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Exam 01 key.pdf
Organic Chemistry I (University of Minnesota, Twin Cities)
Studocu is not sponsored or endorsed by any college or university
Exam 01 key.pdf
Organic Chemistry I (University of Minnesota, Twin Cities)
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Problem
1
(10 points).
Electronic structure. Answer the questions below as described.
a
) Sulforphane (below) is a compound that is released when broccoli is chopped up. In the provided
boxes, supply the answers about the atoms and bonds in its molecule:
Hybridization of sulfur labeled as S1:
Expected C-N-C angle in the molecule
:
Orbitals that make the C=N bond, from each atom’s side:
Bond B1,
σ-bond:
C
-
N
π-bond:
C
-
N
b
) Which of the following molecules will be the most polar
(check box)?
O
2
CO
2
CS
2
SO
2
c
) Which of the following compounds will have the highest boiling point
(check box)?
CF
4
NF
3
OF
2
LiF
Problem 2
(6 points).
Lewis structures.
Answer the questions below as described.
a
) In the following Lewis structure indicate what formal charges should be on each of the specified
atoms. Write “0” for no charge, and “-1”, “-2”, … and “+1”, “+2”, ... for positive and negative charges
Charge on O:
Charge on N:
Charge on C:
b
) What should be the overall charge of this molecule?
c
) How does the structure in a) relate to the structure below (check box)?
isomer
resonance form
not an isomer or a resonance form
N
C
O
O
C
N
B1
S
O
C
N
S
Sulforaphane
S1
sp
3
sp
3
120
sp
sp
2
p
p
-1
+1
-1
-1
LP + 3 bonds
N is sp
2
LP + 2 bonds
C is sp, N is sp
2
O=O bond non-polar, in CO
2
and CS
2
polarities cancel out. In SO
2
they do not – it’s bent
C
O
O
C
S
S
S
O
O
LiF is ionic, so stronges IMF. NF
3
and OF
2
are polar (dipole-dipole), CF
4
is non-polar
Different order of connection: OCN vs. OCN: isomer
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Problem 3
(8 points).
Resonance. Answer the questions below as described.
a)
Draw (as a Lewis structure
, showing lone pairs and formal charges) a significantly contributing
resonance structure for the following
N
N
C
C
H
H
b)
Draw (as a Lewis structure
, showing lone pairs and formal charges) a significantly contributing
resonance structure for the following
O
C
C
O
H
H
H
c
) How do the following resonance forms compare by relative contribution
(check box)
A > B > C
A > C > B
B > A > C
B > C > A
C > B > A
C
H
H
H
O
H
N
B
C
H
H
H
O
H
N
C
A
H
H
H
O
H
C
N
Problem
4
(9 points). IUPAC nomenclature. Answer the questions below as described.
a)
Draw
2,3-dicyclopropylbutane
b)
Draw
trans
-1-ethyl-3-
tert
-butylcyclopentane
c
) Write the IUPAC name for the following structure
3-ethyl-2-methylhexane
or
:A-B=C ↔A=B-C: pattern
C
N
H
H
:A-B□ ↔A=B pattern
C
C
H
H
H
O
Octets; + on N
No octet
on C
Octets;+ on O
Longest chain with most substituents highlighted
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Problem
5
(19 points).
Acid-base reactions. Answer the questions below as described.
a)
Which is a stronger
acid
(check box)
b)
Which is a stronger
base
(check box)
A
B
O
H
O
H
vs.
A
B
A
B
O
S
vs.
A
B
c)
Which is a stronger
acid
(check box)?
A
B
OH
HO
OH
HO
vs.
A
B
d)
Which is a stronger
acid
(check box), and
briefly explain your choice
Briefly explain your choice
A
B
OH
O
OH
O
vs.
A
B
e)
Show the electron flow
and draw
the favored acid-base reaction between the following acid and base
+
O
N
H
+
OH
N
f)
Show the electron flow
and draw
the favored acid-base reaction between the following acid and base
+
O
H
+
O
Conjugate base of B is stabilized by
resonance, conjugate base of A is not
Note: partial credit for inductive effect
reasoning (it is less significant)
H-O vs. HO
⊕
Conjugate base of HOR vs. HSR
O is farther from OH,
closer
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Problem
6
(8 points): Lewis acid-base reactions. For the following Lewis
acid-base reactions show
electron flow
, and draw
the Lewis acid-base adduct resulting from their reaction:
a
)
Al
Cl
Cl
Cl
+
С
O
H
H
С
O
H
H
Al
Cl
Cl
Cl
b
)
H
H
H
C
+
H
H
O
H
H
H
C
O
H
H
Problem
7
(10 points).
Conformations around a single bond.
For questions a-c consider the conformation A of 2-methylpentane over C2-C3 bond shown below,
along with the energy diagram of its rotation around that bond.
C
2
H
5
H
H
H
H
3
C
CH
3
A
a)
What point on the energy diagram corresponds to A (check box)?
I or VI
II or IV
III
V
b)
What is the dihedral angle between H and C
2
H
5
in conformation A?
c)
Draw (as a Newman projection
) the conformation that corresponds to point III on the diagram:
C
2
H
5
H
H
H
3
C
CH
3
H
d
) What is the relative position of C
2
H
5
and H in the conformation shown in c)
eclipsed
gauche
anti
E
dihedral angle
I
IV
III
II
VI
V
60
Staggered: must be a dip. Less repulsion that in another staggered: One of the lower dips
The C-H and C-C
2
H
5
bonds forming the angle highlighted: gauche, 60
o
III is a dip, must be a staggered conformation.
A higher dip – so the staggered with greater repulsion than A:
2x CH
3
– C
2
H
5
gauche repulsions, A only has one.
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Problem
8
(12 points). Chair conformations. Answer the questions below as described.
a)
Using the blank chair templates below, draw the two chair conformations of the following compound
H
3
C
H
3
C
CH
3
CH
3
H
3
C
CH
3
CH
3
CH
3
H
3
C
b)
Indicate which is going to be more stable (check box)
the one on the left
the one on the right
both equal in stability
c)
Briefly explain your choice for b)
Two CH
3
s are equatorial, one axial
vs.
two axial, one equatorial
d)
Which of the following is the most stable conformation of
cis
-
1-isopropyl-4-methylcyclohexane
(check box)
H
3
C
CH
3
H
3
C
H
3
C
A
B
C
D
E
A
B
C
D
E
Will depend on the drawing above. For this one: on the right
Note: Other versions of it are possible
Less stabe: i-Pr axial
Not a cis-
Not a cis-
Not 1,3
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Problem
9
(6 points): Isomers. Answer the questions below as described.
a)
How would the following compounds relate to each other? (check box)
vs.
same
constitutional isomers
stereoisomers
not isomers
b)
How would the following compounds relate to each other? (check box)
H
CH
3
C
2
H
5
C
2
H
5
H
H
vs.
same
constitutional isomers
stereoisomers
not isomers
c)
How would the following compounds relate to each other? (check box)
vs.
same
constitutional isomers
stereoisomers
not isomers
Problem 10
(12 points). Miscellaneous. Check the appropriate box for each question.
a)
How is the following reaction classified?
Reduction
Oxidation
Not a redox reaction
OH
H
H
O
H
H
H
b)
How is the following reaction classified?
Reduction
Oxidation
Not a redox reaction
H
O
Cl
H
H
c)
Which of the following alkanes will have the highest boiling point
?
A
B
C
D
E
A
B
C
D
E
d)
What type of strain is di-axial interaction?
torsional strain
angle strain
ring strain
steric strain
(continued on the next page)
C
5
, 1 ring
C
5
, no rings
Different composition
Different composition
C
2
H
5
C
2
H
5
H
H
H
H
3
C
C
7
C
6
C-H and C-O added
C-H, 2x C-Os, C-Cl added
B contains most Cs and no branches
Di-axial interaction is a repulsion between substituents in two axial positions
Repulsion between groups → steric repulsion → steric strain
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e)
What is a correct electron flow for the following resonance?
A
B
C
D
OH
H
H
OH
H
H
OH
H
H
OH
H
H
OH
H
H
OH
H
H
...
...
...
...
A
B
C
D
f)
Which of the following bonds is expected to be the shortest
?
C-H
C-O
C-C
H-H
The smaller the atoms, the shorter the bond. H is the smallest of atoms, so H-H
bond will be the shortest
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