Module 4: SOLUBILITY OF ORGANIC COMPOUNDS Flashcards

1
Q
  • a physicochemical property that refers to the ability of a given “solute” to be “dissolved” in a given amount of “solvent”
A

Solubility

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2
Q

property of solute to dissolve in a solvent

A

Solubility

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2
Q

a substance dissolved to create a solution

A

solute

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2
Q

dissolving medium

A

solvent

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3
Q

a solution that contains “less amount of solute” than the solvent

A

unsaturated solution

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3
Q

liquid mixture composed of the solute uniformly dissolved in the solvent

A

solution

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3
Q

the process of dissolvin

A

dissolution

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4
Q

a solution that contains “more amount of solute” than the solvent

A

supersaturated solution

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4
Q

a solution with the “maximum amount of solute” dissolved in the given solvent

A

saturated solution

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5
Q

certain substances exhibit “solubility property” wherein they “mix in all proportions”, forming a homogenous mixture, this property is termed as

A

miscibility

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5
Q

predicting solubility is important:

A
  • in “purifying or isolating” a compound
  • when “extracting a molecule” from its natural source
  • when “designing a pharmaceutical product” which needs to be soluble enough to elicit its desired effect
  • when performing “synthesis reactions” especially in the formulation of organic drugs
  • the “partitioning of drug molecules” within the body between the blood and various tissues are governed by the solubility concept
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6
Q

predicting solubility is important:

A
  • “purifying or isolating”
  • “extracting a molecule”
  • “designing a pharmaceutical product”
  • “synthesis reactions”
  • “partitioning of drug molecules”
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6
Q

the solubility is controlled by the energy balance of intermolecular forces of attraction between which molecules?

A
  1. solute-solute
  2. solute-solvent
  3. solvent-solvent
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6
Q

IFA means

A

intermolecular forces of attraction

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7
Q

pertains to the polarity of compounds

A

the rule of “like dissolves like”

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7
Q

Van der Waals dispersion forces

A

non-polar molecules

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7
Q

polar molecules

A

dipole-dipole interaction (or hydrogen bonding under certain circumstances)

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7
Q

dipole-dipole interaction (or hydrogen bonding under certain circumstances)

A

polar molecules

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7
Q

non-polar molecules

A

Van der Waals dispersion forces

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8
Q

depends on the “polarities of the
individual bonds” and the “shape of the molecule”

A

Polarity

! * evaluating these factors are quite complicated because of the “complexities of the molecules”themselves

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8
Q

All hydrocarbons are _____________

A

non-polar

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8
Q

Compounds with electronegative element (O and N) are generally
___________, but the degree of polarity varies from slightly polar to highly polar.

9
Q

The presence of __________ does not alter the polarity of the compound; therefore, these compounds are only slightly polar

9
Q

Adding more “carbon” to the
chain makes the compound more
___________

10
this bonding makes it possible for the solute to be dissolved in the solvent
Hydrogen bonding
11
* this phenomenon is also applicable to organic compounds that can exist as ions - converting the organic molecule to its salt form by ________________ (acid-base reaction)
neutralization reaction (acid-base reaction)
12
Solubility = aspirin
+5% NaOH - S +5% NaHCO3 - S
12
Solubility = chloroform
conc. H2SO4 - INS
12
Solubility = acetaminophen
+5% NaOH - S +5% NaHCO3 - INS
13
Solubility = n-propanol
H2O - S pH test - 5-8 (neutral)
13
Solubility = sulfadiazine
+5% NaOH - S +5% NaHCO3 - INS
13
Solubility = salicylic acid
+5% NaOH - S +5% NaHCO3 - S
13
Solubility = aniline
5% HCl - S
13
SOLUBILILTY CLASSIFICATION = acetaminophen
HMW weakly acidic
13
SOLUBILILTY CLASSIFICATION = aspirin
HMW strongly acidic
14
SOLUBILILTY CLASSIFICATION = chloroform
HMW neutral (does not contain N or O)
14
SOLUBILILTY CLASSIFICATION = n-propanol
LMW neutral
14
Solubility = phenol
+5% NaOH - S +5% NaHCO3 - INS
14
SOLUBILILTY CLASSIFICATION = sulfadiazine
HMW weakly acidic
14
SOLUBILILTY CLASSIFICATION = salicylic acid
HMW strongly acidic
14
SOLUBILILTY CLASSIFICATION = aniline
HMW basic
15
SOLUBILILTY CLASSIFICATION = phenol
HMW weakly acidic
16
pH > 8
LMW basic (i.e. amines)
17
pH 5 – 8
LMW neutral (i.e. contains N or O)
18
pH < 5
LMW acidic (i.e. carboxylic acids)
19
soluble in 5% HCl
HMW basic (i.e. amines)
20
soluble in 5% NaHCO3
HMW strongly acidic (i.e. carboxylic acids)
21
insoluble in 5% NaHCO3
HMW weakly acidic (i.e. phenols)
22
soluble in H2SO4
HMW neutral (i.e. contains N or O)
23
insoluble in H2SO4
HMW neutral (i.e. does not contain N or O)
24
soluble in H2O --> pH test insoluble in H2O -->??
5% HCl test
25
insoluble in 5% HCl?
5% NaOH test
26
5% NaOH test soluble = 5% NaHCO3 insoluble = ??
H2SO4 test