Final-Exam-Practice
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Chem 51A, UCI
Prof. Weiss
Final Exam
Instructions:
You may
use model sets, but
no other
aids, including electronic devices, notes, etc.
Answer clearly with neat figures, which are necessary to ascertain whether you know the correct answer.
You can use the reverse side of the page as additional paper, but specify clearly the answer you would like to
have graded.
For mechanism problems, show all elementary steps including proton transfers.
Time allowed: 110 minutes.
Please make sure you have all
10
pages of this exam including the coverpage.
Part A. Multiple choice (60 pts).
Circle the correct answer(s) below.
Note:
some questions might require circling more than one choice.
1.
Which compound below would you expect to have the
highest
melting point?
2
. Which of the following is
NOT
a valid resonance structure of benzene?
3.
How are the molecules in the following pair related?
A) constitutional isomers
B) racemates
C) diastereomers
D) different molecules
4. Circle
the molecule in Question
3
(above) with the lower p
K
a.
H
N
O
O
H
N
O
A)
D)
B)
C)
:
:
:
H
A)
E)
B)
C)
D)
OH
O
H
O
OH
Possible
Earned
Part A
60
Part B
1
25
2
20
3
25
4
20
5
25
6
25
Bonus
6
Signature: _______
_____________
_
_______
_
__
_
_________
Seat Number
:
_________
_
_______
_
________
_
_
_
__________
Your signature below indicates that you agree
to abide by all U.C. Irvine regulations
concerning academic honesty. If this section is
incomplete, your exam might not be graded,
and a point penalty will be assessed.
Chem 51A, UCI
Prof. Weiss
5.
Which of the following carbons indicated with an arrow is
sp
2
hybridized?
6.
Consider the following molecule having three labeled protons, H
a
, H
b
, and H
c
. Rank these protons in order of
increasing acidity from left to right.
A) H
a
; H
b
; H
c
B) H
b
; H
a
; H
c
C) H
b
; H
c
; H
a
D) H
c
; H
b
; H
a
7.
How many
1
H NMR signals do you expect to see for the following compound?
A) 4
B) 5
C) 6
D) 7
E) 8
8.
Does the equilibrium of the following reaction lie to the left or right?
A) Left
B) Right
C) It cannot be determined. D)
K
eq
= 1
9.
Circle the compound below that you would expect to have the
lower
boiling point.
10.
Identify the enantiomer of the following molecule.
11.
Which of the following conformations of 1,2-dibromoethane is the most stable?
E)
All arrows indicate sp
3
-hybridized carbons.
B)
C)
D)
None of arrows indicate
sp
3
-hybridized carbons.
OH
b
H
c
H
a
Br
O
H
H
+
NH
3
OH
+
NH
4
A)
B)
C)
D)
O
O
O
O
Br
H
O
H
Cl
O
Br
Cl
O
Br
Cl
O
Br
Cl
O
Br
Cl
A)
B)
C)
D)
Chem 51A, UCI
Prof. Weiss
12.
What is the IUPAC name for the following compound?
Don’t worry about the stereochemistry of this
compound.
a. 3,3-diethyl-4-cycloheptyl-5,6-dimethylnonane
b. 3-ethyl-4-cycloheptyl-3,6,7-trimethyldecane
c.
3-ethyl-4-decyl-3,6,7-trimethylcycloheptane
d.
8-ethyl-6-cycloheptyl-4,5,8-trimethyl-decane
13.
Which of the following compound(s) is (are) chiral? Circle one or more compounds.
14.
Which reaction below is slowest?
15.
How many signal are expected to appear in the
13
C NMR spectrum of molecule
2
(right)?
A) 3
B)
4
C)
5
D)
6
16.
Based upon the following mass spectrum, the compound contains ___(choices below)___________.
A) one bromine
B) one chlorine
C) two bromines
D) Both A & B
E) none of the above.
N
H
HO
Br
Br
Br
Br
A)
B)
C)
D)
OH
HO
O
O
2
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Chem 51A, UCI
Prof. Weiss
17, 18, 19, 20.
Use the following reaction coordinate diagram to answer questions below.
17.
What step has a negative
Δ
G?
A) A to B
B) B to C
C) A to C
18.
What is the rate determining (limiting) step?
A) A to B
B) B to C
C) A to C
19.
How many transition states are present in the reaction coordinate diagram?
A) 0
B) 1
C) 2
D) 3
E)
4
20.
This reaction is
A) hyperthermic
B) exobaric
C) endothermic
D) exothermic
E)
Cannot be determined.
Part B.
Short answers and fill in the blanks.
1.
(25 points) The following questions refer to the structure of (+)-psiguadial D below.
A related compound was
recently synthesized by Prof. Sarah Reisman at Caltech.
1.1.
Draw
all lone pairs on the structure of (+)-psiguadial B above.
1.2.
Label
the
hybridization state
of each oxygen atom (place the label close to the O atom).
1.3.
Next to the label for each oxygen atom,
label
the functional group that includes the oxygen.
1.4.
What is molecular formula of the product?
________________________________________
1.5.
What is the absolute configuration of the stereocenter marked with an arrow?
____________________
O
OH
OH
O
H
H
O
H
(+)-psiguadial D
Chem 51A, UCI
Prof. Weiss
2.
(20 points)
2.1.
Draw the most stable Newman projection for the molecule below looking down the bond indicated
by the arrow.
2.2.
Fill-in the box to predict the product of the reaction below.
2.3.
Draw an arrow-pushing mechanism for the reaction shown above using curly arrows to indicate the
movement of electrons.
2.4.
Fill-in the box to show the starting materials for the reaction.
3.
(25 points) Answer questions regarding the molecule
1
shown on the right.
3.1.
Draw both chair conformations of this molecule.
3.2.
Label the more stable and less stable chair conformations above.
3.3.
What is the IUPAC name of molecule
1
? Indicate the compound’s absolute stereochemistry.
3.4.
What type of compound is molecule
1
?___________________________________
3.5.
Is molecule
1
likely to be soluble in water?
(circle one)
YES
or
NO
3.6.
What is the optical rotation of a 1:1 mixture of molecule
1
and its enantiomer?
__________________
HO
NH
2
:
+
H
2
O
N
:
+
H
2
O
:
1
OH
Chem 51A, UCI
Prof. Weiss
4.
(20 points)
4.1.
Draw
an arrow-pushing mechanism for the following reaction.
4.2.
If you double the concentrations of molecule
1
and NaOH, what will happen to the rate of the reaction?
4.3. Draw
a reaction coordinate diagram for this reaction.
Br
NaOH
+
NaBr + H
2
O
1
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Chem 51A, UCI
Prof. Weiss
5.
(25 points) Use the following spectra to answer the questions below for a compound with the molecular
formula of C
4
H
8
O
2
.
5.1. Identify
the spectra above with the correct following labels (not all used):
1
H NMR,
13
C NMR, MS, IR, and
UV-Vis.
5.2.
What is the mass of this compound (include units)?__________________
5.3.
Based on the IR spectrum, what key functionality is present in this molecule?_______________________
5.4.
Propose a structure of this compound:
5.5.
Based on your proposed structure,
add
the
1
H integration associated with each signal in the
1
H NMR
spectrum.
5.6.
Draw a
13
C NMR spectrum for the compound above.
intensity
Chem 51A, UCI
Prof. Weiss
6.
(25 points)
6.1.
Is a carbonyl carbon an
electrophile
or
nucleophile
? To explain your choice, draw a resonance
structure, and use 1 concise sentence.
6.2.
Draw
two
resonances structures for each of the molecules below, and
circle
the lowest energy resonance
structure.
Include curly arrows showing the movements of electrons, resonance arrows, and lone pairs.
6.3. Label
each compound below as chiral, meso, or neither.
6.4.
(Fill-in the blanks to complete the following sentence)
A __________________________accelerates a chemical reaction by _________________________
the ____________________________________ of activation.
Bonus!
(6 points, no partial credit)
Name the two scientists who were awarded the 2003 Nobel Prize in
Medicine or Physiology for their contributions to the development of Magnetic Resonance Imaging.
O
O
NO
2
HO
CH
3
H
3
C
Cl
Cl
OH
H
HO
Chem 51A, UCI
Prof. Weiss
Reference Information
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