Solubility Properties of Organic Compound Flashcards
maximum amount of solute that can be dissolved in a given amount of solvent at certain temperature
SOLUBILITY: PHYSICAL PROPERTY
The solubility of physical property can be expressed as ____________ at a specific temperature
g solute/100 mL
Solubility of Physical Property is affected by these factors except:
a. nature of solute and solvent
b. chemical properties
c. temperature
d. pH
e. pressure
b. Chemical Properties
TRUE OR FALSE:
A compound is soluble when 3 g of solute dissolves in 100 mL of solvent
TRUE
can be dissolved (used for solid solutes)
Soluble
can be dissolved (used for liquid solutes)
Miscible
TRUE OR FALSE:
Solution Process may be endothermic or exothermic
TRUE
heat was absorbed from the
surrounding (decrease in temperature)
Endothermic
heat was released to the surrounding
(increase in temperature)
Exothermic
TRUE OR FALSE:
NH4Cl in water is Endothermic
NaOH in water is Exothermic
TRUE
TRUE OR FALSE:
Solute-Solvent Interaction > Solute-solute interaction, solvent-solvent interaction
TRUE
SOLUTION FORMATION:
* Solvent-Solvent Interaction
* Energy Requiring
Energy Considerations (Enthalpy)
What is the requirement of Dissolution Process?
Compatible IMFA of solute and solvent
SOLUTION FORMATION:
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)
DISSOLUTION PROCESS
macroscopic region in matter that is homogeneous in terms of physical properties and composition
Phase
violet color dispersed formation of a uniform mixture one phase observed
KMnO4 in H2O
FACTORS AFFECTING SOLUBILITY
Rule of Thumb: “Like dissolves like.”
- The stronger the attractive forces between unlike particles, the greater the solubility.
Nature of solute and solvent
FACTORS AFFECTING SOLUBILITY
TRUE OR FALSE:
Polar compounds dissolve in polar solvents. Nonpolar
or weakly polar compounds dissolve in nonpolar or
weakly polar solvents.
TRUE
FACTORS AFFECTING SOLUBILITY
TRUE OR FALSE:
polar – tetrachloride and hexane
nonpolar – water
FALSE; polar - water
nonpolar - tetrachloride and hexane
DISSOLUTION PROCESS
The factor in which a given substance reduces the electrostatic force between charged bodies separated by a vacuum
Dielectric Constant
TRUE OR FALSE:
- ion-dipole interaction - between ions and water molecules
- ion-dipole > h-bonding,
dipole-dipole > LDF - H2O has a low dielectric constant (polar)
- TRUE
- TRUE
- FALSE (water has a high dielectric cosntant (polar)
FACTORS AFFECTING SOLUBILITY
TRUE OR FALSE:
Solubility of gases in liquids increases with
increasing pressure.
TRUE
FACTORS AFFECTING SOLUBILITY
for liquid solutions where solute is a gas
Pressure
FACTORS AFFECTING SOLUBILITY
_____________ – increases the number of collisions of gas particles with the surface of the liquid.*
Increase in Pressure
FACTORS AFFECTING SOLUBILITY
TRUE OR FALSE:
The quantity of dissolved gas increases, thus, the solubility of gases in liquids increases with increasing pressure.
TRUE
FACTORS AFFECTING SOLUBILITY
TRUE OR FALSE:
Solubility of gases in liquids decreases with increasing temperature.
TRUE
FACTORS AFFECTING SOLUBILITY
TRUE OR FALSE:
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.
TRUE
All of the compounds are mainly water soluble EXCEPT 7 compounds:
a. Acetates (CH3COO–)
b. Nitrates, nitrites (NO3– NO2–)
c. Group 1 (Li+ Na+ K+ Rb+ Cs+)
d. Group 17 (Cl– Br – I–)
e. Pb2+
f. Ag+
g. Hg2
h. Ammonium (NH4+)
i. Sulfates (SO42–)
j. Hg22+
k. Ca2+
l. Ba2+
m. Sr2+
n. Chlorates, perchlorates (ClO3–, ClO4–)
e. Pb2+
f. Ag+
g. Hg2
j. Hg22+
k. Ca2+
l. Ba2+
m. Sr2+
All of the compounds are mainly water soluble EXCEPT 3 compounds:
a. Carbonates (CO3 2–)
b. Group 1
c. NH4+
d. Chromates (CrO42–)
e. Hydroxides (OH–)
f. Ba2+
g. Phosphates (PO43–)
h. Sulfides (S2–)
i. Sulfites (SO32–)
b. Group 1
c. NH4+
f. Ba2+
the first step in identification of functional group
Solubility Tests
What are the solvents for solubility tests?
- solubility in water
- nonpolar organic solvent
- 5% NaOH
- 5% NaHCO3
- 5% HCl
- concentrated H2SO4.
What is the measurement and procedure of solubility test for solid samples?
- 0.1 g of solid sample
- add 2 mL of solvent
- tap the tube with finger
- determine whether its soluble or insoluble
What is the measurement and procedure of solubility test for liquid samples?
- 4 drops of liquid sample
- add 2 mL of solvent
- tap the tube with finger
- determine whether soluble or insoluble
What will you do if the substance is water-soluble?
- Perform diethyl ether test
- Determine if it is soluble or insoluble
What are the class S2 (insoluble) substances?
- Salts of organic acids (RCO2Na, RSO3Na);
- amine hydrochlorides (RNH3Cl);
- amino acids,
- polyfunctional compounds with hydrophilic functional groups.
What will you do if the substance is ether-soluble?
- test the pH of the solution using pH paper
- test the pH of water (control)
- acidic, basic, neutral
What are the Class SA (soluble and acidic) substances?
- Monofunctional carboxylic acids (≤5 C)
- arylsulfonic acids.
What are the Class SA (soluble and basic) substances?
Monofunctional amines (≤6 C)
What are the Class S1 (soluble and neutral) substances?
Class S1 – Monofunctional alcohols, aldehydes, ketones, esters, nitriles, and amides (all≤5 C)
What will you do if your substance is water-insoluble?
- Perform 5% NaOH test
- Determine if i is soluble or insoluble
Class A1 – Strong organic acids: carboxylic acids (>6 C); phenols with electron-withdrawing groups in the ortho and/or para positions; β-diketones (1,3-diketones) are examples of:
Naoh soluble
Alcohols, aldehydes, ketones, esters with one functional group and (>5C but <9C), ethers, epoxides, alkenes, alkyls, some aromatic compounds (especially those
with activating groups) are what kind of class?
Class N (96% h2so4 soluble)
What will you do if your substance is NaOH-soluble?
- Perform 5% NaHCO3 test
- Determine if it is soluble or insoluble
Class A2 – Weak organic acids: phenols, enols, oximes, imides, sulfonamides, thiophenols, (all>5 C) β- diketones (1,3-diketones); nitro compounds with α-hydrogens are example of:
NaOH insoluble
What will you do if your substances are HCl-Insoluble?
- perform concentrated H2SO4 test
- determine if it is soluble or insoluble
Saturated hydrocarbons, haloalkanes, aryl
halides, other deactivated aromatic compounds, diaryl ethers are what kind of class?
Class I (06% h2so4 insoluble)
What are the measurement and procedure for Water Soluble Test?
- 4 drops of liquid sample
- add 2 mL of dH2O
- tap the tube with finger
- determine if it is soluble or insoluble
What will you do if your substance is NaOH-insoluble?
- perform 5% HCl test
- determine if it is soluble or insoluble
Aliphatic amines (all ≥ 8 C); anilines (only one
phenyl group attached to nitrogen); some ethers are what class?
Class B (HCl Soluble)
Miscellaneous neutral compounds containing nitrogen or sulfur and having more than five carbon atoms are what kind of class?
Class MN (5% HCL insoluble)
What are the measurement and procedure for Diethyl Ether Solubility Test?
- 4 drops of liquid sample
- add 2 mL of diethyl ether
- tap the tube with finger
- determine if it is soluble or insoluble
What will you do if your sample is soluble in Diethyl Ether Solubility Test?
- Perform pH paper test
- Determine if acidic, basic, neutral
What are the procedure and measurement for 5% Sodium Hydroxide Solubility Test?
- 4 drops of liquid sample
- add 2 mL of 5% Sodium Hydroxide
- tap the tube with finger
- determine if it is soluble or insoluble
What are the procedure and measurement for 5% Sodium Bicarbonate Solubility Test?
- 4 drops of liquid sample
- add 2 mL of 5% Sodium Bicarbonate
- tap the tube with finger
- determine if it is soluble or insoluble
What are the procedure and measurement for 5% Hydrochloric Acid Solubility Test?
- 4 drops of liquid sample
- add 2 mL of 5% HCl
- tap the tube with finger
- determine if it is soluble or insoluble
What are the procedure and measurement for Concentrated Sulfuric Acid Solubility Test?
- 4 drops of liquid sample
- add 2 mL of concentrated H2SO4
- tap the tube with finger
- soluble or insoluble
What are the samples that we will be using?
- alanine
- aniline
- benzoic acid
- methylamine