Professional Documents
Culture Documents
`
3
Alkynes
A m i d es
s
at ic
m
Ar o
Hydration of Alkenes
T hio
ls s
Salt
Acetal Formation
5
USER GUIDE 7
UNIT
I
9
ACIDS
&
BASES
11
1.1 –
ACIDS
&
BASE
CHEMISTRY
13
1.2
–
GRAM
EQUIVALENTS-‐NORMALITY-‐TITRATION
15
1.3 –
PH
-‐
POH
–
[H+]
–
[-‐OH]
17
1.4 –
BUFFERS
19
ALKANES
21
1.5 –
NAMING
ALKANES
23
1.6 –
FUNCTIONAL
GROUPS
25
1.7 –
DRAWING
STRUCTURES
27
1.8 –
CONFORMERS
&
ISOMERS
29
PRACTICE
TESTS
1A
31
1B
39
UNIT
II
47
ALKENES,
ALKYNES
&
AROMATICS
49
2.1
–
NAMING
ALKENES,
ALKYNES,
&
AROMATICS
51
2.2
–
CIS/TRANS
53
2.3
–
POLYMERS
55
2.4
–
REACTIONS
OF
ALKENES,
ALKYNES,
&
AROMATICS
57
ALCOHOLS,
PHENOLS,
ETHERS,
THIOLS,
&
HALOGENS
59
2.5
–
NAMING
ALCOHOLS,
PHENOLS,
ETHERS,
THIOLS,
&
HALOGENS
61
2.6
–
REACTIONS
OF
ALCOHOLS,
PHENOLS,
ETHERS,
THIOLS,
&
HALOGENS
63
PRACTICE
TESTS
2A
65
2B
73
UNIT
III
81
AMINES,
ALDEHYDES,
KETONES,
CARBOXYLIC
ACIDS,
ESTERS,
&
AMIDES
83
3.1
–
NAMING
AMINES,
ALDEHYDES,
&
KETONES
85
3.2
–
NAMING
CARBOXYLIC
ACIDS,
ESTERS,
&
AMIDES
87
3.3
–
REACTIONS
–
TESTS
(LUCAS,
BENEDICTS,
&
TOLLENS)
89
3.4
–
REACTIONS
OF
CARBONYLS
91
CARBOHYDRATES
93
3.5
–
CARBOHYDRATE
NOMENCLATURE
95
3.6
–
REACTIONS
OF
CARBOHYDRATES
97
3.7
–
CONVERTING
FISCHER
TO
CYCLIC
99
PRACTICE
TESTS
3A
101
3B
109
TOOLS
117
NOMENCLATURE
119
COMMON
FUNCTIONAL
GROUPS
120
SIGNIFICANT
FIGURES
121
PERIODIC
TABLE
OF
THE
ELEMENTS
123
7
Thank
you
for
choosing
to
use
this
workbook
provided
by
the
PLUS
program
at
Eastern
Washington
University!
The
purpose
of
this
book
is
to
provide
a
medium
to
which
students
and
tutors
can
enhance
their
subject
knowledge
by
focusing
on
fluency
and
speed,
which
are
fundamental
to
success
on
exams.
This
workbook
is
intended
for
use
by
a
tutor
who
has
successfully
completed
the
course
in
question,
in
a
1-‐on-‐1
or
small
group
format.
In
addition,
this
workbook
assumes
that
the
reader
has
access
to
a
textbook
for
explanations
not
provided
in
this
material.
This
book
is
intended
to
be
supplemental
to
a
textbook
for
use
by
a
tutor
and
a
student.
NO TE:
These worksheets and
Worksheets:
practice exams are
Ø 1
page
of
problems
on
a
focused
topic
intended to be used with
Ø FRONT
=
BLANK
a knowledgeable tutor
Ø BACK
=
ANSWER
KEY
and therefore, the most
Ø Print
off/copy
for
student
problems encountered
Ø Or
work
on
with
student
are NOT meant to be
Ø Consult
textbook
for
detailed
explanation
of
topic
easy.
Practice
Exams:
The theory: if a student
Ø 3-‐4
pages
of
simulated
exam
type
questions
can complete difficult
o There
are
two
types
of
exams:
practice problems with a
§ A
–
very
similar
to
worksheets
tutor, they can excel
§ B
–
more
integrative
concepts
&
analysis
independently on a
Ø TREAT
IT
LIKE
A
REAL
EXAM
standard exam level.
o Grab
a
study
carrel
or
another
quite
place
o No
drinks/food,
cell
phones,
textbooks,
or
computers
Ø Allow
no
more
than
50-‐55
minutes
to
complete.
Ø Answer
key
immediately
follows
the
blank
test
Ø Grade
exam
for
students
just
like
a
professor
would
Ø Or
grade
exam
with
student
–
learn
from
mistakes!
In
order
to
get
the
most
out
of
the
practice
exams,
it
is
imperative
to
simulate
a
test-‐like
environment
when
taking
these
exams.
Many
students
unfortunately
suffer
from
test
anxiety
and
much
of
this
anxiety
can
be
avoided
by
increased
knowledge
of
material,
as
well
as
experience
with
testing
environments.
Once
the
student
has
completed
an
exam,
the
tutor
may
choose
to
grade
the
exam
during
a
normal
session
while
the
student
works
on
other
materials
(such
as
worksheets)
and
return
the
graded
exam
to
the
student.
Alternatively,
a
tutor
could
evaluate
the
exam
with
the
student.
It
is
not
advised,
however,
to
simply
provide
the
student
with
the
answer
key
without
a
tutor
to
review
the
exam
also.
This
is
due
the
simple
fact
that
it
is
hard
to
catch
our
own
mistakes.
Also,
because
the
practice
exam
does
not
directly
affect
the
student’s
course
grade,
the
path
of
least
resistance
(neglecting
to
evaluate)
is
easy
to
be
taken.
The
point
of
this
book
is
to
help
identify
problem
areas
and
provide
a
means
to
address
and
remedy
them.
Happy tutoring!
81
83
Aldehydes
Ketones
• Replace
the
‘e’
• Replace
the
‘e’
at
the
end
of
the
at
the
end
of
the
parent
chain
parent
chain
with
“al.”
with
“one.”
Amines
• Replace
the
‘e’
at
the
end
of
the
parent
chain
with
“amine.”
• Use
a
number
to
identify
the
location
of
the
nitrogen,
either
before
the
parent
name
or
before
“amine.”
• The
name
of
any
alkyl
group
bonded
to
the
nitrogen
is
preceded
by
an
“N.”
Amides
• 1st
name
alkyl
group
off
the
amide
preceding
with
“N.”
• 2nd
name
parent
acid,
replacing
“ic”
with
“amide.”
85
3.1 – Worksheet
Naming Amines, Aldehydes, & ketones
Please
complete
the
following
table
by
either
providing
the
structure
or
the
name
of
the
compound.
Formaldehyde
N,N-‐diethyl-‐5-‐fluoroheptan-‐3-‐
2-‐chloro-‐3-‐methylhexanal
amine
3,4-‐diethyl-‐3-‐methyl-‐2-‐
hexanone
5-‐bromo-‐3-‐methylheptanal
2-‐ethyl-‐N-‐isopropyl-‐N-‐
3-‐methylcyclohexanone
Formaldehyde
methylcyclohexanamine
N,N-‐diethyl-‐5-‐fluoroheptan-‐3-‐ 5-‐bromo-‐2-‐methyl-‐4-‐
2-‐chloro-‐3-‐methylhexanal
amine
heptanone
3,4-‐diethyl-‐3-‐methyl-‐2-‐ N-‐sec-‐butyl-‐2-‐tert-‐butyl-‐N-‐
Acetalaldehyde
hexanone
isobutylcyclopentanamine
3-‐chloro-‐5-‐
5-‐ethyl-‐6-‐methyl-‐4-‐octanone
5-‐bromo-‐3-‐methylheptanal
cyclobutylbenzaldehyde
87
3.2 – Worksheet
Naming Carboxylic Acids, Amides, & Esters
Please
complete
the
following
table
by
either
providing
the
structure
or
the
name
of
the
compound.
N,N,3-‐triethylpentanamide
Butyl
octanoate
3-‐cyclcohexyl-‐N-‐isopropyl-‐ 3-‐chloro-‐4-‐cyclopropyl-‐2-‐
N,2,4-‐trimethyloctanamide
isopropylpentoic
acid
4-‐ethyl-‐5-‐methyl-‐N,N-‐ 2-‐ethyl-‐6-‐iodo-‐3,3-‐
dipropylheptanamide
dimethylheptanoic
acid
3.2 – Worksheet – KEY
Naming Carboxylic Acids, Amides, & Esters
Please
complete
the
following
table
by
either
providing
the
structure
or
the
name
of
the
compound.
4-‐
fluoro-‐N-‐methyl-‐
Ethyl
3-‐methylpentanoate
3-‐chlorobutanoic
acid
hexanamide
Pentyl
3-‐propyl-‐6-‐
4-‐methylpentanamide
N,N,3-‐triethylpentanamide
bromohexanoate
Name:
+
+ Name:
A
Lucas
test
is
performed
on
the
following
alcohols
to
determine
if
the
presence
of
a
primary,
secondary,
or
tertiary
alcohol.
Using
your
knowledge
of
the
Lucas
test
please
identify
which
alcohol
is
in
which
beaker.
Perform
a
Benedicts
test
on
the
following
compound.
Make
sure
to
list
all
reagents
and
the
expected
products
&
colors
associated.
+
Perform
a
Tollens
test
on
the
following
compound,
make
sure
to
list
all
reagents
and
the
expected
products
&
colors
associated.
+
3.3 – Worksheet – KEY
Reactions – Tests (Lucas, Benedicts, & Tollens)
Please
provide
the
name
of
the
following
tests
as
well
as
the
reactants,
products,
or
starting
materials.
A
Lucas
test
is
performed
on
the
following
alcohols
to
determine
if
the
presence
of
a
primary,
secondary,
or
tertiary
alcohol.
Using
your
knowledge
of
the
Lucas
test
please
identify
which
alcohol
is
in
which
beaker.
(I)
Beaker
A:
No
precipitation
after
one
hour
__________________________________
(III)
Beaker
B:
Precipitation
observed
after
four
minutes
______________________
(II)
Beaker
C:
Precipitation
observed
immediately
_____________________________
Write
the
reaction
that
occurs
in
beaker
C:
Perform
a
Benedicts
test
on
the
following
compound.
Make
sure
to
list
all
reagents
and
the
expected
products
&
colors
associated.
Buffer
+
Perform
a
Tollens
test
on
the
following
compound,
make
sure
to
list
all
reagents
and
the
expected
products
&
colors
associated.
+
NH3
Ag(s)
H2O
91
3.4 – Worksheet
Reaction s of Carbonyls
Please
complete
the
following
reactions
by
either
providing
the
reactants,
products
or
starting
materials.
+
+ +
+
3.4 – Worksheet – KEY
Reaction s of Carbonyls
Please
complete
the
following
reactions
by
either
providing
the
reactants,
products
or
starting
materials.
HCN
+
+
+
+ +
+
+
+
93
D
&
L
Sugars
Look
at
last
chiral
carbon
Fischer
à
Cyclic
If
hydroxyl
is
on
right
–
D
RIGHT
in
Fischer
DOWN
in
Cyclic
LEFT
in
Fischer
If
hydroxyl
is
UP
in
Cyclic
on
the
left
–
L
Compounds
to
MEMORIZE
#
of
Stereoisomers
2n
n
=
#
of
chiral
carbons
Classification:
Classification:
D
or
L:
D
or
L:
Please
classify
the
following
compounds
through
use
of
the
terms
aldose
and
ketose,
including
the
#
of
carbons
in
the
name.
Also,
draw
its
enantiomer
and
name
both
compounds
including
the
appropriate
D/L
nomenclature.
Please
draw
Maltose.
Indicate
the
two
monomers
that
make
up
the
disaccharide
as
well
as
the
type
of
bond
between
the
two
monomers.
Briefly
describe
what
amylose,
amylopectin,
and
glycogen
are
and
how
amylopectin
and
glycogen
are
used
in
plants
and
animals.
3.5 – Worksheet – KEY
Carbohydrate Nomenclat ure
Please
classify
the
following
compounds
through
use
of
the
terms
aldose
and
ketose,
including
the
#
of
carbons
in
the
name.
Please
classify
the
following
compounds
through
use
of
the
terms
aldose
and
ketose,
including
the
#
of
carbons
in
the
name.
Also,
draw
its
enantiomer
and
name
both
compounds
including
the
appropriate
D/L
nomenclature.
Please
draw
Maltose.
Indicate
the
two
monomers
that
make
up
the
disaccharide
as
well
as
the
type
of
bond
between
the
two
monomers.
Briefly
describe
what
amylose,
amylopectin,
and
glycogen
are
and
how
amylopectin
and
glycogen
are
used
in
plants
and
animals.
Amylose,
amylopectin,
and
glycogen
are
all
starches
used
for
energy
in
living
organisms.
Amylopectin
and
glycogen
also
have
α-‐1,6
linkages
which
ultimately
store
more
energy.
Amylopectin
does
not
have
as
frequent
branching
as
glycogen.
Due
to
the
frequent
b ranching,
glycogen
holds
more
potential
for
fast
energy,
which
is
why
it
is
used
in
animals,
whereas
plants
use
amylopectin.
97
3.6 – Worksheet
Reaction s of Carbohydrates
Please
complete
the
following
reactions
by
providing
the
product(s),
reactants,
or
the
starting
materials.
+
+
Working
in
a
lab,
your
supervisor
instructs
you
to
perform
both
a
Benedicts
test
and
a
Tollens
test
on
fructose.
You
know
that
ketones
have
to
undergo
a
rearrangement
before
they
can
be
reduced.
Please
show
the
steps
of
the
rearrangement
then
perform
both
tests
with
the
appropriate
reagents.
3.6 – Worksheet – KEY
Reaction s of Carbohydrates
Please
complete
the
following
reactions
by
providing
the
product(s),
reactants,
or
the
starting
materials.
+
+
Working
in
a
lab,
your
supervisor
instructs
you
to
perform
both
a
Benedicts
test
and
a
Tollens
test
on
fructose.
You
know
that
ketones
have
to
undergo
a
rearrangement
before
they
can
be
reducing
sugars.
Please
show
the
steps
of
the
rearrangement
then
perform
both
tests
with
the
appropriate
reagents.
Benedicts
+ +
Tollens
+
+
99
3.7 – Worksheet
Con vertin g Fischer to Cyclic
Please
convert
the
following
from
Fischer
to
cyclic
form.
H O
H OH
HO H
HO H
H OH
OH
H O
H OH
HO H
HO H
H OH
OH
Isopropylisobutylamine
Acetone
Isobutyl
3-‐methylbutanoate
N-‐sec-‐butylpropanamide
3-‐cyclopentyl-‐4-‐
Formaldehyde
methylhexanal
Practice T est – 3A
2.
A
Lucas
test
is
performed
on
the
following
alcohols
to
determine
if
the
presence
of
a
primary,
secondary,
or
tertiary
alcohol.
Using
your
knowledge
of
the
Lucas
test
please
identify
which
alcohol
is
in
which
beaker.
(6)
3.
Please
complete
the
following
reactions
either
by
providing
the
products,
reactants,
or
starting
materials.
(16)
+
103
Practice T est – 3A
Working
in
a
lab,
your
supervisor
instructs
you
to
perform
both
a
Benedicts
test
and
a
Tollens
test
the
following
ketohexose.
You
know
that
ketones
have
to
undergo
a
rearrangement
before
they
can
be
reducing
sugars.
Please
show
the
steps
of
the
rearrangement
then
perform
both
tests
with
the
appropriate
reagents.
Also,
please
name
the
ketohexose.
(12)
Benedicts
Tollens
Name:
Please
classify
and
identify
the
following
carbohydrates
by
name
and
provide
their
enantiomers
structure
and
name.
Be
sure
to
include
appropriate
D
or
L
specification.
(8)
Classification:
Classification:
Original:
Original:
Enantiomer:
Enantiomer:
Please
identify
the
following
disaccharides,
the
two
monomers
that
make
up
the
disaccharides,
and
the
types
of
glycosidic
bonds
between
them.
(8)
Name:
Name:
Monomers:
Monomers:
Type
of
Bond:
Type
of
Bond:
Practice T est – 3A
7.
Briefly
describe
what
amylose,
amylopectin,
and
glycogen
are
and
how
amylopectin
and
glycogen
are
used
in
plants
and
animals.
(4)
8.
Please
complete
the
following
reactions,
either
by
providing
the
products,
reactants,
or
starting
materials.
Also,
when
prompted
provide
the
name
of
the
compound
in
question.
(8)
(6)
+
(2)
H OH
HO H
H OH
H OH
OH
4-‐chloro-‐3-‐ethylpentanoic
Propyl
2-‐bromopropanoate
Isopropylisobutylamine
acid
N-‐ethyl-‐3-‐iodo-‐2-‐propyl-‐N-‐
Acetone
2,2-‐dimethyl-‐3-‐ethylhexanal
methylpentanamide
N-‐tert-‐butyl-‐N-‐isopropyl-‐2-‐
4-‐ethyl-‐6-‐fluoroheptan-‐3-‐one
Isobutyl
3-‐methylbutanoate
methylcyclopentanamine
2,2,5,5-‐Tetrachloro-‐3-‐
N-‐sec-‐butylpropanamide
Formic
Acid
ethylcyclohexanone
3-‐cyclopentyl-‐4-‐ 2-‐Iodo-‐3-‐propyl-‐2-‐
Formaldehyde
methylhexanal
methylhexanoic
acid
Practice T est – 3A – KEY
2.
A
Lucas
test
is
performed
on
the
following
alcohols
to
determine
if
the
presence
of
a
primary,
secondary,
or
tertiary
alcohol.
Using
your
knowledge
of
the
Lucas
test
please
identify
which
alcohol
is
in
which
beaker.
(6)
II
Beaker
A:
Precipitation
observed
immediately
_____________________________
I
Beaker
B:
Precipitation
observed
after
four
minutes
______________________
III
Beaker
C:
No
precipitation
after
one
hour
__________________________________
Write
the
reaction
that
occurs
in
beaker
A:
3.
Please
complete
the
following
reactions
either
by
providing
the
products,
reactants,
or
starting
materials.
(16)
+
107
Practice T est – 3A – KEY
4.
Working
in
a
lab,
your
supervisor
instructs
you
to
perform
both
a
Benedicts
test
and
a
Tollens
test
the
following
ketohexose.
You
know
that
ketones
have
to
undergo
a
rearrangement
before
they
can
be
reducing
sugars.
Please
show
the
steps
of
the
rearrangement
then
perform
both
tests
with
the
appropriate
reagents.
Also,
please
name
the
ketohexose.
(12)
Benedicts –O O
+ + H OH
HO H
Tollens H OH
H OH
+
+
OH
5.
Please
classify
and
identify
the
following
carbohydrates
by
name
and
provide
their
enantiomers
structure
and
name.
Be
sure
to
include
appropriate
D
or
L
specification.
(8)
(4)
(4)
(6)
+
OH
(2)
OH
O
H3C
O
OH OH CH3
H OH
HO H
H OH
H OH
OH
Practice T est – 3B
1.
Please
complete
the
following
reactions
by
either
providing
the
starting
materials,
reactants,
or
product(s).
When
prompted,
please
provide
the
name
of
the
compound
in
question.
(24)
(4)
H O (6)
HO H
HO H
+
H OH
OH Name:
Name:
(8)
(6)
Name:
2.
Ketoses
are
reducing
sugars
because
under
certain
conditions,
they
undergo
a
rearrangement
that
allows
them
to
be
reduced.
Please
show
each
step
of
this
rearrangement
with
D-‐
Fructose.
Be
sure
to
include
any
inorganic
reagents
needed,
and
please
name
the
product.
(8)
Name:
Practice T est – 3B
3.
A
test
is
performed
on
2-‐chloro-‐3-‐ethylpentanal
that
yields
a
silver
precipitate.
Please
identify
which
test
was
performed
as
well
as
show
this
reaction
including
all
starting
materials,
reactants,
and
products.
(10)
4.
In
a
lab,
you
have
two
unlabeled
beakers
containing
either
3-‐ethylcyclohexanone
or
2-‐
isopropylbutanal.
Using
only
a
reduction
reaction
with
NaBH4
and
a
Lucas
test,
show
the
reactions
that
would
help
determine
the
identity
of
the
two
beakers.
Be
sure
to
include
all
starting
materials,
reactants,
products,
and
to
explain
your
deduction.
(12)
5.
A
test
was
performed
on
D-‐Galactose
that
produced
a
red
solution.
Please
identify
which
test
was
performed
as
well
as
show
this
reaction
including
all
starting
materials,
reactants,
and
products.
(10)
6.
Please
provide
the
cyclic
structure
of
the
starting
materials
and
provide
the
reactants
to
this
reaction
involving
α-‐D-‐Glucose.
(4)
111
Practice T est – 3B
7.
Please
complete
the
following
table
by
providing
either
the
name
or
the
structure
of
the
compound.
(12)
Acetic Acid
O
H H
2-‐fluoro-‐4-‐methylpentaonic
acid
8.
Please
classify
the
following
compound
as
an
aldose/ketose,
D/L
sugar,
and
then
draw
its’
enantiomer
then
and
convert
from
the
original
Fischer
structure
to
its
cyclic
form.
(6)
Classification:
D/L:
7.
Briefly
describe
what
amylose,
amylopectin,
and
glycogen
are
and
how
amylopectin
and
glycogen
are
used
in
plants
and
animals.
(4)
8.
Please
circle
all
of
the
chiral
carbons
and
calculate
the
maximum
#
of
stereoisomers
possible.
(4)
Practice T est – 3B
Please
provide
the
structure
for
Lactose,
identify
the
monomers
that
make
up
the
disaccharide,
and
provide
the
type
of
bond
between
the
two
monomers.
(6)
100
113
1.
Please
complete
the
following
reactions
by
either
providing
the
starting
materials,
reactants,
or
product(s).
When
prompted,
please
provide
the
name
of
the
compound
in
question.
(24)
(4)
H O OH (6)
HO H HO H
HO H HO H +
H OH H OH
(8)
(6)
Name:
3-‐ethyl-‐2-‐
hexanone
2.
Ketoses
are
reducing
sugars
because
under
certain
conditions,
they
undergo
a
rearrangement
that
allows
them
to
be
reduced.
Please
show
each
step
of
this
rearrangement
with
D-‐
Fructose.
Be
sure
to
include
any
inorganic
reagents
needed,
and
please
name
the
product.
(8)
Name:
D-‐Glucose
Practice T est – 3B – KEY
3.
A
test
is
performed
on
2-‐chloro-‐3-‐ethylpentanal
that
yields
a
silver
precipitate.
Please
identify
which
test
was
performed
as
well
as
show
this
reaction
including
all
starting
materials,
reactants,
and
products.
(10)
Tollens Test
+ +
4.
In
a
lab,
you
have
two
unlabeled
beakers
containing
either
3-‐ethylcyclohexanone
or
2-‐
isopropylbutanal.
Using
only
a
reduction
reaction
with
NaBH4
and
a
Lucas
test,
show
the
reactions
that
would
help
determine
the
identity
of
the
two
beakers.
Be
sure
to
include
all
starting
materials,
reactants,
products,
and
to
explain
your
deduction.
(12)
Precipitate
will
form
within
5
minutes
No
precipitate
will
form
in
an
hour
5.
A
test
was
performed
on
D-‐Galactose
that
produced
a
red
solution.
Please
identify
which
test
was
performed
as
well
as
show
this
reaction
including
all
starting
materials,
reactants,
and
products.
(10)
H O
H OH
HO H
HO H
H OH
OH
D-Galactose
6.
Please
provide
the
cyclic
structure
of
the
starting
materials
and
provide
the
reactants
to
this
reaction
involving
α-‐D-‐Glucose.
(4)
115
Practice T est – 3B – KEY
7.
Please
complete
the
following
table
by
providing
either
the
name
or
the
structure
of
the
compound.
(12)
N-‐ethyl-‐N-‐methylhexan-‐3-‐
Acetic
Acid
Ethyl
2-‐bromopropanoate
amine
H H
2-‐fluoro-‐4-‐methylpentaonic
N,2-‐diethyl-‐N-‐
Formaldehyde
acid
methylbutanamide
8.
Please
classify
the
following
compound
as
an
aldose/ketose,
D/L
sugar,
and
then
draw
its’
enantiomer
then
and
convert
from
the
original
Fischer
structure
to
its
cyclic
form.
(6)
Please
provide
the
structure
for
Lactose,
identify
the
monomers
that
make
up
the
disaccharide,
and
provide
the
type
of
bond
between
the
two
monomers.
(6)
1,4-‐β linkage
100
117
119
121
123