Simulations as real-time integration of information: Covalence, an organic chemistry game

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Content SIMULATIONS
AS
REAL-‐TIME
INTEGRATION
OF

INFORMATION:

COVALENCE,
AN
ORGANIC
CHEMISTRY
GAME

BY

JASON
MATHIAS

A
THESIS
Presented
to
the

FACULTY
OF
THE
USC
SCHOOL
OF
CINEMATIC
ARTS

UNIVERSITY
OF
SOUTHERN
CALIFORNIA

In
Partial
Fulfillment
of
the

Requirements
For
the
Degree

MASTER
OF
FINE
ARTS

INTERACTIVE
MEDIA

May
2013

Copyright
2013

Jason
Mathias

2

ACKNOWLEDGEMENTS

To
Jeremy
Gibson
and
Marientina
Gotsis,
my
first
teachers
of
Interactive
Media.
Thank
you
for
your

understanding,
and
for
telling
me
when
I
needed
to
work
harder.
But
most
of
all,
thank
you
for
your

faith
in
me,
before
even
I
believed
in
my
abilities.

To
Alex
Beachum
and
Kedar
Reddy,
for
being
tangible
examples
of
successfully
living
a
creative
life,

and
for
carrying
me
through
my
bleakest
moments.

To
Simon
Wiscombe
and
Loan
Verneau
for
creating
such
an
atmosphere
of
creativity,
mutual
respect

and
free
thought,
to
Sarah
Scialli,
Sanghee
Oh
and
Yasaman
Hashemian
for
letting
me
be
myself,
and

to
everyone
in
the
IMD
Class
of
2013
for
your
respect,
your
unending
warmth,
and
for
truly
making

me
feel
like
I’ve
found
a
clan
I
will
always
belong
to.

To
Lisa
Clements,
for
knowing
how
to
keep
me
thinking
calmly
and
practically
when
it
was
far
too

overwhelming,
to
Danny
Bilson
and
Scott
Fisher
for
letting
me
see
my
passion
and
intuition
through,

to
Mark
Bolas
and
Laird
Malamed
for
letting
(or
forcing)
me
see
the
expansive
possibilities
in
my

work,
to
Steve
Anderson
and
William
Huber
for
giving
me
a
pride
in
the
most
abstract
of
intellectual

curiosities,
to
Mallory
Jebbia
for
seeing
the
scientific
potential
of
this
project
and
entertaining
my

repeated
questions
about
Organic
Chemistry.

To
my
family
and
to
Mary
Emory,
for
taking
care
of
me
through
nearly
a
year
of
seemingly
unending

illnesses.

And
most
importantly,
to
my
parents,
who
fearfully,
but
faithfully,
took
the
greatest
risk
of
their

entire
lives
–
trusting
me
when
I
said
I
wanted
to
make
video
games.

3

TABLE
OF
CONTENTS

Acknowledgements
.................................................................................................................
2

Table
of
Figures
........................................................................................................................
4

Abstract
.......................................................................................................................................
5

Paper
Objectives
......................................................................................................................
5

Covalence
Project
Description
.............................................................................................
6

Audience
...............................................................................................................................................
7

Advantages
of
the
Digital
Platform
–
Why
a
Video
Game?
.........................................
7

Visual
Model
Integration
.................................................................................................................
8

Curation
of
Knowledge:
The
Just-‐In-‐Time
Principle
..............................................................
8

Application
of
Rules
and
Logic
......................................................................................................
9

Design
Philosophy:
The
PsychoSocial
Moratorium
.....................................................
9

Challenges
in
Teaching
the
Modern
Organic
Chemistry
Student
...................................
10

Additional
Technical
Challenge:
3-‐Dimensionality
.............................................................
11

The
Problem:
Multiple
Visual
Models,
Overwhelming
information,
Hidden

Knowledge
..............................................................................................................................
11

The
Solution:
Designing
an
Integrated
Visual
Model
for
Covalence
....................
15

The
Electron
Pair
............................................................................................................................
16

Prior
Visual
Models
..............................................................................................................
18

VSEPR
Theory
...................................................................................................................................
19

Lewis
Dot
Diagram
.........................................................................................................................
20

Skeletal
Formula
.............................................................................................................................
21

Information
Not
Included
............................................................................................................
22

Creating
the
Levels:
Nuclear
Substitution
as
a
way
to
explain
Organic

Chemistry’s
Elegance
and
Subtle
Difficulty
.................................................................
22

Why
Nuclear
Substitution?
..........................................................................................................
23

The
Walden
Inversion
...................................................................................................................
25

Prior
Art
...................................................................................................................................
26

Fold
It
(2008)
...................................................................................................................................
26

Dragon
Box+
(We
Want
to
Know
AS,
2012)
...........................................................................
28

The
Chirality
Game
(2002)
..........................................................................................................
29

What
Games
Have
To
Teach
Us
about
Learning
and
Literacy
(Gee,
2007)
..................
30

Thomas
Was
Alone
(Bithell,
2012)
...........................................................................................
32

Ninja
Gaiden
Black
(Team
Ninja,
2005)
..................................................................................
33

Next
Steps
and
Further
Evaluation
.................................................................................
35

Evaluation
..........................................................................................................................................
36

4

Bibliography
...........................................................................................................................
37

TABLE
OF
FIGURES

Figure
1
..............................................................................................................................................................................................
6

Figure
2
..............................................................................................................................................................................................
8

Figure
3
...........................................................................................................................................................................................
12

Figure
4
...........................................................................................................................................................................................
13

Figure
5
...........................................................................................................................................................................................
13

Figure
6
...........................................................................................................................................................................................
15

Figure
7
...........................................................................................................................................................................................
16

Figure
8
...........................................................................................................................................................................................
17

Figure
9
...........................................................................................................................................................................................
17

Figure
10
........................................................................................................................................................................................
18

Figure
11
........................................................................................................................................................................................
19

Figure
12
........................................................................................................................................................................................
20

Figure
13
........................................................................................................................................................................................
21

Figure
14
........................................................................................................................................................................................
23

Figure
15
........................................................................................................................................................................................
25

Figure
16
........................................................................................................................................................................................
26

Figure
17
........................................................................................................................................................................................
27

Figure
18
........................................................................................................................................................................................
28

Figure
19
........................................................................................................................................................................................
30

Figure
20
........................................................................................................................................................................................
34

Figure
21
........................................................................................................................................................................................
35

5

ABSTRACT

College-‐level
Organic
Chemistry
classes
can
be
overwhelming
to
their
students.
In
addition
to

learning
a
relatively
large
amount
of
information,
students
have
to
learn
to
read
multiple
visual

models
and
use
them
to
understand
subtle
differences
in
the
science.
In
making
the
puzzle
game

Covalence
to
address
Organic
Chemistry
education,
I
decided
to
focus
on
three
aspects
of
the
subject’s

education
–
Hidden
information
in
the
various
visual
models,
the
lack
of
integration
of
these

representations
into
a
3D
representation
of
Chemical
phenomena,
and
an
atom-‐based
view
of
the

molecules
and
how
they
contribute
to
the
field’s
subtle
issues.

This
paper
discusses
various
traditional
visual
models
taught
in
Organic
Chemistry
classes,
devising
a

new
visual
model
to
bring
out
hidden
information
in
these
traditional
models,
and
designing
levels

based
on
known
reactions
and
their
consequences,
to
illustrate
Organic
Chemistry’s
elegance
and

subtlety.

PAPER
OBJECTIVES

Before
I
delve
further
into
this
paper,
I
would
like
to
provide
a
framework
for
how
I
decided
to

approach
it.
I
set
out
to
make
Covalence
an
alternative
form
of
education
for
Organic
Chemistry,
and

to
do
that,
I
had
to
analyze
the
strengths
of
this
new
medium,
and
the
problems
with
the
former

media.

I
then
had
to
choose
what
my
audience
was,
what
their
specific
relation
to
Organic
Chemistry

was,
and
how
I
was
going
to
constrain
my
game
to
address
their
issues.
I
then
chose
the
subject

matter
of
the
game,
based
on
how
that
subject
matter
could
further
illustrate
a
sense
of
discovery
of

Organic
Chemistry,
and
a
feeling
of
intuitive
deduction.
Finally,
I
looked
at
a
series
of
prior
art,
games

and
educational
materials
that
have
tackled
similar
(if
not
the
same)
subjects
before,
and
decided

how
these
products
could
provide
inspiration
for
Covalence.
This
paper
addresses
each
of
these
in

turn,
so
that
readers
may
get
a
sense
of
how
these
subjects
were
tackled.

6

In
truth,
many
of
these
processes
were
intertwined
with
each
other
and
occurred
simultaneously,
but

for
the
sake
of
understanding
this
process,
I
am
choosing
to
represent
it
here
in
sets
of
information

rather
than
chronologically.

COVALENCE
PROJECT
DESCRIPTION

Covalence
is
a
puzzle
game
designed
to
make
players
see
atoms
and
molecules
as
tools,
and

then
learn
to
experiment
with
these
tools
to
achieve
new
goals.
Initially,
the
player
is
introduced
to

the
atoms,
and
learns
only
how
they
fit
into
molecules,
and
how
they
attract
and
repel
each
other.
In

the
latter
stages
of
the
game,
the
player
uses
only
this
information
to
deduce
how
a
specific
reaction,

the
SN2
reaction,
comes
about,
and
what
its
consequences
are.

FIGURE
1

AN
EARLY
SCREENSHOT
OF
COVALENCE.
THE
PLAYER
NAVIGATES
AROUND
THE
3D
SPACE
AND
TRIES
TO
RECREATE

THE
MODELS
SHOWN
IN
THE
‘GOAL’
WINDOW.

The
game
plays
in
a
3D
space,
and
the
player
is
free
to
rotate
around
the
world,
pulling
on

the
molecule’s
bonds
and
pushing
atoms
together
to
see
what
will
happen.
The
intention
is
to
make

Organic
Chemistry
something
to
be
pulled
and
prodded,
something
to
aid
player
curiosity
and
allow
a

deduction
of
more
complex
effects
from
a
few
basic
rules.

7

Covalence
has
an
overarching
goal
to
make
Chemistry
an
approachable
science
–
The
game
is

intended
to
be
as
easy
to
pick
up
as
possible,
something
rarely
attributed
to
chemistry.
Furthermore,

Covalence
is
intended
to
integrate
multiple
coexisting
models
to
explain
Organic
Chemistry
into
one

form,
via
the
principles
of
auditory,
visual
and
interactive
aesthetics
afforded
by
the
medium
of
video

games.

AUDIENCE

Covalence’s
audience
is
the
student
itself,
specifically
students
that
are
entering
classes
in

Organic
Chemistry,
after
having
completed
courses
in
General
Chemistry.
In
the
United
States,
this

audience
is
generally
the
University
Student,
ranging
from
future
Chemists
to
Dentistry,
Pharmacy,

Optometry
and
Medical
School
hopefuls.

Organic
Chemistry
is
a
required
class
in
many
college
Pre-‐Med
tracks,
and
is
a
requirement
for
the

Medical
College
Admissions
Test
(MCAT),
as
well
as
the
Pharmacy
Aptitude
Test
(PAT)
and
Dental

Admissions
Test
(DAT).

Since
many
students
in
Organic
Chemistry
courses
may
not
necessarily
be
interested
in
Chemistry

specifically,
and
more
generally
interested
in
health-‐related
fields,
I
chose
to
make
Covalence
as

universally
applicable
as
I
could,
so
that
it
would
apply
to
both
groups.

ADVANTAGES
OF
THE
DIGITAL
PLATFORM
–
WHY
A
VIDEO
GAME?

Interactive,
digital
platforms
hold
a
few
advantages
over
physical,
paper
and
video
demonstrations
of

the
same
reactions.
Information
can
be
relayed
to
the
player
in
real-‐time,
so
they
can
know
instantly

if
they’ve
made
a
wrong
move.
Moreover,
the
system
can
customize
information
for
each
player,
so
if

they
continue
to
make
the
wrong
assumptions,
the
computer
can
directly
address
that
specific

assumption.

8

VISUAL
MODEL
INTEGRATION

Hidden
information
is
often
done
for
simplicity
–
If
everything
was
included
in
a
model,
there
would

be
far
too
much
clutter
on
screen,
as
Chemistry
is
a
complex
science.
However,
if
the
student
can

change
the
models
at
will,
then
she
can
look
at
a
preferred
model
and
understand
how
it
connects

with
a
different
model,
and
then
compare
that
with
a
3-‐dimensional
representation
of
the
atom,
one

that
doesn’t
rely
on
abstracted
models
to
illustrate
that
dimensionality.

FIGURE
2

TWO
MODES
OF
REPRESENTATION
IN
COVALENCE.
THE
PLAYER
CAN
SWITCH
BETWEEN
BOTH
ON
THE
FLY,
AND
SEE

THE
DIFFERENCES
AND
RELATIONSHIPS
BETWEEN
THE
TWO.

In
addition
to
creating
a
newer
visual
model
for
Covalence,
the
interactive
medium
allows
the
game

to
simultaneously
support
two
visual
models,
so
that
the
player
can
swap
between
them
in
real
time.

For
instance,
the
Skeletal
Formula
(discussed
in
‘Prior
Visual
Models’
below)
is
the
most
common

model
seen
on
college
level
exams.
I
wanted
the
player
to
have
quick
access
to
this
model,
so
she

would
have
a
very
easy
way
to
mentally
convert
the
Covalence
model
to
the
model
she
would
see
on
a

test.

CURATION
OF
KNOWLEDGE:
THE
JUST-‐IN-‐TIME
PRINCIPLE

James
Paul
Gee
wrote
about
video
games’
unique
ability
to
provide
relevant
information
to
a
player

“on-‐demand
and
just-‐in-‐time,”
(Gee,
138)
1

because
a
computer
could
‘listen’
for
certain
player

1

James
Paul
Gee,
What
Video
Games
Have
to
Teach
Us
About
Learning
and
Literacy.

Second
Edition:
Revised
and
Updated
Edition,
2nd
ed.
(Palgrave
Macmillan,
2007).

9

actions.
Thus,
if
a
player
was
repeating
an
action
that
was
not
helping
her
beat
the
game,
then
the

game
could
give
the
player
a
hint.
In
the
context
of
education,
that
is
very
valuable
–
If
a
student
is

understanding
a
lesson
wrong,
and
is
demonstrating
that
misunderstanding
through
repeated

interactions,
the
game
can
tell
the
student
what
she
is
doing
wrong.
A
textbook
or
video
simply

cannot
listen
to
the
reader’s
thoughts
in
the
same
way.

APPLICATION
OF
RULES
AND
LOGIC

When
using
a
physical
model,
it
is
difficult
to
ascertain
the
logic
of
a
system
if
the
model
has
not

designed
for
it.
The
user
could,
for
instance,
simply
pop
an
atom
off
of
a
molecule
physically,
even
if

that
atom
could
not
be
so
easily
removed
in
real
life.
An
interactive
simulation
can
be
programmed

such
that
this
could
not
happen
–
Or,
that
these
rules
could
be
relaxed
or
suspended
in
order
to
teach

single
principles,
and
then
enforced
when
the
player
decides
she
understands
their
consequences.

DESIGN
PHILOSOPHY:
THE
PSYCHOSOCIAL
MORATORIUM

James
Paul
Gee
describes
in
What
Video
Games
Have
to
Teach
Us
About
Learning
an
Literacy
an
idea

of
the
Psychosocial
Moratorium
–
A
mental
and
social
space
in
which
one
feels
free
to
fail
and

experiment,
because
of
a
lowered
sense
of
consequence
(Gee,
62)
2
.
In
designing
Covalence,
my

primary
interest
was
to
create
such
a
space
for
the
Chemistry
student
–
a
space
where
learning
can

be
facilitated,
and
the
intimidation
of
Organic
Chemistry
can
be
minimized
or
at
least
temporarily

forgotten.

In
order
to
achieve
this
state,
I
was
interested
in
using
the
paradigm
of
the
puzzle
game
to
create
a

sort
of
scientific
method
within
the
player
–
the
creation
of
a
hypothesis,
the
testing
out
of
that

hypothesis,
and
the
validation
or
correcting
of
that
hypothesis
until
it
aligns
with
reality.
Thus,
each

2

Ibid.

10

puzzle
should
build
upon
what
the
player
knows
from
previous
puzzles,
and
its
answer
should
be

readily
deducible
from
what
the
player
knows
and
what
the
player
can
learn
from
feedback.

Design-‐wise,
this
meant
that
I
had
to
focus
heavily
on
iterating
feedback
and
visual
language
–
an

“accidental
success”
(the
player
succeeding
without
knowing
the
reason
for
the
success)
would
be
a

failure
of
the
game’s
design,
as
the
player
would
not
actually
learn
the
chemistry
behind
completing
a

level.

CHALLENGES
IN
TEACHING
THE
MODERN
ORGANIC
CHEMISTRY
STUDENT

Covalence
is
designed
to
reach
a
very
specific
audience,
at
a
specific
time
in
their
academic
career.

Thus,
understanding
their
issues
regarding
the
learning
of
Organic
Chemistry
allowed
us
to

understand
our
design
constraints.

I
wanted
to
make
the
game
as
an
easy-‐to-‐integrate
supplement
to
the
regular
course,
something
that

would
minimize
the
amount
of
energy
a
player
would
need
in
order
to
acclimate
and
be
familiar
with

the
system.
That
meant
a
few
design
constraints
–
I
couldn’t
re-‐skin
the
world
of
Chemistry
too
far

from
what
is
understood,
nor
could
I
simplify
the
phenomena
too
much,
lest
the
system
become

another
roadblock
to
learning,
and
possibly
not
a
way
to
learn
Organic
Chemistry
at
all.

Based
on
this
criteria,
I
developed
a
list
of
necessary
design
constraints,
and
worked
my
way
around

them:

• The
game’s
design
must
fit
easily
into
what
the
player
already
knows
about
chemistry.

• The
game
must
feel
like
easy
experimentation
will
lead
to
the
answers,
and
that
conclusions

can
be
made
based
solely
on
what’s
known
in
the
game,
not
from
previous
chemistry

knowledge.

• The
look
and
feel
cannot
contradict
known
visual
language;
rather,
it
should
complement

and
integrate
that
language
wherever
possible.

11

ADDITIONAL
TECHNICAL
CHALLENGE:
3-‐DIMENSIONALITY

While
complex
molecules
are
studied
in
General
Chemistry,
their
orientations
in
space
are
not

important.
In
many
ways,
however,
Organic
Chemistry
is
the
study
of
how
atoms
position
themselves

and
move
in
3D
space.
Thus,
Covalence
had
to
be
a
3-‐dimensional
game,
something
which

complicates
the
game
immensely.
For
instance,
the
screen
and
the
mouse
are
both
on
a
2-‐
dimensional
plane.
Programs
such
as
Autodesk’s
Maya
3

and
games
such
as
Homeworld
4

deal
with

translating
3D
movement
onto
a
2-‐D
plane,
these
movements
require
multiple
inputs
to
define
a

specific
point
in
3D
space.

While
3D
illustration
of
molecules
may
be
a
strength
for
Covalence

learning-‐wise,
it
was
also
an
important
obstacle
that
needed
careful
assessment
throughout

development.

THE
PROBLEM:
MULTIPLE
VISUAL
MODELS,
OVERWHELMING

INFORMATION,
HIDDEN
KNOWLEDGE

Many
of
the
visual
models
that
Chemistry
students
learn
omit
or
imply
information
that
is
important

for
the
understanding
of
a
reaction.
Thus,
it
becomes
difficult
for
a
student
to
quickly
ascertain
the

information
without
looking
at
multiple
models
or
having
a
video
demonstration
of
the
reaction.

3

0003
Maya
Movement
Key
Commands,
2011,

http://www.youtube.com/watch?v=gt0yLpQ6uhE&feature=youtube_gdata_player.

4

Homeworld
(Vivendi
Universal,
1999),
http://www.relic.com/games/homeworld/.

12

FIGURE
3

ALL
OF
THESE
IMAGES
REPRESENT
PROPANE,
A
3-‐CARBON
MOLECULE.
THE
DIFFERENT
VERSIONS
OF
THE
SAME

MOLECULE
CAN
BE
CONFUSING
FOR
FIRST
TIME
LEARNERS,
ESPECIALLY
IF
THEY
DO
NOT
KNOW
HOW
TO
TRANSLATE

FROM
ONE
MODEL
TO
ANOTHER.
THE
INTERACTIVE
MEDIUM
ALLOWS
FOR
A
USER
TO
RAPIDLY
SWITCH
BETWEEN

MODELS,
ESPECIALLY
AFTER
MODIFYING
THE
MOLECULE,
TO
SEE
HOW
THESE
MODELS
ARE
RELATED.

5

For
example,
when
starting
an
OChem
class,
students
often
purchase
physical
toy
models,
such
as
the

Molymod
Molecular
Chemistry
set.
6

These
models
will
mimic
the
shapes
of
the
molecules
when

atoms
are
added,
but
they
lack
the
electrons
that
actually
force
the
atoms
into
the
shapes
they
are
in,

so
they
user
won’t
be
able
to
fully
deduce
the
reason
for
this
model
without
further
study.

5

“Propane,”
Wikipedia,
the
Free
Encyclopedia,
March
27,
2013,

http://en.wikipedia.org/w/index.php?title=Propane&oldid=545220208.

6

Molymod
Organic/Inorganic
Molecular
Model
Student
Set
(Carolina
Biological

Supply
Company,
n.d.).

13

FIGURE
4

ORGANIC
CHEMISTRY
MOLECULAR
MODELS
CAN
SHOW
SHAPES,
BUT
IF
A
STUDENT
WANTS
TO
'ADD'
TO
THE

MOLECULE,
HE
WILL
SIMPLY
POP
IT
INTO
THE
STRUCTURE,
WHETHER
OR
NOT
THE
REAL
SYSTEM
WOULD
WORK

THAT
WAY.
THE
GAME
IS
INTENDED
TO
PRESENT
MOLECULES
IN
THIS
SAME
3D
SHAPE,
BUT
ADHERE
TO
REAL

CHEMISTRY
RULES
AND
PROCEDURES.

Much
of
this
difficulty
comes
from
an
imperfect
representation
of
the
3-‐dimensional
study
on
two-‐
dimensional
formats
such
as
a
drawn
model.
Thus,
when
learning
or
being
tested
on
the
material,
the

chemistry
student
has
the
additional
problem
of
discerning
small
differences
through
a
visual
model

that
may
make
those
differences
hard
to
discern.

FIGURE
5

THIS
DRAWN
MODEL
MAKES
IT
DIFFICULT
TO
DISCERN
SPATIAL
SHAPES
–
WHETHER
THE
H3CH2C
IS
UNDERSTOOD

TO
BE
THE
‘FRONT’
OF
THE
MOLECULE
OR
‘BEHIND’
THE
MOLECULE
IS
NOT
AT
ALL
CLEAR
IN
THIS
REPRESENTATION.

14

Organic
Chemistry
is
a
study
of
Carbon-‐based
(“organic”)
compounds,
and
their
creation
through

various
laboratory
procedures.
However,
much
of
the
science’s
difficulty
lies
in
subtle
differences

that
are
nevertheless
vitally
important.
For
instance,
two
Carbon
atoms
connected
to
the
same
four

atoms,
but
in
different
orders,
may
have
completely
different
effects
when
introduced
into
the
human

body.

15

FIGURE
6

AN
ILLUSTRATION
OF
TWO
ENANTIOMERS,
TWO
DIFFERENT
MOLECULES
WITH
THE
SAME
ATOMIC
MAKEUP.

SIMILAR
TO
THE
LEFT
AND
RIGHT
HAND,
THE
TWO
OBJECTS
CANNOT
BE
SUPERIMPOSED
OVER
EACH
OTHER.
7

Because
of
this,
students
must
first
learn
a
naming
and
illustration
convention
before
they
can

reasonably
discuss
the
intricate
details
about
Organic
molecules.
Soon
thereafter,
they
must
use
this

visual
language
to
learn
very
subtle
differences
in
chemical
structure,
such
as
discerning
mirror

images.
Organic
Chemistry
as
a
study
emphasizes
an
attention
to
detail,
as
adding
chemicals
together

in
the
wrong
order,
or
in
the
incorrect
solution,
can
have
devastating
consequences
when
applied
to

medical
or
pharmaceutical
pursuits.

THE
SOLUTION:
DESIGNING
AN
INTEGRATED
VISUAL
MODEL
FOR

COVALENCE

In
designing
Covalence,
it
became
clear
that
a
previous
model,
converted
to
3D,
would
not
be
enough

for
players
to
navigate
through
the
game.
Previous
models
hide
information
to
the
point
that
multiple

models
are
necessary
to
display
all
the
information
necessary
to
understand
why
a
single
reaction

7

Miloslav
Nič
et
al.,
eds.,
“Chirality,”
in
IUPAC
Compendium
of
Chemical
Terminology,

2.1.0
ed.
(Research
Triagle
Park,
NC:
IUPAC),
accessed
March
30,
2013,

http://goldbook.iupac.org/C01058.html.

16

occurs.
For
a
Chemist,
this
makes
sense
–
much
of
this
information
is
so
well
digested
that
putting
it

into
a
model
is
unnecessary.
For
the
student
learning
the
material
for
the
first
time,
however,
this
is
a

thorny
issue.

When
I
designed
Covalence’s
visual
model,
I
decided
to
focus
on
the
core
of
what
makes
the

structures
and
reactions
possible
–
the
electron.
This
allowed
me
to
then
analyze
each
visual
model

for
what
is
relevant,
and
provided
a
basis
for
integration
of
these
models.

THE
ELECTRON
PAIR

If
we
imagine
the
electron
as
a
sort
of
negative
magnet,
we
can
imagine
that
they
repel
other

electrons
while
attracting
an
atom’s
positive
center.
When
they
are
between
two
atomic
centers,
they

vacillate
between
both,
creating
a
certain
closeness
between
the
two
atoms.
Thus,
a
certain
push-‐
and-‐pull
creates
the
structures
we
see
in
molecules.

FIGURE
7

EACH
OUTER
ATOM
REPULSES
THE
OTHER
WHILE
STILL
BEING
ATTRACTED
TO
THE
CENTRAL
ATOM,
THUS

CREATING
THE
SHAPES
WE
SEE
IN
MOLECULES.
NOTE
HOW
THE
ENTRANCE
OF
THE
THIRD
(YELLOW)
ATOM
PUSHES

THE
OTHER
TWO
ATOMS
DOWNWARD.
I
CHOSE
TO
EMPHASIZE
THE
ELECTRONS
(HIDDEN
HERE)
WHEN
MAKING
THE

GAME,
SO
THAT
THE
REASONS
FOR
THIS
WOULD
BE
MORE
CLEAR.
8

Thus,
every
bond
in
a
molecule
is
actually
a
pair
of
electrons,
sitting
between
two
atoms
and
bringing

them
together.

This
was
crucial
to
the
understanding
of
the
system,
so
we
spent
quite
a
bit
of
time
on

8

“VSEPR
Theory,”
Wikipedia,
the
Free
Encyclopedia,
March
29,
2013,

http://en.wikipedia.org/w/index.php?title=VSEPR_theory&oldid=546494233.

17

visualization
of
this
system.
In
the
current
iteration
of
the
design,
this
means
that
the
bond
is

represented
by
two
atoms,
with
the
bond
acting
as
a
charge
that
goes
between
them.

FIGURE
8

BONDS
AS
ELECTRONS
WITH
FORCE
PASSING
BETWEEN
THEM,
FROM
THE
MOST
CURRENT
PROTOTYPE
OF
THE

GAME.

In
addition,
some
atoms
have
a
stronger
pull
on
these
electrons,
and
this
means
that
bonds
can
be

broken,
with
the
atoms
going
to
one
side.

Traditional
models
(such
as
Lewis
Diagrams
and
Skeletal

models,
discussed
below)
represent
bonds
as
straight
lines
or
pairs
of
electrons,
but
rarely

acknowledge
a
one-‐sided
draw
of
electrons.

FIGURE
9

EARLY
COVALENCE
PROTOTYPE
WITH
UNEVEN
BOND.
EMPHASIZING
A
VISUAL
PULL
TO
ONE
SIDE
HELPED
PLAYERS

UNDERSTAND
AN
IMMEDIATE
DIFFERENCE,

18

There
were
a
few
other
issues
that
I
needed
to
illuminate,
such
as
atom
instability,
so
that
they
were

present
in
the
mind
of
the
user.
Much
of
these
designs
came
from
lessons
in
graphic
design
and

cinematography,
noting
that
certain
visual
contrasts
are
very
good
at
catching
the
attention
of
a
user.

Movement
in
an
otherwise
static
screen,
for
instance,
is
almost
certain
to
get
a
player’s
attention

(Block,
2007)
9
,
so
I
could
program
the
game
to
use
movement
as
a
feedback
tool
and
teach
the
player

what
was
successful.

FIGURE
10

USING
MOVEMENT,
SATURATION
OF
COLOR
AND
OBJECT
GROWTH
AS
INDICATORS
OF
A
CARBON’S
INSTABILITY.

PRIOR
VISUAL
MODELS

Not
all
theories
in
Chemistry
agree
as
to
where
electrons
are
on
an
atom,
nor
what
they
are
even

made
of.
Many
of
these
conflict
and
explain
different
phenomena
in
Chemistry,
as
well.
However,
for

the
sake
of
education,
College
level
Organic
Chemistry
classes
choose
to
emphasize
a
certain
series
of

models,
and
teach
their
lessons
based
on
those
models.

In
the
same
vein,
I
chose
to
integrate
the
following
models
into
a
unified
visual
model,
taking
their

individual
strengths
with
an
eye
towards
highlighting
information
from
multiple
levels.
These

9

Bruce
Block,
The
Visual
Story:
Creating
the
Visual
Structure
of
Film,
TV
and
Digital

Media,
2nd
ed.
(Focal
Press,
2007).

19

models
are
mostly
taken
from
texbooks
such
as
Organic
Chemistry
from
T.W.
Solomons
and
Craig

Fryhle
10
.

VSEPR
THEORY

VSEPR
(“Valence
Shell
ElectronPair
Repulsion”)
theory
dictates
the
shapes
of
electrons,
and
that

these
shapes
occur
based
on
the
electrons
that
are
present
in
bonds
and
on
atoms.

FIGURE
11

EACH
BOND
OR
ELECTRON
PAIR
REPULSES
THE
OTHER,
ACCORDING
TO
VSEPR
THEORY,
AND
THIS
EXPLAINS
HOW

MOLECULES
TAKE
THE
SHAPES
THAT
THEY
DO.
11

HERE,
THE
THEORY
IS
ILLUSTRATED
USING
THE
SKELETAL

FORMULA,
EXPLAINED
BELOW.

This
theory
is
important
for
explaining
reactions,
which
are
based
on
one
atom’s
proximity
to

another,
and
their
likelihood
for
bonding.

10

T.
W.
Graham
Solomons
and
Craig
Fryhle,
Organic
Chemistry,
8th
ed.
(Wiley,

2003).

11

Chem
11,
“Chemistry
11:
VSEPR,”
Chemistry
11,
May
5,
2012,

http://mageechemistry11.blogspot.com/2012/05/vsepr.html.

20

More
importantly,
VSEPR
theory
places
electron
pairs
in
specific
locations.
Other
theories
(such
as

Molecular
Orbital
theory
12
)
place
electrons
in
a
certain
area
of
probability,
rather
than
at
a
specific

place,
and
this
becomes
problematic
when
trying
to
understand
why
atoms
repulse
each
other
at

certain
angles,
or
why
certain
reactions
cannot
happen
because
of
electrons
that
stand
in
the
way.

LEWIS
DOT
DIAGRAM

An
electron-‐focused
diagram,
the
Lewis
diagram
illustrates
the
transfer
of
electrons
from
single
atom

"ownership"
to
two-‐atom
bonds,
and
vice
versa.
This
diagram
is
one
of
the
few
that
showcases

electrons
and
their
placement
on
the
atom.

FIGURE
12

THE
LEWIS
DOT
DIAGRAM
OF
PENTANE
(SHOWN
ABOVE).
NOTE
THAT
BONDS
ARE
SHOWN
AS
PAIRS
OF
ELECTRONS

BETWEEN
TWO
ATOMS.

However,
these
diagrams
ignore
3D
space,
and
put
all
four
electron
pairs
on
the
flat
2D
plane.
This
is

in
direct
conflict
with
the
VSEPR
theory
above,
and
makes
the
understanding
of
molecular
structure

difficult.
However,
it
is
very
successful
in
making
the
transfer
of
charge
intuitive
to
the
learner.
Thus,

I
wanted
to
keep
bonds
forever
in
the
player’s
memory
as
a
pair
of
electrons
rather
than
just
a
line.

12

Molecular
Orbitals,
accessed
March
27,
2013,

http://www.sparknotes.com/chemistry/bonding/molecularorbital/.

21

SKELETAL
FORMULA

Perhaps
the
most
visually
recognizable
model
of
Organic
Chemistry,
the
skeletal
formula
(also
often

referred
to
as
the
‘line
drawing’)
represents
atoms
as
letters,
and
bonds
as
straight
lines.
In
some

drawings,
Carbon
and
hydrogen’s
letters
are
omitted,
and
a
Carbon
is
understood
to
be
the

intersection
of
two
lines,
while
Hydrogens
are
removed
entirely,
and
the
viewer
is
meant
to
deduce

their
location.

This
visual
model
also
accounts
for
3-‐dimensional
space
by
drawing
dashed
lines
for
objects
‘behind’

the
plane
of
the
paper,
and
triangular
lines
for
objects
‘in
front’
of
the
paper.

FIGURE
13

SKELETAL
FORMULAE.
IN
THE
LEFT
FORMULA,
THE
BROMINE
AND
CHLORINE
ARE
DRAWN
OUT,
BUT
THE
CARBONS

(LINE
CORNERS)
AND
HYDROGENS
(NOT
PICTURED)
ARE
IMPLIED.
13

IN
THE
RIGHT
FORMULA,
THE
FLOURINE
IS

‘BEHIND’
THE
PAPER,
AND
THE
CHLORINE
IS
‘IN
FRONT
OF’
THE
PAPER,
A
NOD
TO
THE
3-‐DIMENSIONALITY
OF

MOLECULES.

This
drawing
style
is
the
style
most
likely
to
be
seen
on
tests,
and
most
relevant
to
the
chemistry

student.
The
primary
issue
of
this
model
is
the
hiding
of
information,
as
a
single
glance
does
not
show

all
of
the
chemical
model,
and
this
can
cause
the
student
to
misread
the
system
if
they
do
not
fully

understand
the
rules
of
the
model.

13

“2-‐Bromo-‐1-‐chloropropane,”
Wikipedia,
the
Free
Encyclopedia,
March
29,
2013,

http://en.wikipedia.org/w/index.php?title=2-‐Bromo-‐1-‐
chloropropane&oldid=543868745.

22

INFORMATION
NOT
INCLUDED

These
models
also
ignore
some
important
principles
and
atom-‐specific
properties,
especially

electronegativity
and
Carbon
stability,
and
I
wanted
to
make
sure
these
lessons
were
visually
clear
to

the
player.
In
the
case
of
Carbon
Stability,
this
principle
wasn’t
strictly
defined
in
Organic
Chemistry

textbooks,
so
I
had
the
opportunity
to
exert
a
designer’s
touch
and
define
this
property
in
a
way
that

would
organically
fit
the
rest
of
the
game,
instead
of
relying
on
outside
principles.

Electronegativity
is
simply
a
measure
of
how
much
a
specific
atom
pulls
electrons
towards
itself

(Fryhle,
2003).
14

Since
Carbon
is
the
main
backbone
of
Organic
Chemistry,
atoms
that
pull
electrons

more
than
Carbon
have
the
potential
to
pull
those
electrons
away,
and
break
the
bond
between
the

two
atoms.
However,
in
most
molecular
diagrams,
bonds
are
universally
straight,
and
no
clue
is
given

as
to
their
pull
either
way.

CREATING
THE
LEVELS:
NUCLEAR
SUBSTITUTION
AS
A
WAY
TO

EXPLAIN
ORGANIC
CHEMISTRY’S
ELEGANCE
AND
SUBTLE
DIFFICULTY

My
intention
for
this
project
was
not
to
completely
replace
the
Organic
Chemistry
curriculum,
but

rather
to
illustrate
a
method
for
thinking
about
problems
that
the
student
is
likely
to
encounter.
As

such,
it
was
important
for
me
to
provide
a
basis
for
why
the
science
is
viewed
the
way
it
is,
and
how

certain
properties
in
the
field
contribute
to
its
most
important
concerns
and
lessons.

I
decided
to
focus
on
one
type
of
reaction,
the
nuclear
substitution,
and
use
that
reaction
as
a
catalyst

to
teach
the
basis
of
all
reactions,
as
well
as
more
complex
issues
such
as
chirality.

14

Solomons
and
Fryhle,
Organic
Chemistry.

23

WHY
NUCLEAR
SUBSTITUTION?

One
of
the
earliest
reactions
taught
in
an
Organic
Chemistry
classroom
is
the
Nuclear
Substitution,

the
act
of
switching
out
one
atom
(or
group)
for
another.

Specifically
for
Covalence,
I
focused
on
the

Bimolecular
Nuclear
Substitution
(SN2)
reaction,
a
fairly
well-‐known
reaction
in
Organic
Chemistry.

Carbon
can
bond
with
up
to
four
other
atoms,
and
(unless
connected
to
two
or
three
other
Carbons),

will
not
allow
an
atom
to
leave
a
bond,
and
will
force
itself
to
re-‐bond
with
the
leaving
atom
in
order

to
keep
its
four-‐bond
structure.
For
a
leaving
atom
to
successfully
leave,
,
a
replacement
atom
must

approach
from
the
side
opposite
to
the
leaving
atom,
and
start
to
bond
with
the
Carbon.
Then,
the

Carbon
atom
will
have
a
replacement
fourth
bond,
and
the
leaving
group
is
free
to
leave.
In
my

opinion,
this
felt
exactly
like
a
game
mechanic,
and
it
also
illustrated
Organic
Chemistry’s
elegance

rather
well.

FIGURE
14

EXAMPLE
OF
AN
SN2
NUCLEAR
SUBSTITUTION,
WHERE
THE
LEFT
MOLECULE
IS
PUSHING
THE
PURPLE
ATOM
OUT
OF

THE
MOLECULE.

24

The
key
to
this
reaction
lies
in
the
magnetic
repulsion
of
electrons
–
Each
atom
has
a
certain
draw

towards
electrons,
and
between
the
‘leaving’
atom
and
the
Carbon
it
is
bonded
to,
the
‘leaving’
atom

pulls
electrons
more
tightly.
Thus,
if
the
leaving
atom
is
pushed
away
from
the
carbon,
it
will
break

its
bond
and
take
the
electrons
with
it.
When
this
happens,
if
Carbon
is
satisfied
by
having
another

fourth
bond,
the
leaving
atom
can
drift
away
successfully.

Current
visual
models
make
this
difficult
to
explain
to
a
chemistry
student,
as
single
bonds
in
most

models
are
drawn
alike,
so
the
student
cannot
immediately
tell
what
bonds
are
breakable.
Similarly,

merely
implying
that
a
bond
was
breakable
was
not
enough
–
The
player
would
simply
break
the

bond
and
then
wonder
why
the
Carbon
was
re-‐bonding
the
atom,
and
assume
it
was
a
bug.
In
the

end,
we
used
the
fact
that
an
uneven
bond
creates
a
slight
positive
charge
on
the
Carbon,
and
placed

an
indicator
for
where
the
incoming
atom
should
go.
This
then
led
to
the
players
understanding
what

to
do,
and
was
still
within
the
bounds
of
Chemistry.

What
is
most
important
to
teach
here
is
the
spatial
orientation
of
the
molecule,
and
the
location
of

attack
for
the
incoming
atom.
The
location
where
the
incoming
atom
can
enter
is
strictly
defined
to

be
the
opposite
side
of
the
leaving
group,
because
that
is
farthest
away
from
the
leaving
group’s
field

of
repulsion.
Unfortunately,
that
lesson
is
hard
to
impart
through
drawings.

25

FIGURE
15

INCOMING
ATOMS
IN
AN
SN2
REACTION
NEED
TO
ATTACK
AT
A
CERTAIN
SPACE
TO
SUCCEED.
ALSO
NOT
THE
SPATIAL

CHANGE
IN
THE
GREY
MOLECULES
WHILE
THIS
OCCURS
-‐
THE
MOLECULES
'FLATTEN'
IN
RELATION
TO
CARBON,

THEN
BECOME
INVERTED

THE
WALDEN
INVERSION

An
SN2
reaction
always
occurs
at
the
point
of
a
Carbon
atom,
which
is,
at
that
point,
attached
to
four

other
atoms.
When
an
SN2
reaction
occurs,
the
“legs”
of
the
Carbon
(the
three
bonds
that
are
not
the

leaving
group’s
bond)
will
‘flip,’
similar
to
an
umbrella
flipping
backwards
during
a
strong
wind.
This

is
known
as
the
Walden
Inversion
15
,
and
is
one
of
the
more
important
takeaways
of
SN2
reactions.

Whatever
orientation
the
three
‘legs’
were
in
before
the
flip
will
be
reversed
after
the
flip,
and

students
must
take
note
of
this
while
doing
their
experiments
or
answering
exam
questions.

15

Miloslav
Nič
et
al.,
eds.,
“Walden
Inversion,”
in
IUPAC
Compendium
of
Chemical

Terminology,
2.1.0
ed.
(Research
Triagle
Park,
NC:
IUPAC),
accessed
March
30,
2013,

http://goldbook.iupac.org/W06653.html.

26

FIGURE
16

IF
WE
IMAGINE
THE
HYDROGEN,
FLOURINE
AND
OXYGEN
TO
BE
POINTS
ON
A
CIRCLE,
THE
FLUORINE
(F)
IS
COUNTER-‐
CLOCKWISE
FROM
THE
OXYGEN
ON
THE
LEFT,
BUT
CLOCKWISE
TO
THE
OXYGEN
ON
THE
RIGHT.

This
is
a
good
example
of
the
basics
of
the
system
creating
a
problem
that
occurs
as
a
natural

consequences
of
the
system’s
actions.
The
only
reason
that
the
Walden
inversion
occurs
is
because
of

the
magnetic
repulsion
of
the
‘legs’,
rather
than
due
to
some
other
property
of
chemistry
such
as

electronegativity.
Thus,
when
the
player
observes
the
‘flip’
and
notices
how
the
orientation
is

different
when
she
flips
the
molecule’s
legs,
she
will
learn
to
be
observant
of
how
many
‘flips’
she
is

doing,
an
important
lesson
that
is
nonetheless
difficult
to
impart
otherwise.

PRIOR
ART

Of
course,
no
art
is
created
in
a
vacuum.
I’m
indebted
to
a
series
of
books
and
games
for
their

portrayal
of
both
Chemistry
and
three-‐dimensional
navigation,
as
well
as
a
critical
and
philosophical

approach
to
using
games
as
powerful
educational
experiences.

FOLD
IT
(2008)

The
most
directly
connected
prior
art
game
in
the
educational
games
field,
FoldIt
is
a
3D
protein

folding
simulation,
intended
as
a
crowdsourcing
game
to
help
scientists
study
protein
folding

27

patterns.
The
game
uses
a
similar
3D
navigational
style,
and
the
player
grabs
pieces
of
the
protein

and
brings
it
closer
to
or
farther
away
from
other
pieces
of
the
protein,
in
order
to
get
a
better
fit
and

minimize
tension
between
the
pieces
of
the
protein.

FIGURE
17

FOLDIT’S
GRAPHICAL
STYLE
MAKES
IT
EASY
TO
FOCUS
ON
THE
AREAS
OF
STRAIN,
SHOWN
AS
RED
CIRCLES.

Foldit
was
a
useful
example
of
visual
design
and
navigation
around
a
3D
space,
but
as
an
educational

tool,
it
went
in
a
different
direction
than
Covalence.
While
Foldit
does
talk
about
protein
pieces
like

Beta-‐Pleated
Sheets,
Foldit
does
not
focus
on
teaching
the
player
about
these
elements
of
the
protein,

but
rather
boils
the
matter
down
to
a
question
of
strain
and
tension,
indicated
by
red
spheres
and

spiked
balls.
In
doing
so,
the
player
can
understand
visually
where
the
problem
is,
even
if
she
doesn’t

understand
why
it
is
occurring.
The
real
power
in
Foldit’s
design
is
the
ability
to
crowdsource
large

questions
about
protein
folding,
and
it
uses
that
power
to
give
the
designers
information
about
the

game
and
its
levels,
rather
than
the
players.

28

Covalence,
on
the
other
hand,
is
interested
in
using
each
piece
of
information
to
teach
a
larger
picture,

and
to
teach
it
primarily
to
the
player
playing
the
game.
Thus,
the
design
of
the
levels
and
the

experiential
arc
of
the
game
take
a
different
direction
than
Foldit.

DRAGON
BOX+
(WE
WANT
TO
KNOW
AS,
2012)

Dragon
Box
is
a
puzzle
game
designed
to
teach
algebra,
specifically
the
navigation
around
equations.

This
is
done,
however,
without
numbers
or
variables,
but
instead
with
pictures,
for
the
first
few

hours
of
gameplay.
In
fact,
there
isn’t
even
an
“=”
sign
in
the
game,
but
rather
a
pair
of
boxes.
The

object
is
to
keep
one
image
by
itself
on
one
box,
by
dropping
“negative”
(oppositely
colored)
versions

of
images
into
both
boxes,
so
that
the
opposites
in
a
single
box
cancel
each
other
out.

FIGURE
18

ADDING
THE
"POSITIVE"
FLY
TO
BOTH
SIDES
WILL
GET
THE
BOX
ALONE,
AN
ANALOGY
FOR
HAVING
X
ON
ONE
SIDE

OF
THE
EQUATION.

The
game
is
designed
so
that
the
player
gets
used
to
the
movement
and
thought
pattern
of
algebra,

but
without
consciously
realizing
that
she
is
studying
algebra.
The
player
gets
used
to
the
rules
of

adding
to
both
sides,
multiplying
everything
by
the
same
number,
and
that
there
are
multiple
ways
to

attack
the
same
problem,
though
a
certain
order
of
operations
must
be
followed.
Similar
to
Covalence,

the
intent
is
to
make
an
intimidating
system
easier
to
understand.

29

Initially,
there
was
some
impetus
in
Covalence
to
go
away
from
the
familiar
chemical
models,
and
the

ball-‐and-‐stick
visualizations
often
seen
in
Chemistry.
If
the
system
was
seen
in
a
different,
less

abrasive
manner,
perhaps
the
student
playing
the
game
would
have
an
easier
time
getting
the
core

idea
of
the
game
down,
before
slowly
being
revealed
the
chemistry
behind
it.

However,
a
design
decision
was
made
early
on
in
the
development
of
the
game,
to
make
this
system

as
easy
to
integrate
in
to
regular
curriculum
as
possible.
One
of
the
biggest
issues
of
learning
Organic

Chemistry
is
the
multiple
modes
of
literacy
that
Chemists
use
to
explain
the
same
molecule.
During

the
expected
window
that
we
hope
the
player
would
be
using
Covalence,
these
multiple
modes
are

being
introduced
to
students,
and
students
are
expected
to
learn
both
these
reading
systems,
and
the

material
that
they
are
meant
to
represent.
Thus,
if
the
player
had
to
learn
a
new
system
on
top
of

those
modes,
it
seemed
like
an
unattractive
proposition
for
a
potential
customer,
and
would
be
a

barrier
to
engaging
with
the
material,
as
opposed
to
a
smoother
way
to
learn
the
material.

In
fact,
doing
the
opposite
seemed
more
attractive
–
Covalence
would
have
the
opportunity
to

integrate
multiple
systems
of
literacy
into
a
single
interface,
thus
allowing
players
to
understand
how

these
multiple
systems
work
within
each
other.
Thus,
Covalence
would
be
an
attractive
way
to
speed

up
learning,
of
multiple
systems.

THE
CHIRALITY
GAME
(2002)

A
game
designed
for
the
Nobel
Prize
website,
the
Chirality
Game
shows
the
principle
of
chirality
via
a

card-‐matching
game,
in
which
the
player
matches
molecules
and
other
images
that
are
not
exactly

the
same,
but
instead
mirror
images.
16

The
game
takes
a
familiar
game
mechanic
–
card
matching
–

And
uses
it
as
a
way
to
illustrate
how
chiral
molecules
are
very
similar,
and
subtly
different.

16

The
Chirality
Game
-‐
About
(Nobel
Media,
n.d.),

http://www.nobelprize.org/educational/chemistry/chiral/game/game.html.

30

FIGURE
19

TWO
SNAILS
WITH
MIRROR-‐IMAGE
(CHIRAL)
SHELLS
HELP
THE
PLAYER
PICK
OUT
CHIRAL
OBJECTS
SUCH
AS
HANDS

AND
MOLECULES.

The
Chiral
Game
uses
a
pair
of
chiral
mascots
and
a
familiar
game
mechanic
to
emphasize
how
subtle

chirality
is
–
Everything
looks
so
similar,
and
one
must
really
look
carefully
to
discern
the
materials.

However,
The
Chiral
Game
feels
limited
in
that
one
can
only
look
at
the
differences
via
a
two-‐
dimensional
image,
and
if
the
player
does
not
understand
how
to
pick
out
the
difference,
little
help
is

offered
in
the
game
to
do
so,
once
the
cards
are
on
display.

WHAT
GAMES
HAVE
TO
TEACH
US
ABOUT
LEARNING
AND
LITERACY
(GEE,

2007)

In
the
chapter
“Learning
and
Identity,”
Gee
emphasizes
an
idea
of
the
“Player
As
Avatar,”
a
sentence

in
which
a
game
player
is
aware
of
all
three
states
–
the
real
(recognized
as
‘James
Paul
Gee’),
the

virtual
(the
avatar
character
that
he
named
‘Bead
Bead’),
and
projective.
17

“The
projective
identity
of
Bead
Bead
as
a
project
(mine)
in
the
making
can
fail
because
I
(the
real-‐
world
James
Paul
Gee)
have
caused
Bead
Bead
(the
virtual
me)
to
do
something
in
the
game
that
the

character
I
want
Bead
Bead
to
be
would
not
or
should
not
do.
For
example,
on
my
first
try
at
the
game,

17

Gee,
What
Video
Games
Have
to
Teach
Us
About
Learning
and
Literacy.
Second

Edition.

31

early
on
I
had
Bead
Bead
sell
the
ring
the
old
man
had
given
her.
This
is
not
a
mistake
at
playing
the

game…It’s
a
move
allowed
[by
the
game,
and]
not
something
that
Half-‐Elves
can’t
do
or
are,
for
that

matter,
necessarily
too
principled
or
ungreedy
to
want
to
do.
Thus
it
is
not
necessarily
a
violation
of

Bead
Bead
as
a
virtual
identity.

However,
the
act
just
seemed
wrong
for
the
creature
I
wanted
Bead
Bead
to
be
(or
to
have

become…by
the
end
of
the
game).
I
felt
that
when
I
(Bead
Bead)
had
sold
the
ring
that
I
was
forming
a

history
for
Bead
Bead
that
was
not
the
one
she
should
have.
I
wanted
her
to
be
a
creature
who
acted

more
intelligently
and
more
cautiously,
a
creature
who
could
eventually
look
back
on
the
history
of
her

acts
without
regret.
I
felt
I
had
“let
her
down”…Thus,
in
my
projective
identity
–
Bead
Bead
as
my
project

–
I
am
attributing
feelings
and
motives
to
Bead
Bead
that
go
beyond
the
confines
of
the
game
world
and

enter
the
realm
of
a
world
of
my
own
creation.”

This
projective
identity,
then,
is
a
way
that
the
player
imbues
personal
convictions
upon
the
world
of

the
game,
and
decides
how
she
(and
her
avatar)
will
choose
to
play
the
hand
they
are
dealt.
In
large,

expansive
role-‐laying
games,
for
instance,
a
sense
that
one
can
project
in
any
direction
one
desires

will
usually
lead
to
the
game
being
described
positively,
as
an
“immersive”
and
“open”
game.

Gee
argues
that
this
Projection
as
the
unification
of
the
Real
and
Virtual
self
is
at
the
heart
of

choosing
if
one
wants
to
take
a
specific
career
path,
or
if
one
can
take
said
career
path.

“People
cannot
learn
in
a
deep
way
within
a
semiotic
domain
if
they
are
not
willing
to
commit

themselves
fully
to
the
learning
in
terms
of
effort,
and
active
engagement.
Such
a
commitment
requires

that
they
are
willing
to
see
themselves
in
terms
of
a
new
identity,
that
is,
to
see
themselves
as
the
kind
of

person
who
can
learn,
use,
and
value
the
new
semiotic
domain.
In
turn,
they
need
to
believe
that,
if
they

are
successful
learners
in
the
domain,
they
will
be
valued
and
accepted
by
others
committed
to
that

domain…It
has
been
argued
that
some
poor
urban
African-‐American
children
and
teenagers
resist

learning
literacy
in
school
because
they
see
school-‐based
literacy
as
“white,”
as
associated
with
people

who
disregard
them
and
others
like
them.
They
don’t
believe
that
a
society
that
they
view
as
racist
will

32

ever
allow
them
to
gain
a
good
job,
status,
and
power,
even
if
they
do
succeed
at
school-‐based
literacy.

Thus,
they
will
not
[see
themselves]
as
the
“kind
of
person”
who
learns,
values
and
uses
such
literacy
and

gets
valued
and
respected
for
doing
so.”

In
other
words,
if
a
student
believes
they
can’t
be
taken
seriously
as
a
scientist
because
of
some

barrier
(be
it
racial,
sexual,
or
based
on
anything
they
identify
with),
then
they
won’t
be
able
to
be

invested
in
learning
it.
This,
I
suspect,
is
why
many
who
have
not
grown
up
with
games
will
say
they

“aren’t
a
gamer”
before
they
pick
up
a
controller,
and
are
quick
to
put
down
the
controller
if
they

don’t
see
progress
quickly.
This
is
also
why
STEM
fields
can
be
so
incredibly
off-‐putting
to
someone

that
doesn’t
have
the
background
in
it.

Covalence
is
an
attempt
to
use
this
idea
of
projection
as
a
manifesto,
a
design
philosophy
interested
in

acknowledging
the
tension
that
many
students
entering
Organic
Chemistry
feel
regarding
their

current
skills
and
the
complexity
of
the
material.

THOMAS
WAS
ALONE
(BITHELL,
2012)

Thomas
Was
Alone
is
a
platformer
that
uses
a
story,
delivered
by
narration,
to
assign
context,
fears,

and
motivations
to
characters
that
are
otherwise
only
a
set
of
rectangles.

Each
of
the
rectangles
have
a
unique
shape,
color
and
jump
height,
and
perhaps
a
special
ability
such

as
floating
on
water.
Yet
by
attributing
a
certain
size
or
jump
height
to
a
personality
style,
the
game

makes
these
shapes
memorable.

I
was
inspired
by
Thomas
Was
Alone’s
narrative
style
to
try
and
give
a
certain
character
to
each
of
the

atoms,
so
that
the
player
will
recognize
each
atom
by
its
specific
actions.
While
this
sort
of
activity

did
not
ultimately
make
it
into
the
final
game,
it
was
a
very
worthwhile
exercise
to
imagine
the
atoms

as
different
‘characters’
based
solely
in
singular
differences
such
as
the
number
of
electrons
that
they

need
to
find
stability.

33

NINJA
GAIDEN
BLACK
(TEAM
NINJA,
2005)

Ninja
Gaiden
Black
is
an
excellent
example
of
using
elegance
as
a
tool
for
players
to
feel
free
to

experiment.
When
designing
Covalence,
I
had
to
explain
a
few
concepts
that
were
otherwise

nebulously
explained
in
the
science
of
chemistry,
and
give
them
a
defined
system.
In
the
vein
of
Ninja

Gaiden
Black,
I
endeavored
to
make
those
design
decisions
in
such
a
way
that
the
player
could
draw

conclusions
from
whatever
the
system
ended
up
being.

For
instance,
the
idea
of
Carbon
‘shedding’
a
leaving
group
is
not
strictly
defined
in
actual

Chemical
terms,
but
is
a
phenomena
that
is
observed
in
multiple
situations
in
substitution
reactions.

Similarly,
other
mechanics
that
were
ultimately
not
put
into
the
game
dealt
with
‘resonance
stability,’

the
possibility
of
a
Carbon
with
only
3
bonds
being
somewhat
stable
due
to
those
three
bonds
being

to
other
Carbon
atoms.
In
Covalence,
these
phenomena
are
defined
by,
and
reinforce,
the
Substitution

reaction.
This
largely
came
from
looking
at
how
controls
were
defined
in
Ninja
Gaiden
so
that

dodging
and
blocking
were
largely
the
same
mental
space
and
physical
button,
and
as
a
player
I
could

easily
follow
from
one
action
to
the
other
without
imagining
a
whole
new
input
process.

Ninja
Gaiden
is
a
game
developed
for
the
Xbox
platform,
heralded
as
one
of
the
most
difficult

games
of
its
console
generation.

18

The
player
plays
a
ninja
whose
lithe
movements
are
key
to

surviving
combat,
fighting
enemies
that
can
cause
large
amounts
of
damage
with
every
attack.
The

player
must
then
learn
to
navigate
the
world
through
an
“incredibly
intuitive
and
accessible’
control

scheme”
(IGN,
2004)
19

that
allows
the
player
to
learn
how
to
do
complex
movements
such
as

blocking
and
rolling
with
a
minimal
change
in
button
presses.

Holding
down
the
left
trigger
while
not
moving
makes
Ryu
block,
and
moving
in
any
direction
while

in
blocking
causes
the
player
to
roll.
In
playing
through
myself,
I
learned
how
to
roll
before
I
learned

to
block,
as
rolling
and
jumping
were
the
fastest
way
to
get
around
the
levels.
Because
of
this,
rolling

18

Clive
Thompson,
“The
Wonderfully
Difficult
Ninja
Gaiden,”
Slate,
May
6,
2004,

http://www.slate.com/articles/technology/gaming/2004/05/tough_love.html.

19

Hilary
Goldstein,
“Ninja
Gaiden
Review,”
IGN,
February
27,
2004,

http://www.ign.com/articles/2004/02/27/ninja-‐gaiden-‐review-‐2?page=1.

34

was
well-‐understood,
and
I
instinctively
used
it
do
dodge
attacks
from
enemies.
However,
a
curious

thing
happened
because
of
this
–
After
I
finished
a
dodge,
I
left
my
finger
on
the
left
trigger
a
hair
too

long,
and
when
a
ninja
attacked
Ryu,
he
blocked.
Thus,
I
learned
how
to
block
intuitively
without

needing
to
look
at
a
tutorial
or
instructional
image.

FIGURE
20

However,
in
case
players
do
not
learn
dodging
and
blocking
through
button
presses,
however,

prompts
do
appear
in
later
stages
of
the
first
level.
However,
it
is
worth
noting
that
the
intuitive

controls
allow
for
the
player
to
go
from
blocking
to
dodging
to
strong
attacks
fluidly
‘within
the
blink

of
an
eye’
(IGN
2004),
20

and
this
allows
for
a
quick
thinking
on
the
part
of
the
player.

The
first
level
of
Ninja
Gaiden
is
also
a
great
example
of
using
an
open
feel
of
exploration
to

encourage
learning.
Although
the
game
has
a
reputation
for
difficulty,
Ninja
Gaiden
Black
starts
with

an
open
space,
devoid
of
enemies,
and
the
player
must
simply
get
out
of
the
area.

There
are
no

instructional
button
images,
nor
are
there
goal
markers.
Because
of
this,
the
player
naturally

experiments
with
the
controls
by
pressing
buttons
until
she
understands
how
to
move
around
the

space.

20

Ibid.

35

FIGURE
21

THE
RIVERBED
THAT
THE
PLAYER
MUST
ESCAPE
FROM
IN
THE
BEGINNING
OF
THE
GAME.
THERE
IS
NO
INSTRUCTION

OF
WHERE
TO
GO,
AND
ALSO
NO
INSTRUCTION
DEFINING
CONTROLS,
BUT
THERE
ARE
ALSO
NO
ENEMIES,
AND
FALLS

INCUR
NO
DAMAGE.

This
allows
the
player
to
gain
a
certain
understanding
of
the
controls
intuitively,
but
pressing
buttons

to
see
what
happens.
When
designing
the
levels
of
Covalence,
I
tried
to
imagine
each
level
as
a

similarly
open
possibility
space,
one
that
the
player
can
feel
free
to
experiment
with,
even
if
they

don’t
know
exactly
what
everything
is
doing.
However,
Ninja
Gaiden
was
aimed
towards
players
used

to
its
parent
genre,
and
could
assume
a
familiarity
with
conventions
of
that
genre.
My
audience
was

aimed
towards
students
knew
to
this
educational
experience.
Ultimately,
the
science
proved

overwhelming,
and
I
decided
to
opt
for
teaching
the
pieces
of
the
game
more
explicitly.
Thus,
not
all

levels,
could
hold
true
to
this
design
philosophy,
but
in
my
opinion,
a
few
of
them
did.

NEXT
STEPS
AND
FURTHER
EVALUATION

As
this
project
has
continued,
I’ve
inevitably
had
to
contend
with
the
urge
to
grow
it
beyond
the

year’s
timeframe.
Given
the
amount
of
experience
I’ve
gained
from
the
project
already,
I’m
interested

in
possibilities
for
the
project
going
forward,
and
what
a
continuation
of
Covalence
would
look
like.

Early
on
in
the
game’s
design,
there
was
an
intention
to
include
line
drawings,
IUPAC
nomenclature,

and
reaction
temperature
in
the
feedback
of
the
game.
Unfortunately,
due
to
time
constraints,
many

36

of
these
things
were
severely
curtailed
in
the
current
build,
though
they
will
likely
be
important

subjects
to
consider
in
future
iterations.
In
particular,
the
IUPAC
nomenclature
is
a
complex,
but
very

logic-‐driven
system.
That
system
is
something
I
believe
would
be
much
easier
to
understand
if
a

student
could
simply
make
a
molecule
and
watch
as
its
name
changes.

EVALUATION

So
far,
evaluation
has
been
a
more
firmly
rooted
in
the
traditions
of
the
playtest,
bringing
players

(chemistry
students
and
non-‐students
alike)
to
play
builds
of
the
game,
and
gauge
their
response.

While
this
has
been
useful
for
the
purpose
of
building
the
game,
I
am
curious
about
standardizing
and

proving
a
meaningful
change
in
Organic
Chemistry
knowledge.
This
is
especially
true
since
I
have

taken
steps
to
include
the
Skeletal
Formula
model
in
the
game
as
an
optional
view,
so
as
to
provide

an
easy
transition
for
learning
the
material.
I’m
curious
to
gauge
how
many
students
use
this
view,

and
if
it
comes
in
handy,
or
if
it
is
the
only
view
used
by
students.
In
fact,
this
view
could
serve
as
a

‘normal’
by
which
the
Covalence
visual
model
could
be
compared,
to
see
if
there
really
is
any

improvement
due
to
the
new
model,
or
just
due
to
the
game
being
a
3D,
interactive
representation.

37

BIBLIOGRAPHY

0003
Maya
Movement
Key
Commands,
2011.

http://www.youtube.com/watch?v=gt0yLpQ6uhE&feature=youtube_gdata_player.

11,
Chem.
“Chemistry
11:
VSEPR.”
Chemistry
11,
May
5,
2012.

http://mageechemistry11.blogspot.com/2012/05/vsepr.html.

“2-‐Bromo-‐1-‐chloropropane.”
Wikipedia,
the
Free
Encyclopedia,
March
29,
2013.

http://en.wikipedia.org/w/index.php?title=2-‐Bromo-‐1-‐chloropropane&oldid=543868745.

Block,
Bruce.
The
Visual
Story:
Creating
the
Visual
Structure
of
Film,
TV
and
Digital
Media.
2nd
ed.

Focal
Press,
2007.

Gee,
James
Paul.
What
Video
Games
Have
to
Teach
Us
About
Learning
and
Literacy.
Second
Edition:

Revised
and
Updated
Edition.
2nd
ed.
Palgrave
Macmillan,
2007.

Goldstein,
Hilary.
“Ninja
Gaiden
Review.”
IGN,
February
27,
2004.

http://www.ign.com/articles/2004/02/27/ninja-‐gaiden-‐review-‐2?page=1.

Homeworld.
Vivendi
Universal,
1999.
http://www.relic.com/games/homeworld/.

Molecular
Orbitals.
Accessed
March
27,
2013.

http://www.sparknotes.com/chemistry/bonding/molecularorbital/.

Molymod
Organic/Inorganic
Molecular
Model
Student
Set.
Carolina
Biological
Supply
Company,
n.d.

Nič,
Miloslav,
Jiří
Jirát,
Bedřich
Košata,
Aubrey
Jenkins,
and
Alan
McNaught,
eds.

“Chirality.”
In
IUPAC
Compendium
of
Chemical
Terminology.
2.1.0
ed.
Research
Triagle
Park,
NC:

IUPAC.
Accessed
March
30,
2013.
http://goldbook.iupac.org/C01058.html.

“Walden
Inversion.”
In
IUPAC
Compendium
of
Chemical
Terminology.
2.1.0
ed.
Research
Triagle
Park,

NC:
IUPAC.
Accessed
March
30,
2013.
http://goldbook.iupac.org/W06653.html.

“Propane.”
Wikipedia,
the
Free
Encyclopedia,
March
27,
2013.

http://en.wikipedia.org/w/index.php?title=Propane&oldid=545220208.

Solomons,
T.
W.
Graham,
and
Craig
Fryhle.
Organic
Chemistry.
8th
ed.
Wiley,
2003.

The
Chirality
Game
-‐
About.
Nobel
Media,
n.d.

http://www.nobelprize.org/educational/chemistry/chiral/game/game.html.

38

Thompson,
Clive.
“The
Wonderfully
Difficult
Ninja
Gaiden.”
Slate,
May
6,
2004.

http://www.slate.com/articles/technology/gaming/2004/05/tough_love.html.

“VSEPR
Theory.”
Wikipedia,
the
Free
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29,
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http://en.wikipedia.org/w/index.php?title=VSEPR_theory&oldid=546494233.

Asset Metadata

Creator Mathias, Jason (author)

Core Title Simulations as real-time integration of information: Covalence, an organic chemistry game

Contributor Electronically uploaded by the author (provenance)

School School of Cinematic Arts

Degree Master of Fine Arts

Degree Program Interactive Media

Publication Date 04/30/2013

Defense Date 04/30/2013

Publisher University of Southern California (original), University of Southern California. Libraries (digital)

Tag Computer Science,digital media,Interactive Media,media arts,OAI-PMH Harvest,organic chemistry

Format application/pdf (imt)

Language English

Advisor Gibson, Jeremy (committee chair), Clements, Lisa (committee member), Gotsis, Marientina (committee member)

Creator Email jason.mathias@gmail.com

Permanent Link (DOI) https://doi.org/10.25549/usctheses-c3-248899

Unique identifier UC11294511

Identifier etd-MathiasJas-1637.pdf (filename),usctheses-c3-248899 (legacy record id)

Legacy Identifier etd-MathiasJas-1637-1.pdf

Dmrecord 248899

Document Type Thesis

Format application/pdf (imt)

Rights Mathias, Jason

Type texts

Source University of Southern California (contributing entity), University of Southern California Dissertations and Theses (collection)

Access Conditions The author retains rights to his/her dissertation, thesis or other graduate work according to U.S. copyright law. Electronic access is being provided by the USC Libraries in agreement with the a...

Repository Name University of Southern California Digital Library

Repository Location USC Digital Library, University of Southern California, University Park Campus MC 2810, 3434 South Grand Avenue, 2nd Floor, Los Angeles, California 90089-2810, USA

Abstract (if available)

Abstract College-level Organic Chemistry classes can be overwhelming to their students. In addition to learning a relatively large amount of information, students have to learn to read multiple visual models and use them to understand subtle differences in the science. In making the puzzle game Covalence to address Organic Chemistry education, I decided to focus on three aspects of the subject’s education – Hidden information in the various visual models, the lack of integration of these representations into a 3D representation of Chemical phenomena, and an atom-‐based view of the molecules and how they contribute to the field’s subtle issues. ❧ This paper discusses various traditional visual models taught in Organic Chemistry classes, devising a new visual model to bring out hidden information in these traditional models, and designing levels based on known reactions and their consequences, to illustrate Organic Chemistry’s elegance and subtlety.