Fall 2024, CH 301, Unit 2: Bonding – List of Question Types (QTs)

1. Bond Polarity based on ΔElectronegativity

2. Ionic Compounds: Naming and Formulas
3. Ionic Compounds: Lattice Energy
4. Lewis Structures: Octet Rule
5. Lewis Structures: Hypovalency and Radicals
6. Lewis Structures: Hypervalency
7. Lewis Structures: Double and Triple Bonds
8. Lewis Structures: Resonance
9. Lewis Structures: Multiple Central Atoms
10. Lewis Structures: Formal Charge 1
11. Lewis Structures: Formal Charge 2
12. VSEPR Model: Electronic Geometries
13. VSEPR Model: Molecular Shapes
14. VSEPR Model: Bond Angles 1
15. VSEPR Model: Bond Angles 2
16. VSEPR Model: Molecular Polarity
17. The Theory behind Valence Bond Theory
18. Valence Bond Theory: Hybridization
19. Valence Bond Theory: sigma (σ) and pi (π) bonds
20. Valence Bond Theory: Orbitals in Bonding
21. Molecular Orbital Theory: Diagrams 1
22. Molecular Orbital Theory: Diagrams 2
23. Molecular Orbital Theory: Bond Order Calculation
24. Molecular Orbital Theory: Bond Order Application
25. Molecular Orbital Theory: Magnetism
2.1 Bond Polarity based on ΔElectronegativity (∆EN)
What you need to know:
Given a collection of bonds:
 Bond polarity is proportional to the length of the dipole between
2 atoms.  Find ΔEN for each bond
 The dipole is directly proportional to ΔEN. This means the  Rank bond polarity by increasing ΔEN
greater the ΔEN, the more polar the bond.
 Be able to calculate ΔEN using the electronegativity values below
(memorize them). Excellent example. If you can do
this, you will get the question right.
.H . He
2.1 X

.Li Be
. .B .C .N O
. F
. Ne
.
Practice Exam Problem:
1.0 1.5 2.0 2.5 3.0 3.5 4.0 X Consider the labeled bonds in the molecule below and rank them
from least to most polar in terms of difference in electronegativity.

IMPORTANT: Bond polarity is NOT molecular

polarity. A molecular can have polar bonds
a) d<c<a<e<b
and be nonpolar. For example, CF4 is
b) d < c < e < a < b correct
nonpolar.
c) a<b<c<d<e
d) c<d<e<b<a
e) e<b<d<c<a

Explanation:
Using the EN values for each atom, we can calculate a ΔEN for each
bond. For example, bond a has ΔEN = 4.0 – 2.5 = 1.5.
 2.2 Ionic Compounds: Naming and Formulas
Be able to assign correct structure and formula unit to main group salts.
The table below contains the common formulas:
where “A” represents the cation Note that these are all ionic bonds because Practice Exam Problem:
and “B” represents the anion. the ∆EN is large. Cations are matched with Which of the following is not a common
anions from the opposite side of the formula unit for the salts made with
periodic table. main groups cations and anions?
a) AB
A+n has donated n electrons to b) AB2
be like a Noble gas. c) A2B3
d) AB4 correct
B-n
has accepted n electrons
to bethe
The subscript makes likenumber
a Nobleofgas.
e- Explanation:
balance: AB4 is not one of the common formula
units listed in the table.
Al2O32 x 3 e- donated by Al
3 x 2 e- accepted by O Practice Exam Problem:
Which of the following salts has an
incorrect structure?
a) CaCl2
Know the formula, charge, and name of each polyatomic ion listed below. b) NaI
c) CaO
Name Formula Name Formula d) MgBr correct
Nitrate NO3– Perchlorate ClO4–
Explanation:
Nitrite NO2– Chlorate ClO3–
Br has a -1 charge and Mg has a +2
Carbonate CO32– Chlorite ClO2– charge. To correctly balance, the
Sulfate SO42– Hypochlorite ClO– structure should be MgBr2.
Sulfite SO32- Ammonium NH4+
Phosphate PO43– Hydroxide OH–
Permanganate MnO4– Cyanide CN–
2.3 Ionic Compounds: Lattice Energy
2.4 Lewis Structures: Octet Rule
This isn’t a specific question, but you need to use this skill throughout the exam.
IMPORTANT: Your most important skill in Unit 2 is drawing 3D
structures of covalent compounds given a molecular formula. Be Examples:
able to do the following fast!! Draw the 2D structure of H2O.

1. Add up the valence electrons in a molecule (1) 2 x 1 +6 = 8 e-

2. Spread out perimeter atoms around the central atom (2) H O H 4 e- used for the perimeter
3. Put either 2 (for H) or 8 (for all others) electrons around (3) H:O:H atoms. Add 4 e- to O.
perimeter atoms (4) H —:O:— H
4. Dump the rest of the unused valence electrons in the (5) Skip step 5 because central atom has an octet.
middle (central atom)
5. If the central atom does not have 8 or more electrons (the Draw the 2D structure of CHCl3.
“Octet Rule”), share e- from perimeter atoms to make
(1) 4 + 1 + 21 = 26 e-
multiple bonds (double or triple bonds)
(2) (3) (4)
IMPORTANT: This is how you draw 2D structures. However, you
still need to be able to draw 3D pictures.

 There are many variations on Lewis structures. All start

with those 5 steps.
 DO NOT do S = N – A. It does not work all the time. All 26 e- were used in
step 3, so all done.

Practice Exam Problem: Practice Exam Problem:

Which of the following compounds does not have Which of the following compounds has four single bonds?
unpaired electrons on the central atom?
a) NH3
a) NH3 b) CH2O
b) H2 O c) CO2
c) CH4 correct d) SF4 correct
d) PH3
2.5 Lewis Structures: Hypovalency and Radicals

Hint: Do not fight it.

Simply look for Be or B, or
look for odd # valence e-

Do not try to force the

octet rule!!
This isn’t directly on the exam but shows up in Lewis structure questions.

There are two cases in which fewer than 8 e- are available to make Lewis structures.

Hypovalent (too few electrons): occurs with Be and B atoms.

BeCl2 Why? Be has 2 valence e- so it can only make 2 bonds.

BH3 and BF3 Why? B has 3 valence e- so it can only make 3 bonds.

Radicals (odd # of e-): these are also hypovalent cases. Add up the valence e-; if the total is an odd number, then you cannot have a full octet.
NO Why? Total of 11 valence e-

NO2 Why? Total of 17 valence e- (also has resonance)

Practice Exam Problem:

Which of the following compounds is a radical?
a) NH3
b) CH3 correct
c) O3
d) BH3

Explanation:
Count up the valence electrons. NH3 = 8 e-, CH3 = 7 e-, O3 = 18 e-, BH3 = 6 e-.
Although BH3 is hypovalent, it is not a radical. CH3 is a radical and hypovalent.
2.6 Lewis Structures: Hypervalency
2.6 Lewis Structures: Hypervalency
2.7 Lewis Structures: Double and Triple Bonds / C2H6, C2H4, C2H2
Although not a specific question type, these three compounds are very important and appear often.

Organic compounds use carbon as their backbone, and there are three main ways carbon forms bonds. C2H6, C2H4,
and C2H2 highlight these differences. Start by drawing the Lewis structures of each.
rbon
*Easy trick: each ca
e 4 bo nd s and
must mak
H can on ly ma ke 1!

C2H6 C2H4 C2H2

H H
H H
C C H C C H
H C C H Must have multiple
H H bonds between carbons
to have a full octet!
H H

H H H H
C C H C C H
H C C H H H

H H From this, you can determine there are three different types of carbons in organic molecules.
Later in the unit, you will be able to get the following information concerning each:

Each C has 4 single bonds, or 4 e- Each C has 1 double and 2 single Each C has 1 triple and 1 single
rich regions so… bonds, or 3 e- rich regions so… bond, or 2 e- rich regions so…
- C is tetrahedral - C is trigonal planar - C is linear
- C has 109.5° bond angles - C has 120° bond angles - C has 180° bond angles
- C is sp3 hybridized - C is sp2 hybridized - C is sp hybridized
2.8 Lewis Structures: Resonance
 spread out π
bonds above and
σ bonds below the atoms
between
atoms

note that there is a double bond that is

being shared in two structures

sharing of 1 π bond
between two bonds
2.9 Lewis Structures: Multiple Central Atoms
2.10 and 2.11 Lewis Structures: Formal Charge 1 and 2
2.10 and 2.11 Lewis Structures: Formal Charge 1 and 2

Electronic Geometry Molecular Shape

all e- regions just bonds

Tetrahedral Bent
2.12 VSEPR: Electronic Geometries
You need to be able to distinguish electronic vs molecular shapes.
Electronic geometries just ask where the lone pairs of electrons are and delivers the shape.

Molecular shapes ask where the bonds are and delivers shape. (Ignores unbonded electrons.)

Example: Electronic Geometry Molecular Shape  So for electronic

all e- regions just bonds geometry, just count
up e- rich regions on
the central atom in
the Lewis structure
and look at the table.

Tetrahedral Bent

Summary:
Practice Exam Problem: Example Electronic Geometry
# e- Rich Regions Electronic Geometry
For which of the following compounds is the
electronic geometry not the same as the I3- Trigonal Bipyramidal
2 Linear
molecular shape?
XeF4 Octahedral
3 Trigonal Planar
a) BeCl2 PF5 Trigonal Pyramidal
4 Tetrahedral b) BH3
c) SF4 correct SF6 Octahedral
5 Trigonal Bipyramidal
d) CH4
6 Octahedral
Explanation:
A quick way to tell if electronic differs from
molecular is to find out if the central atom
This is the correct answer for electronic geometry has unbonded electron pairs or not. If not, it
regardless of which electron rich regions are will be the same. If so, it will be different.
bonded or unbonded.
2.13 VSEPR: Molecular Shapes
There are 13 molecular shapes with 5 electronic geometries. Memorize them.

AB2 AB3 AB2U AB4 AB3U AB2U2 AB5

Linear Trigonal Planar Bent / Angular Tetrahedral Trigonal Pyramidal Bent / Angular Trigonal Bipyramidal

X—A—X

AB4U AB3U2 AB2U3 AB6 AB5U AB4U2

Seesaw T-Shaped Linear Octahedral Square Pyramidal Square Planar

Practice Exam Problem: Tips on Molecular Shapes: Practice Exam Problem:

Which of the following compounds What is the molecular shape of
has a molecular shape that is  Note the sequence of bonded (B) and unbonded (U) pairs. the IF4– ion?
different from the others?
 Once you can draw these, you will be able to see the names
easily just by looking at the shape. a) Seesaw
a) BeCl2 b) T-shaped
b) O3 correct  Note that you can see polar vs. nonpolar from symmetry.
c) Square planar correct
c) I3– d) Octahedral
d) CO2 So yes, it seems like a lot to learn, but not much to memorize if
e) Tetrahedral
you draw the picture. From the picture, you can get so much
f) Trigonal pyramidal
Explanation: information such as: geometry, polarity, bond angle, hybridization.
All of the other structures are linear
while O3 is AB2U = bent/angular.
2.14 and 2.15 VSEPR: Bond Angles 1 and 2
VSEPR easily explains electronic geometry and bond angles based on the repulsion of → BUT the angles distort if the compound is polar
electron-rich regions (either bonded or unbonded) (asymmetrical).

# e- Rich Regions Shape Bond Angles

2 X—A—X 180°

3 120°

After you learn about polarity, if a molecule is

nonpolar, the bond angles will be as stated in the
table.
4 109.5°

If the molecule is polar, the bond angles will distort.

Practice Exam Problem:

Which of the following has bond angles of 180°?
5 180°, 120°, 90° a) HO2- Explanation: HO2- and NH2- have 4 e-
-
b) I3 correct regions, O3 has 3 regions, and I3- has
c) NH2- 5e-. From those, only I3- can have
d) O3 angles of 180°.

6 180°, 90° Practice Exam Problem:

In which of the following are the bond angles most
distorted by unbonded electron pairs?
a) NH3
b) O3
c) SCl4
Memorize this simple table d) H2O correct
Explanation:
Each of these has one lone pair except H 2O, which has
two. Two lone pairs will cause more distortion than one.
2.16 VSEPR: Molecular Polarity
With additional content on distorted bond angles.
Note that if a molecule is polar, it also has distorted bonds.
If you look for symmetry and it is NOT there, the substance is polar AND has distorted bond angles.

This is the most important thing you will learn in Unit 2. You will Note the 13 molecular shapes tell you symmetrical or asymmetrical if all bonds
are the same just by looking at it.
see why in Unit 3.
1. Draw the 3D picture.
2. Is it symmetrical?
Yes = Nonpolar
No = Polar
 Alternative method: sum the ΔEN for each bond in the
molecule.
∑ ΔEN =0 Nonpolar
Symmetrical Symmetrical Asymmetrical Asymmetrical
∑ ΔEN ≠ 0 Polar
∴ Nonpolar ∴ Nonpolar ∴ Polar ∴ Polar

The formal definition is to find

If bonds are not the same, this causes asymmetry.
three or more planes of symmetry.
Then it is symmetrical. CH4 = symmetrical and nonpolar
CH3F = asymmetrical and polar

Practice Exam Problem:

Famous example of C2F2H2:
Which of the following is polar?
a) CCl4
b) CH3Cl correct Practice Exam Problem:
c) CH4 Which of the following is NOT
d) CO2 polar?
e) NO3 - a) ClF3
b) SF4
Do you see
c) XeF4 correct
the 3 planes
d) IF4+
of symmetry?
e) ClO2-
2.17 The Theory behind Valence Bond Theory
Consider CH4 and where its electrons come from: # e- rich Electronic
Hybridization Character
regions Geometry
First Thought: We can’t make 4 bonds unless an electron
2 sp 1:1 s+p Linear
from the 2s orbital goes to the 2p orbital.
Trigonal
3 sp2 1:2 s+p+p
↑ ↑ ↑ ↑ ↑ Planar
p p
4 sp3 1:3 s+p+p+p Tetrahedral
s
↑↓ ↑s
Trigonal
5 dsp3 1:1:3 d+s+p+p+p
Bipyramidal

Second Thought: There are four bonds in CH4, but the 6 d2sp3 2:1:3 d+d+s+p+p+p Octahedral
bonds suggest there are two different types of bonds.
This is incorrect, for spectroscopy says there is just one
type. The good news: All you need to know to
H C H C assign hybridization is to find the number of
electron rich regions!
σ1s-2s and σ1s-2p

Practice Exam Problem:

Third Thought: So we would need to mix the 2s and 2p Which of the following statements concerning hybrid orbitals is/are true?
I. Hybrid orbitals are energetically degenerate.
orbitals in C in order to create four equal orbitals. The II. Any element can form sp3d2 hybrid orbitals.
four electrons spread out in the four sp3 orbitals to allow III. Hybridizing a 2s and a 2p orbital would produce one single sp hybrid orbital.
four bonds to be created (one electron in each orbital). a) I only correct
b) I, II
c) III only
↑ ↑ ↑ d) I, III
↑ ↑ ↑ ↑
↑
p e) I, II, and III
s sp3 Explanation:
II is false because only elements with six electron rich regions can form sp 3d2 hybrid
orbitals. III is false because it would produce two sp hybrid orbitals – the number of
orbitals you mix = the number of hybrid orbitals you get out.
So CH4 is actually four σ1s-sp3 bonds.
2.18 Valence Bond Theory: Hybridization
If you can draw a 2D or 3D Lewis Structure, Example:
then just count up the number of e- rich Determine the hybridization of each of the numbered atoms.
regions. That determines the hybridization.

# e- rich
Hybridization
regions
2 sp

3 sp2 Numbered Atom # e- Rich Regions Hybridization

1 4 sp3
3
4 sp
2 3 sp2
5 dsp3 3 3 sp2
4 2 sp
6 d2sp3
5 2 sp
Remember that “electron rich regions” are 6 3 sp2
regions of high electron density. A single
7 4 sp3
bond, a double bond, and a triple bond all
count as one region. 8 3 sp2

Practice Exam Problem:

Carbon has a valence of four electrons in nearly all its
compounds and can form chains and rings of C atoms. Consider
the allene structure on the right. What is the hybridization of the
carbon atoms a, b, and c, respectively?
It is really that
2 2 3
a) sp , sp , sp easy!!
b) sp2 , sp, sp2 correct Explanation: Carbon A has three bonding regions,
c) sp2 , sp, sp carbon B has two bonding regions, and carbon C
d) sp3 , sp, sp3 has three bonding regions. None have any
e) sp3 , sp2 , sp3 unbonded regions (lone pairs or lone electrons).
2.19 Valence Bond Theory: Sigma (σ) and Pi (π) Bonds

If you can draw a Lewis structure, even in 2D, you can then count the Example:
3 kinds of electron pairs: σ bonds, 𝜋 bonds, and unbonded e- 11 σ bonds

 σ bonds are made by overlap of orbitals on the bond axis. 3 π bonds

o Single, double, and triple bonds all contain one σ bond.
5 unbonded
o These can be made with any orbital with s character (s pairs
orbitals, sp, sp2, sp3, …) or p orbitals along the bond axis.

 π bonds are made by overlap of orbitals off the bond axis. Practice Exam Problem:
o Double bonds have 1 π bond, triple bonds have 2 π Draw the Lewis structure for acetylene, C2H2. How
bonds. many sigma and pi bonds, respectively, are found in
o These can only be made with p orbitals (or d orbitals, the molecule?
but we don’t go there in this course).
a) 3, 2 correct
b) 1, 2
1σ 1σ 1σ c) 3, 1
0π 1π 2π d) 2, 2

 Any leftover electron pairs that aren’t bonded are an Explanation:

Acetylene has two single bonds (1 σ each) and a triple
unbonded pair (or lone electron, in the case of radicals).
bond (1 σ, 2 π).
2.20 Valence Bond Theory: Orbitals in Bonding
2.21 and 2.22 Molecular Orbital Theory: Diagrams 1 and 2
1. Be able to describe how molecular orbitals are made from AOs, and how they build up to produce the energy levels for H 2 to Ne2
2. Be able to identify individual molecular orbitals by relative order of energy. Know the difference in diagrams between H 2 to N2 and O2 to F2

In molecular orbital theory, 2 atomic orbitals make two molecular Li2 to N2 Energy Levels
orbitals. Just like V.B. theory. But we draw energy diagrams like in σ*2p
Unit 1, NOT structures. antibonding
π*2p
σ*1s 2p2p
This simple picture of two
MO 1s e- making a σ1s bond
1s 1s
for H2 can be σ2p
AO AO
σ1s generalized for all
MO diatomic M.O. 2s2s
π2p
bonding
Note the following: σ*2s
 The kind of atomic orbital it comes from is included (σ 1s,
π2p) 1s1s
*For this problem,
 The antibonding is always above the bonding σ2s
you must be able to
 2 equal energy orbitals is the π σ*1s
label the molecular
 1 equal energy orbital is the σ
orbitals* O2 to Ne2 Energy Levels
σσ*
1s 2p

Practice Exam Question π*2p

2p2p
Consider the molecular orbital diagram on the right. What are the names of the
labeled orbitals, a, b, and c, respectively?

𝜎2p*, 𝜋2p , 𝜎2s* π2p

𝜎2p*, 𝜋2p , 𝜎2s correct 2s2s
𝜎2p*, 𝜋2p , 𝜎1s* σ2p
𝜋2p*, 𝜎2p , 𝜎2s*
σ*2s
1s1s
Explanation: You need to memorize the diagrams for Li through
N2 and O2 through Ne2, including how to label them. Hint:
single MOs are always σ and double MOs are always π. The σ2s
higher energy orbitals of a set are antibonding (*).
σ*1s

σ1s
2.23 Molecular Orbital Theory: Bond Order Calculation
Bond order is the molecular orbital way of saying “bond”
The HARD Way: Example: If you have
→ N≡N is 3 bonds or a bond order of 3 ↑
Draw MO diagram
→ O=O is 2 bonds or a bond order of 2 ↑↓ * Then:
Count up bonding and antibonding B.O. =
↑↓
→ O O O is 1.5 bonds or a B.O. of 1.5 Calculate using the equation ↑↓ * ( 4−3)
=0.5
2
Bond order is a calculation:
B.O. = ¿ ¿

The EASY Way (do this every time!!):

Note that B.O. is directly related to the # e — in diatomic species

So by learning this table, you can do B.O. questions fast.

Example: O2— has 17 e-. Look at the table to see where 17 e- would be.
It is between the B.O. of 1 and 2, so B.O. of O 2— is 1.5!

Practice Exam Question

All of the species below have the same bond order except for one of them.
Which is it?
a) H2–
b) H2+
c) F2–
d) Ne2+
e) B2– correct

Explanation: Count up the total # e- in each. H2— has 3, H2+ has 1, F2— has 19, Ne2+
has 19, and B2— has 11. F2— and Ne2+ have the same # e-, so they have the same
B.O. Using the table, H2+ and H2— each have a B.O. of 0.5. The answer here is B 2—
because it has a B.O. of 1.5.
2.24 Molecular Orbital Theory: Bond Order Application
You need to be able to rank bond length, bond energy, and the existence of diatoms. Example:
Rank the bond length for O2, O2—, and F2.
To do this, remember… (1) Assign B.O.’s:
 The larger the B.O. the stronger the bond energy O2 has 16 e- so B.O. = 2.0
 The larger the B.O. the shorter the bond length O2— has 17 e- so B.O. = 1.5
F2 has 18 e- so B.O. = 1.0
Use the same B.O. table:
(2) Rank: ↑B.O. = ↑ bond energy = ↓ length
# e- 2 4 6 8 10 12 14 16 18 20
O2 < O2— < F2
B.O. 1 0 1 0 1 2 3 2 1 0

B.O. = 0 means the molecule doesn’t exist.

B.O. = 3 is the strongest and shortest bond.

Practice Exam Question

Rank the following by bond length, from shortest to longest: H2+, C2, F2
a) C2 < H2+ < F2
b) F2 < H2+ < C2
c) F2 < C2 < H2+
d) C2 < F2 < H2+ correct
e) H2+ < F2 < C2

Explanation:
Count the total # e- and find B.O. H2+ has 1 e- so B.O. = 0.5, C2 has 12 e-
so B.O. = 2, and F2 has 18 e- so B.O. = 1. Rank, remembering that:
↑B.O. = ↑ bond energy = ↓ length
2.25 Molecular Orbital Theory: Magnetism
Remember from Unit 1, unpaired e- are magnets in atoms, the same is true for Practice Exam Question
molecules. Which of the following species is/are paramagnetic?
2p ↑↓ ↑↓ ↑↓ 2p ↑↓ ↑ ↑ I. Li2—
II. O2
2s ↑↓ 2s ↑↓
III. H2+
1s ↑↓ Paramagnetic
Diamagnetic 1s ↑↓ a) II and III
(Not Magnetic)(Magnetic) b) I and II
c) II only
d) I, II, and III correct
e) III only
So, in diatoms, when drawing M.O.’s and filling according to Hund, Aufbau, and Pauli, Explanation:
if ↑ happens, then it is paramagnetic (magnetic). Li2— and H2+ have an odd total # e- and so must have
at least one unpaired e-. Drawing and filling the MO
↑ ↑ diagram for O2 shows that the top two electrons are
This is why O2
unpaired, so all three molecules are paramagnetic.
is magnetic.
↑↓ ↑↓ ↑↓

↑↓ ↑↓ ↑↓
But N2 is not.
↑↓ ↑↓ Hint: There are three easy ways to
recognize paramagnetism:
↑↓ ↑↓
O2 with 16 e- N2 with 14 e-  Have 10 e- like B2
 Have 16 e- like O2
↑↓  Have an odd total # e- like He+
↑↓

↑↓ ↑↓