1.

Structure and Bonding

Why this chapter?
• Review ideas from general chemistry:
atoms, bonds, molecular geometry
What is Organic
Chemistry?
Living things are made of organic
chemicals
Proteins that make up hair
DNA, controls genetic make-up
Foods, medicines
Examine structures below

2
Origins of Organic
Chemistry
Foundations of organic chemistry from mid-
1700’s.

Compounds obtained from plants, animals hard

to isolate, and purify.

Compounds also decomposed more easily.

Torben Bergman (1770) first to make distinction

between organic and inorganic chemistry.

It was thought that organic compounds must

contain some “vital force” because they were
from living sources.

3
Because of “Vital force”, it was thought that
organic compounds could not be synthesized
in laboratory like inorganic compounds.

1816, Chervrut showed that not to be the case,

he could prepare soap from animal fat and an
alkali

1828, Wholer showed that it was possible to

convert inorganic salt ammonium cyanate
into organic substance “urea”

4
• Organic chemistry is study of carbon
compounds.
• Why is it so special?
- 90% of more than 30 million
chemical compounds contain carbon.
- Examination of carbon in periodic
chart answers some of these
questions.
- Carbon is group 4A element, it can
share 4 valence electrons and form 4
covalent bonds.

5
 1.1 Atomic Structure
 Structure of an atom
◦ Positively charged nucleus (very dense, protons and
neutrons) and small (10-15 m)

◦ Negatively charged electrons are in a cloud (10-10 m)

around nucleus

 Diameter is about 2  10-10 m (200 picometers

(pm)) [the unit angstrom (Å) is 10-10 m = 100 pm]

6
 The Atomic Symbol
A = Atomic mass C = Charge
=# p +#n = + or - values
A C

Z X #

Z = Atomic # # = Number of atoms

in a formula.
#p=#e
 The Atomic Symbol
A = Atomic mass
6
= # protons + # neutrons
6
- -
12

6
X - -
+
+

Z = Atomic number +
- +
+
+
= # protons = # electrons
-
 The Atomic Symbol
A = Atomic mass
= # protons + # neutrons
- -
12

C
-
-
6 +
+

Z = Atomic number - +
+

+ +
= # protons = # electrons -
 The Atomic Symbol
A = Atomic mass C = Charge = +1
11 12
= p + n = 23
23 1+

11
Na
Z = Atomic # = p = 11 # = 1 atom in formula.
Sodium
 Why is the atomic weight on the tables not a whole #?

47 Atomic number
Silver Name of the element

Ag Elemental Symbol

107.87 Atomic mass (weight)

Atomic weight = The average,

average relative
mass of an atom in an element.
 Isotopes of Hydrogen
Isotopes = Atoms of the same element but
having different masses.
1 2 3
1H 1 H 1 H
- - -
+ + +

Protium Deuterium Tritium

99.99% 0.01% Trace %
 Isotopes of Hydrogen
Isotopes = Atoms of the same element but
having different masses.
1 2 3
1H 1 H 1 H
- - -
+ + +

Average Atomic weight of Hydrogen

= 1.00794 amu
 Isotopes of Carbon
12 13 14
6
C 6
C C
6
- -
- - - - -
+ - + +
- + + +
+ + +
+ + +
- + + + + - + +
- - - - - - -
98.89% 1.11% Trace %

Average Atomic weight of C= 12.011 amu

 Radioactive Isotopes
3 14
H-3 1 H C-14
6 C
- -
- -
+
+ +
+
+
- + +
Nucleus - -
Nucleusisisunstable
unstable
So
Sofalls
fallsapart
apart(decays)
(decays)
Giving
Givingradioactive
radioactiveparticles
particles
Electronic arrangement

A new layer is
added for each
row or period in
the table.
 Electron arrangement
24 Electrons
12
Mg
fill layers
32 around nucleus
18 Low  High
8
2

Shells = Energy levels

 IA IIA

1 4
1
H He
2
7 9
3
Li 4
Be

2,
2, 11 2,
2, 22
 IA IIA IIIA

1
1
H
11
7 9
Li Be 5
B
3 4

2,
2, 11 2,
2, 22 2, 3
 IIIA IVA VA

11 12 13
5
B 6
C 7
N

2,
2, 33 2,
2, 44 2,
2, 55
 IA IIA VIIIA

1 4
1
H He
2
7 9 20

Li 4
Be 10 Ne
3
2,
2, 11 2,
2, 22 2,
2, 88

24 40
23
12 Mg 18Ar
11 Na
2,
2, 8,
8, 88
2, 8, 1 2, 8, 2
 11

1 Valence electrons
1
H Where most chemical
22 Reactions occur.
33

7 9 11
Li 4
Be B
3 5

2,
2, 11 2,
2, 22 2, 3

24 27
23
11 Na 12 Mg 13 Al

2,
2, 8,
8, 33
2, 8, 1 2, 8, 2
 11
88

1 Octet Rule 4
1
H He
22 2
9 20
7 Be Ne
3
Li 4
10

2,
2, 11 2,
2, 22 2,
2, 88

24 40
23
12 Mg 18Ar
11 Na
2,
2, 8,
8, 88
2, 8, 1 2, 8, 2
The octet rule
Atoms are most stable if they have a
filled or empty outer layer of electrons.

Except for H and He, a filled layer

contains 8 electrons - an octet.

Atoms gain, lose or share electrons to

make a filled or empty outer layer.

Atoms gain, lose or share electrons

based on what is easiest.
 1.2 Atomic Structure:
Orbitals
Quantum mechanics: describes
electron energies and locations by a
wave equation
◦ Wave function solution of wave equation
◦ Each wave function is an orbital,

26
 Orbitals
Aplot of  2 describes where electron
most likely to be
Electroncloud has no specific boundary
so we show most probable area
s (1) p (3) d (5) f (7)

An f orbital

4 different kinds of orbitals for e-s

 s and p orbitals most important in organic &
biochem
 Orbitals and Shells
 Orbitals are grouped in shells of increasing size and energy
 Different shells contain different numbers and kinds of orbitals
 Each orbital can be occupied by two electrons

28
 Orbitals and Shells
 1st shell contains one s orbital, denoted 1s, holds
2 e-s
 2nd shell contains one s orbital (2s) and three p
orbitals (2p), 8 electrons
 3rd shell contains an s orbital (3s), three p orbitals
(3p), and five d orbitals (3d), 18 electrons

29
 p-Orbitals
 In
each shell there are three
perpendicular p orbitals, px, py, and pz, of
equal energy

 Lobesof a p orbital are separated by

region of zero electron density, a node

30
1.3 Atomic Structure: Electron
Configurations
 Ground-state electron configuration (lowest energy
arrangement) of an atom lists orbitals occupied by its
electrons. Rules:

 1. Lowest-energy orbitals fill first: 1s  2s  2p  3s 

3p  4s  3d (Aufbau (“build-up”) principle)

 2. Electrons act as if they were spinning around an axis.

Electron spin can have only two orientations, up  and
down . Only two electrons can occupy an orbital, and
they must be of opposite spin (Pauli exclusion principle)
to have unique wave equations

 3. If two or more empty orbitals of equal energy are

available, electrons occupy each with spins parallel
until all orbitals have one electron (Hund's rule).

31
 1.3 Atomic Structure: Electron
The Aufbau (“build-up”) principle Configurations
 Electrons fill from the
f
low  high. d
fill n = 1 before n = 2 , p n=4
fill s before p ... s
d
Pauli Exclusion principle p n=3
s
 Each subshell contains p
orbitals which can hold a n=2
s
max of 2 e-s s
n=1
 e’s in same orbital must be
of opposite spins: 1  & 1 .
Hund’s Rule
 Electrons don’t share same orbital unless they need to.
(i.e. no pairing until each orbital of the set has an e-)
 5d
Major trends in electron filling
Exceptions: 4f

◦ Fill 4s before 3d 5p
◦ Fill 5s before 4 d 4d
◦ Fill 5p before 4f
5s
4p
This is why 3d
transition metals 4s
are assigned as 3p
B group elements.
3s
2p

2s
1s
 Electron
5d __ __ __ __Configuration
__
6s __
4f __ __ __ __ __ __ __
5p __ __ __
7
4d __ __ __ __ __ Li
5s __ 3
4p __ __ __
4s __ 3d __ __ __ __ __
3px __ y__ z __ 1s22s1
3s __
2px __ y__ z __
2s __
1s __
 Electron Configuration
5d __ __ __ __ __
6s __
4f __ __ __ __ __ __ __
5p __ __ __ 16
4d __ __ __ __ __8 O
5s __
4p __ __ __
4s __ 3d __ __ __ __ __
3p __ __ __ 1s22s22p4
3s __
2px __ y __z __
2s __
1s __
 Electron Configuration
5d __ __ __ __ __
6s __
4f __ __ __ __ __ __ __
5p __ __ __
4d __ __ __ __ __ Zn
5s __ 30
4p __ __ __
4s __ 3d __ __ __ __ __
3px __ y __z __
3s __ 1s22s22p63s23p64s23d10
2px __ y__ z __
2s __ [Ar] 4s23d10
1s __ [Ar] 3d104s2
 Classification by sublevels
ss

H pp He

Li Be B C N O F Ne
dd
Na Mg Al Si P S Cl Ar

K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe

Cs Ba Ls Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn

Fr Ra Ac

Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu
ff
Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr
3 - 25
 Using the periodic table
s to find sublevels
1 H He
p
2 Li Be 2 B C N O F Ne

3 Na Mg d 3 Al Si P S Cl Ar

4 K Ca 3 Sc Ti V Cr Mn Fe Co Ni Cu Zn 4 Ga Ge As Se Br Kr

5 Rb Sr 4 Y Zr Nb Mo Tc Ru Rh Pd Ag Cd 5 In Sn Sb Te I Xe

6 Cs Ba 5 Ls Hf Ta W Re Os Ir Pt Au Hg 6 Tl Pb Bi Po At Rn

7 Fr Ra 6 Ac

4 Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu
f 5 Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr
 Learning Check:
Which of the following represents the ground-
state electronic configuration for carbon
(atomic number 6)?
1. 1s22s22px22py02pz0
2. 1s22s22px12py12pz0
3. 1s22s12px12py1
2pz1
4. 1s12s22px12py1
2pz1
5. 1s22s22px02py02pz2
39
 Solution:
Which of the following represents the ground-
state electronic configuration for carbon
(atomic number 6)?
1. 1s22s22px22py02pz0
2. 1s22s22px12py12pz0
3. 1s22s12px12py1
2pz1
4. 1s12s22px12py1
2pz1
5. 1s22s22px02py02pz2
40
 1 Octet Rule 4
1
H He
2
1s1 1s2
7 9 20
Li 4
Be 10
Ne
3

1s , 2s
2 1 1s2, 2s2 1s2, 2s2 2p6
24 40
23 Mg
12 18 Ar
11
Na
1s 2
, 2s 2
2p 6
, 3s 2
3p6
1s2, 2s2 2p6, 3s1
[Ne] 3s1 1s2, 2s2 2p6, 3s2
 1 Lewis Structures
1
H
H Show only
7 Valence
3
Li
Electrons
Li

23 Na
11
Na
K
 1 Nonmetals Share e-s 8
with other nonmetals
H 2 3 4 5 6 7 He

Li Be B C N O F Ne

Na Mg Al Si P S Cl Ar
Metals give e-s to nonmetals

K Ca Ga Ge As Se Br Kr
 Common ions
Representative Elements
1+
1+ 4+
4+
4-
4-
H 2+ 3+ 3-
3- 2-
2- 1-
1- He

Li Be Transition Elements B C N O F Ne
Variable
Variable
Na Mg Al Si P S Cl Ar

K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe

Cs Ba Ls Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn

Fr Ra Ac Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu

Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr
 Formation of NaCl
e- moves from Metal  Nonmetal
Stable octets
_
Na + Cl Na + Cl
+

Metal Nonmetal
Cation Anion

+ and - ions attract to form an ionic bond.

 Ionic compounds
• Not individual molecules
• Form crystal arrays
• Ions touch many others
• Formula represents the average ion
ratio
Na Cl NaCl
Cl Na Cl Na sodium chloride
 1 Nonmetals Share e-s 8
with other nonmetals
H 2 3 4 5 6 7 He

Li Be B C N O F Ne

Na Mg Al Si P S Cl Ar
Metals give e-s to nonmetals

K Ca Ga Ge As Se Br Kr
Covalent Bonds
H + H H H

Cl +
Cl Cl Cl

O + O O O

N + N N N
 Covalent Bonds
H H H-H H2

Cl Cl Cl-Cl Cl2

O O O=O O2

N N N N N2
 Covalent Bonds
Carbon monoxide CO
C O C O
Carbon dioxide CO2
O C O O=C=O
May modify rules to improve sound.
ie - monoxide
mon not monooxide.
mono
Review:
Naming covalent compounds
CO carbon monoxide
CO2 carbon dioxide
N2O5 dinitrogen pentoxide
SiO2 silicon dioxide
ICl3 iodine trichloride
P2O5 diphophorous pentoxide
CCl4 carbon tetrachloride
May modify rules to improve the sound.
Example - use monoxide not monooxide.
 Shape
CO2

O C O

O=C=O

Linear Shape (180o)

 Shape
BF3
F
F
B
F B F F F
(120o)
Trigonal Planar
1.4 Development of Chemical
Bonding Theory
 Kekulé and Couper independently observed that
carbon always has four bonds

 van't Hoff and Le Bel proposed that the four bonds

of carbon have specific spatial directions
◦ Atoms surround carbon as corners of a
tetrahedron

60
 Shape
e-’s in 2 directions = 180o

O=C=O Linear

e-’s in 3 directions = 120o

O Trigonal planar

C
H H
 Shape
e-’s in 4 directions = 109.5o

N
H N H H N H H
H H
H H
Pyramidal

(109.5o)
Tetrahedral Configuration of Electrons
Trigonal Pyramid Configuration of Atoms
 Tetrahedral electron-pair
Geometries
Tetrahedral
Pyramidal
Bent
71
 Non-bonding electrons
 Valence electrons not used in bonding are called
nonbonding electrons, or lone-pair electrons
◦ Nitrogen atom in ammonia (NH3)
 Shares six valence electrons in three covalent
bonds and remaining two valence electrons
are nonbonding lone pair

72
 Learning Check
How many hydrogen atoms does phosphorus
bond to in forming phosphine, PH?

Hint: Draw the electron dot structure and then

use Hydrogen to provided the needed bonded
electrons

73
 Solution
How many hydrogen atoms does phosphorus
bond to in forming phosphine, PH?

H H 3
H P H P
H H
Hint: Draw the electron dot structure and then
use Hydrogen to provided the needed bonded
electrons

74
Learning Check
 Howmany hydrogen atoms does Carbon
need in forming chloroform, CH?Cl

H C Cl

75
Solution
 Howmany hydrogen atoms does Carbon
need in forming chloroform, CH?Cl

3
H C Cl

H H
H
Cl H C Cl C
H C HH Cl
H H

76
1.5 The Nature of Chemical Bonds:
Valence Bond Theory
 Covalent bond forms when two atoms
approach each other closely so that a
singly occupied orbital on one atom
overlaps a singly occupied orbital on the
other atom
 Two models to describe covalent bonding.

Valence bond theory, Molecular orbital

theory

Valence Bond Theory:

 Electrons are paired in the overlapping
orbitals and are attracted to nuclei of both
atoms
◦ H–H bond results from the overlap of
two singly occupied hydrogen 1s orbitals
◦ H-H bond is cylindrically symmetrical,
sigma () bond

77
 Bond Energy
 Reaction 2 H·  H2 releases 436 kJ/mol
 Product has 436 kJ/mol less energy than two
atoms:
H–H has bond strength of 436 kJ/mol.
(1 kJ = 0.2390 kcal; 1 kcal = 4.184 kJ)

78
 Bond Length
 Distance
between nuclei
that leads to
maximum
stability
 If too close,
they repel
because both
are positively
charged
 If too far apart,
bonding is weak

79
1.6 sp3 Orbitals and the Structure of
Methane
Carbon has 4 valence electrons (2s2 2p2)
 In CH4, all C–H bonds are identical (tetrahedral)
 sp3 hybrid orbitals: s orbital and three p orbitals
combine to form four equivalent, unsymmetrical,
tetrahedral orbitals (sppp = sp3), Pauling (1931)

80
 The Structure of Methane
 sp3 orbitals on C overlap with 1s orbitals on 4
H atoms to form four identical C-H bonds
 Each C–H bond has a strength of 436 (438)
kJ/mol and length of 109 pm
 Bond angle: each H–C–H is 109.5°, the
tetrahedral angle.

81
1.7 sp3 Orbitals and the Structure of
Ethane
 Two C’s bond to each other by  overlap of an
sp3 orbital from each
 Three sp3 orbitals on each C overlap with H 1s
orbitals to form six C–H bonds
 C–H bond strength in ethane 423 kJ/mol
 C–C bond is 154 pm long and strength is 376
kJ/mol
 All bond angles of ethane are tetrahedral

82
1.8 sp2 Orbitals and the
Structure of Ethylene
 sp2 hybrid orbitals: 2s orbital combines with
two 2p orbitals, giving 3 orbitals (spp = sp2).
This results in a double bond.
 sp2 orbitals are in a plane with120° angles
 Remaining p orbital is perpendicular to the
plane

83
 Bonds From sp2 Hybrid
Orbitals
 Two sp2-hybridized orbitals overlap to form a  bond
 p orbitals overlap side-to-side to formation a pi () bond
 sp2–sp2  bond and 2p–2p  bond result in sharing four
electrons and formation of C-C double bond
 Electrons in the  bond are centered between nuclei
 Electrons in the  bond occupy regions are on either side
of a line between nuclei

84
 Structure of Ethylene
 H atoms form  bonds with four sp2 orbitals
 H–C–H and H–C–C bond angles of about 120°

 C–C double bond in ethylene shorter and stronger than

single bond in ethane
 Ethylene C=C bond length 134 pm (C–C 154 pm)
85
1.9 sp Orbitals and the Structure of
Acetylene
 C-C a triple bond sharing six electrons
 Carbon 2s orbital hybridizes with a single p
orbital giving two sp hybrids
◦ two p orbitals remain unchanged
 sp orbitals are linear, 180° apart on x-axis
 Two p orbitals are perpendicular on the y-axis
and the z-axis

86
 Orbitals of Acetylene
 Two sp hybrid orbitals from each C form sp–sp 
bond
 pz orbitals from each C form a pz–pz  bond by
sideways overlap and py orbitals overlap similarly

87
 Bonding in Acetylene
 Sharing of six electrons forms C C

 Two sp orbitals form  bonds with hydrogens

88
89
 1.10 Hybridization of Nitrogen
and Oxygen
 Elements other than C can have hybridized
orbitals
 H–N–H bond angle in ammonia (NH3) 107.3°
 C-N-H bond angle is 110.3 °
 N’s orbitals (sppp) hybridize to form four sp3
orbitals
 One sp3 orbital is occupied by two nonbonding
electrons, and three sp3 orbitals have one
electron each, forming bonds to H and CH3.

90
 1.11 Molecular Orbital
Theory
A molecular orbital (MO): where electrons are most
likely to be found (specific energy and general shape)
in a molecule

 Additive combination (bonding) MO is lower in energy

 Subtractive combination (antibonding) MO is higher

energy

91
 Molecular Orbitals in
Ethylene
 The  bonding MO is from combining p orbital
lobes with the same algebraic sign
 The  antibonding MO is from combining lobes
with opposite signs
 Only bonding MO is occupied

92
1.12 Drawing Structures
Drawing every bond in organic
molecule can become tedious.
Several shorthand methods have
been developed to write
structures.
Condensed structures don’t have
C-H or C-C single bonds shown.
They are understood.
e.g.
93
3 General Rules:
1) Carbon atoms aren’t usually shown. Instead a
carbon atom is assumed to be at each
intersection of two lines (bonds) and at the end
of each line.

2) Hydrogen atoms bonded to carbon aren’t

shown.

3) Atoms other than carbon and hydrogen are

shown (See table 1.3).

94
Summary
 Organic chemistry – chemistry of carbon compounds
 Atom: positively charged nucleus surrounded by
negatively charged electrons
 Electronic structure of an atom described by wave
equation
◦ Electrons occupy orbitals around the nucleus.
◦ Different orbitals have different energy levels and
different shapes
 s orbitals are spherical, p orbitals are dumbbell-
shaped
 Covalent bonds - electron pair is shared between
atoms
 Valence bond theory - electron sharing occurs by
overlap of two atomic orbitals
 Molecular orbital (MO) theory, - bonds result from
combination of atomic orbitals to give molecular
orbitals, which belong to the entire molecule

95
Summary (cont’d)
 Sigma () bonds - Circular cross-section and are
formed by head-on interaction
 Pi () bonds – “dumbbell” shape from sideways
interaction of p orbitals
 Carbon uses hybrid orbitals to form bonds in organic
molecules.
◦ In single bonds with tetrahedral geometry, carbon has
four sp3 hybrid orbitals
◦ In double bonds with planar geometry, carbon uses
three equivalent sp2 hybrid orbitals and one
unhybridized p orbital
◦ Carbon uses two equivalent sp hybrid orbitals to
form a triple bond with linear geometry, with two
unhybridized p orbitals
 Atoms such as nitrogen and oxygen hybridize to form
strong, oriented bonds
◦ The nitrogen atom in ammonia and the oxygen atom
in water are sp3-hybridized

96
Learning Check:
Based on the octet rule, which line-bond
structures is/are correct?
H H H H H H H H
H C C C H H C C C H H C C C H H C C C H
H H H H
A B C D

1. A and B
2. A and C
3. B and D
4. Only B
5. Only C

97
Solution:
Based on the octet rule, which line-bond
structures is/are correct?
H H H H H H H H
H C C C H H C C C H H C C C H H C C C H
H H H H
A B C D

1. A and B
2. A and C
3. B and D
4. Only B
5. Only C

98
 Learning Check:
Which of these statements concerning p-
orbitals is false?

1. They consist of two equivalent lobes.

2. They are absent from the first shell of
atomic orbitals.
3. They can form π bonds.
4. They only participate in bonding on
carbon atoms.
5. They can hold a maximum of two
electrons.
99
 Solution:
Which of these statements concerning p-
orbitals is false?

1. They consist of two equivalent lobes.

2. They are absent from the first shell of
atomic orbitals.
3. They can form π bonds.
4. They only participate in bonding on
carbon atoms.
5. They can hold a maximum of two
electrons.
100
Learning Check:
What is the hybridization of the oxygen-
bonded carbon atom in the following
molecule?
H3 C
N C O
1. s
2. p
3. sp
4. sp2
5. sp3

101
Solution:
What is the hybridization of the oxygen-
bonded carbon atom in the following
molecule?
H3 C
N C O
1. s
2. p
3. sp
4. sp2
5. sp3

102
Learning Check:
What is the hybridization of nitrogen
atom in trimethylamine :N(CH3)3?

1. sp
2. sp2
3. sp3
4. dsp2
5. unhybridized

103
Solution:
What is the hybridization of nitrogen
atom in trimethylamine :N(CH3)3?

1. sp
2. sp2
3. sp3
4. dsp2
5. unhybridized

104
Learning Check:
What type of orbital is not used in
constructing the molecule shown below?
O

O
1. s
2. p
3. sp
4. sp2
5. sp3
105
Solution:
What type of orbital is not used in
constructing the molecule shown below?
O

O
1. s
2. p
3. sp
4. sp2
5. sp3
106
Learning Check:
What is the molecular formula of the
molecule shown below?
O

1. C8H12O
2. C8H11O
3. C8H7O
4. C7H7O
5. C7H10O
107
Solution:
What is the molecular formula of the
molecule shown below?
O

1. C8H12O
2. C8H11O
3. C8H7O
4. C7H7O
5. C7H10O
108
Learning Check:
Electrons cannot occupy an antibonding
molecular orbital.

1. True
2. False

109
Solution:
Electrons cannot occupy an antibonding
molecular orbital.

1. True
2. False

110
Learning Check:
How many hydrogen atoms are present in the
naturally-occurring terpene α-terpinene shown
below?

1. 14
2. 15
3. 16
4. 17
5. 18

111
Solution:
How many hydrogen atoms are present in the
naturally-occurring terpene α-terpinene shown
below?

1. 14
2. 15
3. 16
4. 17
5. 18

112
Learning Check:
Select the best condensed structural
formula for the following molecule:
HO OH
H

1. (CH3)2CHCH2COHOHCOH
2. CH3CH3CHCH2C(OH)2CHO
3. (CH3)2CHCH2C(OH)2CHO
4. (CH3)2CHCH2C(OH)2COH
5. CH3CHCH3CH2C(OH)2CHO
113
Solution:
Select the best condensed structural
formula for the following molecule:
HO OH
H

1. (CH3)2CHCH2COHOHCOH
2. CH3CH3CHCH2C(OH)2CHO
3. (CH3)2CHCH2C(OH)2CHO
4. (CH3)2CHCH2C(OH)2COH
5. CH3CHCH3CH2C(OH)2CHO
114
Learning Check:
What is the correct order of carbon-
carbon bond lengths in ethane, ethylene
and acetylene?
1. ethane < ethylene < acetylene
2. ethane < acetylene < ethylene
3. ethylene < ethane < acetylene
4. ethylene < acetylene < ethane
5. acetylene < ethane < ethylene
6. acetylene < ethylene < ethane

115
Solution:
What is the correct order of carbon-
carbon bond lengths in ethane, ethylene
and acetylene?
1. ethane < ethylene < acetylene
2. ethane < acetylene < ethylene
3. ethylene < ethane < acetylene
4. ethylene < acetylene < ethane
5. acetylene < ethane < ethylene
6. acetylene < ethylene < ethane

116
Learning Check:
What kind of orbital and with how many
nodal planes is shown in the picture
below?

1. σ antibonding, two nodal planes

2. σ antibonding, one nodal plane
3. π bonding, one nodal plane
4. π antibonding, two nodal planes
5. π antibonding, one nodal plane
117
 Solution:
What kind of orbital and with how many
nodal planes is shown in the picture
below?

1. σ antibonding, two nodal planes

2. σ antibonding, one nodal plane
3. π bonding, one nodal plane
4. π antibonding, two nodal planes
5. π antibonding, one nodal plane
118
Learning Check:
What is the best description of bond
length?
1. a distance between nuclei that yields the
best orbital overlap
2. a distance between nuclei that yields the
smallest nuclear-nuclear repulsion
3. a distance between nuclei that yields the
smallest electron-electron repulsion
4. a distance between nuclei that yields the
largest electron-nuclei attraction
5. a distance between nuclei that is a
compromise of all electrostatic interactions

119
Solution:
What is the best description of bond
length?
1. a distance between nuclei that yields the
best orbital overlap
2. a distance between nuclei that yields the
smallest nuclear-nuclear repulsion
3. a distance between nuclei that yields the
smallest electron-electron repulsion
4. a distance between nuclei that yields the
largest electron-nuclei attraction
5. a distance between nuclei that is a
compromise of all electrostatic interactions

120
Learning Check:
What is the O-C-O bond angle in
potassium carbonate, K2CO3?

1. 60°
2. 90°
3. 109.5°
4. 120°
5. 180°

121
Solution:
What is the O-C-O bond angle in
potassium carbonate, K2CO3?

1. 60°
2. 90°
3. 109.5°
4. 120°
5. 180°

122
Learning Check:
What is the relative orientation of
two π orbitals in acetylene?

1. 60°
2. 90°
3. 109.5°
4. 120°
5. 180°

123
Solution:
What is the relative orientation of
two π orbitals in acetylene?

1. 60°
2. 90°
3. 109.5°
4. 120°
5. 180°

124
 Learning Check:
In relation to σ bonds, which
statement about π bonds is correct?
1. π bonds are weaker and π electrons have
higher energy
2. π bonds are stronger and π electrons have
higher energy
3. π bonds are weaker and π electrons have
lower energy
4. π bonds are stronger and π electrons have
lower energy
5. π bonds and σ bonds have equal strengths,
and their electrons have the same energies
125
 Solution:
In relation to σ bonds, which
statement about π bonds is correct?
1. π bonds are weaker and π electrons have
higher energy
2. π bonds are stronger and π electrons have
higher energy
3. π bonds are weaker and π electrons have
lower energy
4. π bonds are stronger and π electrons have
lower energy
5. π bonds and σ bonds have equal strengths,
and their electrons have the same energies
126
Learning Check:
Which of the orbitals shown below can be
occupied in a hydrogen atom?

A B C D
1. A
2. B
3. C
4. D
5. Any one of these
127
Solution:
Which of the orbitals shown below can be
occupied in a hydrogen atom?

A B C D
1. A
2. B
3. C
4. D
5. Any one of these
128
Learning Check:
Which statement about the antibonding
orbital in H2 is false?

1. It is higher in energy than the

corresponding bonding orbital
2. It is a molecular orbital
3. It has a nodal plane (a node for
short)
4. It can hold up to two electrons
5. The two lobes have different
charges
129
Solution:
Which statement about the antibonding
orbital in H2 is false?

1. It is higher in energy than the

corresponding bonding orbital
2. It is a molecular orbital
3. It has a nodal plane (a node for
short)
4. It can hold up to two electrons
5. The two lobes have different
charges
130
Learning Check:
What is the hybridization of nitrogen
in :NCCH3?

1. sp
2. sp2
3. sp3
4. sp3d
5. nitrogen is not
hybridized

131
Solution:
What is the hybridization of nitrogen
in :NCCH3?

1. sp
2. sp2
3. sp3
4. sp3d
5. nitrogen is not
hybridized

132
 Each shell (floor of the Hotel)
Hotel Model
Has subshells (s,p,d,f)

n = 4 (4th floor) d
p
32 e-
s

n = 3 (3rd floor) d
p 18 e-
s
p
n = 2 (2nd floor) 8 e-
s

n = 1 (1st floor) s 2 e-