Chem 201, Fall 2010

Activity 1, M Aug 30

Activity1.HowtoDrawandReadStructuralFormulas
This activity focuses on how to read and draw structural formulas for molecules. Lewis structures
show how atoms are connected together inside a molecule. They also show how electrons are
organized around atoms. Line formulas and condensed formulas are used to make drawing easier.
You are not expected to complete this activity during this class. However, you should complete it on
your own time before the next class. Instructions for completing this activity and for additional study
have been inserted at various points in the activity so keep this handout for future reference.

GettingStartedwithLearningActivities.FormaGroup.Moveon.
Form a group. If you have not already done so, form a group of three students (its best if one
student has a clicker). Sit in adjacent chairs. Tell each other your names and write them below to help
you remember them (one space is for your name because you belong to the group too).
My group: _____________________ , _____________________ and _____________________.
Some groups find it helpful to assign special jobs. A manager makes sure that the group stays
together and stays on task. The manager should sit in the middle of the group. A managers entire job
might be to ask every so often, are we ready to move on? A manager might also make sure that
every member of the group gets a chance to contribute. Two other potentially useful jobs: a recorder
who makes written notes of group questions and conclusions, and a reflector who calls the groups
attention to strengths and weaknesses in the way they operate.
Assign jobs now (these jobs should rotate in future classes), but if you want to move on without
assigning jobs, thats fine. Suggestion: if you decide to operate without assigned jobs, somewhere down the line your

group should discuss whether assigning jobs might make the group more successful.

Move on. Work your way into this activity by doing the following:
On your own, read a model and answer all of the critical thinking questions (CTQs) that
follow the model. Write and draw your answers to the CTQs in the space provided. The activity
sheets will not be collected so write and draw your answers even if you are unsure about them.
When you reach a CTQ labeled check-in (CI), compare your answer to those of your group
mates. Discuss and resolve all differences. Then continue working individually on the following
material, whether it is a new model or more CTQs.
If you get stuck on a CTQ before you reach the next CI point, or if your group cannot resolve the
different answers it has, try the following:
Have one person read a problematic question out loud.
Peek ahead at the next question or model. These might contain some helpful clues.
Check the answers of a neighboring group (please stay seated).
Construct a group question and put it to the instructor. (Note: Try to ask a question that speaks to
the source of your groups confusion. If you simply ask me, Do we have the right answer? I am likely to
respond Why do you doubt yourselves? instead of saying Yes or No.)

Some additional courtesies that will help make this experience more productive:
Dont blurt out answers while working on your own. It is important for each person to reach
an answer, correct or otherwise, before comparing notes. Likewise, discuss material quietly
so that you dont disturb other groups.
If you reach a CI question way ahead of your group mates, continue working, but come back to
the CI for the group discussion.

Chem 201, Fall 2010

Activity 1, M Aug 30

Model1.ValenceElectrons
An atom consists of a nucleus surrounded by electrons. The nucleus carries a positive charge, +Z,
where Z is the atomic number. The electrons carry identical negative charges of -1. In an electrically
neutral atom, the total negative charge balances the total positive charge. The following periodic
table provides information about atomic numbers and electrons for some common elements.
Memorization note. The shaded boxes represent the elements that appear most often in this
course. Before the next class, memorize the #valence electrons for the shaded elements.
1

2/8

valence
electron

valence
electrons

valence
electrons

valence
electrons

valence
electrons

valence
electrons

valence
electrons

valence
electrons

9
F
17
Cl
35
Br
53
I

2
He
10
Ne
18
Ar
36
Kr
54
Xe

1
H
3
Li
11
Na
19
K

4
Be
12
Mg
20
Ca

5
B
13
Al

6
C
14
Si

7
N
15
P

8
O
16
S

valence
shell

e
e

e
e

Cnucleus
+6

core
shell

It is useful to view the electrons inside an atom as being arranged in shells that hold electrons of
similar energy. To simplify even more, we will group the electrons into just two shells: a core shell
and a valence shell. The drawing to the right of the table shows this highly simplified picture for a
carbon atom. Each shell is represented by a circle; the nucleus and the electrons are represented by a
dot and the letter e, respectively.
A carbon nucleus carries a +6 charge (Z = 6). The two core electrons (e) stay very close to the
nucleus. They have very low energies and are only weakly affected by routine physical and chemical
processes. The four valence electrons have much higher energies than the core electrons. They are
able to wander much farther away from the nucleus, and routine physical and chemical processes
dramatically affect their behavior.
Critical Thinking Questions (remember: write or draw all answers)
1. What is the atomic number of carbon?
2. How many electrons are there in an electrically neutral carbon atom?
3. How many core electrons are there in C? How many valence electrons?
4. (CI) Complete the following atomic models of aluminum (Al) and fluorine (F): 1) by filling
in appropriate nuclear charges, 2) labeling each shell, and 3) adding electrons to each shell.

Alnucleus
+__

Fnucleus
+__

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Activity 1, M Aug 30

5. Consider atoms of F, Cl, Br, I (the halogens). Do these atoms contain the same number of
core electrons, valence electrons, or the same nuclear charge?
6. (CI) Consider atoms of B, C, N, and O. Do these atoms contain the same number of core
electrons, valence electrons, or the same nuclear charge?
7. T or F. An atom always contains more valence electrons than core electrons. (If F, illustrate
this by identifying an atom that contains more core electrons than valence electrons.)

Model2.TheLewisOctetRule
In 1916, G.N. Lewis, a chemist at University of California-Berkeley, described a system of chemical
bonds. His ideas were extended and popularized in 1919 by I. Langmuir, another well-known
scientist. We still use the Lewis-Langmuir system today because it provides a quick and meaningful
way to represent electrons in molecules. (For convenience, we usually call this the Lewis system.
Sorry Dr. Langmuir.)
In Lewis system, stable, long-lived molecules can be represented using special formulas called Lewis
structures. Unstable molecules cannot. 1 A Lewis structure shows elements surrounded by electrons,
where the element symbol represents the nucleus and core electrons, dots represent nonbonding valence
electrons, and line segments represent pairs of shared valence electrons. Drawing note: If an element
symbol contains two letters, capitalize the first letter only. The correct symbol for neon is Ne, not
NE.

H
Li

He
B

Ne

He, Ne and other inert gas atoms occur naturally as stable atoms. The atoms of other elements are
always found as ions (charged species) or as parts of molecules. Ions and molecules can be
represented by drawings called Lewis structures that embody Lewis system of chemical bonding.
Lewis structure checklist I. A satisfactory Lewis structure must obey every item on this checklist:
all valence electrons appear in the drawing
a nonbonding electron is associated with a single atom. Nonbonding electrons are drawn
using dots
covalent bonding electrons occur in pairs. Each pair is associated with two atoms and is
drawn using a line segment
ionic bonds are implied wherever two species carry different electrical charges
2 valence electrons (usually bonding electrons) are associated with each hydrogen atom
8 valence electrons (octet) are associated with each non-hydrogen atom.
(the last two items are called the Octet Rule)

1 Organic chemists typically refer to ANY formula that shows bonding and nonbonding electrons as a Lewis
structure and I will follow this usage myself, but this is sloppy. Originally, Lewis structure meant a drawing
that obeyed all of the rules on checklists I and II. Drawings that disobeyed one of these rules were not Lewis
structures. Unfortunately, I dont have a good name for these drawings, so I will call them Lewis structures too.

Chem 201, Fall 2010

Activity 1, M Aug 30

The next figure shows how one combines atoms and electrons to make Lewis structures for CH4,
HO-, and CH3Cl. A temporary drawing is provided to help you count all of the electrons, but only
the right-most drawings are suitable for our course.

C
H

C
H

8electronstotal

"1"

1
O

8electronstotal

C
H

H
Cl

14electronstotal

C
H

Cl

Cl

Critical Thinking Questions (remember: write or draw all answers)

8. Confirm that the Lewis structure of CH3Cl satisfies every item on checklist I by filling in the
blanks:
a. Number of bonding electrons in Lewis structure = ____
b. Number of nonbonding electrons in Lewis structure = ____
c. Total number of electrons in Lewis structure = ____
d. ____ electrons are associated with each H (____ bonding + ____ nonbonding)
e. ____ electrons are associated with C (____ bonding + ____ nonbonding)
f. ____ electrons are associated with Cl (____ bonding + ____ nonbonding)
9. The following species are ions. Draw the appropriate electrical charge next to each ion by
comparing the number of electrons with those found on neutral fluorine. Which ion(s)
satisfy the Octet Rule?

10. (CI) Draw a Lewis structure for NH3. Confirm that your drawing satisfies checklist I by
counting electrons the way you did in CTQ 8.

11. It is impossible to draw a satisfactory Lewis structure for neutral NH4 (and this is not a longlived species).
a. How many valence electrons does neutral NH4 contain?
b. How many valence electrons does NH4+, the +1 ion or cation, contain?

Chem 201, Fall 2010

c.

Activity 1, M Aug 30

(CI) Draw a Lewis structure of NH4+ (draw brackets [ ] around your ion and draw

+ outside the right bracket). Could this be a long-lived ion? Explain.

12. BF4 contains 31 valence electrons. How many valence electrons does BF4+ contain? BF4-?

Model3.FormalCharge
In order to decide whether an atom satisfies the Octet Rule, you must count all of the electrons
associated with that atom, i.e., all nonbonding electrons plus all bonding electrons. A Lewis structure
also needs to show whether an atom is charged, i.e., whether it has gained or lost electrons. To
determine this, you must disassemble each bond so that one electron is assigned to each atom. This is
shown below for NH3 and NH4+.

H
N

N
H

N
H

Disassembly of NH3 in this fashion produces N with 5 valence electrons. Disassembly of NH4+, on
the other hand, gives N only 4 valence electrons. Because neutral N contains 5 valence electrons, the
latter N must carry a positive charge. Since this method of breaking bonds and counting electrons is
completely arbitrary, we refer to the +1 charge on N as its formal charge (FC).2
The FC on any atom in a Lewis structure can be quickly calculated using the following formula:
FC = #valence electrons on neutral atom #bonds #nonbonding electrons
Applying this formula to N in NH3, we write FC = 5 3 2 = 0 where 5 is the #valence electrons
on neutral N, 3 is the #bonds made by N in the Lewis structure, and 2 is the #nonbonding electrons
on N. Since FC = 0, N is neutral.
Critical Thinking Questions
13. Apply the FC formula to N in NH4+ and confirm that it yields the correct FC.

2 Although bonds do not spontaneously disassemble themselves as shown above, formal charges can often
suggest the location of electrical charges inside a molecule. The electrons in a bonding pair have the same
negative charge and they repel each other. This electron-electron repulsion drives the electrons towards
different atoms. For example, at any given moment one N-H bonding electron will stay close to N and the
other will stay close to H. When this occurs, the FC indicates the atoms actual electrical charge.

Chem 201, Fall 2010

Activity 1, M Aug 30

14. Most atoms in organic molecules have FC = 0. Use the FC formula to check the charges on
each molecule below. (These calculations show why it is helpful to memorize the number of
valence electrons on commonly encountered atoms.)

H
H

Br

15. Atoms with +1 and -1 formal charges appear frequently in Lewis structures (larger charges
seldom appear for energy reasons3). By convention, only non-zero charges are drawn in a
Lewis structure, and the single charges (+1, -1) are circled to distinguish FC from other +
and symbols. Use the FC formula to check the charges that have been assigned below
(check only the charged atoms).

H
H

O H

Lewis structure checklist II. A satisfactory Lewis structure should show

all non-zero formal charges
no valence electrons on alkali metal ions (Li+, Na+, K+) and alkaline earth ions (Mg+2, Ca+2)
(the last item is the third and final part of the Octet Rule)
16. None of these drawings are satisfactory Lewis structures. Correct each drawing by adding
non-zero formal charges where needed. Do NOT add or remove electrons.

O
F

By convention, organic chemists never draw molecular ions inside brackets with a total charge
outside. Instead, they draw formal charges where these are needed inside the Lewis structure. The
two drawing styles are compared here.
H
correct

C
H

H
O

H
H

C
H

H
incorrect

O
H

17. Every molecule in CTQ #16 is neutral (total charge = 0). The relationship between the FC
that appear in these drawings and the total charge applies to all molecules. Define this
relationship by answering CTQ #17a/b (next page).
A +1 or -1 ion can be created by removing or adding an electron (charge = -1) to a neutral atom. To create a
+2 atomic ion, an electron (-1) must be removed from a +1 ion. This is much more difficult because of the
electrical attraction between the electron and the ion. Likewise, to create a -2 atomic ion, an electron (-1) must
be added to a -1 ion. This time electrical repulsion between like charges makes the process difficult.

Chem 201, Fall 2010

a.

Activity 1, M Aug 30

T or F. A molecules total charge equals the sum of the FC that appear in its Lewis
structure. (If F, identify a molecule on the preceding page that demonstrates this.)

b. T or F. If a molecules total charge equals 0 (neutral molecule), FC equals 0 on

every atom in the molecule. (if F, identify a molecule on the preceding page that
demonstrates this.)

Model4.RecognizingFormalChargesVisually
The following chart shows the way commonly encountered atoms appear in Lewis structures (X
signifies a halogen: F, Cl, Br, or I; Z represents any atom that can make covalent bonds). The central
atoms are listed on the left and the formulas are grouped together by FC (listed across the top). All
possible C structures have been drawn, but some structures for other atoms are missing.
FC = +1

FC = 0
Z

C
Z

Z
Z

C
Z

Z
Z

Draw 2 structures

N
Z

Z
Z

One can also imagine ZC+, but this structure is

never encountered in practice

FC = 1

Draw 1 more structure

Draw 1 more structure

Draw 3 structures

Draw 1 structure

Draw 2 structures

Draw 1 structure

Draw 1 structure (Hint: atomic anion)

Carefully read the structures in each box of the C row. Notice that all of the structures in a given box
place the same number of bonds and nonbonding electrons around C. Also notice that the structures
in the N/+1 box are essentially identical to the structures in the C/0 box (this must be true because

Chem 201, Fall 2010

Activity 1, M Aug 30

the structures contain the same number of electrons, but Ns nucleus contains one more proton than
Cs nucleus). As you practice drawing and reading Lewis structures, you will naturally learn these
visual patterns and the correct FC without resorting to the calculations used in Model 3.
Critical Thinking Questions
18. Complete the box in Model 4 for N+ by drawing one other structure that places a +1 formal
charge on N. (Hint: The 4 structures in N/+1 should resemble the 4 structures in C/0.)
19. (CI) Complete the rest of the chart by drawing all of the missing structures. (Hint: structures
in diagonally related boxes, such as N/+1 and C/0, are identical except at the central atom.)
20. S and P are also commonly encountered atoms in organic chemistry. Which boxes contain
structures that apply to P? To S? (Write the letters in the left-most column of the chart.).
21. (CI) Which FC = . 1 boxes and FC = +1 boxes contain the same structures? Take one of
these pairs and explain why these charged atoms must be surrounded by identical electron
patterns.

22. Compare the non-hydrogen atoms in the following structures to those in the chart. Add
non-zero formal charges to atoms as needed. Do NOT add or remove electrons.
H

H
H

H
N
N

C
H

H
H

O
S
C

Model5.CondensedFormulas
Long before the discovery of the electron, organic chemists had already noticed empirical patterns in
the ways atoms combined. Simply stated, one could draw a structural formula for most stable neutral
molecules by having each C make 4 bonds, N make 3 bonds, O make 2 bonds, and H and X make 1.
With this rule in mind, it is possible write certain molecular structures as a single line of text. These
are called condensed formulas because the bonds are generally not shown. Most or all of the
bonding information is implied by the sequence of atoms in the formula. In the following examples,
the condensed formula is shown above a structural formula.
CH4

CH3CH3

CH3NH2

CH3OCH2CH2OH

H
H C H
H

H H
H C C H
H H

H
H C N H
H H

H H
H
H C O C C O H
H H
H

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Activity 1, M Aug 30

Condensed formulas can be simplified further when:

several identical groups are attached to a common atom. The repeated group is written
inside parentheses and a subscript is placed outside to indicate the number of instances of
that group
a chain of CH2 groups separates two other groups or atoms. The CH2 group is written inside
parentheses and a subscript indicates the number of CH2 groups in the chain.
(CH3)3CH
CH3
H C CH3
CH3

((CH3)3Si) 2NH
H3C H CH3
H3C Si N Si CH3
H3C
CH3

(CH3O) 2CH(CH2)4Br
H3C

O H H H H
H C C C C C Br
O H H H H
H3C

Rings cannot be drawn easily using condensed formulas, but double and triple bonds are easily
handled (see below). It is common practice to draw the multiple bond in the condensed formula, but
the bond can be omitted when its placement will be obvious. For example, the last molecule could
also be drawn as NCCH2CH3.
CH2=CH2 or H2C=CH2

CH3CH=CHCH3

N CCH2CH3

H H
C C
H H

H CH3
C C
H3C H

H H
N C C C H
H H

Critical Thinking Questions

23. Organic molecules can contain single, double, and triple bonds. Which of these kinds of
bonds do not appear in a condensed formula?
24. Which of these statements best captures the motivation for using condensed formulas:
a. 19th century chemists didnt know about electrons and couldnt draw Lewis
structures.
b. Useful ideas about chemical bonding predate Lewis.
c. Condensed formulas simplify the drawing of structural formulas. They also make it
possible for certain formulas to be typed.
d. Condensed formulas highlight the fact that most organic compounds exist in a
condensed state of matter (liquid or solid).
25. (CI) Draw a Lewis structure for CH3OCF3.

26. Although H and X (halogen) atoms might appear anywhere in a condensed formula, they
always represent the end of an atom chain, never the middle. Why?

Chem 201, Fall 2010

Activity 1, M Aug 30

Model6.LineFormulas
The following drawings compare condensed formulas with line formulas for some simple
hydrocarbons. Line formulas do not show carbon or hydrogen atoms. Line segments show carboncarbon bonds, with a carbon atom assumed to lie at the end of each segment (there is one carbon at
the intersection of two or more segments). The number of hydrogen atoms is determined by
assuming that each carbon must make four bonds. Thus, a carbon that makes two CC bonds must
also be bonded to two hydrogens.

CH3CH2CH2CH2CH3

H3C

H
C

CH3

H3C

CH2

C
H

CH2
CH3

Critical Thinking Questions

27. Circle the locations of carbon atoms in the following line formulas.

28. (CI) Show the number of hydrogens attached to each carbon in the following formula by
writing a number next to each carbon atom (one has been done for you).

All atoms other than carbon and hydrogen, i.e., the so-called heteroatoms (N, O, S, X, etc.) must be
drawn in a line formula. In addition, hydrogens bonded to heteroatoms must be drawn (it is
sometimes wise to draw carbons for clarity, but this is optional). Although line formulas are not
Lewis structures, formal charges must be drawn next to atoms with non-zero formal charges.

CH3CH2CN

(CH3)3CNH3

29. Draw a line formula for (CH3)2C=CHCH2F

NH3

Chem 201, Fall 2010

Activity 1, M Aug 30

Summary
Lewis structures, condensed formulas, and line formulas represent three tools for showing molecular
structures. Lewis structures provide the most information, but they are the hardest to draw. Chemists
routinely use all three formulas and often combine them (see below).
H3C

N
N

CH3

The key to learning to draw Lewis structures is to get multiple bonds, nonbonding electrons, and
formal charges drawn correctly. Multiple bonds and formals charges are also a key part of condensed
formulas and line formulas.

AdditionalReading+PracticeProblems

Lewis structures are described in Loudon 1.2ABC and online at

http://academic.reed.edu/chemistry/roco/Lewis/index.html (ROCO: Lewis Structures).
Practice problems: Loudon 1.24, 1.25, 1.26, 1.27, 1.28, 1.29
Condensed formulas of alkanes are described in Loudon 2.2 (see Table 2.1) and 2.4D.
Loudon 2.2 does not address the drawing of compounds with multiple bonds or
heteroatoms. Practice problems are provided below.
Line formulas of alkanes and cycloalkanes (Loudon calls them skeletal formulas) are
described in Loudon 2.5. Loudon 2.5 does not address the drawing of compounds with
multiple bonds or heteroatoms. Practice problems: Loudon 2.12 and the problems provided
below.

1. Convert the following formulas into line formulas.

O
O

CHCH2CH(CH3)2

HC
HC

C H
C

CH3

CH3CH2OC

C(CH2)4N(CH3)3

CH2

2. Convert the following line formulas into condensed formulas.

Cl

Cl

Si

Chem 201, Fall 2010

Activity 1, M Aug 30

3. An empirical formula, like C10H24, provides information about composition, but not
structure. Write empirical formulas for each of the following molecules.
HO
O
O
N

OH

NH

Answers to these problems will be posted later this week on the Syllabus web page.