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Carleton
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CHEMISTRY
2203/2207
Final
Exam
Date:
Tuesday
15
December
2020
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m&_&i&;fi"'a
[
Corlefan.g,
Do
not
open
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exam
paper
until
instructed
to
do
so.
Before
starting
the
examination,
read
and
do
the
following
1.
Complete
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above
section.
2.
This Final
Exam
includes
this
1
question
booklet
(14
pages).
You
are
responsible
for
ensuring
that
your
copy
of
the
paper
is
complete.
Bring
any
discrepancy
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the
attention
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proctor.
You
will
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hours)
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test.
Use
pen
to
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question
booklet.
Neatly
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marked.
5.
A
periodic
table
is
provided
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the
end
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booklet;
however,
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is
an
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book
test.
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means
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Wiley
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your
textbook).
6.
Non-programmable
calculators
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permitted.
7.
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but not
limited
to
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watches,
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phones,
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tablets)
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An
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annotate
the
midterm
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Please
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8.
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Please
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otherwise
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marked.
9.
Marking
scheme:
Each
question
clearly
indicates
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points
associated
with each.
There
are
8
questions
worth
a
total
of
120
marks.
The
exam
will
be
marked
out
of
100
marks
so
there
are
20
extra
marks
available.
rw
10.
Appeals:
You
may
note
here
any
question
that
you
feel
was
unfair
or
not
clearly
worded.
QMx
100
—7
1.
Fillin
the
missing
starting
organic
molecule,
reagents
necessary,
or
final
major
product(s)
for
the
following
reactions.
Be
sure
to
include
proper
stereochemistry
where
necessary.
If
there
is
no
reaction,
write
“N.R*
and
if
there
is
more
than
one
major
product
(e.g.
enantiomers),
please
specify
this
by
drawing
them
(or
writing
“+
en.”
for
enantiomers)
(38
points;
2
points
for
each
reaction)
b)
HOE!
e
N.R
Hoge
=
SNI/swg
Corhn
=
g
)
\/kr\
B,
g
'y
2
oo
B
d)
c\
/\/?:
HC
(dilute,
cold)
A
/°S°
-3
-sN1/swg
2P
=N
e)
a0
o
V02
9
Cl;
e
T
XL,
Ay
S
Tak
=K
U
A
A
\)@/\
conc.
H;SOy/heat
M
N
OH
\
)
Ak
)
UM,
A
\
Prookuct
n
oy
3
>u©
Sl
..
4
‘Jm/l
B—o
g
|
—_—
:
(3
H
8
B
Y
excess
HBr
)&/
=g
)
m)
AV
dree
dilute
HSOJH,0
—
)\/
cold
ta
—~<_/a.
)
H}j),b,
Wi
ST
*3
1
Your preview ends here
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)
o
L
TR4R
Y
PP
CCly
C
L)
)
O
e
3
N
an
e
3.
The
following
molecule
was
made
from
a
bicyclic
ring
involving
a
single
tworstep
reaction/process.
Draw
and
name
the
original bicyclic
ring,
including
the
proper
location
of
it
functional
groups,
and
provide
the
reagent
that
was
used
to
make
the
product,
(5
points;
2
for
the
structure,
1for
the
reagents,
2
for
the
IUPAC
name)
Name:
|~
Cgclohexence
-
agdo
pent
-
Complete
the
following
multistep
syntheses
by
showing
the
major
intermediate
products
and
the
reagents
necessary
for
each
step.
(25
points;
5
points
each)
a)
lon
DEBR
S
TRES
oS
A\,
05
,
Na
OB
-
<\£Q
To
t
ok
&
oM
——
o
o
&
-
A
T
T
(/
S
/\7)-
i
4T
9
NH
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d)
racemic
mixture
90%
enantiomeric
exces
\)\&AM\A/\
L}
N\
-
)
‘«7'*
(
5.
i3
e)
y
oo,
@
P&
)
D%
t
A
A
oL
n
(N
bk
?
—
%/\/‘
ity
></\\
4.a).
Provide
the
reagent
and
reaction
mechanism
to
show
how
the
reactants
and
products
in
the
following
reaction
can
interconvert.
(S
points)
/Y\
\72‘
SOy
aPH;O1—/Y\
o
DH,e
OH
b)
Under
what
conditions
would
the
reaction
i)
favour
reactants,
i)
favour
products,
and
iii)
why?
(3
points)
e
M8
—vhen
o
dSUENEERE
“L‘_§Q4
3
.
VSuasel
cecordd
orsast
A8
L\
C\\Q“\E\‘\g
Vs
Y(“'\Q“f"e
wowul
RS
Y
mm:\;é
Q‘C«vcur
e
Praducky
e
e
~
C
N\-ey
\
b
R
_\,\N“\Lv
on%{'t&f'd
+\1(oq
{&
taaoily
e
y
bRcCaun
“nciple
Payon
Shall
e
$
\/C)D‘(’k“fiu>b<<<t
L
dhatelien
x
Qa
R
5.
Indicate
the
necessary
reagents
above
the
reaction
arrow
for
the
following
reaction
and
provide
the
mechanism
to
achieve
the
product
indicated.
Be
sure
to
include
proper
stereochemistry.
(7
points)
6.a)
Draw
the
final
major
product(s)
for
the
following
reaction.
Be
sure
to
include
proper
stereochemistry.
(2
points)
ron<
{
u
@u
1
-t
2
=Ez
=
g-
£
1\
-
(
el
S}
ecorge
i
i
W
b)
Circle
the
more
appropriate
solvent
for
the
reaction
in
a)
(1
mark):
5
W
\~
A
/
Polar
Protic
m
C
Non-polar
Protic
Cy,
=
Non-Polar
Aprotic
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<)
Draw
the
intermediate
conformer
involved
in
reaction
a) (2
marks):
Note:
Feel
free
to
use the
abbreviations
Me
for
methyl;
sec-but
for
sec-butyl;
and
t-but
for
thutylgroups
()
V)
)‘o,l//\:
"
-
Cis3¢
Stabie
C
masy)
d)
if
the
conformer
in
c)
is
the
most
stable
conformer
write
“most
stable”,
otherwise,
draw
the
most
stable
conformer
below
(2
marks).
/
v
b
N
B
Ycans
=
most
SHsble
7.
The
following
organic
molecule
was
treated
with
an
excess
of
t-BuOK.
The
major
product
was
isolated
and
subsequently
reacted
with
ozone
(0s),
followed
by
a
water
workup.
Ff‘mww-w)w
¢
'
7
-bo
Brg
>
D&
?
r
o
"
Using
the
following
spectra
and
the
reactions
above,
identify the
final
product
and labe
all
relevant
peaks
in
the
IR,
’H-
and
13C-
spectra.
(10
marks)
Final
Product:
B
1
IH
NMR:
NOTE:
The
integration
of
the
peaks
from
left
to
right
is:
1.68;
1.73;
and
10.23
Ba
A
(-
S5
Poe
NfegE
N
|
S
He
150~
Peopy!
N
ol
i
Gc
—
¢
A
T
T
T
T
T
T
b
1.6312
10
8
6
4
1’73
2
“mihmadband-decoupled):
?{7
Ccu
o
M-
lfl,—r—
o
(&)
3
(&
c
G
]
e
—Cié?
~
gh}
8
5
-~
™
e
W
5
g
12
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8.
Starting
from
the
organic
molecules
shown
below
(each
could
be
used
more
than
once...)
as
your
only
sources
of
carbon
in
the
final
product,
provide
the
reaction
scheme
(reagents
and
\)intermediates)
(S?
obtain
the
fingl
product
indicated.
——*
P
A&"’v
Y
/M
s
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O SUBSTITUTION REACTIONS
Predicting the effect of carbocation stability on the rate of...
For each pair of substrates below, choose the one that will react faster in a substitution reaction, assuming that:
1. the rate law for the substitution reaction has a first-order dependence on the concentration of the alkyl halide, and
2. doesn't depend on the concentration of the other reactant at all.
Substrate A
age
Explanation
CI
Check
Br
B
Substrate B
CI
Faster Rate
(Choose one)
(Choose one)
Choose one)
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A ALEKS - Natalie Drury - Learn
G A major component of gasoline x
A www-awn.aleks.com/alekscgi/x/Isl.exe/1o_u-IgNslkr7j8P3jH-IJgt8PIGunmDn7WsVrRAXK6XnHkiRvH2tl800vdbuH6lkCnssocifJxkN3ax2TWa6AXXqcyFaLE6ceOfbJICanm28fOOHz
O CHEMICAL REACTIONS
Solving for a reactant using a chemical equation
Natalie
A major component of gasoline is octane (C,H,8). When octane is burned in air, it chemically reacts with oxygen gas (0,) to produce carbon dioxide (CO,)
18
and water (H,0).
What mass of water is produced by the reaction of 3.05 g of octane?
Round your answer to 3 significant digits.
x10
Explanation
Check
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O CHEMICAL REACTIONS
Jasmine V
Using molarity to find solute mass and solution volume
A chemist adds 0.90 L of a 2.53M zinc
nitrate (Zn(NO3),) solution to a reaction flask. Calculate the mass in kilograms of zinc nitrate the chemist has added to
the flask. Be sure your answer has the correct number of significant digits.
kg
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For the following, identify the most likely value for x:
BHx
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Use the References to access important values if needed for this question.
Cyclopentasilane (SigH10) is a liquid with a density of 0.963 g cm3. It reacts with oxygen to give silicon dioxide (SiO2) and water. Calculate the mass of
water that would form if 29.4 cm³ of cyclopentasilane reacted completely with excess oxygen.
g water
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