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Course: CHEM 2536, Spring 2012School: Virginia Tech
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1a O Test Chem 2536 Spring 2010 Name______________________________________ Opscan Instructions: For questions 1- 12 you will fill in the correct opscan choice. For questions 12 17, you will draw your answer in the space provided on the opscan sheet. All answers must be on the opscan, both multiple choice and written. Use a #2 Lead Pencil. Fill circles completely. Choose only one answer for each question. Be...
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1a
O Test Chem 2536
Spring 2010
Name______________________________________
Opscan Instructions: For questions 1- 12 you will fill in the correct opscan choice. For questions 12 17, you will
draw your answer in the space provided on the opscan sheet. All answers must be on the opscan, both multiple choice
and written. Use a #2 Lead Pencil. Fill circles completely. Choose only one answer for each question. Be sure to fill
in your ID number.
Multiple Choice fill in opscan circles for questions 1 - 12 (5 pts ea)
1) What is the intermediate formed in the first step of the electrophilic aromatic substitution below?
2) What is the rate determining step in the reaction above?
Formation of the electrophile (E+)
Pi electrons from the ring (Nu:) bonding to the electrophile (E+)
Base (Ba:) removing a hydrogen from the cationic intermediate
Chlorine bonding as a nucleophile (Nu:)
3) Choose a resonance contributor for this compound
4) Which compound below is antiaromatic?
Matching Use the following choices to answer 5) 8). Some choices may be used more than once or not at all.
5)
6)
7)
8)
aniline
para-bromobenzaldehyde
Considering electronegativity of the substituent, choose the most nucleophilic, 1), 5), or 6)
Choose the starting compound that yields only the given product when brominated.
Absorbance
9) Which compound is shown in the IR above?
10) When considering an IR spectrum, the C=O stretch of an amide, HCONR2, vibrates at a(n) ____________
frequency compared to the C=O stretch of a ketone, RCOR.
higher (faster)
lower (slower)
Identical
Cannot determine with this information
11) For question 10), this is because the C=O in the amide
has lighter atoms.
is more polar.
is more like a single bond.
is more like a double bond.
12) Rank the following rings from most (1) to least (3) reactive in a bromination with Br 2/FeBr3.
a
abc
b
acb
c
bac
bca
cab
cba
Written
13) Draw both molecules on the opscan. For each, give another resonance contributor below it on the opscan. Label
the major and minor contributor in each set. Circle the molecule with the nitrile ( CN) stretch that is expected
to absorb at the highest IR frequency (highest wavenumber). (10 pts)
show on opscan
14) Give the major organic of product(s) the following reaction. (5 pts)
show on opscan
15) Give the major organic product(s) of the following reaction. (5 pts)
show on opscan
16) Propose a mechanism to explain the following product. Show intermediates and curved arrows for all electron
movement. Do not add any reagents. (10 pts)
show on opscan
17) Multistep synthesis - Add reagents and methods to show how the following starting material can be converted into
the desired product. This will take more than one reaction. You do not need to show the reaction mechanisms.
(10 pts)
show on opscan
Extra credit (3pts): A group of students in our class are raising money for Partners In Health to help what
countrys earthquake victims? Answer on opscan
Table of some reagents: Zn(Hg)/HCl
NaNO2/HCl/0C
NBS
KMnO4 K2Cr2O7
MnO2
Class,functionalgroup
Groupfrequency(cm1)
Relativeabsorptionintensity
Alkanes,alkylgroups
CHstretch
29802850
mediumtostrong
CHbend
14701450,14001360
medium
=CHstretch
30903010
medium
C=Cstretch
16801620
veryweak(trans)tomedium(cis,term)
CHstretch
33003250
medium,(terminalalkynesonly)
CCstretch
22502200
weak(internal)tomedium(terminal)
CHstretch
31003000
medium
arom.CCstretch
16301590,15201480
medium
OHstretch
36503300
strong,broad
COstretch
11501030
strong
34503280
weaktomedium,broad
11401100
verystrong
Alkenes
Alkynes
Aromatics
Alcohols
Amines
NHstretch
Ethers
COstretch
Aldehydes
"CHstretch"
27402720
medium
C=Ostretch
17351720
verystrong
17251705
verystrong
OHstretch
33002400
strong,verybroad
C=Ostretch
17101680
verystrong
18101790
strong
C=Ostretch
17501735
verystrong
COCstretch
12901180
verystrong
NHstretch
35403380
medium,broad(prim.&sec.only)
C=Ostretch
16801640
verystrong
22602240
weak
Ketones
C=Ostretch
Carboxylicacids
Carboxylicacidchlorides
C=Ostretch
Esters
Amides
Nitriles
CNstretch
Top of Periodic Table
1
1
H
3
Li
11
Na
19
K
37
Rb
2
4
Be
12
Mg
20
Ca
38
Sr
3
21
Sc
39
Y
4
22
Ti
40
Zr
5
23
V
41
Nb
6
24
Cr
42
Mo
7
25
M
43
Tc
8
26
Fe
44
Ru
9
27
Co
45
Rh
10
28
Ni
46
Pd
11
29
Cu
47
Ag
12
13
14
15
16
17
30
Zn
48
Cd
5
B
13
Al
31
Ga
49
In
6
C
14
Si
32
Ge
50
Sn
7
N
15
P
33
As
51
Sb
8
O
16
S
34
Se
52
Te
9
F
17
Cl
35
Br
53
I
18
2
He
10
Ne
18
Ar
36
Kr
54
Xe
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