the IUPAC name.
Recommended video:
Guided course
02:36
Identifying Functional Groups
Related Practice
Textbook Question

Draw the correct structure from the following IUPAC names:

(a) (4R,2Z)-4-methylhex-2-en-1-ol

2
views
Textbook Question

Draw the correct structure from the following IUPAC names:

(b) 4-methoxybut-1-yne

1
views
Textbook Question

Draw the correct structure from the following IUPAC names:

(f) (S)-4-isopropoxypent-2-yne.

1
views
Textbook Question

Draw the correct structure from the following IUPAC names:

(c) (1S,4R)-4-bromocyclohex-2-en-1-ol

2
views
Textbook Question

Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (iii) H2SO4 , H2O . If there is no reaction, write 'no reaction.'

(a)

6
views
Textbook Question

Draw the correct structure from the following IUPAC names:


(e) (R)-2,2-dimethyl-1-phenylpropane-1-thiol

2
views