LAST NAME :______ ________________
FIRST NAME :___ _________________________
(Please print your name on next page also – If you do this you get 1 EC pt!!)
Total Pages: 7
Questions: 14
Some of you missed this sadly!!
EXAM I
Spring 2015 (1/30/15)
Dr. Kingston
There are 7 pages to this exam. Check to make sure you have a complete exam. During tests and quizzes, all electronic devices (e.g., cell phones, iPods, laptops etc) and papers other than your test sheets must be put away and completely out of sight. All book bags, books, etc., as well as jackets, coats and hats, etc., are to be on the floor UNDER your seat. Please refrain from conversation until you leave and are outside the door. Thank you.

2
LAST NAME :___________________________________
FIRST NAME :__________________________________
EXAM I
Spring 2015 (1/30/15)
Dr. Kingston
Page
3
4
5
6
Total
Points
35 pts
17 pts
26 pts
25 pts
103 pts
Score
________
________
________
________
________

3
1.
True/False (2pts each) Circle T or F as appropriate. a. T | F
The following two structures are resonance structures. b. T | F
The molecule of ammonia, NH
3
is example of a Lewis base. c. T | F
When comparing the relative strengths of acids, the stronger acid has the smaller value of K a
. d. T | F If ammonia, NH
3
were to behave as an acid, its conjugate base would be NH
2

ion. e. T | F A primary amine contains one N-H bond, a secondary amine contains two N-H bonds, and a tertiary amine contains three N-H bonds.
2. (6 pts) Circle ALL the correct structures in the following list.
(3 pts) Fix the error(s) in the molecule/ion that you did not select in Question-2. 3.
4. Draw at least one structure meeting each of the following criteria. There could be more than one possible structure. But, just draw one structure for each of the following. a) (3 pts) Tertiary alcohol with a molecular formula, C
6
H
14
O b) (3 pts) Secondary amine with a molecular formula, C
5
H
13
N arene
5. (10 pts) Circle and label all the functional groups present in the artificial sweetener Aspartame whose structure is shown 
Carboxylic acid amide
Ester
1 o amine

4
6. a) (6 pts) Complete the following acid-base reaction between benzoic acid and dimethylamine by drawing the correct structure of the products (include lone pairs of electron and formal charges
Benzoic acid p K a
4.19 if any). Label acid, base, conjugate acid and conjugate base . Also,
Dimethyl ammonium ion show curved arrows to show how this acid-base reaction is happening between these two reactants.
10.7 b) (2 pts) Predict whether the above acid-base equilibrium reaction would favor reactant side (left) or product side (right)? Circle your choice.
Reactant side (left) Product side (right) c) (3 pts) Justify your answer for part-b by properly choosing an appropriate statement below. i) because, benzoic acid is stronger acid compared to dimethylammonium ion. ii) because, dimethylammonium ion is stronger acid compared to benzoic acid. iii) because, dimethylamine is a stronger acid compared to benzoic acid. iv) because, the conjugate base of benzoic acid is less stable. v) because, the reaction is irreversible.
7. (6 pts) Choose ANY THREE of the following and draw a correct Lewis structure. Include lone pairs of electrons, formal charges, if any. a) Butane b) Nitromethane, CH
3
NO
2
(Taken from Sapling) [Hint: Both oxygens are connected directly with N] c) The conjugate acid of nitromethane (Taken from Sapling) d) The conjugate base of acetic acid

8.
9.
5
Captopril is an angiotensin-converting enzyme (ACE) inhibitor used for the treatment of hypertension and some types of congestive heart failure. Answer the following questions related the structure of Captopril. a) (2 pts) Number of sp
3
– hybridized carbon atoms: ___ 7 ______ b) (2 pts) Number of sp
2
– hybridized carbon atoms: ____ 2 _____ c) (2 pts) Total number of pi bonds: _____ 2 ________ d) (2 pts) Total number of hydrogens present in this molecule: ___ 15 ____ e) (2 pts) Total number of lone-pairs of electrons present in this molecule: ___ 9 _____
[a lone pair is 2 electrons, so list only the total number of pairs of electrons] f) (2 pts) What is the approximate bond angle at the sulfur atom indicated by an arrow-x . __ 109.5
o __ g) (4 pts) Give a brief bonding description for the single bond indicated by an arrow-y by completing the following sentence.
“It is a __ Sigma _____ ( sigma or pi ) bond formed by the __ head-on _____ ( head-on or side-way ) overlap of __
sp
2
– hybridized
_ orbital of Carbon with ___
sp
3
– hybridized
__ orbital of Nitrogen ”
(10 pts) Draw ALL the possible resonance structures for the starting carbocation shown in the box. To save you time, some blank skeletal structures are given which you could use to show different resonance structures. Remember to include necessary double bonds and formal charges, if any.
Put ‘X’ on the unused structures.
Show arrow-pushing of electrons when you go from one structure to another.

6
10. a) (3 pts) Circle the carbon that has the relatively more acidic hydrogen in the following molecule. b) (4 pts) Why did you choose that carbon? Justify your answer by briefly explaining the reason.
Include any structures if needed.
When the Hydrogen is removed, the resultant conjugate base can be stabilized by 2 resonance structures as shown in the picture.
11. (4 pts) Circle the molecule(s) that are non-polar . [Taken from Sapling] a) PCl
3 b) CO
2 c) SO
2
d) CH
2
Cl
2
e)
12.
Try to draw the Lewis structure and look at the molecular structure. If the bond polarity is cancelled due to the symmetrical structure, then the molecule will be non-polar
(4 pts) Show the direction of the polarity using the crossed arrow ( ) and assign δ+ and δ  on the atoms in each of the following bonds. Also, Circle the least polar bond .
δ+ δ 
P  Cl
δ+ δ
C 

N
δ
O
 δ+
 H
13. (4 pts) Which of the following is an example of a Lewis acid but not a Brønsted acid ? a) H
2
SO
4 b) HCl c) BCl
3 d) NaOH e) CH
3
OH
14. (6 pts) In each pair of compounds, circle the stronger acid.

7
Rb
0.8
Cs
0.7
F r
0.7
Na
0.9
K
0.8
1A
H
2.1 2A
Li
1.0
Be
1.5
Mg
1.2
Ca
1.0
Sr
1.0
Ba
0.9
Ra
0.9
3B
Sc
1.3
Y
1.2
La-Lu
1.0-1.2
Zr
1.4
Hf
1.3
4B
Ti
1.5
Nb
1.6
Ta
1.5
5B
V
1.6
Mo
1.8
W
1.7
6B
Cr
1.6
Increasing electronegativity
7B
Mn
1.5
Tc
1.9
(------8B------)
Fe
1.8
Ru
2.2
Co
1.9
Rh
2.2
Re Os Ir
1.9 2.2 2.2
Ni
Pt
1.9
Pd
2.2
2.2
Au
2.4
1B
Cu
1.9
Ag
1.9
Cd
1.7
Hg
1.9
2B
Zn
1.6
3A
B
2.0
Al
1.5
Ga
1.6
In
1.7
Tl
1.8
Si
1.8
Ge
1.8
4A
C
2.5
Sn
1.8
Pb
1.9
P
2.1
As
2.0
5A
N
3.0
Sb
1.9
Bi
1.9
S
2.5
Se
2.4
6A
O
3.5
Te
2.1
Po
2.0
I
2.5
At
2.2
Cl
3.0
Br
2.8
8A
7A
F
4.0
Pe rio d ic Ta b le o f t he Ele m e nt s
1 A
1
1
H
1 .0 1
3
Li
6 .9 4
1 1
Na
2 3 .0
1 9
K
3 9 .1
2 A
2
3 7
Rb
8 5 .5
5 5
Cs
1 3 3
8 7
Fr
( 2 2 3 )
2 0
Ca
4 0 .1
3 8
Sr
8 7 .6
5 6
Ba
1 3 7
8 8
Ra
2 2 6
4
Be
9 .0 1
1 2
Mg
2 4 .3
3 B
3
4 B
4
5 B
5
6 B
6
7 B
7 8
8 B
9 1 0
1 B
1 1
2 1
Sc
4 5 .0
3 9
Y
8 8 .9
5 7
La
1 3 9
8 9
Ac
2 2 7
2 2
Ti
4 7 .9
4 0
Zr
9 1 .2
2 3
V
5 0 .9
4 1
Nb
9 2 .9
2 4
Cr
5 2 .0
4 2
Mo
9 5 .9
2 5
Mn
5 4 .9
4 3
Tc
( 9 8 )
7 2
Hf
1 7 8
1 0 4
Rf
( 2 6 1 )
7 3
Ta
1 8 1
1 0 5
Db
( 2 6 2 )
7 4
W
1 8 4
1 0 6
Sg
( 2 6 3 )
7 5
Re
1 8 6
1 0 7
Bh
( 2 6 2 )
2 6
Fe
5 5 .8
2 7
Co
5 8 .9
2 8
Ni
5 8 .7
4 4
Ru
1 0 1
7 6
Os
1 9 0
1 0 8
Hs
( 2 6 5 )
4 5
Rh
1 0 3
7 7
Ir
1 9 2
1 0 9
Mt
( 2 6 6 )
1 1 0
Ds
( 2 8 1 )
4 6
Pd
1 0 6
7 8
Pt
1 9 5
2 9
Cu
6 3 .5
4 7
Ag
1 0 8
7 9
Au
1 9 7
2 B
1 2
3 0
Zn
6 5 .4
4 8
Cd
1 1 2
8 0
Hg
2 0 1
3 A
1 3
5
B
1 0 .8
4 9
In
1 1 5
8 1
Tl
2 0 4
1 3
Al
2 7 .0
3 1
Ga
6 9 .7
4 A
1 4
5 A
1 5
6
C
1 2 .0
1 4
Si
2 8 .1
3 2
Ge
7 2 .6
5 0
Sn
1 1 9
8 2
Pb
2 0 7
7
N
1 4 .0
1 5
P
3 1 .0
3 3
As
7 4 .9
5 1
Sb
1 2 2
8 3
Bi
2 0 9
6 A
1 6
8
O
1 6 .0
1 6
S
3 2 .1
3 4
Se
7 9 .0
5 2
Te
1 2 8
8 4
Po
( 2 0 9 )
7 A
1 7
8 A
1 8
2
He
4 .0 0
9
F
1 9 .0
1 0
Ne
2 0 .2
1 7
Cl
3 5 .5
1 8
Ar
3 9 .9
3 5
Br
7 9 .9
3 6
Kr
8 3 .8
5 3
I
1 2 7
5 4
Xe
1 3 1
8 5 8 6
At
( 2 1 0 )
Rn
( 2 2 2 )
La nt ha nid e s
Ac t inid e s
5 8
Ce
1 4 0
9 0
Th
2 3 2
5 9
Pr
1 4 1
9 1
Pa
2 3 1
6 0
Nd
1 4 4
9 2
U
2 3 8
6 1
Pm
( 1 4 5 )
9 3
Np
( 2 3 7 )
6 2
Sm
1 5 0
9 4
Pu
( 2 4 4 )
6 3
Eu
1 5 2
9 5
Am
( 2 4 3 )
6 4
Gd
1 5 7
9 6
Cm
( 2 4 7 )
6 5
Tb
1 5 9
9 7
Bk
( 2 4 7 )
6 6
Dy
1 6 2
9 8
Cf
( 2 5 1 )
6 7
Ho
1 6 5
9 9
Es
( 2 5 2 )
6 8
Er
1 6 7
1 0 0
Fm
( 2 5 7 )
6 9
Tm
1 6 9
1 0 1
Md
( 2 5 8 )
7 0
Yb
1 7 3
1 0 2
No
( 2 5 9 )
7 1
Lu
1 7 5
1 0 3
Lr
( 2 6 0 )