210 Fa 15 Exam 1 KEY

Chem 210 Feldman & Maslak
FORM A KEY
Exam 1 Fall 2015
Chem 210 Sections 001 003

Exam 1
September 14, 2015
Printed Name: _KEY_____________________________ Section: _________

PSU eMail: ______________________________________
Signature: _______________________________________
FILL OUT AND TURN IN THIS FRONT PAGE WITH YOUR SCANTRON FORM. WE
WILL NOT PROCESS YOUR SCANTRON WITHOUT THIS COMPLETED AND SIGNED
FRONT PAGE.
1) There are 25 multiple-choice questions on this exam. Make sure that you have them all. Each
question is worth 4 pts.
2) On the Scantron sheet, make sure that you fill in your name (print), section, your student ID
number, and the test form (white cover = Form A, yellow cover = test form B).
3) You may take the exam booklet with you. Your score will be based solely on the information on
your Scantron form.
4) Needed data will be provided. The data values provided with the exam will be the ones that you
must use to arrive at an answer.
5) There is no penalty for guessing.
6) No electronic devices of any kind are allowed. This proscription includes, but is not limited to,
calculators, cell phones, cameras, etc. Exposing such devices during the exam, even if they are
not in use, is grounds for imposing a "zero" grade on the exam.
7) Use of molecular model kits is encouraged.
8) Blank paper is provided at the end of the exam for your convenience. You may not use any other
source of paper during the exam.
9) An answer key will be posted soon after the end of the exam.
1
Copyright 2015 Ken Feldman & Pshemak Maslak Use of this document by any third-party forprofit concern (i.e., PSU KnowHow, Nittany Notes) is in violation of US copyright law. All rights
reserved.
FORM A KEY
Exam 1 Fall 2015
2
reserved.

1.
FORM A KEY
Exam 1 Fall 2015
Mike Joyce is the person to see for

(a) a lost exam score.
(b) signing up for a make-up or conflict exam.
(c) an exam scheduling issue.
(d) all of the above.
(d) is the correct answer.
2.
The square of the 4p atomic orbital wavefunction is plotted below. Where is the nucleus of the
atom?
(b)
2 (a)
(c)
0
0
(d)
The nucleus of the atom is always at r = 0, since r is the distance from the nucleus. (a) is the
correct answer.
3.
For atoms in the same row of the periodic table, why is the s orbital lower in energy than the p
orbital?
(a) The s orbital is more electronegative than the p orbital.
(b) The s orbital is less electronegative than the p orbital.
(c) The s orbital has less electron density near the nucleus than the p orbital.
(d) The s orbital has more electron density near the nucleus than the p orbital.
Orbitals are not electronegative that is a property of atoms, so (a) and (b) can't be right. s
Orbitals hold their electrons closer to the nucleus compared to the same row's p orbitals,
leading to a stronger electrostatic attraction. (d) is the correct answer.
3
reserved.
4.
FORM A KEY
Exam 1 Fall 2015
Which electronic state of tellurium (Te) best describes the tellurium in TeH2 shown below?
(c) p
(a) sp3
Te
H
sp2
H
90o
5
(d) sp
(b) p
sp2
The 90o HTeH angle is the clue that indicates the hybridization ("geometry specifies
hybridization"). Of the choices listed, this angle is only consistent with the angle between two
p orbitals. Unhybridized Te (answer (b)) has two open valences that are pure p orbitals. The
other answers would have a geometry other than 90o between the open valence orbitals. (b) is
the correct answer.
5.
Which hybrid orbitals overlap to form the bond indicated by in the structure below?
(a) Two sp hybrid orbitals.

(b) Two sp3 hybrid orbitals.
(c) An sp and an sp3 hybrid orbital.
(d) Two s orbitals.
The bond indicated by is a single bond that is defined by the overlap of two sp orbitals, one
each contributed from the two sp-hybridized carbons. (a) is the correct answer.
4
reserved.

6.
FORM A KEY
Exam 1 Fall 2015
Which of the following individual molecules has (have) a dipole moment? Note that these
Lewis dot structures don't necessarily show the actual geometry of the molecule.
F
C
H
(a) 1
(b) 2
H
C
F
3
(c) 3
(d) 1 and 2
(e) 1 and 3
A molecule will show a dipole moment if it has polar bonds (bond dipoles) and a threedimensional structure in which the bond dipoles do not cancel. Molecules 1 and 3 are planar
with all atoms (and bond dipoles) in one plane. Since the matching bond dipole vectors are
pointing in the opposite direction (180o) there is no net molecular dipole. In molecule 2 the
central carbon is sp hybridized and the two bonds have to be 90o to each other as each uses a
different atomic p orbital on carbon for its construction. As a consequence, the two H-C-F
groups at the termini of the molecule are also perpendicular. In this case, the bond dipoles do
not cancel. Note that in 3 there are two sp hybridized carbons with the central bond
perpendicular to both terminal bonds which results in coplanar H-C-F groups. The correct
answer is (b).
F
H
H
F
1
7.
F
H
H
C
F
F
H
C C
Which molecule contains a nitrogen atom of an sp hybridization type?

(a) HNNH
(b) HNCH2
(c) HCN
(d) H2NNH2
The Lewis dot structures are illustrated below. Only (c) has an sp-hybridization-type nitrogen.
(c) is the correct answer.
(a)
H
N N
sp2
(b)
H
N
sp2
(c) H
N
sp
HH
(d) H N N
H sp3
5
reserved.

8.
FORM A KEY
Exam 1 Fall 2015
What are the formal charges on the nitrogen and oxygen atoms in the following structure?
(a)
(b)
+1
+1
(c)
(d)
+1
Neutral nitrogen has 5 valence electrons and 4 electrons in the Lewis structure (LSE), thus the
formal charge of +1. Neutral oxygen has 6 valence electrons and 7 electrons in the Lewis
structure (LSE) and therefore a formal charge of 1. (d) is the correct answer.
9.
The hybrid orbital that carbon contributes to one CF bond in difluoromethane (1) below has
22% s-character. How much s-character can be assigned to the hybrid orbital that carbon
contributes to one CH bond?
F
(a) 22%
(b) 28%
H
H
(c) 25%
(d) 56%
The % s-character in the hybrid orbital that carbon uses in one CH bond can be calculated as
follows: There is 22% s-character in the hybrid of one CF bond, and so there must be 44% scharacter committed by carbon to both equivalent CF bonds. Since there is a total of 100% scharacter, 56% remains to use in the two equivalent CH bonds, or 28% s-character in each C
H bond. (b) is the correct answer.
10.
The FCF bond angle in 1,1-difluorocyclopropane (1) is 109.5o. What are the hybrid orbitals
used to form the CC bonds from the CF2 carbon to the adjacent carbons?
1
F
F
(a) sp3
(b) sp2
(c) sp5
(d) pure p
A 109.5o FCF bond angle indicates that the canonical sp3 hybrids are used (i.e., cos(109.5) =
1/3, or m = 3). If two of the four hybrid orbitals on the CF2 carbon are sp3 hybrids, then the
symmetry of the molecule demands that the other two orbitals that form the two equivalent C
C bonds are sp3 hybrids also. (a) is the correct answer.
6
reserved.
11.
FORM A KEY
Exam 1 Fall 2015
Which bond angle between orbitals on the same atom is not possible?
(a) 80o
(b) 90o
(c) 94.3o
(d) 180o
The bond angle between hybrids can't be any smaller than the 90o angle between pure p
orbitals, or m (via cos() = 1/m) would be a negative number. (a) is the correct answer.
12.
Which carbanion has the largest amount of s-character in the hybrid orbital holding the lone
pair?
(a)
A
A
109.5 o
(b)
B
B
(c)
119 o
C
C
107 o
(d)
D
D
98o
The smaller the angle between the same groups, the less s-character in the hybrids extending
from the central atom. If the central atom invests less s-character in the bonds to the attached
groups, then it can invest more s-character in the lone pair-containing hybrid orbital. By this
logic, answer (d), with the smallest bond angle, would have the most s-character in the lone
pair's hybrid orbital. (d) is the correct answer.
7
reserved.

13.
FORM A KEY
Exam 1 Fall 2015
Which structures are resonance forms of each other?

H
and
II
III
(a) I only
(b) II only
(c) III only
and
R2
R2
R1
R1
and
(d) I and II only

(e) I and III only
(f) II and III only
(g) I, II, and III

(h) none
The definition of resonance forms involves only electron motion but no nuclear motion. Both I
and II involve nuclear motion; in I, the explicitly shown "H" shifts between C and O. In II, the
radical inverts, which involves nuclear motion note that the two species are not identical. In
III, however, all of the atoms remain in the same location for the two structures; only the
electron pair that defines the bond moves. This electron pair is in the bond in the left-hand
structure, but it is localized on the right-hand carbon in the right-hand structure. So, the
structures shown in III are legitimate resonance forms of each other. (c) is the correct answer.
14.
Which statement best describes the negative charge's location in 1a/1b below?
O
O
a
1a
1b
(a) It is more on carbon a.

(b) It is more on the oxygen.
(c) It is equally distributed on carbon a and the oxygen.
Whereas resonance forms do shown the (re)distribution of charge, that charge distribution does
not necessarily have to be equal between the atoms involved. In the case of 1a/1b, the
electronegative oxygen is better able to accommodate the excess electron density of the
negative charge, so the resonance form 1a will be a larger contributor to the overall structure.
(b) is the correct answer.
8
reserved.

15.
FORM A KEY
Exam 1 Fall 2015
Which species is not a resonance form of munchnone 1?

O
(a)
1
H
N
+
O+
(b)
O+
(c)
+
H
(d)
N
N
+
Answer (c) has a positive charge on a carbon that has a full complement of valence electrons,
which is an impossible situation. All of the other answers meet the criteria for resonance
forms. (c) is the correct answer.
16.
The MOs for O2 molecule are built by pairwise overlap of atomic orbitals on both oxygen
atoms. Atomic s and p orbitals do not mix because of the large energy difference between
them. One set of p orbitals overlaps head-on giving a /* combination, while the other two
sets of p orbitals overlap sideways, giving / * combinations. How many unpaired electrons
are there in the O2 molecule?
(a)
(b)
(c)
(d)
(e)
The MOs for O2 can be constructed as shown in the scheme below:
9
reserved.
FORM A KEY
Exam 1 Fall 2015
The mixing of oxygens s orbitals results in bonding and antibonding MOs. These are the two
lowest energy orbitals in the scheme. Mixing of two p orbitals head-on gives a -type MO, which
is third from the bottom in energy and the corresponding * MO of highest energy. Sideway
mixing of the remaining two sets of two p orbitals results in two and two * MOs.
The 12 valence electrons from the two oxygens occupy the 7 lowest energy MOs, with the two
highest energy (*) MOs singly occupied.
The two highest-energy MOs each contain one electron, which, according to Hunds rule, have
parallel spins. There are two unpaired electrons in O2 (c) is the correct answer.
10
reserved.

17.
FORM A KEY
Exam 1 Fall 2015
Amine borane 1 prefers to exist as the planar form 2.

+
B N
B N
1
What does the LUMO of the B=N bond look like?

(a)
B N
(b)
(c)
B N
(d)
B N
B N
To solve this problem, two types of insight are necessary: (1) The B=N bond and antibond
(B=N) are formed like any other system, by combining the atomic p orbitals contributed
from the individual atoms. The and * bonds are formed from an empty p orbital on B and a
filled p orbital on N (see below); the construction of this MO scheme differs from a typical
system like C=C or C=O, where each atom contributes a single electron. Nevertheless, it is a
strength of the MO approach to describing bonding that it can accommodate any electron
contribution scheme; first the AO's mix, and then the electrons, however many and wherever
they start from, are added in to the derived MO's. (2) The atom with the greater
electronegativity (N in this case, inspect the periodic table at the end of the exam) contributes
more to the HOMO, leading to large lobes on N compared to B. It also follows that the least
electronegative atom (= B) contributes more to the LUMO, leading to larger lobes on the B.
This description fits the MO picture shown in answer (a). (a) is the correct answer.
B N
E
B
N
B N
11
reserved.

18.
FORM A KEY
Exam 1 Fall 2015
Which molecular orbital shown below is the lowest energy one for the methyl cation 1?
1 H
+ H
H
(a) H
(b) H
(c) H
(d) H
The lowest energy MO always has zero nodes. That description only applies to the orbital
shown in (d). (d) is the correct answer.
19.
Which is the highest energy MO of carbonate 1?

O
O
O
1
(a) O
(b) O
(c) O
(d) O
The highest energy -type orbital will have the most nodes. That criterion is met only by
answer (b). (b) is the correct answer.
12
reserved.

20.
FORM A KEY
Exam 1 Fall 2015
The reaction between the allyl anion 1 and the allyl cation 2 to form 1,5-hexadiene (3) can best
be represented by interaction of which MO's?
(a)
(b)
(c)
(d)
MO from 1
MO from 2
HOMO
LUMO
HOMO
LUMO
HOMO
LUMO
LUMO
HOMO
This problem is particularly challenging because it requires you to apply the paradigm
presented in the hyperconjugation section (MO mixing leads to stabilization when one orbital
is filled and one is empty, and the most stabilization accrues when the two orbitals are more
similar in energy) to a chemical reaction. The MO's of 1 and 2 are illustrated below. The
filled/empty orbitals that are closest in energy (actually exactly the same in energy in this
simple MO picture) are the HOMO of 1 and the LUMO of 2. Their interaction upon bond
formation will lead to the most MO-based stabilization at the transition state. (c) is the correct
answer.
LUMO
LUMO
HOMO
HOMO
1
13
reserved.

21.
FORM A KEY
Exam 1 Fall 2015
Consider the hyperconjugative interaction between a CH orbital and a carbocation's empty p

orbital illustrated below left:
H
H
+
ao
vs.
do
no hyperconjugation
d
hyperconjugation
What effect will this hyperconjugative interaction have on the bond angle a and the bond
distance d, compared to the normal bond angle (ao) and normal bond distance (do) in a nonhyperconjugating system?
(a) a bigger than ao, d longer than do
(b) a bigger than ao, d shorter than do
(c) a smaller than ao, d longer than do
(d) a smaller than ao, d shorter than do
The hyperconjugative interaction illustrated above left actually increases the bonding between
the two carbons. So, the angle a decreases compared to ao and the distance d shortens
compared to do in order to maximize overlap of the MO's underlying this bonding increase. (d)
is the correct answer.
22.
Which of the marked bonds can participate in hyperconjugation?

(c)
(b)
H
(d)
+
(e)
(a)
Only bonds that can overlap with the p orbital of the carbocation can participate in
hyperconjugation. Of the marked bonds, only CC bond (b) is properly disposed for such
overlap. Examination of a 3D model may help to appreciate the shape of this molecule. (b) is
the correct answer.
14
reserved.

23.
FORM A KEY
Exam 1 Fall 2015
All of the systems illustrated below benefit from stabilization through aromatic resonance
energy to some degree. How many electrons are contained in the systems of each species?
H
H
_
(a)
(b)
(c)
(d)
(e)
(f)
4
4
6
6
4
6
6
6
6
6
4
4
6
8
8
6
6
8
Each system has 6 electrons in the cyclic system. With 1, two of these electrons happen to
reside on a single carbon (in the resonance form shown), whereas in 3, on carbon (in the
resonance form shown) has no electrons to contribute to the system. (d) is the correct
answer.
24.
How many constitutional isomers of dibromoadamantane (C10H14Br2) exist? [Hint: Building a

plastic model should prove helpful.]
adamantane, C10H16
(a) 5
(b) 6
(c) 7
(d) 8
There is no systematic way to calculate the number of constitutional isomers. You just have to
draw them out and count them. There are six. (b) is the correct answer.
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
15
reserved.

25.
FORM A KEY
Exam 1 Fall 2015
How many secondary hydrogens are there in the cycloalkane shown below?
(a)
(b)
(c)
(d)
(e)
The molecule has only two secondary carbons and four 2 hydrogens. (c) is the correct answer.
H
16
reserved.

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Chem 210 Feldman & Maslak

Exam 1 Fall 2015

Chem 210 Sections 001 003

September 14, 2015

Printed Name: _KEY_____________________________ Section: _________

Chem 210 Feldman & Maslak

Exam 1 Fall 2015

Chem 210 Feldman & Maslak

Exam 1 Fall 2015

Mike Joyce is the person to see for

Chem 210 Feldman & Maslak

Exam 1 Fall 2015

(a) Two sp hybrid orbitals.

Chem 210 Feldman & Maslak

Exam 1 Fall 2015

Which molecule contains a nitrogen atom of an sp hybridization type?

Chem 210 Feldman & Maslak

Exam 1 Fall 2015

Chem 210 Feldman & Maslak

Exam 1 Fall 2015

Chem 210 Feldman & Maslak

Exam 1 Fall 2015

Which structures are resonance forms of each other?

(d) I and II only

(g) I, II, and III

(a) It is more on carbon a.

Chem 210 Feldman & Maslak

Exam 1 Fall 2015

Which species is not a resonance form of munchnone 1?

The MOs for O2 can be constructed as shown in the scheme below:

Chem 210 Feldman & Maslak

Exam 1 Fall 2015

Chem 210 Feldman & Maslak

Exam 1 Fall 2015

Amine borane 1 prefers to exist as the planar form 2.

What does the LUMO of the B=N bond look like?

Chem 210 Feldman & Maslak

Exam 1 Fall 2015

Which is the highest energy MO of carbonate 1?

Chem 210 Feldman & Maslak

Exam 1 Fall 2015

Chem 210 Feldman & Maslak

Exam 1 Fall 2015

Consider the hyperconjugative interaction between a CH orbital and a carbocation's empty p

Which of the marked bonds can participate in hyperconjugation?

Chem 210 Feldman & Maslak

Exam 1 Fall 2015

How many constitutional isomers of dibromoadamantane (C10H14Br2) exist? [Hint: Building a

Chem 210 Feldman & Maslak

Exam 1 Fall 2015

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Printed Name: _KEY_____________________ Section: _