Alkyl Halides, Alcohols, Ethers & Solubility

11/10/2016
Adapted from Chapter 8 - Overview

Organic Chemistry, 6th ed.
Marc Loudon and Jim Parise 8.1 – Definitions and Classification of Alkyl Halides, Alcohols,
Thiols, Ethers, and Sulfides.
8.2 – Nomenclature of Alkyl Halides, Alcohols, Thiols, Ethers,
and Sulfides
8.3 – Structures of Alkyl Halides, Alcohols, Thiols, Ethers, and
Chapter 8 Sulfides
8.4 – Noncovalent Intermolecular Interactions: Introduction
Noncovalent Intermolecular Interactions
8.5 – Homogeneous Noncovlanet Intermolecular Attractions:
Boiling Points and Melting Points
8.6 – Heterogeneous Intermolecular Interactions: Solutions
and Solubility
8.7 – Applications of Solubility and Solvation Principles
8.8 – Strengths of Noncovalent Intermolecular Attractions
Alkyl Halides Alcohols and Thiols

• -F, -Cl, -Br, or -I bound to the carbon of an alkyl • An alcohol is a compound that has a _________
groups. group (-OH) bound to the carbon of an alkyl
group.
• A thiol is a compound that has a mercapto group

or sulfhydryl group (-_____) bound to the carbon
of an alkyl group.
8.1 Definitions and Classification 3 8.1 Definitions and Classification 4
Alcohols Ethers and Sulfides

• Don’t confuse an alcohol with a phenol. • Ethers are compounds in which an oxygen is
bound to _____ carbon groups.
• Don’t confuse an alcohol with an enol. • Sulfides (thioethers) are the sulfur analogs of
_______.
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The Alpha Carbon Classification

• The carbon bonded to the halogen in an alkyl • Alkyl halides and alcohols are classified by the
halide or the oxygen in an alcohol is called the number of alkyl groups attached to the a-carbon.
alpha-carbon.
Chapter 8 - Overview Nomenclature of Alkyl Halides

8.1 – Definitions and Classification of Alkyl Halides, Alcohols, Common Nomenclature
8.2 – Nomenclature of Alkyl Halides, Alcohols, Thiols, Ethers, • The common name uses the name of the alkyl
and Sulfides group followed by the halide.
Sulfides
and Solubility
9 8.2 Nomenclature 10
Nomenclature of Alkyl Halides Nomenclature of Alkyl Halides

Common Nomenclature Substitutive Nomenclature
•Other common names to learn: • IUPAC – Apply the rules of alkane and alkene
nomenclature. Halogens are treated as
substituents (fluoro, chloro, bromo, & iodo).
•The phenyl and benzyl groups:
8.2 Nomenclature 11 8.2 Nomenclature 12
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Nomenclature of Alcohols & Thiols Nomenclature of Alcohols & Thiols

Common Nomenclature Common Nomenclature
• Specify the alkyl group to which the –OH is attached, • Compounds that contain two or more hydroxy
followed by the word _________. groups on different carbons are called glycols.
• Thiols are named in the common system as mercaptans.
Nomenclature of Alcohols & Thiols Principal Group and Principal Chain

Substitutive Nomenclature 1. Identify the principle group (e.g., -OH > -SH).
•The substitutive name is generated from the 2. Identify the principle chain which is the chain
_____________ group (-OH or –SH).
a. with the greatest number of principle groups.
•The principle group is the chemical group on which
b. with the greatest number of double and triple
the name is based and is always the ________ in bonds.
the name.
c. of greatest length.
d. with the greatest number of other substituents.
•The priorities of principle groups will be given as

they are encountered in upcoming chapters. Apply criteria a-d in order until a decision is made.
Principal Group and Principal Chain Principal Group and Principal Chain
3. Number the carbons of the principle chain giving 4. Begin construction of the name with the name of
the lowest numbers to the hydrocarbon corresponding to the principle
a. the principle groups. chain.
b. multiple bonds (C=C > CC). a. Cite principle group by its suffix and number; its
number is the last one cited in the name.
c. other substituents.
b. If there is no principle group, name the compound
d. the substituent cited first in the name. as a substituted hydrocarbon.
c. Cite the names and numbers of other substituents
in alphabetical order.
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Alcohols With More Than One -OH Nomenclature of Ethers and Sulfides
• For alcohols with more than one –OH group use Common Nomenclature
diol, triol, etc.
• The common name is constructed by citing the
• Do not drop the final e of the alkane. two groups attached to O or S followed by ether
or sulfide, respectively.
Nomenclature of Ethers and Sulfides Heterocyclic Nomenclature

Substitutive Nomenclature • Some important ethers and sulfides are part of a
• Ethers and sulfides are never treated as principle cyclic structure.
groups. • Cyclic compounds that contain at least one atom
• The substitutive name makes use of the terms other than carbon are called heterocyclic
alkoxy (RO-) and alkylthio (RS-) as substituents. compounds.
Heterocyclic Nomenclature Chapter 8 - Overview

• Oxirane is the parent compound of a special class 8.1 – Definitions and Classification of Alkyl Halides, Alcohols,
of cyclic ethers, called epoxides. Thiols, Ethers, and Sulfides.
and Sulfides
Sulfides
• Some expoxides are named as oxides of the Boiling Points and Melting Points
corresponding alkene. 8.6 – Heterogeneous Intermolecular Interactions: Solutions
and Solubility
8.2 Nomenclature 23 24
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Bond Angles and Lengths Bond Lengths of Methyl Derivatives

Alkyl Halides, Alcohols, Thiols, Ethers, and Sulfides
•In all of these compounds, the bond angles at
carbon are nearly_______________.
•The a-carbons are ______ hybridized.
8.3 Structures of Alkyl Halides, Alcohols, Thiols, Ethers, and Sulfides 25 8.3 Structures of Alkyl Halides, Alcohols, Thiols, Ethers, and Sulfides 26
Chapter 8 - Overview Noncovalent Interactions

8.1 – Definitions and Classification of Alkyl Halides, Alcohols, • Molecules can interact in ways that do not involve
Thiols, Ethers, and Sulfides. covalent bonds (i.e. noncovalent interactions).
and Sulfides • Steric effects is one example of noncovalent
8.3 – Structures of Alkyl Halides, Alcohols, Thiols, Ethers, and interactions between molecules.
Sulfides • Intramolecular _________ – energetically
8.4 – Noncovalent Intermolecular Interactions: Introduction favorable noncovalent interactions.
Boiling Points and Melting Points • Intramolecular __________– energetically
8.6 – Heterogeneous Intermolecular Interactions: Solutions unfavorable noncovalent interactions.
and Solubility • Many biological structures (DNA, proteins) owe
8.7 – Applications of Solubility and Solvation Principles their very existence to noncovalent interactions.
27 8.4 Noncovalent Intermolecular Interactions: Introduction 28
Chapter 8 - Overview Boiling Points

8.1 – Definitions and Classification of Alkyl Halides, Alcohols, • If there were no attractions between molecules in
Thiols, Ethers, and Sulfides. a solid or a liquid, the substance would be a gas.
8.2 – Nomenclature of Alkyl Halides, Alcohols, Thiols, Ethers, • The attraction between molecules in a solid or
and Sulfides
liquid are noncovalent because no chemical
8.3 – Structures of Alkyl Halides, Alcohols, Thiols, Ethers, and reaction occurs when a substance undergoes a
Sulfides
phase change.
8.5 – Homogeneous Noncovlanet Intermolecular Attractions: • The boiling point is the temperature required to
Boiling Points and Melting Points raise the vapor pressure of a liquid to atmospheric
8.6 – Heterogeneous Intermolecular Interactions: Solutions pressure.
and Solubility
• As the boiling point increases, then, more energy
is required to break the intermolecular attractions
in the liquid state.
29 8.5 Homogeneous Noncovalent Intermolecular Attractions 30
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van der Waals (Dispersion) Forces van der Waals (Dispersion) Forces
• BP increases with molecular size for a homologous
series.
• The electron clouds in some molecules are rather
“squishy.”
• Rapid and random electron cloud distortion
results in a temporary dipole within a molecule.
• A second nearby molecule distorts to form a
complementary dipole called an induced dipole.
• The d+ of one molecule is attracted to the d- of
another. This attraction is called van der Waals
attraction or dispersion interaction.
8.5 Homogeneous Noncovalent Intermolecular Attractions 31 8.5 Homogeneous Noncovalent Intermolecular Attractions 32
van der Waals (Dispersion) Forces Boiling Point

Why do larger molecules have higher boiling points? Comparing several compound classes with
• van der Waals attractions increase with surface unbranched carbon chains:
area.
van der Waals (Dispersion) Forces Polarizability

Summary • The polarizability of a molecule is a direct measure
of how easy it is energetically for an external charge
• BP increases with increasing molecular weight
(or dipole) to alter its electron distribution.
within a homologous series (20-30 °C per C atom).
• Molecules or groups that have “squishy,” easily
• BP tends to be lower for highly branched molecules
deformed electron clouds are polarizable.
because they have a smaller surface area.
• Very electronegative atoms – typically not very
polarizable.
• Less electronegativity atoms – typically more
polarizable.
• Iodine is 10x more polarizable than Fluorine.
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Polarizability Polarizability
• Perfluoroethane is much less polarizable than • Despite its much larger mass, perfluorohexane has a
2,2,3,3-tetramethylbutane. lower boiling point than hexane due to it being less
• This polarizability difference is reflected in the polarizable.
boiling points.
• Teflon is valued precisely because it has weak

noncovalent interactions with nearly everything.
Attractions between Permanent Dipoles Attractions between Permanent Dipoles

• Molecules with permanent dipoles can show • The higher boiling point of ether results from
enhanced intermolecular attractions. greater attractions between molecules in the liquid
• Molecules with permanent dipoles can have higher state.
boiling points than alkanes of the same size and
shape.
• The electronegativity of the oxygen reduces the

ethers polarizability, but this is more than offset by
the attractions between the permanent dipoles.
Attractions between Permanent Dipoles Attractions between Permanent Dipoles

• Nitriles have particularly high boiling points. They • All of the alkyl halides have significant dipole
also have unusually large dipole moments resulting moments.
from the two parallel bond dipoles. • Alkyl chlorides have about the same boiling points
as alkanes of the same molecular mass.
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Attractions between Permanent Dipoles Hydrogen Bonding

• Alkyl bromides and alkyl iodides have lower boiling • Alcohols have unusually high boiling points when
points than alkanes of similar molecular mass. compared to structurally similar compounds.
• The unusual boiling points of alcohols is due to a

phenomenon known as_________ ___________.
Hydrogen Bonding Hydrogen Bonding

• Hydrogen bonding is an intermolecular ________ • Formation of a hydrogen bond requires a H-bond
that results from the association of a hydrogen on donor and a H-bond acceptor.
one atom with an unshared electron pair on
another.
Best donors: O, N, halogens

Best acceptors: O, N, F
Hydrogen Bonding Melting Points

• Sometimes atoms can act as both H-bond donors • The melting point is the temperature above which
and H-bond acceptors. a solid is spontaneously transformed into a liquid.
• At the melting point, a solid and its liquid are in
equilibrium.
• Like boiling points, melting points are a reflection
of noncovalent interactions between molecules.
• Thus, melting points reflect the noncovalent
interactions in both the solid and liquid states.
• Water and alcohols exist in hydrogen-bonded
networks.
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Melting Points Melting Points

Important Observations: • Symmetrical molecules can pack into the crystal
• Within a homologous series, we often find a more closely than unsymmetrical molecules.
“sawtooth” pattern when melting points are • Closer molecules have stronger noncovalent
plotted against number of carbons. interactions.
• Symmetrical compounds tend to have • The crystalline state is stabilized by symmetry and
considerably higher melting points than less more energy is required to convert the crystal into
symmetrical isomers. a liquid.
Chapter 8 - Overview Solutions

8.1 – Definitions and Classification of Alkyl Halides, Alcohols, • In a solution, a solute, A, (present in the lesser
Thiols, Ethers, and Sulfides. amount) is added to a solvent, S, (present in the
8.2 – Nomenclature of Alkyl Halides, Alcohols, Thiols, Ethers, greater amount).
and Sulfides
8.3 – Structures of Alkyl Halides, Alcohols, Thiols, Ethers, and • If the two compounds persist in separate phases,
Sulfides then A is insoluble in S.
8.4 – Noncovalent Intermolecular Interactions: Introduction • If A and S forma single clear liquid phase, then A is
8.5 – Homogeneous Noncovlanet Intermolecular Attractions: soluble in S.
and Solubility
51 8.6 Heterogeneous Intermolecular Interactions 52
Solutions Solution Energetics

• The process of forming a solution involves the • When a solute A is dissolved in a liter of solvent S,
interplay of noncovalent intermolecular the free-energy change, DGs, is called the free
interactions. energy of solution.
• DGs < 0 Favorable solution process

• DGs > 0 Unfavorable solution process
8.6 Heterogeneous Intermolecular Interactions 53 8.6 Heterogeneous Intermolecular Interactions 54
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Solution Energetics Solution Energetics

• Regardless of the intermolecular interactions • Because we are considering only probabilities, not
involved, there is a statistical driving force for the energy changes, DHmixing = 0
formation of a solution called the entropy of
• Thus,
mixing, DSmixing.
Why then doesn’t every liquid dissolve in every
• Entropy is a measure of probability.
other liquid?
• When a solute is added to a solvent, the solute • Noncovalent interactions also make contributions
disperses. The dispersed state is simply more to the free energy.
probable.
• Forming a solution involves replacing some S-S
interactions and all A-A interactions with S-A
interactions.
Solution Energetics Solution Energetics

• The free-energy change associated with the
noncovalent interactions involved in forming a
solution is represented as DGinter • If S-S or A-A interactions are significant and are
• The overall free energy change of solution is then not replaced by compensating S-A interactions in
a balance between DGinter and the always solution, then DGinter > 0.
favorable DGmixing • If DGinter becomes large enough, it overcomes the
entropy of mixing and DGs > 0.
• As DGs increases, the amount of A that dissolves in
S decreases.
• Whether or not a solution forms depends on the
balance between DGinter and DGmixing.
Classification of Solvents Classification of Solvents

A solvent can be: • Polar solvents consist of molecules that have
significant dipole moments.
•Protic (H-bond _________) or aprotic.
• Apolar solvents, however, may or may not contain
Protic Examples: water, alcohols, carboxylic acids
dipolar molecules.
Aprotic Examples: ether, dichloromethane, hexane
• Consider acetic and formic acids:
•Polar (high dielectric constant) or apolar.
•Donor (Lewis base) or nondonor.
The dielectric constant is a property of many molecules of

a solvent acting together while the dipole moment is a Apolar Polar
property of individual molecules. Solvent Solvent
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Solubility of Covalent Compounds Solubility of Covalent Compounds

• Rule of thumb: Like dissolves like. • Pentane and dichloromethane are miscible.
• Miscible liquids form a solution when mixed in any • When the two are mixed, the dipoles of
proportions. dichloromethane can induce temporary dipoles in
nearby pentane molecules.
Solubility in Water Solubility in Water

• The ability to both donate an H-bond to water and Rule of Thumb
accept an H-bond from water is an important •Compounds containing one –OH group for every
factor in water solubility. five carbons usually have significant water solubility.
Xenobiotic Metabolism Solubility of Hydrocarbons in Water

• Xenobiotic – any substance that is not a normal • Hydrocarbons do have a very small solubility in
constituent of a living organism. water that can be measured.
• If the body encounters a xenobiotic that has low water
solubility it converts it into a more water soluble
compound that can be excreted in the urine.
• The concentration of pentane in water is very

small, but not zero.
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Solubility of Hydrocarbons in Water Solubility of Hydrocarbons in Water

• The unfavorable standard free energy for • Moving pentane into water causes an enthalpy
dissolving pentane in water is use to the large, reduction (-DHinter), but due to the large negative
negative entropy associated with intermolecular entropy, the free-energy DGs is positive.
interactions.
• The association of hydrocarbon groups in aqueous
solution is called hydrophobic bonding.
• When hydrocarbon groups associate, low-entropy
solvation water is released to become ordinary,
high-entropy, water.
• Many biological processes are driven by
hydrophobic bonding.
Solubility of Solid Covalent Compounds Solubility of Solid Covalent Compounds

• Two hypothetical steps:
1.Solid must become a liquid. • The free-energy change for step 1 is the energy of
2.The resulting liquid must dissolve in the solvent. fusion of the solid at 298K.
• DGofusion is < 0, because we are forming a solution
at a temperature below the compounds melting
point.
• In effect, the solid is converted into a
“supercooled” liquid.
Solubility of Solid Covalent Compounds Solubility of Solid Covalent Compounds

• Recall that symmetrical compounds generally have • Liquid nifedipine is 30x as soluble in water as liquid
higher melting point. 9,10-dihydroanthracene.
• Solids with higher melting points have a greater • The solubility of the two solids, however, is similar.
Dgofusion, 298 and are less soluble. • This is due to the higher mp of nifedipine.
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Solubility of Ionic Compounds Ions in Solution

• Ionic compounds in solution can exist as ion pairs
or dissociated ions.
• In an ion pair, each ion is closely associated with
an ion of opposite charge.
• Dissociated ions are surrounded by a solvent shell
and move more or less independently.
• The ability of a solvent to separate ions is

measured by its dielectric constant.
Solvation of NaCl in Water Solubility of Ionic Compounds

Dissolved ions are stabilized by:
1. Charge-dipole interactions.
2. Hydrogen-bonding interactions.
3. Donor interactions.
Solubility of Ionic Compounds Chapter 8 - Overview

• The effect of solvation by ions of water can lead to 8.1 – Definitions and Classification of Alkyl Halides, Alcohols,
significant solubility changes as a result of acid- Thiols, Ethers, and Sulfides.
base reactions. 8.2 – Nomenclature of Alkyl Halides, Alcohols, Thiols, Ethers,
and Sulfides
Sulfides
and Solubility
8.6 Heterogeneous Intermolecular Interactions 77 78
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Cell Membrane and Drug Solubility Lipids and Phospholipids

• Solubility is crucial for drug action. • A lipid is a compound that shows significant
solubility in apolar solvents.
• Water solubility is important, but the drug must
also be able to arrive at its target site. • Lipids are defined by behavior rather than a
precise structure.
• The drug must be able to pass through the cell
membrane that surrounds the cell. • They typically contain polar functional groups, but
• Cell membranes are composed of phospholipids. have significant hydrocarbon character.
• Phospholipids are lipids that contain the
phosphate group.
8.7 Applications of Solubility and Solvation Principles 79 8.7 Applications of Solubility and Solvation Principles 80
Lipids and Phospholipids Lipids and Phospholipids

• Membrane phospholipids are built on a glycerol 2. The remaining hydroxy group of the glycerol
“scaffold” backbone is connected to a phosphoric acid
1.Two of the hydroxy groups of glycerol form ester molecule as a phosphate ester.
linkages to fatty acids.
Lipids and Phospholipids Structure of Phospholipids

3. Finally, the phosphate is connected to a • Polar head group: A hydrophilic group that
protonated ethanolamine molecule in another interacts favorably with water.
phosphate ester linkage.
• Nonpolar tail: A hydrophobic group that is not
well solvated by water; oftentimes referred to as a
“greasy group.”
• Molecules that contain these two discrete regions
are called amphipathic.
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Structure of Phospholipids Structure of Phospholipids

• When membrane phospholipids are added to
water, they undergo a self-assembly to
spontaneously form a phospholipid bilayer.
Cell Membrane Cell Membrane

• Chemically, the living cell can be thought of as a • The phospholipid bilayer is generally impermeable
large phospholipid vesicle in which the cell to ions.
membrane is a phospholipid bilayer. • Unlike ions, a number of uncharged molecules (i.e.
O2) diffuse readily through the cell membrane.
• Drugs that completely insoluble in hydrocarbons
do not pass through the cell membranes.
• Drugs that are highly soluble in hydrocarbons get
stuck in the phospholipid bilayer.
• Drugs must be carefully designed such that their
solubility allows them to pass through the
phospholipid bilayer and enter the cell.
Cation-Binding Molecules [18]-Crown-6 and Potassium Ion

• Ionophores are molecules that form strong • The oxygens of the “host” crown ether wrap
complexes with specific ions. around the “guest” metal cation.
• Crown ethers are heterocyclic ethers with
regularly spaced oxygen atoms.
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Cation-Binding Molecules Ionophore Antibiotics

• An antibiotic is a compound that interferes with the
• Cryptands are nitrogen- growth or survival of one or more microorganisms.
containing analogs of the • Ionophore antibiotics form strong complexes with
crown ethers. metal ions much like crown ethers and cryptans.
Ion Channels Ion Channels

• Ion channels or “ion gates,” provide passageways
for ions into and out of cells.
• A typical channel is a large protein molecule
imbedded into a cell membrane.
• Ion channels can be opened or closed to regulate
the concentration of ions in the interior of the cell.
Chapter 8 - Overview Strengths of Attraction

8.1 – Definitions and Classification of Alkyl Halides, Alcohols, • Attraction between ions can be very strong.
8.2 – Nomenclature of Alkyl Halides, Alcohols, Thiols, Ethers, • van der Waals attractions, dipole-dipole
and Sulfides attractions, and hydrogen bonds are all relatively
8.3 – Structures of Alkyl Halides, Alcohols, Thiols, Ethers, and weak.
Sulfides • The strengths of noncovalent attractions have
8.4 – Noncovalent Intermolecular Interactions: Introduction nothing to do with the stabilities of the molecules
8.5 – Homogeneous Noncovlanet Intermolecular Attractions: involved.
and Solubility
95 8.8 Strengths of Noncovalent Intermolecular Attractions 96
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SUMMARY SUMMARY
97 98
SUMMARY SUMMARY
99 100
SUMMARY
101
17

Alkyl Halides, Alcohols, Ethers & Solubility

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11/10/2016

Adapted from Chapter 8 - Overview

Alkyl Halides Alcohols and Thiols

• A thiol is a compound that has a mercapto group

8.1 Definitions and Classification 3 8.1 Definitions and Classification 4

Alcohols Ethers and Sulfides

8.1 Definitions and Classification 5 8.1 Definitions and Classification 6

The Alpha Carbon Classification

8.1 Definitions and Classification 7 8.1 Definitions and Classification 8

Chapter 8 - Overview Nomenclature of Alkyl Halides

Nomenclature of Alkyl Halides Nomenclature of Alkyl Halides

•The phenyl and benzyl groups:

8.2 Nomenclature 11 8.2 Nomenclature 12

Nomenclature of Alcohols & Thiols Nomenclature of Alcohols & Thiols

• Thiols are named in the common system as mercaptans.

8.2 Nomenclature 13 8.2 Nomenclature 14

Nomenclature of Alcohols & Thiols Principal Group and Principal Chain

•The priorities of principle groups will be given as

8.2 Nomenclature 15 8.2 Nomenclature 16

8.2 Nomenclature 17 8.2 Nomenclature 18

8.2 Nomenclature 19 8.2 Nomenclature 20

Nomenclature of Ethers and Sulfides Heterocyclic Nomenclature

8.2 Nomenclature 21 8.2 Nomenclature 22

Heterocyclic Nomenclature Chapter 8 - Overview

Bond Angles and Lengths Bond Lengths of Methyl Derivatives

Chapter 8 - Overview Noncovalent Interactions

27 8.4 Noncovalent Intermolecular Interactions: Introduction 28

Chapter 8 - Overview Boiling Points

van der Waals (Dispersion) Forces Boiling Point

van der Waals (Dispersion) Forces Polarizability

• Teflon is valued precisely because it has weak

Attractions between Permanent Dipoles Attractions between Permanent Dipoles

• The electronegativity of the oxygen reduces the

Attractions between Permanent Dipoles Attractions between Permanent Dipoles

Attractions between Permanent Dipoles Hydrogen Bonding

• The unusual boiling points of alcohols is due to a

Hydrogen Bonding Hydrogen Bonding

Best donors: O, N, halogens

Hydrogen Bonding Melting Points

Melting Points Melting Points

Chapter 8 - Overview Solutions

51 8.6 Heterogeneous Intermolecular Interactions 52

Solutions Solution Energetics

• DGs < 0 Favorable solution process

8.6 Heterogeneous Intermolecular Interactions 53 8.6 Heterogeneous Intermolecular Interactions 54

Solution Energetics Solution Energetics

8.6 Heterogeneous Intermolecular Interactions 55 8.6 Heterogeneous Intermolecular Interactions 56

Solution Energetics Solution Energetics

8.6 Heterogeneous Intermolecular Interactions 57 8.6 Heterogeneous Intermolecular Interactions 58

Classification of Solvents Classification of Solvents

The dielectric constant is a property of many molecules of

8.6 Heterogeneous Intermolecular Interactions 59 8.6 Heterogeneous Intermolecular Interactions 60

Solubility of Covalent Compounds Solubility of Covalent Compounds

8.6 Heterogeneous Intermolecular Interactions 61 8.6 Heterogeneous Intermolecular Interactions 62

Solubility in Water Solubility in Water

8.6 Heterogeneous Intermolecular Interactions 63 8.6 Heterogeneous Intermolecular Interactions 64

Xenobiotic Metabolism Solubility of Hydrocarbons in Water

• The concentration of pentane in water is very

8.6 Heterogeneous Intermolecular Interactions 65 8.6 Heterogeneous Intermolecular Interactions 66

Solubility of Hydrocarbons in Water Solubility of Hydrocarbons in Water

8.6 Heterogeneous Intermolecular Interactions 67 8.6 Heterogeneous Intermolecular Interactions 68

Solubility of Solid Covalent Compounds Solubility of Solid Covalent Compounds

8.6 Heterogeneous Intermolecular Interactions 69 8.6 Heterogeneous Intermolecular Interactions 70