SYLLABUS

CHEM 201 ORGANIC CHEMISTRY I

SPRING 2014

Text book :Organic Chemistry, T.W.Graham Solomons, JohnWiley andSons, Inc.

M2 M3
Instructor : Prof.Dr.Turgut Nugay ( office hour )

Topics to be covered 1. Carbon Compounds and Chemical Bonds

Writing Lewis Structures
Exceptions to the Octet Rule
Formal Charge
Resonance
2. Functional Groups.
3. Acids and Bases.
4. Alkanes.
5. Stereochemistry.
6. Nucleophilic Substitution and Elimination Reactions
of Alkyl Hallides.
7. Alkenes and Alkynes I
8. Alkenes and Alkynes II
9. Radical Reactions.

Course evaluation : 3 Mid-term exams 60% (20% each), Final exam 40%

Exam dates M1
M2
M3
Final exam: to be announced

Make-up exam If a mid-term exam is missed, you must present an acceptable excuse to your instructor
within one week. One comprehensive make-up exam will be given at the end of the
semester. If you miss the final, see the register.

Ch. 1 - 1
 Chapter 1
Carbon Compounds and
Chemical Bonds

Ch. 1 - 2
1774- Lavoisier, «Law of concervation of mass» : The
total mass of substances present after the chemical
reaction is the same as the total mass of before the
reaction.

1779- Proust, «Law of definite proportions» : All

samples of a compound have the same composition-the
same proportions by mass of the constituant elements.

1780- Scientists began to distinguish between organic

compounds and inorganic compounds.

Ch. 1 - 3
1. Introduction
 The name Organic Chemistry came
from the word organism
 Organic Chemistry is the study of
carbon compounds. Carbon, atomic
number 6, is a second-row element.
Although carbon is the principal
element in organic compounds, most
also contain hydrogen, and many
contain nitrogen, oxygen, phosphorus,
sulfur, chlorine, or other elements
Ch. 1 - 4
 Most of the compounds found in nature -
those we rely on for food, medicine,
clothing (cotton, wool, silk), and energy
(natural gas, petroleum) - are organic as
well
 Important organic compounds are not,
however, limited to the ones we find in
nature
 Chemists have learned to synthesize millions
of organic compounds never found in
nature, including synthetic fabrics, plastics,
synthetic rubber, medicines, and even things
like photographic film & Super glue
Ch. 1 - 5
Chemical structures of different
classes of antibiotics

Ch. 1 - 6
Classification by Application
a. Plastics (sheets, films)
polyethylene

isotactic
polypropylene
polyvinylchloride

polystyrene
polycarbonate
(life magazine)
polycarbonate (life magazine)
 (life magazine)
polydimethylsiloxane
Polytetrafloroethylene
(Teflon)
 b. (Semi-) Synthetic fibers
Poly(-caprolactam) Poly(hexamethylene adipamide)
(Nylon 6) (Nylon 6,6)

Polyethyleneterephthalate
(Polyester fiber) Polyacrylonitrile
(Acrylic fiber)
c. Elastomers and rubbers

Poly(cis-1,4-isoprene)

Styrene-butadiene rubber
(SBR)
yellow

blue

red

Rubber Life magazine)

…
d. Coatings and adhesives

Polymethylmetacrylate
(PMMA)

Polyvinylacetate
(PVAc)
Life magazine)
2. Atomic Structure
 Compounds
● made up of elements combined in
different proportions
 Elements
● made up of atoms
 Atoms
● positively charged nucleus
containing protons and neutrons
● with a surrounding cloud of
negatively charged electrons Ch. 1 - 18
 Each element is distinguished by its
atomic number (Z)

 Atomic number = number of protons

in nucleus

Ch. 1 - 19
Ch. 1 - 20
2A. Isotopes

 Although all the nuclei of all atoms of

the same element will have the same
number of protons, some atoms of
the same element may have different
masses because they have different
numbers of neutrons. Such atoms are
called isotopes

Ch. 1 - 21
 Examples

(1) 12C 13C 14C

(6 protons (6 protons (6 protons

6 neutrons) 7 neutrons) 8 neutrons)

(2) 1H 2H 3H

Hydrogen Deuterium Tritium

(1 proton (1 proton (1 proton
0 neutrons) 1 neutron) 2 neutrons)

Ch. 1 - 22
2B. Valence Electrons
 Electrons that surround the nucleus exist in
shells of increasing energy and at increasing
distances from the nucleus. The most
important shell, called the valence shell,
is the outermost shell because the electrons
of this shell are the ones that an atom uses
in making chemical bonds with other atoms
to form compounds
 The number of electrons in the valence shell
(called valence electrons) is equal to the
group number of the atom
Ch. 1 - 23
 e.g. Carbon is in group IVA
● Carbon has 4 valence electrons

 e.g. Nitrogen is in group VA

● Nitrogen has 5 valence electrons

 e.g. Halogens are in group VIIA

● F, Cl, Br, I all have 7 valence
electrons

Ch. 1 - 24
3. The Structural Theory of
Organic Chemistry
 Number of covalent bonds usually
formed by some elements typically
encountered in organic compounds

Element # of covalent bonds Element # of covalent bonds

H 1 F 1
C 4 Cl 1
N 3 (or 4) Br 1
O 2 I 1
Ch. 1 - 25
 Thus
● C is tetravalent
● O is divalent
● H and halogens are monovalent

C O H Br

(tetravalent) (divalent) (monovalent)

Ch. 1 - 26
 Important:
● Do not draw any structure with
more than 4 bonds on a carbon

C C C

4 bonds

Ch. 1 - 27
 3 bonds on carbon  need a charge
on carbon
Br
C C
Carbenium ion
C (Carbonium ion)
B
H
C C
Carbanion

C Never draw 5 (or more) bonds on carbon

Ch. 1 - 28
 Oxygen
● Usually divalent
O

O H3C O H H3C CH3

(diethyl ether) (methanol) (acetone)

Ch. 1 - 29
 Lone pair electrons on oxygen can
donate electrons to a Lewis acid
● 3 bonds on oxygen (with a positive
charge on oxygen)
e.g.

H3C H3C H3C

O H+ O H O H
H H H
dative
covalent bond

Ch. 1 - 30
 BF3
O F O
B
H3C CH3 H3C CH3
F F

empty p-orbitals

Ch. 1 - 31
 One bond on oxygen
● Usually need a negative charge on
oxygen

e.g.

O O
H OH
R O R O

Ch. 1 - 32
3A. Isomers: The Importance of
Structural Formulas
 Different compounds that have the
same molecular formula. Such
compounds are called isomers

e.g.
OH O
1-Butanol Diethyl ether

Ch. 1 - 33
● Both have the molecular formula
C4H10O

● They are constitutional isomers

● Constitutional isomers usually have

different physical properties (e.g.,
melting point, boiling point, and
density) and different chemical
properties (reactivity)

Ch. 1 - 34
3B. The Tetrahedral Shape of
Methane

Ch. 1 - 35
4. Chemical Bonds:
The Octet Rule
 Ionic (or electrovalent) bonds are
formed by the transfer of one or more
electrons from one atom to another to
create ions

 Covalent bonds result when atoms

share electrons

Ch. 1 - 36
 Octet Rule
● In forming compounds, they gain,
lose, or share electrons to give a
stable electron configuration
characterized by 8 valence electrons
● When the octet rule is satisfied for
C, N, O and F, they have an
electron configuration analogous to
the noble gas Ne

Ch. 1 - 37
 Recall: electron configuration of noble
(inert) gas

# of e-s in outer shell

He [1s2] 2
Ne 1s2[2s22p6] 8
Ar 1s22s22p6[3s23p6] 8

Ch. 1 - 38
4A. Ionic Bonds

 Atoms may gain or lose electrons and

form charged particles called ions

● An ionic bond is an attractive force

between oppositely charged ions

Ch. 1 - 39
 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)

Ch. 1 - 40
 element H
(EN) (2.1)
Li Be B C N O F
……..………
(1.0) (1.6) (2.0) (2.5) (3.0) (3.5) (4.0)
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)

Ch. 1 - 41
 give 1 e- to
Na Cl
1s 2s 2p 3s
2 2 6 1 1s 2s 2p 3s 3p
2 2 6 2 5

(1 e- in outermost shell) (7 e- in outermost shell)

ionic bonding
+ –
Na Cl
1s2 2s2 2p6 1s2 2s2 2p6 3s2 3p6
8 8
Ch. 1 - 42
4B. Covalent Bonds & Lewis Structures
 Covalent bonds form by sharing of
electrons between atoms of similar
electronegativities to achieve the
configuration of a noble gas

 Molecules are composed of atoms

joined exclusively or predominantly by
covalent bonds

Ch. 1 - 43
 Example

:Cl.
: : . Cl:

: :
[Ne] 3s2 3p5 [Ne] 3s2 3p5
covalent bonding
: :
: :
:Cl—Cl:
Ch. 1 - 44
 Ions, themselves, may contain covalent
bonds. Consider, as an example, the
ammonium ion

H
H+ N
N H H
H H
H H
(ammonia) (ammonium cation)
(3 bonds on N) (4 bonds on N with
a positive charge on N)

Ch. 1 - 45
5. How to Write Lewis Structures
 Lewis structures show the connections
between atoms in a molecule or ion
using only the valence electrons of the
atoms involved
 For main group elements, the number
of valence electrons a neutral atom
brings to a Lewis structure is the same
as its group number in the periodic
table
Ch. 1 - 46
 If the structure we are drawing is a
negative ion (an anion), we add one
electron for each negative charge to
the original count of valence electrons.
If the structure is a positive ion (a
cation), we subtract one electron for
each positive charge
 In drawing Lewis structures we try to
give each atom the electron
configuration of a noble gas

Ch. 1 - 47
 Examples

(1) Lewis structure of CH3Br

● Total number of all valence

electrons:

C H Br

4 + 1 x 3 + 7 = 14

Ch. 1 - 48
● H
H C Br
H

● H

: :
H C Br:
8 H remaining
valence 6 valence
electrons electrons
Ch. 1 - 49
(2) Lewis structure of methylamine
(CH5N)

● Total number of all valence

electrons:

C H N

4 + 1 x 5 + 5 = 14

Ch. 1 - 50
● H
H C N H
H H
2 valence
● H electrons left

:
H C N H
12 valence H H
electrons
Ch. 1 - 51
6. Exceptions to the Octet Rule
 Elements in the 2nd row in the periodic
table usually obey the Octet Rule (Li,
Be, B, C, N, O, F) since they have one
2s and three 2p orbitals available for
bonding
 Elements in the 3rd row in the periodic
table have d orbitals that can be used
for bonding and may not obey the
Octet Rule
Ch. 1 - 52
 Examples Expanded octet
Cl Cl Cl
Cl Cl Cl
Cl P P P
Cl Cl Cl Cl Cl
Cl Cl Cl
(PCl5) Phosphorus pentachloride
m.p. = 179oC
2-
F
F F
Si
F F
F

(SiF62-)
Ch. 1 - 53
 Electron defficient octet
 Some highly reactive molecules or ions
have atoms with fewer than eight
electrons in their outer shell

F
B
F F

Ch. 1 - 54
7. Formal Charges and How to
Calculate Them
 Formal charge number of valence electrons
1/2 number of shared electrons – number
of unshared electrons

or F = Z - S /2 - U

where F is the formal charge, Z is the

group number of the element, S equals the
number of shared electrons, and U is the
number of unshared electrons
Ch. 1 - 55
 Examples
(1) The Ammonium ion (NH4+)
H
H NH Recall: F = Z - S /2 - U
H

Formal charge of H:
= 1 – 2/2 – 0 = 0
group number number of
number of shared unshared
of H electrons electrons
Ch. 1 - 56
 Formal charge of N:
= 5 – 8/2 – 0 = +1
group number number of
number of shared unshared
of N electrons electrons

Charge on ion = 4 x 0 +1 = +1

 The arithmetic sum of all the formal

charges in a molecule or ion will equal
the overall charge on the molecule or
ion
Ch. 1 - 57
 -
(2) The Nitrate ion (NO3 )

O
N Recall: F = Z - S /2 - U
O O

Formal charge of O:
= 6 – 2/2 – 6 = -1
group number number of
number of shared unshared
of O electrons electrons
Ch. 1 - 58
 Formal charge of O:
= 6 – 4/2 – 4 = 0
group number number of
number of shared unshared
of O electrons electrons

Formal charge of N:
= 5 – 8/2 – 0 = +1
group number number of
number of shared unshared
of N electrons electrons

Charge on ion = 2 x (-1) + 0 +1 = -1

Ch. 1 - 59
(3) Water (H2O)
The sum of the formal charges on
each atom making up a molecule
must be zero
O
H H

Formal charge of O = 6 – 4/2 – 4 = 0

Formal charge of H = 1 – 2/2 – 0 = 0

Charge on molecule = 0 + 2 x 0 = 0
Ch. 1 - 60
7A. A Summary of Formal Charges

Ch. 1 - 61
8. Resonance Theory
 In a Lewis structure, we draw a well-
defined location for the electrons in a
molecule. In many molecules and ions
(especially those containing p bonds),
more than one equivalent Lewis
structure can be drawn which
represent the same molecule

Ch. 1 - 62
 We can write three different but
equivalent structures, 1–3

O O O
C C C
O O O O O O
1 2 3

Ch. 1 - 63
 O O O
becomes becomes
C C C
O O O O O O
1 2 3

 Structures 1–3, although not identical

on paper, are equivalent; all of its
carbon–oxygen bonds are of equal
length

Ch. 1 - 64
 Resonance theory states that whenever a
molecule or ion can be represented by two
or more Lewis structures that differ only in
the positions of the electrons, two things
will be true:
● None of these structures, which we call
resonance structures or resonance
contributors, will be a realistic representation
for the molecule or ion. None will be in
complete accord with the physical or
chemical properties of the substance
● The actual molecule or ion will be better
represented by a hybrid (average) of
these structures
Ch. 1 - 65
 ● Resonance structures, then, are not
real structures for the actual
molecule or ion; they exist only on
paper

O O O
C C C
O O O O O O

Ch. 1 - 66
● It is also important to distinguish
between resonance and an equilibrium

● In an equilibrium between two or more

species, it is quite correct to think of
different structures and moving (or
fluctuating) atoms, but not in the case
of resonance (as in the carbonate ion).
Here the atoms do not move, and the
“structures” exist only on paper. An
equilibrium is indicated by and
resonance by
Ch. 1 - 67
8A. How to Write Resonance
Structures
 Resonance structures exist only
on paper. Although they have no real
existence of their own, resonance
structures are useful because they
allow us to describe molecules and ions
for which a single Lewis structure is
inadequate

Ch. 1 - 68
 We write two or more Lewis structures,
calling them resonance structures or
resonance contributors. We connect
these structures by double-headed
arrows , and we say that the
real molecule or ion is a hybrid of all of
them

Ch. 1 - 69
 We are only allowed to move electrons
in writing resonance structures

These are resonance structures

H2C CH2 CH CH2

This is not a proper resonance

structure of 1 and 2 because a
hydrogen atom has been moved
Ch. 1 - 70
 All of the structures must be proper
Lewis structures
H
H C O H
H

This is not a proper

resonance
structure of methanol

Ch. 1 - 71
 The energy of the resonance hybrid is
lower than the energy of any
contributing structure. Resonance
stabilizes a molecule or ion. This is
especially true when the resonance
structures are equivalent. Chemists
call this stabilization resonance
stabilization. If the resonance
structures are equivalent, then the
resonance stabilization is large

Ch. 1 - 72
 The more stable a structure is (when
taken by itself), the greater is its
contribution to the hybrid
 The more covalent bonds a structure
has, the more stable it is
 Charge separation decreases stability

Resonance structures for formaldehyde

Four O O Three
covalent covalent
C C
bonds H H H H bonds
more stable less stable Ch. 1 - 73
 Structures in which all the atoms have
a complete valence shell of electrons
(i.e., the noble gas structure) are more
stable

Ch. 1 - 74
 Examples
(1) Benzene

(2) Carboxylate ion (RCOO-)

O O O

R O R O R O

(3) Ozone (O3)

O O
O O O O Ch. 1 - 75
10. Atomic Orbitals and Electron
Configuration

Ch. 1 - 76
10A. Electron Configurations
 The relative energies of atomic orbitals in
the 1st & 2nd principal shells are as follows:
● Electrons in 1s orbitals have the lowest
energy because they are closest to the
positive nucleus
● Electrons in 2s orbitals are next lowest in
energy
● Electrons of the three 2p orbitals have
equal but higher energy than the 2s orbital
● Orbitals of equal energy (such as the three
2p orbitals) are called degenerate
orbitals
Ch. 1 - 77
 Aufbau principle
● Orbitals are filled so that those of
lowest energy are filled first

 Pauli exclusion principle

● A maximum of two electrons may
be placed in each orbital but only
when the spins of the electrons are
in opposite directions

Ch. 1 - 78
 Hund’s rule
● When we come to orbitals of equal
energy (degenerate orbitals) such as the
three p orbitals, we add one electron to
each with their spins unpaired until
each of the degenerate orbitals contains
one electron. (This allows the electrons,
which repel each other, to be farther
apart.) Then we begin adding a second
electron to each degenerate orbital so
that the spins are paired

Ch. 1 - 79
Ch. 1 - 80
11. Molecular Orbitals

Ch. 1 - 81
 We cannot simultaneously know the
position and momentum of an electron
 An atomic orbital represents the
region of space where one or two
electrons of an isolated atom are likely
to be found
 A molecular orbital (MO) represents
the region of space where one or two
electrons of a molecule are likely to be
found

Ch. 1 - 82
 An orbital (atomic or molecular) can
contain a maximum of two spin-paired
electrons (Pauli exclusion principle)

 When atomic orbitals combine to form

molecular orbitals, the number of
molecular orbitals that result always
equals the number of atomic orbitals
that combine

Ch. 1 - 83
 A bonding molecular orbital (ymolec)
results when two orbitals of the same
phase overlap

Ch. 1 - 84
 An antibonding molecular orbital
(y*molec) results when two orbitals of
opposite phase overlap

Ch. 1 - 85
Ch. 1 - 86
12. The Structure of Methane and
Ethane: sp3 Hybridization

Ground state of a carbon atom

C
1s 2s 2px 2py 2pz

Ch. 1 - 87
 Hybridization
● sp3
sp3
covalent hybridized
bond H carbon
H C H
H
(line bond structure)

Ch. 1 - 88
 Hybridization
● sp3 H
H C H
H
(Lewis structure)

109o H Tetrahedral
structure
C H
H H
Carbon with
(3-D stucture) 4 bonds
Ch. 1 - 89
12A. The Structure of Methane

Ch. 1 - 90
Ch. 1 - 91
Ch. 1 - 92
Ch. 1 - 93
12B. The Structure of Ethane

Ch. 1 - 94
Ch. 1 - 95
13. The Structure of Ethene
(Ethylene): sp2 Hybridization
 sp2
1  bond + 1 p bond
o
~120
H H
~120o C C sp2 hybridized carbon
H H
~120o

Ch. 1 - 96
 sp2
3-Dimensional View

p-bond
(p-orbitals overlap)
H H
C C
H H

Planar structure
Carbon with (3 + 1p) bonds
Ch. 1 - 97
Ch. 1 - 98
Ch. 1 - 99
Ch. 1 - 100
Ch. 1 - 101
Ch. 1 - 102
Ch. 1 - 103
13A. Restricted Rotation and the
Double Bond
 There is a large energy barrier to
rotation associated with groups joined
by a double bond
● ~264 kJmol-1 (strength of the p
bond)
● To compare: rotation of groups
joined by C-C single bonds ~13-26
kJmol-1

Ch. 1 - 104
Ch. 1 - 105
13B. Cis–Trans Isomerism
 Stereochemistry of double bonds
H R
H identical to H
R H
H H

H H
i
H3C identical to Pr
H H
i
Pr CH3

Ch. 1 - 106
H3C different from
CH3 CH3

(trans) CH3 (cis)

● Restricted rotation of C=C

Ch. 1 - 107
 ● Cis-Trans System
 Useful for 1,2 disubstituted
alkenes
e.g.
(1) H Br
Cl Cl
Br vs. H
H H
trans -1-Bromo- cis-1-Bromo-
2-chloroethane 2-chloroethane

Ch. 1 - 108
(2) H

vs. H
H H
trans -3-Hexene cis -3-Hexene

(3)
Br

Br Br vs. Br
trans -1,3- cis -1,3-
Dibromopropene Dibromopropene

Ch. 1 - 109
14. The Structure of Ethyne
(Acetylene): sp Hybridization
 sp
1  bond + 2 p bond
H C C H
180o
sp2 hybridized carbon

Linear structure
Carbon with (2 + 2 p) bonds

Ch. 1 - 110
Ch. 1 - 111
Ch. 1 - 112
Ch. 1 - 113
 sp orbital
● 50% s character, 50% p character

 sp2 orbital
● 33% s character, 66% p character

 sp3 orbital
● 25% s character, 75% p character

Ch. 1 - 114
Ch. 1 - 115
15. A Summary of Important
Concepts That Come from
Quantum Mechanics
1) An atomic orbital (AO) corresponds
to a region of space about the nucleus
of a single atom where there is a high
probability of finding an electron. s
orbitals are spherical, p orbitals are like
two almost-tangent spheres. Orbitals
can hold a maximum of two electrons
when their spins are paired
Ch. 1 - 116
2) When atomic orbitals overlap, they
combine to form molecular orbitals
(MOs)

3) When atomic orbitals with the same

phase sign interact, they combine to
form a bonding molecular orbital

4) An antibonding molecular orbital

forms when orbitals of opposite phase
sign overlap
Ch. 1 - 117
5) The energy of electrons in a bonding
molecular orbital is less than the
energy of the electrons in their
separate atomic orbitals
6) The number of molecular orbitals
always equals the number of atomic
orbitals from which they are formed
7) Hybrid atomic orbitals are obtained
by mixing (hybridizing) the wave
functions for orbitals of different types
(i.e., s and p orbitals) but from the
same atom Ch. 1 - 118
8) Hybridizing three p orbitals with one s
orbital yields four sp3 orbitals and
they are tetrahedral

9) Hybridizing two p orbitals with one s

orbital yields three sp2 orbitals and
they are trigonal planar

10) Hybridizing one p orbital with one s

orbital yields two sp orbitals, a linear
molecule
Ch. 1 - 119
11) A sigma () bond (a type of single
bond) is one in which the electron
density has circular symmetry when
viewed along the bond axis

12) A pi (p) bond, part of double and

triple carbon–carbon bonds, is one in
which the electron densities of two
adjacent parallel p orbitals overlap
sideways to form a bonding pi
molecular orbital
Ch. 1 - 120
16. Molecular Geometry: The
Valence Shell Electron Pair
Repulsion Model
 Valence shell electron pair repulsion
(VSEPR) model:
1) We consider molecules (or ions) in
which the central atom is
covalently bonded to two or more
atoms or groups

Ch. 1 - 121
2) We consider all of the valence
electron pairs of the central
atom—both those that are shared
in covalent bonds, called bonding
pairs, and those that are
unshared, called nonbonding pairs
or unshared pairs or lone pairs

Ch. 1 - 122
3) Because electron pairs repel each
other, the electron pairs of the
valence shell tend to stay as far
apart as possible. The repulsion
between nonbonding pairs is
generally greater than that
between bonding pairs

Ch. 1 - 123
4) We arrive at the geometry of the
molecule by considering all of the
electron pairs, bonding and
nonbonding, but we describe the
shape of the molecule or ion by
referring to the positions of the
nuclei (or atoms) and not by the
positions of the electron pairs

Ch. 1 - 124
16A. Methane

Ch. 1 - 125
16B. Ammonia

 A tetrahedral arrangement of the electron

pairs explains the trigonal pyramidal
arrangement of the four atoms. The bond
angles are 107° (not 109.5°) because the
nonbonding pair occupies more space than
the bonding pairs
Ch. 1 - 126
16C. Water

Ch. 1 - 127
16D. Boron Trifluoride

Ch. 1 - 128
16E. Beryllium Hydride

Ch. 1 - 129
16F. Carbon Dioxide
o
180

Ch. 1 - 130
Ch. 1 - 131
17. How to Interpret and Write
Structural Formulas

Ch. 1 - 132
17A. Dash Structural Formulas
 Atoms joined by single bonds can
rotate relatively freely with respect to
one another
H
H HH H H H H
H HO H
C C H H C O
C C
H C O C C
H C H
H H H HH H
H H
Equivalent dash formulas for propyl alcohol

Ch. 1 - 133
17B. Condensed Structural Formulas

Ch. 1 - 134
17C. Bond-Line Formulas

Ch. 1 - 135
Ch. 1 - 136
17D. Three-Dimensional Formulas
H
H H H
C H H
OR C C etc.
H C H
H H H
H
Ethane

H H Br
C OR C OR C etc.
H H H
Br Br H
H H H
Bromomethane
Ch. 1 - 137
 Br
H

H OH Cl
H
Examples of bond-line formulas that include
three-dimensional representations

H NH2 Br H
HO

An example involving An example involving

trigonal planar geometry linear geometry
Ch. 1 - 138