Lecture 3-11102022

Table of Contents
Chapter 2 1.
2.
Hydrocarbons
Polar Covalent Bonds
3. Polar and Nonpolar Molecules
4. Functional Groups
Alkyl Halides or Haloalkanes
Families of Carbon
5.
6. Alcohols and Phenols
7. Ethers
Compounds 8.
9.
Amines
Aldehydes and Ketones
10. Carboxylic Acids, Esters, and Amides
11. Nitriles
Functional Groups, 12. Summary of Important Families of Organic Compounds
Physical Properties and Molecular Structure
Intermolecular Forces, 13.
14. Summary of Attractive Electric Forces
& Infrared (IR) Spectroscopy
Created by 15. Infrared Spectroscopy
16. Interpreting IR Spectra
Professor William Tam & Dr. Phillis Chang 17. Applications of Basic Principles
Copyright © 2014 by John Wiley & Sons, Inc. All rights reserved. © 2014 by John Wiley & Sons, Inc. All rights reserved.
1 2
In this chapter we will consider: 1. Hydrocarbons

 The major functional groups  Hydrocarbons are compounds that
contain only carbon and hydrogen
 The correlation between properties of atoms
functional groups and molecules and ● Alkanes
intermolecular forces  hydrocarbons that do not have
multiple bonds between carbon
 Infrared (IR) spectroscopy, which can atoms
be used to determine what functional e.g.
groups are present in a molecule
pentane cyclohexane
© 2014 by John Wiley & Sons, Inc. All rights reserved. © 2014 by John Wiley & Sons, Inc. All rights reserved.
3 4
1A. Alkanes 1B. Alkenes

 The primary sources of alkanes are natural gas and  Ethene and propene, the two simplest alkenes, are among
petroleum the most important industrial chemicals produced in the
United States
 The smaller alkanes (methane through butane) are gases
under ambient conditions  Ethene is used as a starting material for the synthesis of
many industrial compounds, including ethanol, ethylene
 Methane is the principal component of natural gas oxide, ethanal, and the polymer polyethylene
 Higher molecular weight alkanes are obtained largely by

refining petroleum
H H
H C
H C
H H H
H
5 6
1
1C. Alkynes
● Alkenes  The simplest alkyne is ethyne (also called
 contain at least one acetylene)
H C C H
carbon–carbon double bond
 Examples of naturally occurring alkynes
O Br Cl
e.g.
C C C C C CH3
Capillin O
propene cyclohexene (an antifungal agent)
Br Dactylyne
(an inhibitor of
pentobarbital
metabolism)
7 8
● Alkynes ● Aromatic compounds

 contain at least one  contain a special type of ring,
carbon–carbon triple bond the most common example of
which is a benzene ring
CH3 COOH
e.g.
benzene toluene benzoic acid
9 10
1D. Benzene  3-Dimensional structure of benzene
 All C C bond lengths are the same p-electrons above

(1.39 Å) (compare with C–C single and below ring
bond 1.54 Å, C=C double bond 1.34 Å)
 Extra stabilization due to resonance

● Planar structure
 aromatic
● All carbons sp2 hybridized
11 12
2
2. Polar Covalent Bonds
 The lobes of each p orbital above and
below the ring overlap with the lobes
Li F
of p orbitals on the atoms to either
side of it  Lithium fluoride has an ionic bond
 the six electrons associated with these H H
p orbitals (one electron from each H C C H
orbital) are delocalized about all six
carbon atoms of the ring H H
 Ethane has a covalent bond. The electrons
are shared equally between the carbon
atoms
13 14
electronegativity element
(EN) H
(2.1)
Li Be B C N O F
+ - (1.0) (1.6) (2.0) (2.5) (3.0) (3.5) (4.0)
d d
Increasing EN
Na Mg Si P S Cl
C C C O (0.9) (1.2) (1.8) (2.1) (2.5) (3.0)
2.5 3.5 K Br
(0.8) (2.8)
Rb I
equal sharing unequal sharing (0.8)
Cs
(2.5)
of e⊖ of e⊖ (0.7)
(non-polar bond) (polar bond)
Increasing EN
 Electronegativity (EN): The intrinsic ability of an atom to
attract the shared electrons in a covalent bond
15 16
3. Polar and Nonpolar Molecules

+ - + -
d d d d
C N C Cl Dipole distance between the
= 
2.5 3.0 2.5 3.0 moment the charges charge
m=rQ
+ - + -
d d d d  Dipole moments are expressed in
H C Si C debyes (D), where 1 D = 3.336  10–30
2.1 2.5 1.8 2.5 coulomb meter (C•m) in SI units
17 18
3
 Molecules containing polar bonds are
d- not necessarily polar as a whole, for
Cl example
(1) BF3 (m = 0 D) (2) CCl4 (m = 0 D)
>
C net dipole Cl
H (1.87 D) F
H 120o C
Cl
H B Cl
F F Cl
d+ (trigonal planar) (tetrahedral)
19 20
 Dipole moment of some compounds 3A. Dipole Moments in Alkenes

Dipole Dipole cis- trans-
Compound Compound
Moment Moment 1,2-Dichloroethene 1,2-Dichloroethene
NaCl 9.0 H2O 1.85 H H H Cl
CH3NO2 3.45 CH3OH 1.70
C C C C
CH3Cl 1.87 CH3COOH 1.52
Cl Cl Cl H
CH3Br 1.79 NH3 1.47
resultant dipole
CH3I 1.64 CH4 0 moment
CHCl3 1.02 CCl4 0 (m = 1.9 D) (m = 0 D)
21 22
 Physical properties of some cis-trans isomers Indicate the direction of the important bond moments in
the each of the following compounds (neglect C-H
m.p. b.p. bonds). You should also give the direction of the net
Compound (m)
(oC) (oC) dipole moment for the molecule. If there is no net dipole
moment, state that µ=0
cis-1,2-Dichloroethene -80 60 1.90
a) cis-CHF=CHF b) trans-CHF=CHF
c) CH2=CF2 d) CF2=CF2
trans-1,2-Dichloroethene -50 48 0
cis-1,2-Dibromoethene -53 112.5 1.35
trans-1,2-Dibromoethene -6 108 0
23 24
4
4. Functional Groups 4A. Alkyl Groups and the Symbol R
 Functional groups are common and

specific arrangements of atoms that
impart predictable reactivity and
properties to a molecule
25 26
4B. Phenyl and Benzyl Groups

CH3 Methyl
 Phenyl group
CH3CH2 Ethyl
These and
others can be
designated
CH3CH2CH2 Propyl
by R
CH3CHCH3 Isopropyl
 Benzyl group
CH2
 General formula for an alkane is R–H or or C6H5CH2
or Bn
27 28
5. Alkyl Halides or Haloalkanes

 R–X (X = F, Cl, Br, I)
● Examples
Attached to Attached to Attached to

1 carbon atom 2 carbon atoms 3 carbon atoms
The same terminology is used for
carbocations.
C C C
C Cl C Br C I
a 1o chloride a 2o bromide a 3o iodide
© 2014 by John Wiley & Sons, Inc. All rights reserved.
29 30
5
6. Alcohols and Phenols
an alkenyl bromide  R–OH
(Br bonded to an alkene carbon)
● Examples
an aryl chloride
(Cl bonded to an aromatic ring)
31 32
 Alcohols may be viewed structurally in Circle the atoms that comprise (a) the phenol and
alcohol functional groups in following molecules
two ways:
● As hydroxyl derivatives of alkanes 2o Alcohol
● As alkyl derivatives of water
ethyl group
CH3CH2 H
CH3CH3 109.5o O104.5o O Phenol
H hydroxyl H
group
Ethane Ethyl alcohol Water
(ethanol)
33 34
One way of naming ethers is to name the two alkyl groups

7. Ethers attached to the oxygen atom in alphabetical order and add
the word ether. If the two alkyl groups are the same, we
 R–O–R use the prefix di-. Write bond-line stuctual formulas for
(a) diethyl ether,

● Examples (b) ethyl propyl ether
(c) ethyl isopropyl ether
~100o What name would you give to

(d) (e)
OMe
O O
O
Acyclic Cyclic (f) CH3OC6H5
35 36
6
Euenol is the main constituent of the natural oil
from cloves. Circle and label all of the functional
8. Amines
groups in eugenol.  R–NH2
H H CH3
Ether N N N
H3C H H3C CH3 H3C CH3
(1o) (2o) (3o)
Alkene
N N
Phenol H
(cyclic) (aromatic)
37 38
One way of naming amine is to name in alphabetical order

HO NH2
the alkyl groups attached to the nitrogen atom using the
H NH2 the prefixes di- and tri-. Write bond-line formulas for
HO
(a) propylamine
Amphetamine Dopamin (b) trimethylamine
(1o) (1o)
(c) ethylisopropylmethylamine
What are names for

N
H (d) (e) NH2
N
N 3
H
Nicotine H
N N
(3o) (f) (g)
39 40
9. Aldehydes and Ketones

 Aldehydes and ketones have a trigonal
O O planar arrangement of groups around
the carbonyl carbon atom
R H R R
(aldehydes) (ketones)
O
121o 121o
O O O O
H , , H H H
o
ketone aldehyde 108
41 42
7
Some specific examples of aldehydes 10. Carboxylic Acids, Esters, and
and ketones Amides
O
O O O
O O
H
H H H R OH R OR R Cl
(carboxylic (ester) (acid
Benzaldehyde
Methanal Ethanal acid) chloride)
(Formaldeyde) (Acetaldehyde)
O O O
O O
R NR2 R O R
2-Butanon (amide) (acid anhydride)
Propanon
(Ethyl methyl ketone)
(Acetone)
43 44
11. Nitriles 12. Summary of Important Families

of Organic Compounds
 R–C≡N
45 46
Circle and label all of the functional groups in the

following compound.
47 48
8
Circle and label all of the functional groups in the 13. Physical Properties & Molecular Structure
following compound.
13A. Ionic Compounds: Ion-Ion Forces
 A large amount of thermal energy is required to break up
the orderly structure of the crystal into the disorderly open
structure of a liquid high melting points
ion–ion forces
 The boiling points of ionic compounds are higher still, so

high that most ionic organic compounds decompose before
they boil
49 50
 Physical properties of selected compounds 13B. Intermolecular Forces (van der

Compound Structure mp (oC) bp (oC) Waals Forces)
(1 atm)
 The forces that act between molecules are
Ethane CH3CH3 -172 -88.2 not as strong as those between ions
Chloroethane CH3CH2Cl -138.7 13.1
 These intermolecular forces, van der Waals
Ethyl alcohol CH3CH2OH -114 78.5 forces, are all electrical in nature
Acetaldehyde CH3CHO -121 20
● Dipole-dipole forces
● Hydrogen bonds
Acetic acid CH3CO2H 16.6 118 ● Dispersion forces
Sodium acetate CH3CO2Na 324 dec
51 52
● Dipole-dipole forces ● Hydrogen bonds

 Dipole-dipole attractions between  Dipole-dipole attractions between hydrogen atoms
polar molecules bonded to small, strongly electronegative atoms (O, N, or
F) and nonbonding electron pairs on other such
electronegative atoms
-1
+ - +  Hydrogen bonds (4 – 38 kJ mol ) are weaker than
d O d d O -
d ordinary covalent bonds but much stronger than the
dipole–dipole interactions
dipole-dipole attraction d+ d+
d+H d+H H H
d+ d+
H H d-O d-O H N- H N-
d d
d H
+
C Cl d
-
d H
+
C Cl - d+ H d+ H H H
d d+ d+
H H
© 2014 by John Wiley & Sons, Inc. All rights reserved. hydrogen bond
53 54
9
● Hydrogen bonds ● Hydrogen bonds
• Hydrogen bonds hold the base pairs of double-stranded DNA
together.
bp 78°C bp 25°C
C2H6O C2H6O
Which compound would you expect to have a higher boiling point?

 The boiling point of a liquid is the temperature at which
(d) NH
the vapor pressure of the liquid equals the pressure of the N CH3
atmosphere above it.
bp (CH4)
>> -161.6°C
55 56
● Dispersion forces (London forces)

 The relative polarizability of electrons of the atoms
 At any given instant, because electrons move, the involved
electrons and therefore the charge may not be
uniformly distributed.
 Electrons may, in one instant, be slightly
• The electrons of large
accumulated on one part of the molecule, and, as a atoms such as iodine
consequence, a small temporary dipole will occur. are loosely held and are
 This temporary dipole in one molecule can induce easily polarized, while
the electrons of small
opposite (attractive) dipoles in surrounding atoms such as fluorine
molecules. are more tightly held
and are much less
polarizable
 Two important factors determine the magnitude of

dispersion forces:
57 58
 The relative surface area of the molecules involved

e.g. Pentane vs. Neopentane (both C5H12) -
Summary of van der Waals Forces
- -
d d- - d
d d Dispersion forces (London forces) exist between in all
- •
d H HH d
- -
- d -
-
d H H H H d - H H molecules.
larger surface
d H H d d H C C H d
- -
area
H H C H • When comparing substances of roughly comparable molecular
 stronger H C
+ + dispersion + C + masses, dipole-dipole forces can produce significant
d H H d d d
d H+ H +
+
+ d forces H H H differences in physical properties (i.e. bp, mp).
d d+ + d+ d + +
d d +
d
d • When comparing substances of widely different molecular
- masses, dispersion forces are usually more significant than
-
d d- -
d d
-
- d - d
-
dipole forces.
d H H H H d -
d H HH d
- - -
d H H d smaller surface
area H C H
H H  weaker d
- C H d-
H
H C C C H
+
d
+ dispersion
d H+
+ H H H + d
+ d forces + +
d d+ + d+ d d d
d Neopentane H H H
+ +
Pentane (bp 36oC) (bp 9.5oC) d +
d
d
59 60
10
Solubilities 13D. Solubilities
 “like dissolves like” in  A general rule for solubility is that “like
terms of comparable dissolves like” in terms of comparable polarities
polarities ● Polar and ionic solids are usually soluble in
polar solvents
● Hydrophobic means incompatible with water ● Polar liquids are usually miscible
● Hydrophilic means compatible with water ● Nonpolar solids are usually soluble in
nonpolar solvents
Hydrophilic
group
● Nonpolar liquids are usually miscible
Hydrophobic portion
● Polar and nonpolar liquids, like oil and
O water, are usually not soluble to large
S O Na extents
O
O
A typical detergent molecule © 2014 by John Wiley & Sons, Inc. All rights reserved.
61 62
Which of the following solvents should be capable

e.g. MeOH and H2O are miscible in all
of dissolving ionic compounds?
proportions
a) Liquid SO2
H3C - b) Liquid NH3
d +
d Benzene
O H c)
d) CCl4
hydrogen
bond H H +
d+ O d
d-
 Usually compounds with one to three carbon atoms are water soluble,
compounds with four or five carbon atoms are borderline, and
compounds with six carbon atoms or more are insoluble.
63 64
Summary of Attractive Electric Forces 15. Infrared Spectroscopy

intramolecular
intermolecular
65 66
11
 The position of an absorption band
(peak) in an IR spectrum is specified in
units of wavenumbers (  )
1 ∵ DE = h
= 
∴E
( = wavelength in cm)
(E = energy) c
∵=
( = frequency of radiation) 
hc
∴ DE =

67 68
Interpreting IR Spectra
octane
1-octene
69 70
IR Spectra of Some Functional  Carboxylic Acids

Groups Containing Heteroatoms ● IR spectrum of propanoic acid
 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) (amide)
1710-1780 cm-1 1630-1690 cm-1
71 72
12
 IR spectrum of toluene Summary
 The functional groups defining the families to which
organic compounds belong.
3D structure
↓
 EN → charge distribution → polarity of a molecule
↓
Relative strength of
electrostatic forces
↓
physical properties
(mp, bp)
 IR spectroscopy → suggests which functional groups are

present in a molecule.
73 74
13

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Table of Contents

In this chapter we will consider: 1. Hydrocarbons

1A. Alkanes 1B. Alkenes

 Higher molecular weight alkanes are obtained largely by

● Alkynes ● Aromatic compounds

benzene toluene benzoic acid

1D. Benzene  3-Dimensional structure of benzene

 All C C bond lengths are the same p-electrons above

 Extra stabilization due to resonance

3. Polar and Nonpolar Molecules

(1) BF3 (m = 0 D) (2) CCl4 (m = 0 D)

 Dipole moment of some compounds 3A. Dipole Moments in Alkenes

cis-1,2-Dibromoethene -53 112.5 1.35

 Functional groups are common and

4B. Phenyl and Benzyl Groups

5. Alkyl Halides or Haloalkanes

Attached to Attached to Attached to

One way of naming ethers is to name the two alkyl groups

(a) diethyl ether,

~100o What name would you give to

One way of naming amine is to name in alphabetical order

What are names for

© 2014 by John Wiley & Sons, Inc. All rights reserved.

9. Aldehydes and Ketones

11. Nitriles 12. Summary of Important Families

Circle and label all of the functional groups in the

 The boiling points of ionic compounds are higher still, so

 Physical properties of selected compounds 13B. Intermolecular Forces (van der

● Dipole-dipole forces ● Hydrogen bonds

Which compound would you expect to have a higher boiling point?

● Dispersion forces (London forces)

 Two important factors determine the magnitude of

 The relative surface area of the molecules involved

Which of the following solvents should be capable

Summary of Attractive Electric Forces 15. Infrared Spectroscopy

© 2014 by John Wiley & Sons, Inc. All rights reserved.

IR Spectra of Some Functional  Carboxylic Acids

 IR spectroscopy → suggests which functional groups are

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