CH 01

Organic Chemistry
Original Slides by:

Professor William Tam
Dr. Phillis Chang
Edited by:
Assoc. Prof. Dr. Abdulilah ECE
Biruni University, İstanbul
http://ece.biruni.edu.tr
Copyright © 2022 by ABECE & 2016 by John Wiley & Sons, Inc. All rights reserved.
Chapter 1
Families of Carbon
Compounds
Functional Groups
& Intermolecular Forces
Table of Contents
1. Hydrocarbons
2. Polar Covalent Bonds
3. Polar and Nonpolar Molecules
4. Functional Groups
5. Alkyl Halides or Haloalkanes
6. Alcohols and Phenols
7. Ethers
8. Amines
9. Aldehydes and Ketones
10. Carboxylic Acids, Esters, and Amides
11. Nitriles
12. Summary of Important Families of Organic Compounds
13. Physical Properties and Molecular Structure
14. Summary of Attractive Electric Forces
In this chapter we will consider:
 The major functional groups
 The correlation between properties of

functional groups and molecules and
intermolecular forces
Organic chemistry provides the power
 to synthesize new drugs
 to engineer molecules that can make computer processors run more
quickly,
 to understand why grilled meat can cause cancer and how its effects
can be combated to design ways
 to knock the calories out of sugar while still making food taste
deliciously sweet
It can do almost anything.

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
● Alkenes
 contain at least one
carbon–carbon double bond
e.g.
propene cyclohexene
● Alkynes
 contain at least one
carbon–carbon triple bond
1 2
e.g. H C C H
3 5
4
ethyne 1-pentyne
4 3 2 1
5
2-pentyne
● Aromatic compounds
 contain a special type of ring,
the most common example of
which is a benzene ring
CH3 COOH
e.g.
benzene toluene benzoic acid
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 by refining petroleum
H
H H
H
1B. Alkenes
 Ethene is used as a starting material for the
synthesis of many industrial compounds,
including ethanol, ethylene oxide, ethanal, and
the polymer polyethylene
H H
C
C
H H
 Examples of naturally occurring alkenes
β-Pinene An aphid alarm

(a component of pheromone
turpentine)
1C. Alkynes
 The simplest alkyne is ethyne (also called
acetylene)
H C C H
 Examples of naturally occurring alkynes
O Br Cl
C C C C C CH3
Capillin O
(an antifungal agent)
Br Dactylyne
(an inhibitor of
pentobarbital
metabolism)
1D. Benzene
 All C C bond lengths are the same

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

⇒ aromatic
 3-Dimensional structure of benzene
π-electrons above
and below ring
● Planar structure
● All carbons sp2 hybridized
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
electronegativity
+ −
δ δ
C C C O
2.5 3.5
equal sharing unequal sharing

⊖ ⊖
of e of e
(non-polar bond) (polar bond)
 Electronegativity (EN)
● The intrinsic ability of an atom to
attract the shared electrons in a
covalent bond
● Electronegativities are based on an

arbitrary scale, with F the most
electronegative (EN = 4.0) and Cs
the least (EN = 0.7)
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)
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
+ − + −
δ δ δ δ
C N C Cl
2.5 3.0 2.5 3.0
+ − + −
δ δ δ δ
H C Si C
2.1 2.5 1.8 2.5
3. Polar and Nonpolar Molecules
Dipole distance between the

= ×
moment the charges charge
µ=r×Q
 Dipole moments are expressed in
debyes (D), where 1 D = 3.336 × 10–30
coulomb meter (C•m) in SI units
 Molecules containing polar bonds are
not necessarily polar as a whole, for
example
(1) BF3 (µ = 0 D) (2) CCl4 (µ = 0 D)

Cl
F
o C
120 Cl
B Cl
F F Cl
(trigonal planar) (tetrahedral)
 Dipole moment of some compounds
Dipole Dipole
Compound Compound
Moment Moment
NaCl 9.0 H2O 1.85
CH3NO2 3.45 CH3OH 1.70
CH3Cl 1.87 CH3COOH 1.52
CH3Br 1.79 NH3 1.47
CH3I 1.64 CH4 0
CHCl3 1.02 CCl4 0
3A. Dipole Moments in Alkenes
cis- trans-
1,2-Dichloroethene 1,2-Dichloroethene
H H H Cl
C C C C
Cl Cl Cl H
resultant dipole
moment
(µ = 1.9 D) (µ = 0 D)
 Physical properties of some cis-trans isomers
m.p. b.p.
Compound (µ)
(oC) (oC)
cis-1,2-Dichloroethene -80 60 1.90
trans-1,2-Dichloroethene -50 48 0
cis-1,2-Dibromoethene -53 112.5 1.35
trans-1,2-Dibromoethene -6 108 0
4. Functional Groups
 Functional groups are common and

specific arrangements of atoms that
impart predictable reactivity and
properties to a molecule
4A. Alkyl Groups and the Symbol R
CH3 Methyl
CH3CH2 Ethyl These and

others can be
designated
CH3CH2CH2 Propyl
by R
CH3CHCH3 Isopropyl
 General formula for an alkane is R–H
4B. Phenyl and Benzyl Groups
 Phenyl group
or or C6H5
or Ph or φ
 Benzyl group
CH2
or or C6H5CH2
or Bn
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
C C C
C Cl C Br C I
a 1o chloride a 2o bromide a 3o iodide
Br
an alkenyl bromide
(Br bonded to an alkene carbon)
Cl
an aryl chloride
(Cl bonded to an aromatic ring)
6. Alcohols and Phenols
 R–OH
● Examples
OH
, OH , OH ,
OH
o o o
(1 ) (2 ) (3 ) (aromatic)
(phenol)
 Alcohols may be viewed structurally in
two ways:
● As hydroxyl derivatives of alkanes
● As alkyl derivatives of water
ethyl group
CH3CH2 H
CH3CH3 109.5o O104.5o O
H hydroxyl H
group
Ethane Ethyl alcohol Water
(ethanol)
7. Ethers
 R–O–R
● Examples
o
~100
O
O
Acyclic Cyclic
8. Amines
 R–NH2
H H CH3
N N N
H3C H H3C CH3 H3C CH3
o o o
(1 ) (2 ) (3 )
N N
H
(cyclic) (aromatic)
9. Aldehydes and Ketones
O O
R H R R
(aldehydes) (ketones)
O O O O
H , , H
ketone aldehyde
 Aldehydes and ketones have a trigonal
planar arrangement of groups around
the carbonyl carbon atom
o
O
121 121o
H H
108o
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)
11. Nitriles
 R–C≡N
2
2 1 1
3
H3 C C N C N C N
Ethanenitrile Propenenitrile Benzonitrile

(acetonitrile) (acrylonitrile) (benzenecarbonitrile)
12. Summary of Important Families
of Organic Compounds
13. Physical Properties & Molecular
Structure
13A. 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
 If the substance is an ionic compound,
the ion–ion forces are the strong
electrostatic lattice forces that act
between the positive and negative ions
 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
 The boiling points of ionic
compounds are higher still, so high
that most ionic organic compounds
decompose before they boil
 Physical properties of selected compounds
Compound Structure mp (oC) bp (oC)
(1 atm)
Ethane CH3CH3 -172 -88.2
Chloroethane CH3CH2Cl -138.7 13.1
Ethyl alcohol CH3CH2OH -114 78.5
Acetaldehyde CH3CHO -121 20
Acetic acid CH3CO2H 16.6 118
Sodium acetate CH3CO2Na 324 dec
13B. Intermolecular Forces (van der
Waals Forces)
 The forces that act between molecules
are not as strong as those between ions
 These intermolecular forces, van der
Waals forces, are all electrical in
nature
● Dipole-dipole forces
● Hydrogen bonds
● Dispersion forces
● Dipole-dipole forces
 Dipole-dipole attractions
between polar molecules
+ − +
δ O δ δ O −
δ
dipole-dipole attraction
H H
H
δ H C
+ − +
δ C Cl δ Cl −
δ
H H
● 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 bonds (bond dissociation
-1
energies of about 4 – 38 kJ mol )
are weaker than ordinary covalent
bonds but much stronger than the
dipole–dipole interactions
● Hydrogen bonds
δ+H δ+H
− −
δO δO
δ+ H δ+ H
hydrogen bond
+ +
δ δ
H H
δ+ δ+
H N− H N−
δ δ
+H +H
δ δ
● Hydrogen bonds
 Hydrogen bonding explains why
water, ammonia, and hydrogen
fluoride all have far higher boiling
points than methane (bp −161.6°C),
even though all four compounds
have similar molecular weights
 One of the most important

consequences of hydrogen bonding
is that it causes water to be a liquid
rather than a gas at 25°C
● Hydrogen bonds
 Calculations indicate that in the
absence of hydrogen bonding, water
would have a bp near −80°C and
would not exist as a liquid at room
temperature
Hydrogen bonds
Location of the substituents
Weak
H-Bond
H Strong
O H-Bond H
(increased Binding Region
activity) O (H-Bond)
Binding Region
Binding Binding (for Y)
site site
Y Y
para Substitution meta Substitution
© 2016 by ABECE & 2013 Oxford University Press, All rights reserved.
● 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 a consequence, a small temporary
dipole will occur
● Dispersion forces (London forces)
 This temporary dipole in one molecule

can induce opposite (attractive) dipoles in
surrounding molecules
 These temporary dipoles change

constantly, but the net result of their
existence is to produce attractive forces
between nonpolar molecules
● Two important factors determine
the magnitude of dispersion forces
 The relative polarizability of electrons
of the atoms involved
 The electrons of large atoms such
as iodine are loosely held and are
easily polarized, while the electrons
of small atoms such as fluorine are
more tightly held and are much less
polarizable
− stronger
+
δ δ δ− δ+
− + dispersion forces − +
δ δ δ δ
− + − +
δ I δ δ I δ
+
−
δ −
δ δ δ+
δ − C I δ+ δ − C I δ+
−
δ I δ+ δ
− I δ+
δ− I δ+ δ−
I δ+
− + − +
δ δ δ δ
weaker
dispersion forces
δ− F δ+ δ− F δ+
− + − +
δ C Fδ δ C Fδ
F F
δ−
F δ+ δ−
F δ+
 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
e.g. Pentane vs. Neopentane (both C5H12)
−
δ −
−
δ δ −
− − δ
δ δ δ H H−H δ−
δ− H H H H δ−
H H
δ− H H δ− larger surface −
δ H
C C
δ
−
area H
H H
⇒ stronger H C C C H
δ+ +H H H Hδ+ δ+ dispersion δ+ +
δ
δ forces H H H
δ+ δ+ + δ+ δ+
δ δ+ δ+
δ+
− −−
−δ δ δ −
− δ δ − δ
−
δ H H H H δ − H − −
δ H −
H δ smaller surface δ H H δ
area H H
H H − C C −
⇒ weaker δ H H δ
δ+ +H H H Hδ+ δ+ dispersion
H C C C H
δ + + forces + +
δ δ+ + δ+ δ δ δ
δ H H H
+ +
δ +
δ
Copyright © 2022 by ABECE & 2016 by John Wiley & Sons, Inc. All rights reserved. δ
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
 the boiling points of liquids are

pressure dependent, and boiling points
are always reported as occurring at a
particular pressure
 Examples
CH3 t
Bu
CH3
NO2
OH
bp: 245oC / 760 mmHg bp: 260oC / 760 mmHg
(74oC / 1 mmHg) (140oC / 20 mmHg)
1 atm = 760 torr = 760 mmHg

13D. Solubilities
 A general rule for solubility is that “like
dissolves like” in terms of comparable polarities
● Polar and ionic solids are usually soluble in

polar solvents
● Nonpolar solids are usually soluble in
nonpolar solvents
● Polar and nonpolar liquids, like oil and
water, are usually not soluble to large
extents
e.g. MeOH and H2O are miscible in all
proportions
H3C −
δ +
δ
O H
hydrogen
bond
+H H +
δ O δ
−
δ
● Hydrophobic means incompatible
with water
● Hydrophilic means compatible
with water
Hydrophilic
Hydrophobic portion group
OH
Decyl alcohol
O
S O Na
O
O
A typical detergent molecule
13E. 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 carbon atoms or more are
insoluble
14. Summary of Attractive Electric
Forces
 END OF LECTURE 1 
Abdulilah October, 2022

CH 01

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CH 01

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Organic Chemistry

Original Slides by:

 The major functional groups

 The correlation between properties of

It can do almost anything.

benzene toluene benzoic acid

β-Pinene An aphid alarm

 All C C bond lengths are the same

 Extra stabilization due to resonance

equal sharing unequal sharing

● Electronegativities are based on an

Dipole distance between the

(1) BF3 (µ = 0 D) (2) CCl4 (µ = 0 D)

cis-1,2-Dibromoethene -53 112.5 1.35

 Functional groups are common and

CH3CH2 Ethyl These and

 General formula for an alkane is R–H

Attached to Attached to Attached to

Ethanenitrile Propenenitrile Benzonitrile

 A large amount of thermal energy is

Ethane CH3CH3 -172 -88.2

Chloroethane CH3CH2Cl -138.7 13.1

Ethyl alcohol CH3CH2OH -114 78.5

Acetaldehyde CH3CHO -121 20

Acetic acid CH3CO2H 16.6 118

Sodium acetate CH3CO2Na 324 dec

 One of the most important

 The average distribution of charge in a

 This temporary dipole in one molecule

 These temporary dipoles change

 The larger the surface area, the

 the boiling points of liquids are

1 atm = 760 torr = 760 mmHg

● Polar and ionic solids are usually soluble in

Abdulilah October, 2022

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