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Ch.5 - Stereochemistry
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook
All textbooksWade 9th EditionCh.5 - StereochemistryProblem 23b
Chapter 5, Problem 23b

Which of the following pairs of compounds could be separated by recrystallization or distillation?
(b)

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Step 1: Analyze the chemical structures of the two compounds provided in the image. Both compounds are esters with similar functional groups, but their structural arrangement differs slightly. One compound has the ethyl group attached to the oxygen atom, while the other has the ethyl group attached to the carbon atom.
Step 2: Consider recrystallization as a separation method. Recrystallization is effective for separating compounds with different solubilities in a given solvent. Evaluate whether the two compounds have significantly different solubility properties based on their structural differences.
Step 3: Consider distillation as a separation method. Distillation is effective for separating compounds with different boiling points. Analyze the boiling points of the two compounds, which depend on factors such as molecular weight, intermolecular forces, and structural arrangement.
Step 4: Determine the feasibility of separation by recrystallization or distillation. If the compounds have sufficiently different solubilities or boiling points, they can be separated using these methods. If the differences are minimal, alternative methods such as chromatography may be required.
Step 5: Conclude the analysis by identifying the most suitable separation method based on the structural and physical properties of the compounds. Provide reasoning for why recrystallization or distillation would be effective or ineffective in this case.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Recrystallization

Recrystallization is a purification technique used to separate compounds based on their solubility differences. In this process, a solid compound is dissolved in a hot solvent, and as the solution cools, the compound crystallizes out, leaving impurities in solution. The effectiveness of recrystallization depends on the solubility of the compounds at different temperatures.

Distillation

Distillation is a separation technique that exploits differences in boiling points of compounds. In this method, a mixture is heated to vaporize the more volatile component, which is then condensed back into liquid form. This technique is particularly useful for separating liquids or volatile compounds from non-volatile impurities or other liquids with significantly different boiling points.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the context of the provided compounds, the presence of hydroxyl (-OH) and carbonyl (C=O) groups influences their physical properties, such as boiling points and solubility, which are critical for determining the feasibility of separation methods like recrystallization and distillation.
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Textbook Question

Which of the following pairs of compounds could be separated by recrystallization or distillation?

a. meso-tartaric acid and (±)-tartaric acid (HOOC—CHOH—CHOH—COOH)

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Textbook Question
Which configuration (R or S) does the bottom asymmetric carbon have for the D series of sugars? Which configuration for the L series?
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Textbook Question

Which of the following pairs of compounds could be separated by recrystallization or distillation?

(c)

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Textbook Question
Draw the mirror images of glucose and fructose. Are glucose and fructose chiral? Do you expect them to be optically active?
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Textbook Question

The following four structures are naturally occurring optically active compounds. Star (*) the asymmetric carbon atoms in these structures.

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Textbook Question

To show that (R)-2-butyl (R,R)-tartrate and (S)-2-butyl (R,R)-tartrate are not enantiomers, draw and name the mirror images of these compounds.

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