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Chapter 2 student notes

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gdaaku09
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Chapter 2

Acids & Bases; Functional Groups


• Patterns of bonded atoms within the structure of an organic
compound can impart a unique distribution of electron density and
create a reactive site within the molecule.
• This can be used to anticipate the chemical reactions and the
physical properties of the compound.
• The presence of polarity within the compound is very important in
determining both the physical and chemical behaviors.
Polarity of Bonds & Molecules
• Bond polarity can range from:
• Nonpolar covalent, C-C, C-H
• Polar covalent, C-O, O-H, N-H
• Ionic, NH4 +Cl-
• The polarity of bonds is related to the electronegativity of atoms
• It is one the most important topics to remember in order to
understand organic chemistry.
Figure 1-7: Electronegativity Values 8th
Ed
• Bond dipole moments are due to differences in
electronegativity.
• They depend on the amount of charge separation
and distance of separation.
• Bond Dipole Moments (See Table 2-1)
• The measure of a bond’s polarity
• Expressed in Debye (D)

m = 4.8 x d x d

m = measurable dipole moment


Charge of electron is constant ( 1.6X 10-19 C)
d = charge separation between atoms
d = bond length (Å)
• These are experimentally determined values
• Example 2-1

Calculate the amount of charge separation, d, for a typical C-O single


bond, with a bond length of 1.43A and a dipole moment of 0.86 D.
• Molecular dipole moment (does the molecule
‘turn’ when exposed to an electrical field?)
• The dipole moment of the molecule must
consider i) The polarity of any bonds.
ii) The placement of the polar bonds
within the molecule.
• The value is the vector sum of the individual
bond dipole moments, not taken from
experimental measurements
ex. H2O, CH2O, CH3OCH3, CH4
• Lone pair electrons contribute to the dipole
moments of bonds & molecules
• Because of bond dipoles, partial positive and negative charges
are induced within a neutral molecule
• This is important in reactivity as well as in interactions that exist
between molecules (intermolecular forces)
Intermolecular Forces
• 3 major kinds of attractive forces cause molecules to associate
into solids & liquids:

1. London Dispersion forces (affect all molecules)


2. Dipole-Dipole forces (polar molecules)
3. Hydrogen bonds (molecules with NH or OH groups)
• London Dispersion Forces
• The principal attractive force in non polar molecules.
• Arise from temporary dipole moments that are induced by other
nearby molecules.
• These are not permanent charges within the molecule.
• Temporary shifts in electron density create or induce movement
of electrons on neighbouring atoms.
• Molecules with larger surface are will have a higher
boiling/melting point.
• Dipole – dipole Forces
• Attractive intermolecular forces resulting from the attraction of
the positive & negative ends of polar molecules.
• These are permanent dipoles.
• The greater the forces, the higher will be the boiling point and
melting point of a given compound.
• Also, increased solubility in polar solvents
• Hydrogen bonding
• Not a true bond but a particularly

• These bonds are stronger than regular dipole


interactions because of
• An H atom can participate in H-bonding if it is
bonded to O or N
• Ex. ethanol, b.p. = 78°C; dimethyl ether, b.p. = -25°C

• Ex. ethyl amine, b.p. 17°C compared to ethanol


How do intermolecular forces impact
solubility of an organic compound?
• “Like Dissolves Like”
• Polar substances dissolve in polar solvents
• A polar solvent (ex. Water) can separate ions
because it solvates them as the water molecules
overcome the lattice energy of the ionic compound
Polar solvent with polar solute:
• Nonpolar substances dissolve in nonpolar solvents
The weak intermolecular attractions of a nonpolar
substance are overcome by the weak attractions for
a nonpolar solvent (ex. Hexane)
• Which compound is more soluble in H2O?

CH3CH2OCH2CH3 VS CH3CH2CH2OH
Bronsted Lowry Acids & Bases
• Acidity & basicity are two important aspects of organic chemistry.
Many organic reactions will occur because the compound is either
acidic or basic. Organic compounds can often act as either and will do
one over the other based on the environment they are placed in
• Bronsted-Lowry Acid –
• Bronsted-Lowry Base –
• These proton transfers are and the
acid and base reacting to products form their
conjugate partners.

• A strong acid has a weak conjugate base


• A weak acid has a strong conjugate base

• The acid-base equilibrium favors the formation of the


• Recall,
The acid reacts with the base, water, in an acid
dissociation equation:
• The smaller the value of the pKa, the more acidic the compound
• Ex. HCl strong acid pKa =
• Ex. Methanol weak acid pKa =
• Ex. Which is the strongest base: Cl- or CH3O-?
• Classify the following compounds in order of
increasing (least to most) acidity

A: benzoic acid
B: hydrobromic acid
C: propanol
D: pentane
• 1. The acid-base equilibrium favors formation of the weaker acid and
the weaker base.
• 2. Weaker acids have pKa values and weaker bases
have larger
• 3. The weaker acid and weaker base are on the of the
equation.
• Complete the reaction that occurs between the following and use pKa
and pKb values to predict the side of the reaction that is favored:
HCOOH + CN-
Lewis Acids & Bases
• This is a different concept that is used to describe
organic reactions
• Lewis Acids:

• Lewis Bases:
• When forming a bond, the attacks the
so the arrow goes from negative to
positive.
• Use curved arrows
• When breaking a bond, the more atom
the electrons.
• The is always the attacking species
• Electrons flow from the electron donor (electron
rich source) to the electron acceptor (electron
deficient source)

• Refer to Section 2-14 in your text


• We will cover the nomenclature of the various
functional groups as they are introduced but you
should be familiar with the different types & have
a rough understanding of the names
• See the inside front cover of your book!
• 3 general classes of organic compounds
Hydrocarbons

• Alkanes: Single bonds between the carbons; all carbons are

• : sp3 carbons form a ring.


• Alkenes: Double bonds are present in the molecule;

• Cycloalkenes: Double bond in a


• : Triple bonds are present; sp carbons
• Aromatic: Contain a
See Table 2-3 in your text
• If a molecule contains a non-alkane part, that part
is referred as the
• Distinct chemical units where reactions usually
occur
• The alkane portion is then referred to as the

• The alkyl group is derived from the alkane


• When the structure of the alkyl group is not
important it is often replaced by as a
generalization
O Containing Functional Groups
N Containing Functional Groups

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