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Families of Carbon
Compounds
Functional Groups,
Intermolecular Forces,
& Infrared (IR)
Spectroscopy
Created by
Professor William Tam & Dr. Phillis
Chang Ch. 2 - 1
About The Authors
These Powerpoint Lecture Slides were created and prepared by
Professor William Tam and his wife Dr. Phillis Chang.
Dr. Phillis Chang received her B.Sc. at New York University (USA) in
1994, her M.Sc. and Ph.D. in 1997 and 2001 at the University of
Guelph (Canada). She lives in Guelph with her husband, William, and
their son, Matthew. Ch. 2 -
1. Hydrocarbons
Hydrocarbons are compounds
that contain only carbon and
hydrogen atoms
Alkanes
hydrocarbons that do not
have multiple bonds
between carbon atoms
e.g.
pentane cyclohexane
Ch. 2 - 3
Alkenes
contain at least one
carboncarbon double bond
e.g.
propene cyclohexene
Ch. 2 - 4
Alkynes
contain at least one
carboncarbon triple bond
e.g. H C C H
ethyne 1-pentyne
2-pentyne
Ch. 2 - 5
Aromatic compound
contain a special type of
ring, the most common
example of which is a
benzene ring
CH3 COOH
e.g.
Ch. 2 - 6
1A. Alkanes
The primary sources of alkanes are
natural gas and petroleum
The smaller alkanes (methane through
butane) are gases under ambient
conditions
Methane is the principal component of
natural gas
Higher molecular weight alkanes are
obtained largely
H by refining petroleum
H H
H Methane
Ch. 2 - 7
1B. Alkenes
Ethene and propene, the two simplest
alkenes, are among the most
important industrial chemicals
produced in the United States
Ethene is used as a starting material
for the synthesis of many industrial
compounds, including ethanol,
ethylene oxide, ethanal, and the
polymer Hpolyethylene
H
C
C
H H Ethene
Ch. 2 - 8
Propene is the important starting
material for acetone, cumene and
polypropylene
Examples of naturally occurring
alkenes
-electrons
above and
below ring
Planar structure
All carbons sp2 hybridized
Ch. 2 -
The lobes of each orbital above
and below the ring overlap with
the lobes of orbitals on the
atoms to either side of it
the six electrons associated with
these orbitals (one electron from
each orbital) are delocalized
about all six carbon atoms of the
ring
Ch. 2 -
2. Polar Covalent Bonds
Li F
Lithium fluoride has an ionic bond
H H
H C C H
H H
Ethane has a covalent bond. The
electrons are shared equally between
the carbon atoms Ch. 2 -
electronegativity
C C C O
2.5 3.5
Ch. 2 -
Electronegativity (EN)
The intrinsic ability of an atom
to attract the shared electrons
in a covalent bond
Increasing EN
Na Mg Si P S Cl
(0.9) (1.2) (1.8) (2.1) (2.5) (3.0)
K Br
(0.8) (2.8)
Rb I
(0.8) (2.5)
Cs
(0.7)
Increasing EN
Ch. 2 -
C N C Cl
2.5 3.0 2.5 3.0
H C Si C
2.1 2.5 1.8 2.5
Ch. 2 -
3. Polar and Nonpolar Molecules
=rQ
Dipole moments are expressed in
debyes (D), where 1 D = 3.336
1030 coulomb meter (Cm) in SI
units
Ch. 2 -
Cl
>
C net dipole
H (1.87 D)
H
H
+
Ch. 2 -
Molecules containing polar bonds
are not necessarily polar as a
whole, for example
cis- trans-
1,2-Dichloroethene 1,2-Dichloroethene
H H H Cl
C C C C
Cl Cl Cl H
resultant dipole
moment
( = 1.9 D) ( = 0 D)
Ch. 2 -
Physical properties of some cis-
trans isomers
m.p. m.p.
Compound ()
(oC) (oC)
cis-1,2-Dichloroethene -80 60 1.90
trans-1,2-
-50 48 0
Dichloroethene
cis-1,2-Dibromoethene -53 112.5 1.35
trans-1,2-
-6 108 0
Dibromoethene
Ch. 2 -
4. Functional Groups
Alkane Alkyl Group Abbrev. Bond-Line Model
CH3CH2 Ethyl
These and
others can
be
CH3CH2CH2 Propyl
designated
by R
CH3CHCH3 Isoprypyl
or or C6H5
or Ph or or Ar
Benzyl group
CH2
or or C6H5CH2
or Bn Ch. 2 -
5. Alkyl Halides or Haloalkanes
RX (X = F, Cl, Br, I)
Examples
Attached to Attached to Attached to
1 carbon atom 2 carbon atoms 3 carbon atoms
C C C
C Cl C Br C I
a 1o chloride a 2o bromide a 3o iodide
Ch. 2 -
6. Alcohols
ROH
Examples
OH
OH OH,
CH3OH , ,
Examples
~100o
O
O
Acyclic Cyclic
Ch. 2 -
8. Amines
RNH2
H H CH3
N N N
H3C H H3C CH3 H3C CH3
o o o
(1 ) (2 ) (3 )
N N
H
(cyclic) (aromatic) Ch. 2 -
9. Aldehydes and Ketones
O O
R H R R
(aldehydes) (ketones)
O O O O
H, , H
ketone aldehyde
Ch. 2 -
Aldehydes and ketones have a
trigonal planar arrangement of
groups around the carbonyl
carbon atom
o
O
121 121o
H H
108o
Ch. 2 -
10.Carboxylic Acids, Esters, and
Amides
O O O
R OH R OR R Cl
(carboxylic (ester) (acid
acid) chloride)
O O O
R NR2 R O R
(amide) (acid
anhydride) Ch. 2 -
11.Nitriles
RCN
2
2 1 1
3
H3C C N C N C N
Ch. 2 -
12. Summary of Important Families
of Organic Compounds
Ch. 2 -
Ch. 2 -
13.Physical Properties and
Molecular Structure
.Ionic Compounds: Ion-Ion Forces
The melting point of a substance
is the temperature at which an
equilibrium exists between the
well-ordered crystalline state and
the more random liquid state
Ch. 2 -
If the substance is an ionic
compound, the ionion forces
that hold the ions together in the
crystalline state are the strong
electrostatic lattice forces that act
between the positive and negative
ions in the orderly crystalline
structure
Ch. 2 -
Physical properties of selected
compounds
Compound Structure mp ( C)
o
bp (oC)
(1 atm)
O
O
dipole-dipole attraction
H H
H Cl H Cl
C C
H H Ch. 2 -
Hydrogen bonds
Dipole-dipole attractions
between hydrogen atoms
bonded to small, strongly
electronegative atoms (O, N, or
F) and nonbonding electron
pairs on other such
electronegative atoms
hydrogen bond
H H
H N H N
H H
Ch. 2 -
Hydrogen bonds
Hydrogen bonding explains why
water, ammonia, and hydrogen
fluoride all have far higher
boiling points than methane (bp
161.6C), even though all four
compounds have similar
molecular weights
Ch. 2 -
Dispersion forces (London
forces)
The average distribution of
charge in a nonpolar molecule
over a period of time is uniform
At any given instant, however,
because electrons move, the
electrons and therefore the
charge may not be uniformly
distributed
Electrons may, in one instant,
be slightly accumulated on one
part of the molecule, and, as
Ch.a
2-
Dispersion forces (London
forces)
This temporary dipole in one
molecule can induce opposite
(attractive) dipoles in
surrounding molecules
I I
I I
weaker
dispersion forces
F F
C F
C F
F F
F F
Ch. 2 -
The relative surface area of
the molecules involved
The larger the surface
area, the larger is the
overall attraction
between molecules
caused by dispersion
forces
Ch. 2 -
e.g. Pentane vs. Neopentane (both C5H12)
H H H
H H H H H C H
H H larger
C H
surface H
H H C H
area H
C C
H H H H stronger
dispersion H H H
forces
H H H H H H H
H H smaller
surface area H C H
H H weaker C H
H
H H dispersion
H C H
H H C C
forces
Neopentane H H H
Ch.2 -
Pentane (bp 36oC) (bp 9.5 C)
o
13C. Boiling Points
The boiling point of a liquid is the
temperature at which the vapor
pressure of the liquid equals the
pressure of the atmosphere above
it
NO2
OH
o
bp: 245 C / 760 mmHg bp: 260oC / 760 mmHg
o
(74 C / 1 mmHg) (140oC / 20 mmHg)
H3C
O H
hydrogen
bond
H H
O
Ch. 2 -
Hydrophobic means
incompatible with water
Hydrophilic means
compatible with water
Hydrophil
Hydrophobic portion ic group
OH
Decyl alcohol
O
S O Na
O
O
A typical detergent molecule Ch. 2 -
E. Guidelines for Water Solubility
Organic chemists usually define a
compound as water soluble if at
least 3 g of the organic
compound dissolves in 100 mL of
water
Usually compounds with one to
three carbon atoms are water
soluble, compounds with four or
five carbon atoms are borderline,
and compounds with six carbonCh. 2 -
14. Summary of Attractive Electric Forces
Ch. 2 -
15.Infrared Spectroscopy
Ch. 2 -
The position of an absorption band
(peak) in an IR spectrum is
specified in units of wavenumbers
( ) 1 E = h
=
E
( = wavelength in cm)
(E = energy) = c
( = frequency of radiation)
E = hc
Ch. 2 -
Ch. 2 -
Characteristic IR absorptions
Intensity: s = strong, m = medium, w = weak, v =
variable
Group Freq. Range (cm Intensity
-
1
)
Alkyl
CH (stretching) 28532962 (ms)
Alkenyl
CH (stretching) 30103095 (m)
C=H (stretching) 16201680 (v)
cis-RCH=CHR 675730 (s)
trans-RCH=CHR 960975 (s)
Alkynyl
CH (stretching) ~3300 (s)
CC (stretching) 21002260 (v) 2 -
Ch.
Characteristic IR absorptions
Intensity: s = strong, m = medium, w = weak, v =
variable
Group Freq. Range (cm ) Intensity
-1
Aromatic
ArH (stretching) ~3300 (v)
- monosubstituted 690710 (very s)
730770 (very s)
- o-disubstituted 735770 (s)
- m-disubstituted 680725 (s)
750810 (very s)
- p-disubstituted 800860 (very s)
Ch. 2 -
Characteristic IR absorptions
Intensity: s = strong, m = medium, w = weak, v =
variable
Group Freq. Range (cm ) Intensity
-1
Ch. 2 -
IR spectrum of toluene
Ch. 2 -
6B. IR Spectra of Hydrocarbons
IR spectrum of 1-heptyne
Ch. 2 -
IR spectrum of 1-octene
Ch. 2 -
B. IR Spectra of Some Functional
Groups Containing
Carbonyl Functional Groups
O O O
R H R R R OR
(aldehyde) (ketone) (ester)
1690-1740 cm-1 1680-1750 cm-1 1735-1750 cm-1
O O
R OH R NR2
(carboxylic acid) (amid)
1710-1780 cm-1 1630-1690 cm-1 Ch. 2 -
Alcohols and phenols
The IR absorption of an alcohol or
phenol OH group is in the 3200
3550 cm-1 range, and most often it
is broad
Ch. 2 -
Carboxylic Acids
IR spectrum of propanoic acid
Ch. 2 -
Amines
1o and 2o amines give absorptions
of moderate strength in the 3300
3500 cm-1 region
1o amines exhibit two peaks in this
region due to symmetric &
asymmetric
stretching of the two NH bonds
2o amines exhibit a single peak
3o amines show no NH absorption
because they have no such bond
A basic pH is evidence for any class
Ch. 2 -
of amines
Amines
IR spectrum of 4-methylaniline
Ch. 2 -
RNH2 (1 Amine) R2NH (2 Amine)
Two peaks in One peak in
33003500 cm-1 33003500 cm-1
region region
symmetric asymmetric
stretching stretching
Ch. 2 -
END OF CHAPTER 2
Ch. 2 -