Practice Exam I - Ocred
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307
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Chemistry
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Feb 20, 2024
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MCI. Sabinene is shown below. How many hydrogen atoms does a molecule of sabinene have? [You MUST fill in your
answer under the MULTIPLE CHOICE RESPONSE SECTION on the FRONT PAGE to receive credit for this question.]
(3 points)
a. >16
b. 16
c. 15
d. 14
e. <14
sabinene
MC2. Which of the following structures is 2-chloro-3-ethyl-4-nitrophenol? [You MUST fill in your answer under the
MULTIPLE CHOICE RESPONSE SECTION on the FRONT PAGE to receive credit for this question.]
(3 points)
None of the other answers
OH d
MC3. How many non-bonded electron pairs need to be added to the structure shown to make it correct? How many positive charges need to be added? How many negative charges need to be added? [You MUST fill in your answer
under the MULTIPLE CHOICE RESPONSE SECTION on the FRONT PAGE to receive credit for this question.]
(3 points)
a. 4 pairs, one positive charge, one negative charge
b. 3 pairs, no positive charge, no negative charge ))
c. 3 pairs, no positive charge, one negative charge N
d. 2 pairs, one positive charge, one negative charge H,C__
(__ H
e. None of the other answers \,
MC4. The lone pair of electrons on the nitrogen in pyrrole derivative 1 is expected to be localized or delocalized over which atoms? [You MUST fill in your answer under the MULTIPLE CHOICE RESPONSE SECTION on the FRONT PAGE
to receive credit for this question.]
(3 points)
a. Delocalized overall the ring atoms
b. Localized only on nitrogen
c. Delocalized only on the nitrogen and two of the carbons
d. Delocalized only on the carbon atoms
e. None of the other answers
H
3
C
H
3
C
CHa
CHa
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MC5. Two of the possible conformations of methylcyclopentane are shown below. Select the statement that correctly indicates which is expected to be more
stable and correctly justifies the answer. [You MUST fill in your answer
under the MULTIPLE CHOICE RESPONSE SECTION on the FRONT PAGE to receive credit for this question.]
(3 points)
A
H
B
a. A, because there are no diaxial interactions between the methyl group and the ring in A, but there are two such interactions in B.
b. B, because there are no diaxial interactions between the methyl group and the ring in A, but there are two such interactions in B.
c. A, because there are two gauche interactions between the methyl group and the ring in A but there are no such interactions in B.
d. B, because there are two gauche interactions between the methyl group and the ring in A but there are no such interactions in B.
e. The other answers are not correct.
MC6. Given a process in which conformer A in equilibrium with conformer B, which expression is equal to the free energy of the process? [You MUST fill in your answer under the MULTIPLE CHOICE RESPONSE SECTION on the
FRONT PAGE to receive credit for this question.]
(3 points)
a. [B]/[A]
b. -RTInKeq
c. 100(K
eq
/l+K
eq
)
j e-(AG/RT)
e. The other answers are not correct.
MC7. For the structure drawn, a relationship between A and B is which of the following? [You MUST fill in your answer
under the MULTIPLE CHOICE RESPONSE SECTION on the FRONT PAGE to receive credit for this question.]
(3 points)
a. staggered
b. 1,3-diaxial
c. eclipsing
d. gauche
e. The other answers are not correct.
MC8. How many of these structures represent identical molecules (drawn differently or in different conformations)? [You MUST fill in your answer under the MULTIPLE CHOICE RESPONSE SECTION on the FRONT PAGE to receive
credit for this question.]
(3 points)
a. 3
b. 2
c. 1
d. 0
e. The other answers are not correct.
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MC9. Which of the following statements best describes the relationship between compounds shown? [You MUST fill In
your answer under the MULTIPLE CHOICE RESPONSE SECTION on the FRONT PAGE to receive credit for this
question.]
(3 points)
a. They are constitutional isomers.
b. They are diastereomers.
c. They are stereoisomers.
d. They are the meso structures.
e. The other answers are not correct.
1. OA. Use the template provided to draw both chair conformers of the compound shown. (3 points)
2. OA. Use the template provided in the box to convert the structure shown into Newman projections sighting down the C2-C1 bond and the C4-C5 bond. Note that the C3 and C6 carbons are labeled and your answer must maintain this orientation. Add the appropriate hydrogens and functional groups to the Newman projections (ignore the hydrogen atoms on C3 and C6). (3 points)
3. OA Indicate the number of sp
1
, sp
2
, and sp
3
carbon
atoms in the structure shown. Place your answer in the appropriate box. Only the answers in the boxes will be graded. (3 points)
4.
OA. Give an acceptable systematic name for the structure drawn. Assume it is racemic. Place your answer in the box. Only the answer in the box will be graded. (3 points)
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M CIO. Carefully study this structure. How many chiral centers are there in this molecule? [You MUST fill in your answer
under the MULTIPLE CHOICE RESPONSE SECTION on the FRONT PAGE to receive credit for this question.]
(3 points)
a. 3
b. 2
c. 1
d. 0
e. The other answers are not correct.
5.
OA. Use the template to draw the structural formula of (/?)-4-bromo-trans-2-pentene. Draw in the hydrogens on the
double bond and add carbons to the main chain if necessary. Use wedges and/or dashes to clearly indicate the
configuration of the chiral center. (3 points)
6. OA. Using ONLY ONE of the templates provided convert the structure of the difluoro compound shown into the lowest energy Newman projection looking down the C3-C4 bond. (3 points)
C(CH
3
)
3
7. OA. Draw a square around the alcohol, a triangle around the aldehyde, and a circle around the alkene functional groups of the molecule shown. Be clear, ambiguous answers will not receive credit. (3 points)
OA. Using ONLY ONE of the templates provided convert the structure shown below into the lowest energy chair conformation. Base your answer on the energy difference for equilibration of monosubstituted cyclohexanes of ethyl [AG° (equatorial-axial) = -1.8 kcal/mol] and of vinyl (AG° (equatorial-axial) = -1.7 kcal/mol). (3 points)
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MCII. What is the relationship between the two structures drawn? [You MUST fill in your answer under the MULTIPLE
CHOICE RESPONSE SECTION on the FRONT PAGE to receive credit for this question.]
(3 points)
a. These are diastereomers.
b. These are the same.
c. These are enantiomers.
d. These are not stereoisomers nor are they identical.
e. The other answers are not correct.
9. OA. Rank the expected boiling points of the compounds shown below from highest to lowest.
Place your answer appropriately in the box. Only the answer in the box will be graded. (3 points)
10. OA. A carbanion is a species in which a carbon atom has eight electrons and is bonded to only three groups. What is the expected hybridization of a carbanion - when the charge is delocalized over other atoms in addition to that
carbon?
Place your answer in the box. Only the answer in the box will be graded. (2 points)
11.
OA. Guanidinium ion has four important contributing resonance forms, shown below. Mark the box below the least important resonance form with an X. If two or more contribute equally and are least important, mark them with an X. Place your 'X' marks) in the appropriate box(es). Only the answers in the boxes will be graded. (2 points)
12. OA. Draw a structural formula for 2-fert-butylcyclobutanone. Indicate the number of stereocenters in this molecule in the small box. Draw the structure in the large box. Only the answers in the boxes will be graded. (3 points)
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MC12. Is it possible for a meso compound to have a molecular dipole? [You MUST fill in your answer under the MULTIPLE
CHOICE RESPONSE SECTION on the FRONT PAGE to receive credit for this question.]
(3 points)
a. Yes, because the molecular dipole is always aligned with the bond dipole.
b. Yes, because a mirror plane does not necessarily cancel dipoles.
c. No, because meso compounds are superimposable with their mirror image.
d. No, because meso compounds are necessarily symmetric which will lead to bond dipoles canceling.
e. The other answers are not correct.
13.
OA. For the structures shown below, draw a square
around each compound that can function as a hydrogen bond
donor to water in aqueous solution. (2 points)
14.
OA. Design a cyclic anion composed of only five carbons and five hydrogens such that the negative charge is shared equally by each of the five carbon atoms. Draw the structure of this anion in the box. Only the answer in the box will be graded. (3 points)
15. OA. Use the template provided to convert the cyclohexane derivative shown below into the lowest energy chair conformation. Be sure to clearly depict axial and equatoral correctly. (2 points)
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MC13. Which of the following statements best describes the compound shown? [You MUST fill in your answer under the
MULTIPLE CHOICE RESPONSE SECTION on the FRONT PAGE to receive credit for this question.]
(3 points)
a. E and chiral
b. Zand chiral
c. E and achiral
d. Zand achiral
e. The other answers are not correct.
16. OA. Use the template provided to draw a Fischer projection of the compound drawn. Show all the atoms in this compound - including hydrogen. (2 points)
17. OA. Use the template provided to draw the condensed structure of (Z)-3-chloro-2-methyl-2-butenoic acid. Add the hydrogen(s) on the double bond and show all the atoms in this compound. (2 points)
18.
OA. A standard solution of a reference compound of enantiomerically pure l-(-)-ta rta ri c acid has an optical rotation of: -12°. A standard solution of a sample that contained only tartaric acid - but in an unknown ratio of the two enantiomers (d and I) - was found to have an optical rotation of: +6°. Based on these data what percent of each enantiomer of tartaric acid is in the sample? Place your answer in the box. Only the answer in the box will be graded. (2 points)
% of d (+) tartaric acid
% of 1 (-) tartaric acid
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MC14. Which statement best describes the stereochemistry of the inositol derivative shown? [You MUST fill in your
answer under the MULTIPLE CHOICE RESPONSE SECTION on the FRONT PAGE to receive credit for this question.]
(3 points)
a. The chiral centers are all of the 5 configurations and the molecule is chiral.
b. The chiral centers are all of the R configurations and the molecule is achiral.
c. The chiral centers include both R and S configurations and the molecule is chiral.
d. The chiral centers include both R and S configurations and the molecule is achiral.
e. The other answers are not correct.
19. OA. Give the approximate bond angles indicated below for l-penten-4-yne: (3 points)
HO—C CH2—CH— CHa
a) C2-C3-C4 b) C3-C4-C5 c) H-Cl-H 20. OA. What is the correct (IUPAC) name for l,l-dimethyl-l-propen-3-ol? Place your answer in the box. Only the answer in the box will be graded. (3 points)
21. OA. For the structure shown, rank the bond lengths (labeled a, b and c) from shortest to longest. Place your answer in the box. Only the answer in the box will be graded. (2 points)
H
O=N------O----C--- CH,
4 I ------- ------ a
H
c b
22. OA. Draw alanine, C:H7NO2, a molecule that has a carboxylic acid group, a methyl group, and a primary amino group (the nitrogen has two hydrogen atoms directly attached to it). Place your answer in the box. Only the answer in the box will be graded. (3 points)
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Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
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Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY