Mock Final Exam
Chemistry 212 - Meyer
Section I: Structure Exploration & Drawing Structures
1) In the box below each compound, list as many lipid categories as possibleto
which the compound belongs. If a substance is NOT a lipid, write “not a lipid” in
the box.
2) Circle all isoprene units in all terpenes shown in question 1.
3) Three out of the 4 structures drawn in question 1 are colored white. The other
structure has a yellow color. Circle the structure that you expect to be colored
yellow. Retinol is yellow.
4) Draw a wax derived from Lauric Acid and “Compound X” from question
1.
O
H
O
H
O
H
1
H
Mock Final Exam
Chemistry 212 - Meyer
5) When a certain triacylglycerol is hydrolyzed with sulfuric acid and water,
the only products are glycerol and lauric acid. Draw this triacylglycerol
O
O
O
O
O
O
6) Draw a disaccharide that a β–1,4' glycosidic linkage between two
D-glucopyranose carbohydrates. If there are any anomeric carbons that can
spontaneously interconvert between two forms, put a star (*) next to each of
these and draw them all in the α conformation. Make sure you draw this
disaccharide using Haworth projections.
HO
HO
O
O
HO
HO
O
*
HO
OH
OH
OH
7) In the space below, draw a tripeptide at biological pH with the following
amino acid sequence: Ala–Phe–Ala. The side chains are as follows: Ala = CH3;
Phe = CH2Ph
H3N
H
N
O
Ph
O
O
N
H
O
2
Mock Final Exam
Chemistry 212 - Meyer
8) In the space below, draw a phospholipid that would form one saturated
fatty acid with twelve carbons and one unsaturated fatty acid with 14 carbons
when it is hydrolyzed with acid and water. The phospholipid that you draw should
contain a nitrogen atom that has bonds to three methyl groups.
O
O
O
O
P
O
O
O
N
O
Section II: Predict the products and reagents
9. In the space provided, draw the correct structure of the major organic
product(s). Indicate stereochemistry when appropriate. Also, indicate if a pair of
enantiomers has been formed.
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Mock Final Exam
Chemistry 212 - Meyer
H
CN
H
H
Δ
CN
OMe
CN
OMe
OMe
Br
O
HBr
OH
10. Fill in the reactants necessary to convert iso-propyl ethyl ketone into
the following substances:
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Mock Final Exam
Chemistry 212 - Meyer
11. Fill in the missing products in the following roadmap synthesis
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Mock Final Exam
Chemistry 212 - Meyer
Section III: Mechanisms
12. Draw the complete mechanism and predict the major product(s) of the
following reaction.
O
O
O
H3O+
O
Δ
tautomerize
CO2
OH
O
H
O
H2O H
O
O
O
H
O
O
H
H+ transfer
O
O
H
O
O
HO H
OH
H2O
O
O
O
H
H
+ EtOH
OH
13. Draw the complete mechanism and predict the major product(s) for the
following reaction.
O
Ru
O
Ru
Ru
(regenerated
catalyst)
O
O
O
Ru
Ru
Ru
H2C CH2
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Mock Final Exam
Chemistry 212 - Meyer
Section IV: Retrosynthesis
14. Synthesize the following target molecule using acetylene as your only source
of carbons. You may use as many equivalents of acetylene necessary. Other
organic byproducts may be formed.
H H
O
H
O
H
H H
O
H
H
O
O3
DMS
H2/Lindlar
1. H2/Lindlar
2. HBr
Br
H
Br2
Br
Br
H
H2/Lindlar
H
HBr
Br
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Mock Final Exam
Chemistry 212 - Meyer
15. Synthesize the following target molecule using acetone as your only source of
carbons. You may use as many equivalents of acetone necessary.
O
OH
O
O
O
LAH
OH
O
O
NaOEt
PBr3
Br
Mg
MgBr
OH
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Mock Final Exam
Chemistry 212 - Meyer
16. Synthesize the following target molecule using dibromomethane and
acetylene as your only source of carbons. You may use as many equivalents of
acetylene necessary. Other organic byproducts may be formed.
Br Br
H
H
NaH
Br
Br
H
H
1.H2/Lindlar
2. a. BH3/THF
b. H2O2/NaOH
PBr3
Br
(2 eq.)
HO
Br
OH
1. H2/Lindlar
2. O3 / DMS
3. LAH
Ru
H2SO4
heat
HO
HO
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Mock Final Exam
Chemistry 212 - Meyer
Section V: Spectroscopy
17. Answer the following questions about the structure given below.
a. How many signals do you expect to see in the 13C NMR
spectrum?____6____
b. How many signals do you expect to see in the 1H NMR
spectrum?____4____
c. How many signals do you expect to see in the DEPT 135
spectrum?____4_____
18. Deduce the structure that corresponds to the spectral data on the remaining
pages of this exam. If the answer is incorrect, your analysis of the spectra can be
worth significant partial credit, so show your work clearly in the space below each
set of data only. Answers outside of these places will be ignored.
Mass spectrum: m/z = 160 (M; 100%), m/z = 161 (9.0%), and m/z = 162 (0.9%).
No fluorine or iodine.
Molecular Formula: C8H16O3
DUN__________1_________
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Mock Final Exam
Chemistry 212 - Meyer
IR
1H-NMR: 4.93 ppm (septet; integral = 1), 3.73 ppm (triplet; integral = 2), 3.50
ppm (quartet; integral = 2),2.42 ppm (triplet; integral = 2), 1.32 ppm (doublet;
integral = 6), and 1.10 ppm (triplet; integral = 3).
Two Answers are acceptable:
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