Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

5. Chirality

Constitutional Isomers vs. Stereoisomers

Organic Chemistry

5. Chirality

Constitutional Isomers vs. Stereoisomers

Previous problemNext problem

3:31 minutes

Problem 23b

Textbook Question

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

Verified step by step guidance

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.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

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.

Watch next

Master Determining when molecules are different. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

b. Draw the six stereoisomers of octa-2,4,6-triene. Explain why there are only six stereoisomers, rather than the eight we might expect for a compound with three stereogenic double bonds.

Textbook Question

Draw the six stereoisomers of octa-2,4,6-triene. Explain why there are only six stereoisomers, rather than the eight we might expect for a compound with three stereogenic double bonds.

Textbook Question

For each pair, give the relationship between the two compounds. Making models will be helpful.

(c)

(d)

Textbook Question

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

Textbook Question

How many would there be if stereoisomers are included?

Textbook Question

Draw the enantiomer of each of the molecules you drew in Assessment 6.52.

Textbook Question

Draw all possible stereoisomers for each of the following. Indicate those compounds for which no stereoisomers are possible.