Solubility of Organic Compounds Flashcards
The _______ of a compound depends on the type of bonds present in the molecule
chemical behavior
Compounds are grouped according to their _______.
functional groups
_______________ test for the different functional groups have been developed to be carried out easily and quickly
Standard chemical tests
The positive signs to look for include the ff:
- change in color
- evolution of gas
- development of odor
- formation of precipitate
- changes in color of litmus paper
Solvent-Solvent Interaction + Solute-Solute Interaction < Solute-Solvent Interaction (Energy - releasing)
Energy Considerations (Enthalpy)
Maximum amount of solute that can be dissolved in a given amount of solvent at certain temperature
Solubility
It is affected by nature of solute and solvent, temperature, pH, and pressure.
Solubility
Can be dissolved (used for solid solutes)
Soluble
Can be dissolved (used for liquid solutes)
Miscible
heat was absorbed from the surrounding (decrease in temperature)
Endothermic
heat was released to the surrounding (increase in temperature)
Exothermic
As the randomness or degree of disorder increases in a system during a process, the higher the tendency for the process to occur spontaneously.
Degree of Disorder (Entropy)
macroscopic region in matter that is homogeneous in terms of physical properties and composition
Phase in Dissolution Process
violet color dispersed formation of a uniform mixture one phase observed
KMnO4 in H2O of Dissolution Process
In the solubility of organic compounds, polar compounds dissolve in polar solvents. While, nonpolar or weakly polar compounds dissolve in nonpolar or weakly polar solvents.
True or False
True (due to the Rule of thumb: “Like dissolves like”
In the solubility of organic compounds, most ionic compounds are soluble in water but insoluble in organic solvent
True or False
True
In the solubility of organic compounds, for an organic compound with one functional group, a compound is water soluble only if it has <5 C atoms and contains O or N atoms.
True or False
True
In the solubility of organic compounds, organic compounds are soluble in organic solvents regardless.
True or False
True
The factor in which a given substance reduces the electrostatic force between charged bodies separated by a vacuum.
Dielectric constant
- Solubility of gases in liquids increases with increasing pressure.
- Increase in pressure – increases the number of collisions of gas particles with the surface of the liquid.
- The quantity of dissolved gas increases, thus, the solubility of gases in liquids increases with increasing pressure.
Pressure (for liquid solutions where solute is a gas)
- Solubility of gases in liquids decreases with increasing temperature.
- Solubility of solids in liquids may either increase or decrease depending on whether the solution process is endothermic or exothermic.
- Endothermic - ↑T ↑solubility
- Exothermic - ↑T ↓solubility
- In general, the solubility of a solid increases with increasing temperature.
Temperature
Acetic is ______ in water and _______ ether.
Soluble and soluble
Benzoic acid is ______- in water and ___________ in ether
insoluble and soluble
Sodium benzoate is _______ in water and _________ in ether
soluble and insoluble
Cyclohexanol is _________ in water and ___________ in ether
insoluble and soluble
Glucose is _________ in water and ___________ in ether
soluble and insoluble
Cellulose is _________ in water and ___________ in ether
insoluble and insoluble
More hydrophilic portion, higher solubility in polar solvent
True or False
True
More hydrophobic portions, higher solubility in organic solvent
True or False
True
Higher degree of branching, weak IMFA of solute, high solubility in solvent
True or False
True
High Temperature, High kinetic energy interaction between solute and solvent particles has
high solubility or low solubility?
high solubility
In pH as a solubility factor (Neutralization), Amines act as bases with a variety of organic and inorganic acids
True or False
True
Equilibrium favors the product of an acid-base reaction when the weaker acid and base are formed
True or False
Aniline
acid or base
base
diethylamine
acid or base
base
naphthalene
acid or base or neutral
neutral
benzoic acid
acid or base
acid
phenol
acid or base
acid
toluene
acid or base or neutral
neutral
Alkylamines are more basic than NH3
True or False
True
Higher pka more basic is the substance
True or False
True
The sample is soluble in water but insoluble in ether. What is the solubility class?
Class S2
The sample is soluble in water and ether. The litmus paper turns red. What is the solubility class?
Class Sa
The sample is soluble in water and ether. The litmus paper turns blue. What is the solubility class?
Class Sb
The sample is soluble in water and ether. The litmus paper remains red and blue. What is the solubility class?
Class S1
The sample is insoluble in water but soluble in 5%NaOH and 5% NaHCO3. What is the solubility class?
Class A1
The sample is insoluble in water but soluble in 5%NaOH. While insoluble in 5% NaHCO3. What is the solubility class?
Class A2
The sample is insoluble in water and in 5%NaOH but soluble in 5% HCl. What is the solubility class?
Class B
The sample is insoluble in water, in 5%NaOH and in 5% HCl but soluble in 96% H2SO4. What is the solubility class?
Class N
The sample is insoluble in water, in 5%NaOH, in 5% HCl and in 96% H2SO4. What is the solubility class?
Class I
If aqueous solution is neutral - low molecular weight (monofunctional) Monofunctional alcohols, aldehydes, ketones, esters, nitriles, and amides.
What solubility class is this?
Class S1
- If aqueous solution acidic to litmus - low molecular weight (≤5 C; monofunctional) carboxylic acids or arylsulfonic acids.
- Monofunctional carboxylic acids (≤5 C) ; arylsulfonic acids.
What solubility class is this?
Class Sa
- If aqueous solution basic to litmus - low molecular weight (≤5 C; monofunctional) amines.
What solubility class is this?
Class Sb
Salts of organic acids (RCO 2Na, RSO 3Na); amine hydrochlorides (RNH3Cl); amino acids, polyfunctional compounds with hydrophilic functional groups.
What solubility class is this?
Class S2
Strong organic acids: carboxylic acids (>6 C); phenols with electron-withdrawing groups in the ortho and/or para positions; β-diketones (1,3-diketones).
What solubility class is this?
Class A1
Weak organic acids: phenols, enols, oximes, imides, sulfonamides, thiophenols, (all>5 C) β- diketones (1,3-diketones); nitro compounds with α-hydrogens.
What solubility class is this?
Class A2
Aliphatic amines (all ≥ 8 C); anilines (only one phenyl group attached to nitrogen); some ethers.
What solubility class is this?
Class B
Alcohols, aldehydes, ketones, esters with onefunctional group and (>5C but <9C), ethers, epoxides, alkenes, alkyls, some aromatic compounds (especially those with activating groups).
What solubility class is this?
Class N
Saturated hydrocarbons, haloalkanes, aryl halides, other deactivated aromatic compounds, diaryl ethers.
What solubility class is this?
Class I
Miscellaneous neutral compounds containing nitrogen or sulfur and having more than five carbon atoms.
What solubility class is this?
Class MN
