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Name: SV1r~ P°'+J

Exam 1
Chemistry 333
Spring 2019

Question 1 10 points ID_

Question 2 7 points 6
Question 3 16 points \12_
Question 4 8 · points T
Question 5 12 points
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--
Question 6 18 points l3
Question 7 16 points lb
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Question 8 13 points

&Joints
Extra Points 5 points

Total

Early chemists describe the first dirt molecule.

Chemistry 333 Exam 1

1) Draw one valid Lewis Structut t lR oth structural formulas below.

To get full credit: a) Show ALL electrons, as either bonds or lone pairs.

j
b) Assign atoms with formal charges.
c) Draw structures where all atoms have full valence
shells.
[CHN02Cl]·1 . /the last element is Cl= chlorine)
I ':l IJ. 'I

, .
Js) / CHN30 @)
't I r5' =
c,,1 --------;-,T\_______
•• (:£) ' • .. •• 0
-N=N~C "'-:- (N ====-0:
-. I
I~
40
I I
For the following structure: (All formal charges are shown. But, implicit lone
2
> pairs and hydrogens are NOT shown.)
•• © e
9.=9.-Cr
4 4
'' ''
' ' (c) (d)
/ (a) (b)

-J a) Which of the labeled atoms are SP3 hybridized? (Circle ALL that apply)

(a) (b) (d) (none)

b) Which orbital(s) form the 0=0 pi-bond? ..§Pa,, 5p,_

1 PJ- f
c) Which orbital(s) form the N-C sigma-bond? '5P~ 1 SP
-2-
I Chemistry 333
Exam 1

Draw a resonance structure for the following molecules. (Note: All bonds and formal
charges are shown. But implicit lone pairs are NOT shown.)
a) If possible, draw resonance structures that have full valence shells for all atoms.
b) Use curved arrows to show the movement of electrons on both sides of the
double-headed arrow.

4 OH

~ A)

+ '--l C) For each of the following pairs of structures, circle the major resonance
structure. If the resonance structures are equal, then circle both. If they
are not resonance structures, cross-out the double headed arrow. (You
do not have to ow the movement of electrons for these.)
H H
I e I
=C-C-H O=C-C-C-H
I I I I I
i) H H H H H

ii)

(±)
(±) n ,
H-C-N=C-H H-C=N=C-H
I I I \J' I
iii) H H H H

-3-
1// Chemistry 333 Exam 1

+6 4)
l
J e/False (Note: If a statement is only partially true, then it is false.)

An SP3 hybridized orbital Is made up of 33% s and 66% P orbitals

I
JT The weakest attractive force between two molecules is the London
Dispersion interactions.

Molecules with resonance are more stable than molecules without

resonance because the electrons are distributed over a larger number of
atoms

In an acid-base reaction, the proton will move from acid to base but the O
electrons will move from base to acid. /
Q
, I -

1:9?~h(o
~l~c
~I\~
5) a) Write out the IUPAC names for both structures below.· ()
hL~I - bm;o L,ri,5"10 '-c1"'b ~l
(__ (JI I 5 ol
2- '1 - l9 5

1- 6roMo-l- ~ j \ - 3-hmMo-
5- b'(Z)~o- Gi- nt~l ~vtt_

I);~ -t r:~to"'o- 'l....- -,..x\\..'11 ,-r~"trl~

r

C )'C ID\-e pfell\~

(1ot a carlor
-4- 3-- c~lo-ro- 3Jq_ J ;(zi\ ~;__·1- r\voro
e-S- ·l"'e-t"'0 QCt®e
,/ Chemistry 333 Exam 1

+l3 6) Multiple GhGlGe guess:

.CALVIN - HOBBES
A.T llST, Clllt1Tf! l ~
S'EMlQG l'l Elffl~ Ml£.
~~QR~'fll.E.,
~'IUPfllll.E \.IE! CME
at..Mc<fflU!
~!
I

+"3 b)
HCN e
Circle all molecules where the center atom is trigonal planar.

Sifa

Circle all the molecules that have a molecular dipole.

e·
NQ3- (£) 8 N3·

+U c) Crossout all structures that would lead to an invalid Lewis structure. (Note:
some of the arrows may lead to very unlikely but still valid Lewis structures.)

c:~ /"\
0 ~;@_,,CH3
0 C
I
CH 3

d) Circle and label all the functional groups in the two pharmaceuticals below.
You do not have to i. ~kane, alkene, or aromatic groups.

CcH b~lt ho-

~ Ji{'(' I •
p,._~,,_g_ &w o I - - -: ~6--'l\-:,~
o -7
H O....._ --:::
0-l'Yl \;\J.. 0 r-~ 't.'
L- L , (
INX NH 2 I h"

~ \ °' d.fi -~~te r o...MiN--

Amlodlplne Amphetamine
(treatment of hypertension)

-5-
/ Chemistry 333
Exam 1

+ l2
7
) a) From the four molecules below, circle the molecule with the lowest boiling
point and cross-out the molecule with the highest boiling poi,Dl (Assume
that all the molecules have the same molecular weights.)

+9 c) For each set of four acids below, circle the strongest acid and cross-out
the weakest acid . (If a molecule has different types of protons, compare
the most acidic proton in the molecule.)

(±),H
H-0 CI-H
H

~ . ?1

k
---- --- -- ----- ---- ---- ---------
..-:><--...

H-C::C-H

'""'
~ ) c) For each set of three molecules below, circle the strongest base and
cross-out th we est base.

H ~>
H
:c,8 .• H
19
Ne
·,4:,
Hsf;

-6-

J
I/ Chemistry 333

+
Exam 1

8) +La) In the space below, draw the most likely acid-base reaction between:
CH3CH20Na and CH3CCH, showing both the reactants and the products.

W·
~- A-ciJ
"'
.,/4~c"l H :::::=~==-' _/'\. ll-\-\ -r A E)

p\l°"" \lo pk(A = a5 PK~ ICD p Kc.. : J.5

+4- b) Estimate the pKa's of all molecules acting as acids.(± 3 pKa units)

d) Which is more acidic, th@r the on·~;g

c) Which is more basic, t h e r th conjugate base . (circle one)

e) Which side will the equilibrium lie or@ o right)

(circle one)

Draw curved arrow(s) to show the movement of electrons on the left-hand

side of the reaction, which will transform the reactants into the products. /

.+-L-9>Draw curved arrow(s) to show the movement of electrons on the right-hand

· side of the reaction, which will transform the products back into the reactants. /

Ac.,c}. CU"I.J••
~-

-
Ac.icl
/"-e
0 No.£>
-'--?
~A ....- o-~ e
C-1--1
~s ICP a.

-7-
 Exam 1
Chemistry 333

Extra Credit.
Draw all possible unique Lewis Structures with the formula CaH60,
(2 points)
a)
r\ r\ \'\
H '
rl-C,,-C
\ '
C=O
I
I \
H- C H
I

~Ar\l
1-\ \-{
1-1

... o,
H
b) (3 points) One difficulty with resonance structures is that they may predict
different hybridizations for the same atom.
I. Draw an example of a carboxylic amide resonance structures with an SP3
hybridized nitrogen atom in one resonance structure and an SP2
hybridized nitrogen atom in the other resonance structure.

II. The actual hybridization of the carboxylic amide nitrogen is better

described as SP2 hybridized. Propose an explanation on why.