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CHEM 131 - Spriqg 201 1
Your Name:
Final Take-Home Exam (75 points)
+
Instructions: Work on your own. You may use your notes, any book, internet and your instructor as a
resource. The exam is due on Thursday, June 161hduring the regularly scheduled final exam time. I'll be
in the regular classroom to collect the exam and to answer questions. You may also drop it off in my
mailbox any time before the end of the regularly scheduled final exam time.
1. (4 pts) Draw the chemical structure of a sphingolipid containing a linolenic acid and serine. Draw a box
around the backbone and circle the hydrophilic head.
7
/
8wkbBa
2. (4 pts) The skeletal for the compound
-arachidonic acid is given below.
a) Draw all the double bonds at the appropriate places indicated by the delta naming system (2 pts).
0
4
z
6
8
3
LI
2
1
6
b) Using the omega system. What would the name be? (1 pt)
Y
2
c) The double bonds in naturally occurring arachidonic acid would exist in the cis or trans form? (1 pt)
-
hms
inromple &
3.
k r e o b b d
7
kyahpah'ofl3
O ~ L
O&
J;
(4 pts) Draw the structure of FAD after it accepted 2 electrons and 2 protons and formed FADH,.
the two protons that FADH, accepted
Circle
CHEM 131 - Spring 2011
4. (4 pts) How would you be able to convert compound A into B, where the hydroxyl group is transferred
from carbon 4 to carbon 3? You might have to perform several reaction steps to get from A to B. Draw
out all necessary reaction steps.
-
H0+5
OH
4
OH
2
Compound B
Compound A
5. (4 pts) Show how the enzyme activity or rate changes as a function of temperature for part a) and
substrate concentration for part b).
Temperature
[Substrate]
6. (8 pts) Give a short definition of each of the following terms:
a) Dextrin:
3 - 12
3 1 1 * ~ ~ 3wei d .
Jm3 P /Y%~ch-'de
b) Glycogenesis:
c) Chylomicrons:
QL
,!
+CI
~ D P ~ O W ; Ah a dlce f 0 ~ 5 d&,
9~
~cpqomk;fi. w t t l e
h r ~ l y f t - ~ 3 l y m '7
&
-
-
mrrsde~and
d) proton pump:
p(gLJ
d s . .
G J ~ ~ L ~a
~ Cp*n
3 p r mQ ~
mov;n
fradiw+
CHEM 131 - Spring 201 1
7. (10 pts) Compare the net outcome of ATP's from the complete hydrolysis and catabolism of maltose (a
disaccharide containing two glucose units) through glycolysis to the fatty acid, lauric acid (a 12 Carbon
fatty acid), which undergoes P-oxidation. Each acetyl CoA produces 12 ATP, each NADH produces 3
ATP and each FADH, produces 2 ATP. Consider any loss of ATP in the second to last row.
CH3-(CH2)10-COOH
Lauric Acid
I
I
OH
I
Maltose
OH
Glycolysis
# of Cmpds
produced
produced
ATP
Equivalent
NADH
4
x 2.5 ATP
ATP1sused
(activation)
I
TOTALATP
PRODUCED
~
1
1
0
f3-Oxidation
Total ATP
Producded
# of Cmpds
produced
A‘TP
Equivalent
Total ATP
Producded
=
10
&
x2.5ATP
=
/
-
0
=
-2
6
5
I
1
5 8 (
=
8. (5 pts) Consider the following sugars drawn in the open-ring form:
a) (2 pts) Identify the two sugars that are enantiomers to each other, by circling them.
b) (3 pts) Indicate whether each sugar is either a D or L sugar.
CHO
D or L sugar
2
.
78
CHEM 131 - Sprirrg 201 1
9.
(8 pts) Answer the following questions
a) What type of reaction does the coenzyme NAD+ help facilitate? Please be specific (type of
functional groups or compounds and give a specific reaction name.
b) What type of reaction does the coenzyme FAD help facilitate? Please be specific (type of functional
groups or compounds and give a specific reaction name.
c) Name the names of the enzymes that are involved in the regulation of the citric a c ~ dcycle.
h ) k ~
d) Draw the structure of coenzyme A
10. (6 pts) Answer the following questions about the electron transport chain.
.
L!
a) What is the last chemical species that accepts electrons and protons, which have been shuttled
through the electron transport chain?
b) What is the final product resulting from this electron and proton transfer onto the last species?
c) What chemical is synthesized as a result of the proton gradient across the inner membrane
(between the intermembrane space and the matrix)?
CHEM 131 .- Spring 201 1
11. (12 pts) Draw the major product that results from the following reactions. If there is no reaction, please
state "no reactions"
Oh
excess Hz, Pt
/
'
-
A
-
0
+ H20
CH -OH
I
CH.1
pH'
iH2
iH2
H', heat
+
I,,,\
G)- a -1Lc-OH +
1
c-44 -OU
I
(3
Q3
-a-&a-l
I
I
2Jq
CHEM 131 - Spring 201 1
12. (6 pts) The following names are not quite correct according to IUPAC rules. Draw the structure that
results from these names and then give the correct IClPAC name.
a) N,N,3-triethylbutaneamide
Extra Credit
A. (2 pts) For many disaccharides one of the monosaccharide components can exist in the open chain
structure. Redraw the following disaccharide showing the open chain structure of the appropriate sugar
with the other monosaccharide still in ring form. (2 pts)
flH
a
B. (2 pt) Based on !he sugars shown in question 8, give an example of 2 of the sugars that would represent
diastereomers.