PHSC20400 2026

Chapter 2 (and some Chapter 1)

Lecture 1: Ch. 2.1-2.5; Skillbuilders (optional); Lecture 1 Problems
Lecture 2: Ch. 2.6-2.10; Skillbuilders (optional); Lecture 2 Problems
Lecture 3: Ch 1.12-1.14; Skillbuilders (optional); Lecture 3 Problems

Note: WileyPlus lecture problems and Gradescope homeworks are due Wed. Jan 21 by 10:30
am (different from usual Monday because of MLK day)

Note: First quiz will be Wed. Jan 21 (different from usual Monday because of MLK day)

Professor office hours: Friday 2:30-3:30, BRNG B232

TA recitations: Adam Lovato TBD

Chloe Delnicki TBD

Copyright ©2021 John Wiley & Sons, Inc. 1

2.1 Representing Molecules / Introduction
• There are many ways to represent molecules.

Butane Molecular Formula:

Lewis Structure Partially condensed structure Condensed structure

All atoms and bonds C-H bonds not drawn, Bonds not drawn,
are explicitly drawn out all other bonds are drawn out groups of atoms are
clustered together

H3CCH2CH2CH3

Copyright ©2021 John Wiley & Sons, Inc. 2

 2.1 Representing Molecules / Introduction
• Molecular formula is inadequate to distinguish the structure of the molecule.
• : compounds have same molecular formula
but different structures.

Isobutane Molecular Formula:

Lewis Structure Partially condensed structure Condensed structure

All atoms and bonds C-H bonds not drawn, Bonds not drawn,
are explicitly drawn out all other bonds are drawn out groups of atoms are
clustered together

(H3C)3CH

Copyright ©2021 John Wiley & Sons, Inc. 3

 Representing Molecules / Introduction
Octet rule: 2nd row atoms (e.g. C, N, O, and F) prefer to be surrounded by a total of
____ electrons in a stable molecule.
Helpful hints:

Element Typical # bonds for a Typical # lone pairs for a

neutral atom neutral atom
C
H
O
N
F, Br, Cl, I

Exceptions to the octet rule:

• Group 3A (B, Al) only need 6 electrons
• Hydrogen and helium follow the “duet” rule (need 2 e-)
• Phosphorous may have 8 or 10 electrons
• Sulfur may have up 8, 10, or 12 electrons
Copyright ©2021 John Wiley & Sons, Inc. 4
2.1 Representing Molecules / Practice
Converting a condensed structure into a Lewis structure:
1) Draw out linear atom chain
2) Add hydrogens to the carbons (or heteroatoms)
3) Ensure all atoms have an octet, if not add pi-bonds (i.e. double or triple bonds)

H2CCHOCH2CH(CH3)2

• Practice converting from one type of representation to another with SkillBuilder 2.1 –
Converting a Structure.

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iClicker Questions
[Link]
and-remotes/apps

[Link]
Sign in using the campus portal

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2.1 Representing Molecules / iClicker
Which is the correct Lewis structure for CO2?

A) B)

C) D)

• Practice converting from one type of representation to another with SkillBuilder 2.1 –
Converting a Structure.

Copyright ©2021 John Wiley & Sons, Inc. 7

 2.2 Bond-Line Structures / Introduction
• Lewis structures are too impractical to represent a compound
like Amoxicillin, because of its size. But condensed formulas
would tell very little about its shape and atom connectivity.

Lewis structure Bond-line structure

• The Bond-line structure (also called a skeletal structure) is easier to read and to draw.
• Bond-line structures are the benchmark representations for organic compounds.
• It is critical to know how to draw these structures, for any compound, without
difficulty, to succeed in any organic chemistry course.

Copyright ©2021 John Wiley & Sons, Inc. 8

 2.2 How to Read Bond-Line Structures / Introduction
• Each or represents a .

• Carbon atoms are not labeled, but a carbon is assumed to be located at every corner or
endpoint on the zigzag.
• Double bonds are shown with 2 lines; Triple bonds are shown with 3 lines
• H atoms bonded to carbon are not drawn, they are implied.
• See Chapter 1.6 for more details!
Copyright ©2021 John Wiley & Sons, Inc. 9
2.2 How to Read Bond-Line Structures / Hydrogen Atoms
• You must also be able to use the bond-line structure language to interpret the number
and location of H atoms in a molecule.
• H atoms bonded to carbon are not shown, but it’s assumed there are enough to
complete the octet (4 bonds) for each carbon.
How many carbons?
How many hydrogens at each carbon?

Copyright ©2021 John Wiley & Sons, Inc. 10

2.2 How to Read Bond-Line Structures / iClicker

Which of the following structures has 5

carbons and 10 hydrogens?
B) C)
A)

D) A and B E) A and C

Copyright ©2021 John Wiley & Sons, Inc. 11

2.2 How to Draw Bond-Line
Structures / Rule One
• If you are given a Lewis structure or condensed structure, you must also be able to
draw the corresponding bond-line structure
Rule 1: sp2 and sp3-hybridized atoms in a straight chain should be
drawn in zigzag format, sp-hybridized atoms are straight.

H3CCH2CH2CH3 H3CCHCHCH3 H3CCCCH3

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2.2 How to Draw Bond-Line
Structures / Rules Two and Three
Rule 2: When drawing double bonds, draw all bonds as far apart as possible.

acetone

(CH3)2CO

Rule 3: When drawing single bonds, the direction in which the bonds are drawn
is irrelevant

is the same as

Copyright ©2021 John Wiley & Sons, Inc. 13

2.2 How to Draw Bond-Line
Structures / Rule Four
Rule 4: All heteroatoms (atoms other than carbon and hydrogen)
must be drawn, as well as the H atoms attached to them.

H3CCH(OH)CH2CH3
Rule 5: The cardinal rule – Never draw more than four bonds to a
carbon atom (recall the octet rule). No Texas carbons!
For extra practice do Skillbuilder 2.2

Copyright ©2021 John Wiley & Sons, Inc. 14

2.2 How to Draw Bond-Line Structures/iclicker
Which of the following structures is the best
Bond-Line structure for the below molecule?
CH3CH2CH(OH)CHCH2

A) B) C)

Copyright ©2021 John Wiley & Sons, Inc. 15

 2.3 Bond-Line Structures in 3-D / Dashes and Wedges
• All molecules take up spaced in 3 dimensions, but it is difficult to represent a
3-D molecule on a 2-D piece of paper or blackboard
• We will use dashed to show groups that point back into the paper
• We will use solid wedges to show groups that point out of the paper

Tetrahedral carbon

Not enough information on the Provides more information on the 3-D structure
3-D structure of the molecule of the molecule. Can draw hydrogens or not.
They are implied. Either way is acceptable.

Copyright ©2021 John Wiley & Sons, Inc. 16

2.4 Identifying Functional Groups
(1 of 4)

• Bond-line structures make it easier to see the bonds

made/broken in a chemical reaction.
• Compare the condensed formula with the bond-line structure
below for the same reaction:

• The bond-line structures make it more obvious to see the

functional group transformation that takes place.

Copyright ©2021 John Wiley & Sons, Inc. 17

2.4 Identifying Functional Groups / Definition
• When certain atoms are bonded together in specific arrangements,
they undergo specific chemical reactions.
• These characteristic groups of atoms/bonds are called functional
groups. 16 that you need to know!

Ethanol 4
CH3CH2OH

5
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2.4 Identifying Functional Groups / List (continued)

acetone
6

Acetic acid 8

10

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2.4 Identifying Functional Groups / List (continued)

11

12

13

14

15

16

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2.4 Identifying Functional Groups / List (continued)

You should be able to label functional groups in molecules

Fexofenadine (Allegra)

Copyright ©2021 John Wiley & Sons, Inc. 21

2.4 Identifying Functional Groups / iClicker
Not including alkanes, how many different types of
unique functional groups are in simvastatin?

Simvastatin (Zocor)
• Cholesterol lowering drug
• One of top pharmaceutical products by
US prescription
• HMG-CoA reductase inhibitor

A) 5 B) 4 C) 3 D) 2

Copyright ©2021 John Wiley & Sons, Inc. 22

2.5 Bond-Line Structures: Identifying Lone Pairs /
Oxygen
• Use the bond patterns to identify formal charge.
• Oxygen is in the 6th group in PTE – must have 6 valence electrons to be neutral
• Oxygen has three possible bonding patterns that determine formal charge.

when O has 7 when O has 6 when O has 5

valence e− valence e− valence e−
bond + lone pairs bond + lone pairs bond + lone pairs

• Practice with SkillBuilder 2.4 – Identifying Lone Pairs.

Copyright ©2021 John Wiley & Sons, Inc. 23
2.5 Bond-Line Structures: Identifying Lone Pairs /
Nitrogen
• Nitrogen is in the 5th group of PTE, so needs 5 valence electrons to be neutral
• Nitrogen has three possible bonding patterns with 4, 5, or 6 valence electrons
that determine formal charge.

When N has 6 When N has 5 When N has 4

valence e− valence e− valence e−
bond + lone pairs bond + lone pairs bond + lone pairs

• Practice with SkillBuilder 2.4 – Identifying Lone Pairs.

Copyright ©2021 John Wiley & Sons, Inc. 24

 2.6 Carbon Atoms with Formal Charges / Common
Scenarios
• A carbon atom will have when it does not have a formal charge.
• When a carbon has a charge (carbocation), it will have a
total of bonds and one empty orbital.

• A carbanion will also have three bonds, but

also a lone pair and no empty orbitals.

Copyright ©2021 John Wiley & Sons, Inc. 25

 2.6 Carbon Atoms with Formal Charges / Practice
• Formal charge affects the and of molecules,
so you must be able to identify formal charges in bond-line representations.
• Formal charges must always be drawn.
How many hydrogens are on the carbon with the formal charge?

Draw the Lewis structure to convince yourself!

Copyright ©2021 John Wiley & Sons, Inc. 26

2.6 Carbon Atoms with Formal Charges / iClicker
How many hydrogens are on the carbon with the formal charge?

A) 0

B) 1

C) 2

D) 3

E) 4

Draw the Lewis structure to convince yourself!

Copyright ©2021 John Wiley & Sons, Inc. 27

 2.7 – Introduction to Resonance / Definition
• Resonance: When a molecule or ion is best described by two or more structures.
• Pi bonds and/or formal charges are often more “spread out” than a bond-line
structure can imply.
2

1 Vs.
3

• All three overlapping p-orbitals allow the electrons to move throughout the
overlapping area, and so we say the molecule has ,
meaning it has electrons.
• The resonance arrow, and the brackets, indicate these two structure
contributors are describing one compound.
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 2.7 Resonance
• Because neither of the contributors exists exclusively, the average
or is much more appropriate
Contributing resonance structures Resonance hybrid

• Delocalized electrons are more spread out, thus lower energy, thus more
stable. So resonance a molecule.
• Delocalization of charge
o The charge is spread out over more than one atom. The resulting partial
charges are more stable than a full +1 charge.
o The more atoms the charge is delocalized over the more the
molecule
Copyright ©2021 John Wiley & Sons, Inc. 29
2.8 Curved Arrows / Introduction
• Throughout Organic Chemistry, we will be using curved arrows to show
electron movement
electron density electron density
• The sooner you master this skill, the easier the course will be
o The arrow starts where the electrons are located
o The arrow ends where the electrons are after the electron
movement

Copyright ©2021 John Wiley & Sons, Inc. 30

2.8 Curved Arrows / Resonance: Rule One
• There are specific rules for using curved arrows to describe
resonance.
Rule 1: Do not break a single (sigma - 𝜎) bond in resonance structures.
Do use pi-bonds and lone pairs.

• Single bonds break in a chemical reaction, not resonance.

• Resonance occurs for electrons existing in overlapping p orbitals (pi-bonds
and lone pairs… not sigma bonds).

Copyright ©2021 John Wiley & Sons, Inc. 31

2.8 Curved Arrows / Resonance: Rule Two
Rule 2: Never exceed an octet for 2nd row elements (B, C, N, O, F).
• The valence shell of an atom in the 2nd row has only 4 orbitals, holding a
max. of 8 electrons.
• But you can have less than an octet…

For more practice do Skillbuilder 2.5

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2.9 Formal Charges in Resonance / Importance
• When using curved arrows to derive resonance structures, you will often
have one or more formal charges to contend with.
• You have to indicate formal charge to draw a valid structure.
• Each resonance structure must have the same net charge!

Neutral charge

Negative charge For more practice do Skillbuilder 2.6

Copyright ©2021 John Wiley & Sons, Inc. 33
 2.10 Resonance Pattern Recognition / Five Patterns
How to spot if a molecule will have resonance

• There are five general bonding patterns in which resonance occurs.

Recognize these patterns to predict when resonance will occur
1. Allylic lone pair
2. Allylic carbocation
3. Lone pair of electrons adjacent to a carbocation
4. A pi-bond between two atoms with different electronegativities
5. Conjugated pi-bonds in a ring
• The only way to recognize these patterns is to do lots and lots of practice
problems and examples.

Copyright ©2021 John Wiley & Sons, Inc. 34

2.10 Resonance Pattern Recognition / Pattern One
Pattern #1 – Allylic Lone pair
• Vinyl refers to the atoms of the pi-bond/C=C double bond
• Allyl refers to the atoms next door to the C=C double bond
• We look for allylic lone pairs because they will be resonance delocalized.
• Can be charged OR neutral!

REQUIRES TWO ARROWS – moving 2 pairs of electrons

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• Practice with CONCEPTUAL CHECKPOINT 2.18 – Locate the Pattern.
 2.10 Resonance Pattern Recognition / iClicker

Which of the below is a valid resonance structure? Draw the arrows that
would form this resonance structure.

A B C D

Copyright ©2021 John Wiley & Sons, Inc. 36

 2.10 Resonance Pattern Recognition / Pattern Two
Pattern #2
2. Allylic carbocations
Only one curved arrow is needed to show resonance
• If there are multiple double bonds (conjugated), then multiple contributors
are possible. They are drawn by moving one electron pair at a time

Practice with CONCEPTUAL CHECKPOINT 2.19 – Draw Resonance

Structures.
Copyright ©2021 John Wiley & Sons, Inc. 37
2.10 Resonance Pattern Recognition / Pattern Three
Pattern #3
3. A lone pair adjacent to a carbocation
• Only one arrow is needed

• Recognize how the formal charges are affected by the electron movement in
these two examples
Practice with CONCEPTUAL CHECKPOINT 2.20 – Locate the Lone Pair.
Copyright ©2021 John Wiley & Sons, Inc. 38
2.10 Resonance Pattern Recognition / Pattern Four
Pattern #4
4. A pi-bond between atoms of different electronegativity
• The pi-electrons will be more attracted to the more electronegative atom,
causing the pi-bond to be unequally shared.

• These two structure represent the “extreme” descriptions of the pi-bonded

electrons (equally shared versus not shared). The actual compound is a hybrid
of the two (unequally shared).
• Practice with CONCEPTUAL CHECKPOINTS 2.21-2.23 – Draw Resonance
Structures.
Copyright ©2021 John Wiley & Sons, Inc. 39
 2.10 Resonance Pattern Recognition / iClicker

Which of the below is the more stable valid resonance structure? Draw the
arrows that would form this resonance structure.

C
A B

Copyright ©2021 John Wiley & Sons, Inc. 40

2.10 Resonance Pattern Recognition / Pattern Five
Pattern #5
5. Conjugated pi-bonds in a ring
• Each atom in the ring has an unhybridized p-orbital that can overlap with its
neighbors

• The pi-bonds can be pushed over by one position (clockwise or

counterclockwise, doesn’t matter, the result is the same).
• Practice with CONCEPTUAL CHECKPOINT 2.24 – Draw a
Resonance Structure.
Copyright ©2021 John Wiley & Sons, Inc. 41
2.10 Resonance Pattern Recognition /
Summary
Summary of the five main patterns

Practice with CONCEPTUAL CHECKPOINT 2.25 – Draw

Resonance Structures.

Copyright ©2021 John Wiley & Sons, Inc. 42

 2.11 Relative Importance of Resonance
Structures
Not all structures contribute equally to the resonance structure!

Preference is given to structures with:

1. Complete valence shell (complete octet)
2. Fewest formal charges
3. Negative charge on more electronegative atom and positive charge
on least electronegative atom

List is in order of importance with #1 being most importance

Copyright ©2021 John Wiley & Sons, Inc. 43

 2.12 The Resonance Hybrid
• The resonance hybrid represents the pi bond of an allylic
carbocation as being delocalized over all three carbon atoms.

For more practice do Skillbuilder 2.8

Copyright ©2021 John Wiley & Sons, Inc. 44
 2.13 Delocalized Lone Pairs vs. Localized Lone Pairs
• Localized electrons are not in resonance.
• Delocalized electrons are in resonance, and are more stable.

• The lone pair is delocalized, which is only possible through overlapping p-

orbitals. So, the nitrogen must be sp2 hybridized – Trigonal planar

• A lone pair does not participate in resonance if it cannot overlap with an

adjacent p-orbital… it is a localized lone pair.
• So the nitrogen is sp3 hybridized - tetrahedral
Copyright ©2021 John Wiley & Sons, Inc. 45
1.12 Molecular Polarity & Dipoles / Introduction to
Dipole Moment
• Electronegativity differences result in bonds.
• (shifting of electrons within an orbital)
results in a dipole moment.
• Dipole moment = (the amount of partial charge) × (the
distance the δ+ and δ− are separated).
• Dipole moments are reported in units of debye (D).
• Vector sum of individual dipole
moments.

• Practice with SkillBuilder 1.9: Identifying the presence of molecular dipole moments.
Copyright ©2021 John Wiley & Sons, Inc. 46
1.12 Molecular Polarity & Dipoles / iClicker
Which of the following molecules have a non-zero dipole moment?

H2O CO2 CCl4 CH3NHCH2CH3

A) All have non-zero dipole moments

B) None have non-zero dipole moments

C) Only H2O has a non-zero dipole moment

D) H2O and CH3NHCH2CH3 have non-zero dipole moments

Copyright ©2021 John Wiley & Sons, Inc. 47
 1.13 Dipole-Dipole Attractions / Introduction
• Dipole-dipole forces result when polar molecules line up their
opposite charges. Attractive forces

Boiling Point = 56 ºC
Acetone is more polar, and so
Acetone it has a higher BP
• Note acetone’s dipole results from the difference in
electronegativity between C and O.
• The dipole-dipole attractions between acetone molecules acetone’s
boiling and melting points while similar molecules without dipole-dipole
interactions, such as isobutylene, have boiling and melting points.

Boiling Point = -7 ºC
Isobutylene is less polar, has
isobutylene weaker dipole-dipole attractions
and therefore a lower BP
Copyright ©2021 John Wiley & Sons, Inc. 48
1.13 Hydrogen Bonding / Introduction
• Hydrogen bonds are an especially strong type of dipole-dipole attraction.
• Hydrogen bonds are strong because the partial + and − charges are relatively
large.
• H-bonding is the attractive force between a bonded to
an atom (N, O or F) and a on another
electronegative atom.

H-bonding increases boiling point:

Copyright ©2021 John Wiley & Sons, Inc. 49

1.13 Hydrogen Bonding / Protic and Aprotic
• Solvents that engage in H-bonding are called . Solvents that
do not H-bond are . This will be important later in the
course when discussing different reactions.

ethanol

Dimethylsulfoxide, DMSO Acetone Water

Copyright ©2021 John Wiley & Sons, Inc. 50

 1.13 London Dispersion Forces / Introduction
• If two molecules are nonpolar (dipole = 0 D), they still will have an attractive
force between them.
o This occurs due to an induced, transient dipole moment, called London
dispersion forces.
The constant random motion of the electrons in the molecule will sometimes
produce an electron distribution that is not evenly balanced with the positive charge
of the nuclei. Such uneven distribution produces a dipole,
which can induce a temporary dipole in a neighboring molecule.

• The result is a weak fleeting attraction between the two molecules.

Copyright ©2021 John Wiley & Sons, Inc. 51

 1.13 London Dispersion Forces
• Effect of Mass
o Larger mass in general has greater temporary dipole-dipole attraction.

MW = 58 g/mol MW = 72 g/mol MW = 86 g/mol

• Effect of branching
o Less branching has greater temporary dipole-dipole attraction.

C5H12 Smallest SA
Largest SA
MW = 72 g/mol

Copyright ©2021 John Wiley & Sons, Inc. 52

1.14 Solubility / Polar vs Apolar

• As you learned in general chemistry, “like dissolves like.”

• Polar compounds generally mix well with other polar
compounds
o If the compounds mixing are all capable of H-bonding
and/or strong dipole-dipole interactions, then there is no
reason why they shouldn’t mix.
• Nonpolar compounds generally mix well with other
nonpolar compounds
o If none of the compounds are capable of forming strong
attractions, then no strong attractions would have to be
broken to allow them to mix.

Copyright ©2021 John Wiley & Sons, Inc. 53

Major Takeaways
• Draw Lewis structures and assign formal charges to atoms
• Know the octet rule/typical number of bonds and lone pairs for
C, H, O, N, and halogens
• Convert between Lewis structures and bond-line structures
• Identify and name functional groups in molecules
• Identify molecules with resonance structures and draw them
• Use curved arrows to track the movement of electrons in
resonance structures
• Determine the major resonance contributors
• Identify polar bonds, dipole moments, and molecular dipoles
• Know the types of intermolecular forces and how they affect
boiling point/melting point and solubility
Copyright ©2021 John Wiley & Sons, Inc. 54