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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
Chapter 12, Problem 7b

Draw the structure that corresponds to the name provided.
(b) (2R,3R,4S)-heptane-2,3,4-triol

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Step 1: Understand the name of the compound. The name '(2R,3R,4S)-heptane-2,3,4-triol' indicates a heptane backbone (a seven-carbon chain) with three hydroxyl (-OH) groups attached at positions 2, 3, and 4. The stereochemistry (R or S) at each of these positions is specified.
Step 2: Draw the heptane backbone. Start by sketching a straight chain of seven carbon atoms, ensuring each carbon is connected by single bonds.
Step 3: Add the hydroxyl (-OH) groups. Attach an -OH group to the second, third, and fourth carbon atoms in the chain. These are the functional groups that make the compound a triol.
Step 4: Assign stereochemistry. Use wedge and dash bonds to represent the stereochemistry at positions 2, 3, and 4. For (2R), the substituents on the second carbon should be arranged such that the configuration matches the R designation. Similarly, for (3R) and (4S), arrange the substituents on the third and fourth carbons to match their respective stereochemical designations.
Step 5: Verify the structure. Double-check that the stereochemistry matches the given (2R,3R,4S) configuration and that the hydroxyl groups are correctly placed on the heptane backbone. Ensure all other hydrogens are added to satisfy the valency of each carbon atom.

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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 context of the given compound, the (2R,3R,4S) notation indicates specific configurations at the chiral centers, which are crucial for determining the molecule's three-dimensional shape and properties.
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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 (2R,3R,4S)-heptane-2,3,4-triol, the 'triol' suffix indicates the presence of three hydroxyl (-OH) groups, which significantly influence the compound's reactivity and solubility.
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IUPAC Nomenclature

IUPAC nomenclature is a systematic method for naming organic chemical compounds. It provides a way to convey the structure of a compound through its name, as seen in (2R,3R,4S)-heptane-2,3,4-triol, where the name indicates the carbon chain length (heptane) and the positions and configurations of the hydroxyl groups, allowing chemists to deduce the molecular structure.
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