So I went ahead and took the luxury of pre-drawing this little diagram for you. It's very scientific. And, I thought that it would help you guys understand the rule of solubility, which is just that, like dissolves like. Alright? So you might have heard this in lab before, and all it means is this, this has to do with polarity. Okay? So remember that we learned how to figure out if molecules have a net dipole? That's all there is to it. We're going to figure out, okay, what we're dissolving or, yeah, what we're dissolving, is it going into something that has the same polarity as itself? So this is, you know, a very common scene from Friday night, maybe this was a few nights ago for you. You're pouring a bottle and you're pouring it into a cup of water, and you've got your ethanol little molecules spilling out, and they go into the water molecules, which are right down here. And you're not thinking for a second that they're gonna split apart and you're gonna have like alcohol on the top and water on the bottom. That would be really weird. In fact, what happens is that they just mix together and you can't even tell the difference, except you can tell the difference the next morning. You know that obviously you weren't just drinking water. So that has to do with the fact that both have the same polarity or similar polarity. Think about it. Water, let's just expand this a little bit. Water has a net dipole. Right? We said that the net dipole was pretty strong. Well, in the same way, ethanol also has a net dipole. Okay? So in this case, I drew it so that the net dipole would face the other direction, but it doesn't matter. It doesn't really matter what direction it's facing because obviously I could rotate that alcohol. The important thing is that they both have a strong net dipole. Since they're both polar, they're going to dissolve into each other. Okay? So that's the entire concept between like dissolves like.
- 1. A Review of General Chemistry5h 5m
- Summary23m
- Intro to Organic Chemistry5m
- Atomic Structure16m
- Wave Function9m
- Molecular Orbitals17m
- Sigma and Pi Bonds9m
- Octet Rule12m
- Bonding Preferences12m
- Formal Charges6m
- Skeletal Structure14m
- Lewis Structure20m
- Condensed Structural Formula15m
- Degrees of Unsaturation15m
- Constitutional Isomers14m
- Resonance Structures46m
- Hybridization23m
- Molecular Geometry16m
- Electronegativity22m
- 2. Molecular Representations1h 14m
- 3. Acids and Bases2h 46m
- 4. Alkanes and Cycloalkanes4h 19m
- IUPAC Naming29m
- Alkyl Groups13m
- Naming Cycloalkanes10m
- Naming Bicyclic Compounds10m
- Naming Alkyl Halides7m
- Naming Alkenes3m
- Naming Alcohols8m
- Naming Amines15m
- Cis vs Trans21m
- Conformational Isomers13m
- Newman Projections14m
- Drawing Newman Projections16m
- Barrier To Rotation7m
- Ring Strain8m
- Axial vs Equatorial7m
- Cis vs Trans Conformations4m
- Equatorial Preference14m
- Chair Flip9m
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- A-Values17m
- Decalin7m
- 5. Chirality3h 39m
- Constitutional Isomers vs. Stereoisomers9m
- Chirality12m
- Test 1:Plane of Symmetry7m
- Test 2:Stereocenter Test17m
- R and S Configuration43m
- Enantiomers vs. Diastereomers13m
- Atropisomers9m
- Meso Compound12m
- Test 3:Disubstituted Cycloalkanes13m
- What is the Relationship Between Isomers?16m
- Fischer Projection10m
- R and S of Fischer Projections7m
- Optical Activity5m
- Enantiomeric Excess20m
- Calculations with Enantiomeric Percentages11m
- Non-Carbon Chiral Centers8m
- 6. Thermodynamics and Kinetics1h 22m
- 7. Substitution Reactions1h 48m
- 8. Elimination Reactions2h 30m
- 9. Alkenes and Alkynes2h 9m
- 10. Addition Reactions3h 18m
- Addition Reaction6m
- Markovnikov5m
- Hydrohalogenation6m
- Acid-Catalyzed Hydration17m
- Oxymercuration15m
- Hydroboration26m
- Hydrogenation6m
- Halogenation6m
- Halohydrin12m
- Carbene12m
- Epoxidation8m
- Epoxide Reactions9m
- Dihydroxylation8m
- Ozonolysis7m
- Ozonolysis Full Mechanism24m
- Oxidative Cleavage3m
- Alkyne Oxidative Cleavage6m
- Alkyne Hydrohalogenation3m
- Alkyne Halogenation2m
- Alkyne Hydration6m
- Alkyne Hydroboration2m
- 11. Radical Reactions1h 58m
- 12. Alcohols, Ethers, Epoxides and Thiols2h 42m
- Alcohol Nomenclature4m
- Naming Ethers6m
- Naming Epoxides18m
- Naming Thiols11m
- Alcohol Synthesis7m
- Leaving Group Conversions - Using HX11m
- Leaving Group Conversions - SOCl2 and PBr313m
- Leaving Group Conversions - Sulfonyl Chlorides7m
- Leaving Group Conversions Summary4m
- Williamson Ether Synthesis3m
- Making Ethers - Alkoxymercuration4m
- Making Ethers - Alcohol Condensation4m
- Making Ethers - Acid-Catalyzed Alkoxylation4m
- Making Ethers - Cumulative Practice10m
- Ether Cleavage8m
- Alcohol Protecting Groups3m
- t-Butyl Ether Protecting Groups5m
- Silyl Ether Protecting Groups10m
- Sharpless Epoxidation9m
- Thiol Reactions6m
- Sulfide Oxidation4m
- 13. Alcohols and Carbonyl Compounds2h 17m
- 14. Synthetic Techniques1h 26m
- 15. Analytical Techniques:IR, NMR, Mass Spect6h 50m
- Purpose of Analytical Techniques5m
- Infrared Spectroscopy16m
- Infrared Spectroscopy Table31m
- IR Spect:Drawing Spectra40m
- IR Spect:Extra Practice26m
- NMR Spectroscopy10m
- 1H NMR:Number of Signals26m
- 1H NMR:Q-Test26m
- 1H NMR:E/Z Diastereoisomerism8m
- H NMR Table21m
- 1H NMR:Spin-Splitting (N + 1) Rule17m
- 1H NMR:Spin-Splitting Simple Tree Diagrams11m
- 1H NMR:Spin-Splitting Complex Tree Diagrams8m
- 1H NMR:Spin-Splitting Patterns8m
- NMR Integration18m
- NMR Practice14m
- Carbon NMR4m
- Structure Determination without Mass Spect47m
- Mass Spectrometry12m
- Mass Spect:Fragmentation28m
- Mass Spect:Isotopes27m
- 16. Conjugated Systems6h 13m
- Conjugation Chemistry13m
- Stability of Conjugated Intermediates4m
- Allylic Halogenation12m
- Reactions at the Allylic Position39m
- Conjugated Hydrohalogenation (1,2 vs 1,4 addition)26m
- Diels-Alder Reaction9m
- Diels-Alder Forming Bridged Products11m
- Diels-Alder Retrosynthesis8m
- Molecular Orbital Theory9m
- Drawing Atomic Orbitals6m
- Drawing Molecular Orbitals17m
- HOMO LUMO4m
- Orbital Diagram:3-atoms- Allylic Ions13m
- Orbital Diagram:4-atoms- 1,3-butadiene11m
- Orbital Diagram:5-atoms- Allylic Ions10m
- Orbital Diagram:6-atoms- 1,3,5-hexatriene13m
- Orbital Diagram:Excited States4m
- Pericyclic Reaction10m
- Thermal Cycloaddition Reactions26m
- Photochemical Cycloaddition Reactions26m
- Thermal Electrocyclic Reactions14m
- Photochemical Electrocyclic Reactions10m
- Cumulative Electrocyclic Problems25m
- Sigmatropic Rearrangement17m
- Cope Rearrangement9m
- Claisen Rearrangement15m
- 17. Ultraviolet Spectroscopy51m
- 18. Aromaticity2h 31m
- 19. Reactions of Aromatics: EAS and Beyond5h 1m
- Electrophilic Aromatic Substitution9m
- Benzene Reactions11m
- EAS:Halogenation Mechanism6m
- EAS:Nitration Mechanism9m
- EAS:Friedel-Crafts Alkylation Mechanism6m
- EAS:Friedel-Crafts Acylation Mechanism5m
- EAS:Any Carbocation Mechanism7m
- Electron Withdrawing Groups22m
- EAS:Ortho vs. Para Positions4m
- Acylation of Aniline9m
- Limitations of Friedel-Crafts Alkyation19m
- Advantages of Friedel-Crafts Acylation6m
- Blocking Groups - Sulfonic Acid12m
- EAS:Synergistic and Competitive Groups13m
- Side-Chain Halogenation6m
- Side-Chain Oxidation4m
- Reactions at Benzylic Positions31m
- Birch Reduction10m
- EAS:Sequence Groups4m
- EAS:Retrosynthesis29m
- Diazo Replacement Reactions6m
- Diazo Sequence Groups5m
- Diazo Retrosynthesis13m
- Nucleophilic Aromatic Substitution28m
- Benzyne16m
- 20. Phenols55m
- 21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
- Naming Aldehydes8m
- Naming Ketones7m
- Oxidizing and Reducing Agents9m
- Oxidation of Alcohols28m
- Ozonolysis7m
- DIBAL5m
- Alkyne Hydration9m
- Nucleophilic Addition8m
- Cyanohydrin11m
- Organometallics on Ketones19m
- Overview of Nucleophilic Addition of Solvents13m
- Hydrates6m
- Hemiacetal9m
- Acetal12m
- Acetal Protecting Group16m
- Thioacetal6m
- Imine vs Enamine15m
- Addition of Amine Derivatives5m
- Wolff Kishner Reduction7m
- Baeyer-Villiger Oxidation39m
- Acid Chloride to Ketone7m
- Nitrile to Ketone9m
- Wittig Reaction18m
- Ketone and Aldehyde Synthesis Reactions14m
- 22. Carboxylic Acid Derivatives: NAS2h 51m
- Carboxylic Acid Derivatives7m
- Naming Carboxylic Acids9m
- Diacid Nomenclature6m
- Naming Esters5m
- Naming Nitriles3m
- Acid Chloride Nomenclature5m
- Naming Anhydrides7m
- Naming Amides5m
- Nucleophilic Acyl Substitution18m
- Carboxylic Acid to Acid Chloride6m
- Fischer Esterification5m
- Acid-Catalyzed Ester Hydrolysis4m
- Saponification3m
- Transesterification5m
- Lactones, Lactams and Cyclization Reactions10m
- Carboxylation5m
- Decarboxylation Mechanism14m
- Review of Nitriles46m
- 23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
- 24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
- Tautomerization9m
- Tautomers of Dicarbonyl Compounds6m
- Enolate4m
- Acid-Catalyzed Alpha-Halogentation4m
- Base-Catalyzed Alpha-Halogentation3m
- Haloform Reaction8m
- Hell-Volhard-Zelinski Reaction3m
- Overview of Alpha-Alkylations and Acylations5m
- Enolate Alkylation and Acylation12m
- Enamine Alkylation and Acylation16m
- Beta-Dicarbonyl Synthesis Pathway7m
- Acetoacetic Ester Synthesis13m
- Malonic Ester Synthesis15m
- 25. Condensation Chemistry2h 9m
- 26. Amines1h 43m
- 27. Heterocycles2h 0m
- Nomenclature of Heterocycles15m
- Acid-Base Properties of Nitrogen Heterocycles10m
- Reactions of Pyrrole, Furan, and Thiophene13m
- Directing Effects in Substituted Pyrroles, Furans, and Thiophenes16m
- Addition Reactions of Furan8m
- EAS Reactions of Pyridine17m
- SNAr Reactions of Pyridine18m
- Side-Chain Reactions of Substituted Pyridines20m
- 28. Carbohydrates5h 53m
- Monosaccharide20m
- Monosaccharides - D and L Isomerism9m
- Monosaccharides - Drawing Fischer Projections18m
- Monosaccharides - Common Structures6m
- Monosaccharides - Forming Cyclic Hemiacetals12m
- Monosaccharides - Cyclization18m
- Monosaccharides - Haworth Projections13m
- Mutarotation11m
- Epimerization9m
- Monosaccharides - Aldose-Ketose Rearrangement8m
- Monosaccharides - Alkylation10m
- Monosaccharides - Acylation7m
- Glycoside6m
- Monosaccharides - N-Glycosides18m
- Monosaccharides - Reduction (Alditols)12m
- Monosaccharides - Weak Oxidation (Aldonic Acid)7m
- Reducing Sugars23m
- Monosaccharides - Strong Oxidation (Aldaric Acid)11m
- Monosaccharides - Oxidative Cleavage27m
- Monosaccharides - Osazones10m
- Monosaccharides - Kiliani-Fischer23m
- Monosaccharides - Wohl Degradation12m
- Monosaccharides - Ruff Degradation12m
- Disaccharide30m
- Polysaccharide11m
- 29. Amino Acids3h 20m
- Proteins and Amino Acids19m
- L and D Amino Acids14m
- Polar Amino Acids14m
- Amino Acid Chart18m
- Acid-Base Properties of Amino Acids33m
- Isoelectric Point14m
- Amino Acid Synthesis: HVZ Method12m
- Synthesis of Amino Acids: Acetamidomalonic Ester Synthesis16m
- Synthesis of Amino Acids: N-Phthalimidomalonic Ester Synthesis13m
- Synthesis of Amino Acids: Strecker Synthesis13m
- Reactions of Amino Acids: Esterification7m
- Reactions of Amino Acids: Acylation3m
- Reactions of Amino Acids: Hydrogenolysis6m
- Reactions of Amino Acids: Ninhydrin Test11m
- 30. Peptides and Proteins2h 42m
- Peptides12m
- Primary Protein Structure4m
- Secondary Protein Structure17m
- Tertiary Protein Structure11m
- Disulfide Bonds17m
- Quaternary Protein Structure10m
- Summary of Protein Structure7m
- Intro to Peptide Sequencing2m
- Peptide Sequencing: Partial Hydrolysis25m
- Peptide Sequencing: Partial Hydrolysis with Cyanogen Bromide7m
- Peptide Sequencing: Edman Degradation28m
- Merrifield Solid-Phase Peptide Synthesis18m
- 32. Lipids 2h 50m
- 34. Nucleic Acids1h 32m
- 35. Transition Metals5h 33m
- Electron Configuration of Elements45m
- Coordination Complexes20m
- Ligands24m
- Electron Counting10m
- The 18 and 16 Electron Rule13m
- Cross-Coupling General Reactions40m
- Heck Reaction40m
- Stille Reaction13m
- Suzuki Reaction25m
- Sonogashira Coupling Reaction17m
- Fukuyama Coupling Reaction15m
- Kumada Coupling Reaction13m
- Negishi Coupling Reaction16m
- Buchwald-Hartwig Amination Reaction19m
- Eglinton Reaction17m
How To Determine Solubility - Online Tutor, Practice Problems & Exam Prep
The principle of solubility, "like dissolves like," emphasizes the importance of polarity in determining whether substances will mix. Polar molecules, such as water and ethanol, dissolve in each other due to their similar net dipoles. Understanding the polarity of various organic compounds, like pyridine and DMSO, is crucial for predicting their solubility in aqueous solutions. Drawing Lewis structures can help identify molecular dipoles, guiding conclusions about miscibility. This knowledge is foundational for organic chemistry, influencing reactions and interactions among different functional groups.
Only one rule to know here:Like polarity dissolves like polarity.
Understanding “like dissolves like”.
Video transcript
Want a vodka tonic right about now? The reason they mix together is due to similar polarity between molecules. Not that you should know about this if you are under the age of 21! Duh.
Introducing common solvents and other molecules in organic chemistry.
Video transcript
I'm going to use this opportunity to teach you about some really weird molecules that you're going to see for the rest of organic chemistry, and maybe this will give you an opportunity to get a little bit more familiar with them. Alright? So let me go ahead and introduce these molecules first. We've got Pyridine over here. He's like an all-star. Pyridine looks like a benzene ring. I know we haven't been over that yet, but that's a benzene ring with a nitrogen. Alright. Very commonly used in reactions. Then on top, we've got DMSO. DMSO looks a lot like acetone except that it has a sulfur instead of the carbon. Okay? Then we've got THF. It's called Tetrahydrofuran. You don't need to know the full name, but it's basically just an oxygen in a 5-membered ring. Then we've got carbon tetrachloride. That one is a carbon with 4 chlorines all around. The polarity is going to be interesting for that one. And then we've got basically just a sulfur compound, basically that's called a thiol group. And then we've got nitrogen, which has basically 3 carbon groups around it. Okay? And for these 2, we're going to wind up having to draw Lewis structures to figure out what the solubility is. So what I want you guys to do is go through all of these and tell me if you would expect them to dissolve in an aqueous or be miscible in an aqueous solution. Okay? Now what aqueous means, this is tricky, it's not that tricky, but aqueous just means water. Okay? So what I want you guys to do is think about the polarity of water. Think about whether it is polar or apolar, and then look for dipoles on these 6 molecules. Once you think you've found if they have a dipole or not, a net dipole or not, then you can draw your conclusion: is this soluble or is this not going to be soluble? Alright? Now for the last 2, like I said, you are going to have to draw proper Lewis structures in order to know if it has its dipole or not. Okay? Because it can get a little tricky if you don't draw the Lewis structure.
An aqueous solution is one with water. That’s pretty much it. The following molecules are commonly used in organic chemistry - so it’s a good idea to know what their solubilities are.
Would you expect the following molecule to be miscible in an aqueous solution?
Would you expect the following molecule to be miscible in an aqueous solution?
Would you expect the following molecule to be miscible in an aqueous solution?
Would you expect the following molecule to be miscible in an aqueous solution?
Hint: Draw the Lewis structure before deciding!
Would you expect the following molecule to be miscible in an aqueous solution?
Hint: Draw the Lewis structure before deciding!
Would you expect the following molecule to be miscible in an aqueous solution?
Do you want more practice?
More setsHere’s what students ask on this topic:
What does 'like dissolves like' mean in terms of solubility?
The phrase 'like dissolves like' refers to the principle that substances with similar polarity will dissolve in each other. Polar molecules, which have a net dipole moment, will dissolve in other polar substances. Conversely, nonpolar molecules, which lack a net dipole moment, will dissolve in other nonpolar substances. For example, water (a polar molecule) will dissolve ethanol (another polar molecule) because both have similar polarities. This principle is crucial for predicting solubility in various solvents.
How do you determine the polarity of a molecule?
To determine the polarity of a molecule, you need to consider its molecular geometry and the electronegativity of its atoms. First, draw the Lewis structure to visualize the arrangement of atoms. Then, assess the electronegativity differences between bonded atoms. If there is a significant difference, the bond is polar. Finally, consider the molecule's shape to see if the dipoles cancel out or create a net dipole moment. If the dipoles do not cancel, the molecule is polar; otherwise, it is nonpolar.
Why is it important to draw Lewis structures when determining solubility?
Drawing Lewis structures is important for determining solubility because it helps visualize the arrangement of atoms and the distribution of electrons in a molecule. This visualization allows you to identify the presence and direction of dipole moments, which are crucial for assessing the molecule's polarity. Understanding the polarity helps predict whether the molecule will dissolve in a given solvent, based on the 'like dissolves like' principle.
What is the solubility of pyridine in water?
Pyridine is a polar molecule due to the presence of a nitrogen atom with a lone pair of electrons, which creates a net dipole moment. Because water is also polar, pyridine is soluble in water. The similar polarities of pyridine and water allow them to interact and dissolve in each other, following the 'like dissolves like' principle.
How does the polarity of DMSO affect its solubility in water?
DMSO (dimethyl sulfoxide) is a polar molecule due to the presence of a highly electronegative oxygen atom bonded to sulfur, creating a significant dipole moment. Because water is also polar, DMSO is highly soluble in water. The similar polarities of DMSO and water allow them to mix well, adhering to the 'like dissolves like' principle.
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