Chem 2300
Exam 2
October 25, 2013
Name:
(first)
(last)
Last 4 digits of
A number
Score
I. Multiple Choice
(
/90
/30)
II
/10
Total score
/100
Note: Periodic table and pKa Values are on page 13.
1
I. Multiple choice questions. (3 points each). Please put your answers on Scantron sheet. Your score will
be graded based only on your answers from Scantron sheet.
1. What is the systematic name for the following compound?
(a)
(b)
(c)
(d)
(e)
3-methyl-1-vinylcyclohexene
2-methyl-4-vinylcyclohexene
1-methyl-3-vinylcyclohexene
1-methyl-5-vinylcyclohexene
None of the above
2. What is the systematic name for the following compound?
(a)
(b)
(c)
(d)
(e)
(R)-5-methylcyclohexene
(S)-4-methylcyclohexene
(R)-4-methylcyclohexene
(S)-5-methylcyclohexene
None of the above
CH3
3. What is the systematic name for the following compound?
(a)
(b)
(c)
(d)
(e)
1-ethyl-1,4-cyclohexadiene
1-ethyl-1,3-cyclohexadiene
2-ethyl-1,4-cyclohexadiene
1-ethyl-1,3-cyclohexadiene
None of the above
4. What is the systematic name for the following compound?
(a)
(b)
(c)
(d)
(e)
cis-4-methyl-3-hexene
trans-3-methyl-3-hexene
(Z)-3-methyl-3-hexene
(E)-3-methyl-3-hexene
None of the above
5. What is the systematic name for the following compound?
(a)
(b)
(c)
(d)
(e)
(Z)-2-fluoro-4-methyl-2-heptene
(E)-1-fluoro-4-methyl-2-heptene
(E)-2-fluoro-4-methyl-2-heptene
(Z)-1-fluoro-1,3-dimethyl-1-hexene
None of the above
2
CH2CH3
6. What is the systematic name for the following compound?
(a)
(b)
(c)
(d)
(e)
(E)-1-bromo-1-fluoro-3-methyl-1-pentene
(Z)-1-fluoro-1-bromo-3-methyl-1-pentene
(E)-1-fluoro-1-bromo-3-methyl-1-pentene
(Z)-1-bromo-1-fluoro-3-methyl-1-pentene
None of the above
7. What is the systematic name for the following compound?
(a)
(b)
(c)
(d)
(e)
3-fluorocyclohexene
(Z)-3-fluorocyclohexene
Cis-3-fluorocyclohexene
(R)-3-fluorocyclohexene
None of the above
8. Which of the following compounds have Z configuration (carbon-carbon double bond)?
O
HO
Br
Br
Br
II
I
IV
III
Cl
Cl
(a)
(b)
(c)
(d)
(e)
I, III, IV
I, II, III
I, IV
I, II, III, IV
None of the above
9. What is the correct order of stability for the following alkenes (most to least)?
II
I
(a)
(b)
(c)
(d)
(e)
IV
III
I>II>III>IV>V
V>I>III>IV>II
V>I>IV>III>II
V>IV>III>II>I
None of the above
3
V
Based on the potential energy diagram for the following reaction, answer the questions from 10 to 13.
HCl
II
Cl
IV
potential
energy
A
III
B
I
C
V
reaction coordinate
10. What could best describe the reaction above?
(a)
(b)
(c)
(d)
(e)
This is a one-step endothermic reaction.
This is a one-step exothermic reaction.
This is a two-step endothermic reaction.
This is a two-step exothermic reaction.
None of the above
11. Which of the following represents the heat of reaction?
(a)
(b)
(c)
(d)
(e)
A
B
C
A and B
III
12. Which represent the activation energy of the rate-determining step of the reaction?
(a)
(b)
(c)
(d)
(e)
A
B
C
A and B
II
4
13. Which of the following description is correct?
(a)
(b)
(c)
(d)
(e)
This reaction will lead to the formation of meso compounds.
This reaction will lead to the formation of achiral compounds.
This reaction will lead to the formation of a racemic mixture.
This reaction will lead to the formation of structural isomers.
None of the above
14. What is the systematic name for the following compound?
(a)
(b)
(c)
(d)
(e)
(R)-4-bromo-2-hexyne
(R)-3-bromo-1-hexyne
(S)-4-bromo-2-hexyne
(S)-3-bromo-1-hexyne
None of the above
Br
15. Arrange these carbocations in order of stability (most to least).?
(a)
(b)
(c)
(d)
(e)
I>II>III>IV
III>II>I>IV
III>I>II>IV
II>III>I>IV
I>III>II>IV
16. What could be the possible product for the following reaction?
5
17. The second reaction in glycolysis involves the conversion of -D-glucopyranose 6-phosphate (I) to
-D-fructofuranose 6-phosphate (II) under the catalysis of phosphoglucoisomerase. Which of the
following can best describe the relationship between compound I and II?
-D-glucopyranose 6-phosphate
(a)
(b)
(c)
(d)
(e)
-D-fructofuranose
6-phosphate
They are structural isomer to each other.
They are diastereomer to each other.
They are enantiomer to each other.
They are identical.
None of the above
18. What could be the major product for the following reaction?
HBr
major product?
Br
Br
(a)
Br
Br
(c)
(b)
(d)
(e) None of the above
19. What will be the major product in its most stable conformation from the following reaction?
H2
Pd/C
(a)
product?
(b)
(c)
(d)
OH
6
(e) None of the above
20. Brominated vegetable oil (BVO) has been used to stabilize citrus-flavored soft drinks since 1931. Its
high density helps the droplets of natural fat-soluble citrus flavors stay suspended in the drink. BVO can
be prepared by reacting vegetable oil, which contains unsaturated fatty acid, such as oleic acid, with
bromine. Without specifying the R group for the following representative structure of vegetable oil,
what will be the products from bromination?
(a)
(b)
(c)
(d)
(e)
I, IV
I, II
III, IV
II, III
None of the above
21. Which is a diastereomer to the compound circled in the box?
(a)
(b)
(c)
(d)
(e)
I
II
III
IV
None of the above
7
22. Coniine is a poisonous alkaloid found in poison hemlock and the yellow pitcher plant as a mixture of
R and S isomers. One method to separate the R and S coniine is by addition of a chiral acid and
separation of the salt of diastereomers by recrystalization, a process called resolution.
Which of the following acid can be used to achieve the separation of R and S coniine?
23. How many chiral carbons (not chiral amines) are present on Amoxicillin, an antibacterial drug?
(a)
(b)
(c)
(d)
(e)
2
3
4
5
6
24. Which of the following compound is achiral?
(a)
(b)
(c)
(d)
(e)
I
II
III
IV
None of the above
8
25. What are the R and S assignments for carbon 2 (C2) and carbon 3 (C3) of cocaine?
(a)
(b)
(c)
(d)
(e)
C2 is R and C3 is R.
C2 is R and C3 is S.
C2 is S and C3 is R.
C2 is S and C3 is S.
None of the above
26. Which of the following compound is chiral?
(a)
(b)
(c)
(d)
(e)
I
II
III
IV
V
27. Ephedrine in its natural form, known as má huáng (麻黄) in traditional Chinese medicine, has been
documented in China since the Han Dynasty (206 BC – 220 AD) as an antiasthmatic and stimulant.
What are the correct R and S assignments that match the given systematic name of ephedrine?
(a)
(1R,2S)-2-(methylamino)-1-phenylpropan-1-ol
(b)
(1R,2R)-2-(methylamino)-1-phenylpropan-1-ol
(c)
(1S,2R)-2-(methylamino)-1-phenylpropan-1-ol
(d)
(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol
(e) None of the above
9
Terbinafine hydrochloride (commonly marketed as Lamisil) is a synthetic allylamine antifungal from
Novartis. Answer Q.28 based on the following structure and atom-labeling of Lamisil.
28. Which of the following description regarding Lamisil is incorrect?
(a)
(b)
(c)
(d)
(e)
Lamisil contains a chiral nitrogen atom (N2).
Lamisil contains a chiral carbon atom as C8.
Lamisil contains both cis and trans C=C.
Lamisil contains alkyne functional group.
None of the above.
29. How many chiral carbons are present on sucrose?
(a)
(b)
(c)
(d)
(e)
7
8
9
10
11
10
Mupirocin (Bactroban or Centany) is an antibiotic of the monoxycarbolic acid class. It was originally
isolated from Pseudomonas fluorescens NCIMB 10586. Mupirocin is bacteriostatic at low
concentrations and bactericidal at high concentrations. It is used topically and is effective against Grampositive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA).
30. How many chiral carbons are present on mupirocin?
(a)
(b)
(c)
(d)
(e)
7
8
9
10
11
Continue to the Next Page
11
II. The 7th reaction in citric acid cycle is the conversion of furamate into malate, a hydration reaction
catalyzed by furamase. Provide an electron-pushing mechanism for this reaction (Note: no need to
involve furamase in the mechanism but use H+ as the catalyst.). The resulting malate is in S
configuration (assignment). Draw the specific structure of (S)-malate. (10 points)
Next Page: Periodic Table & pKa Values
12
pKa Values for Some organic and Inorganic Acids
Acid
Formula
pKa
Conjugate Base
Ethane
CH3CH3
51
CH3CH2Ammonia
NH3
38
NH2Ethanol
CH3CH2OH
15.9
CH3CH2OWater
H2O
15.7
HO+
Ethylammonium ion
CH3CH2NH3
10.64
CH3CH2NH2+
Bicarbonate ion
HCO310.33
CO32Phenol
C6H5OH
9.95
C6H5OAmmonium ion
NH4+
9.24
NH3
Carbonic acid
H2CO3
6.36
HCO3Acetic acid
CH3CO2H
4.76
CH3CO2Benzoic acid
C6H5CO2H
4.19
C6H5CO2Phosphoric acid
H3PO4
2.1
H2PO4Hydronium ion
H3O+
-1.74
H2O
Sulfuric acid
H2SO4
-5.2
HSO4Hydrogen chloride
HCl
-7
ClHydrogen bromide
HBr
-8
BrHydrogen iodide
HI
-9
I-
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