Arizona State CHM 233 exam1key

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Published on 7 Mar 2019
School
ASU
Department
Chemistry
Course
CHM 233
Professor
Midterm #1 Ian R. Gould
Person on your LEFT (or Empty or Aisle)
H He
Li Be B C N O F Ne
Na Mg Al Si P S Cl Ar
K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr
Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe
Cs Ba Lu Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn
CHEM 233, Spring 2016
H/H ~1.0
Eclipsing
H/Me ~1.4
Me/Me ~2.6
Me/Me ~0.9
Et/Me ~0.95
i-Pr/Me ~1.1
t-Bu/Me ~2.7
Gauche
Me/Et ~2.9
Interaction Energies, kcal/mol
Person on your RIGHT (or Empty or Aisle)
1____________/12
2____________/22
3____________/24
4____________/40
5____________/30
6____________/16
7____________/31
Extra Credit_____/5
Total (incl Extra)________/175+5
CNR2
RC CR
R2CCR2
Aromatic
C
ROH
O
CX
RNH2
ROH
020406080100120140160180200220
–H2CX
H2CNR2
–OCH2
01234567891011
CCH
CH
O
C
ROH
OAromatic Ar H Alkyl
mainly 8 - 6.5 CCH2
CCH3
O
3° > 2° > 1°
Alkyl
–OCH2
C
O
(δ, ppm)
variable and condition dependent,
ca. 2 - 6 δ
RCN
OHCN
C
N
C
C
H
C O
N H
CH
CN
O
HC
O
C
H
CCH
COR
O
N H
CH
C
O
OH
C O H
O
CNR2
O
3000–
3100
2850–2960
3300
broad ~3300
broad with spikes ~3300
2200
broad ~3000 1710
2200
1650
2720–2820
2 peaks
1735
1600–1660
1680
range of values
broad peak
small range usually
strong
1600
Infrared Correlation Chart
NMR Correlation Charts
3000 2000
2500
3500 1500
(cm-1)
!PRINT YOUR NAME ON EACH PAGE!
• READ THE DIRECTIONS CAREFULLY!
• USE BLANK PAGES AS SCRATCH PAPER
work on blank pages will not be graded...
• WRITE CLEARLY!
• MOLECULAR MODELS ARE ALLOWED
• DO NOT USE RED INK
• DON'T CHEAT, USE COMMON SENSE!
3° > 2° > 1°
ASU or Posting ID
The room where most students will take the test for your
class, i.e. LS A-191 for onground and PS H-152 for hybrid)
COMPLETE THIS SECTION : Up to TWO POINTS will be removed for incorrect/missing information!
**YOU ARE NOT ALLOWED TO TAKE SPARE COPIES OF THIS EXAM FROM THE TESTING ROOM**
Points Removed
(cover errors) ____/2
PRINTED FIRST NAME PRINTED LAST NAME
ANSWER KEY
Class you are REGISTERED FOR (onground or hybrid)
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- 2 - NAME
CHEMISTRY 233, Fall 2016, MIDTERM #1
N
O
N
HN
FO
OH
Question 1 (12 pts.) Circle and identify all functional groups in the following structure, ignore alkyl
groups. Indicate any amines, amides or alcohols as primary, secondary or tertiary, as appropriate.
aromatic
halide
carboxylic
acid
ketone
amine
amine
amine Ciprofloxacin, the only drug
specifically approved by the FDA
for treatment of inhalation
anthrax exposure
Question 2 (22 pts.) Rank the pairs of electrons indicated, A, B, C and D in order of increasing
energy. Give an explanation for your choice, most of the points are for the explanation, not the
order.
O
H
P
H
C
(non-bonding)
D (π-bonding)
A (non-bonding)
B (σ-bonding)
lowest
energy highest
energy
< < <
ADB C
non-bonding electrons are higher in energy than bonding electrons, therefore A and C are highest
in energy, phosphorus is larger and less electronegative than oxygen, C are thus highest
π-bonding electrons are higher in energy than σ-bonding electrons, thus D is next highest and B is
lowest
CN
Question 3 (24 pts.) For the structures A and B below:
a) Indicate (in words, do not draw on the structures) the largest BOND DIPOLE moment(s) in each
b) Between these two largest bond dipole moments (the one from A and the one from B), which
would be larger? Give a brief explanation.
c) Draw the MOLECULAR DIPOLE MOMENTS ON TOP OF THE STRUCTURES. Your drawings
do not need to illustrate the size of the dipole, only the direction. If there is no molecular dipole,
indicate so. BRIEFLY explain which structure would have the larger MOLECULAR dipole moment.
F
Br
the largest bond dipole moment in A is that associated with the C-N triple bonds
the largest dipole moment in B is that associated with the C-F bond
AB
A has a larger MOLECULAR dipole moment because it has two larger bond dipole
moments that add in (roughly) the same direction as the two smaller bond dipole moments
in B
C
N
the C-N triple bond dipole moment is larger because even though F is more electronegative than N,
the electrons in the pi-bonds in the triple bond are highly polarizable
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Document Summary

Complete this section : up to two points will be removed for incorrect/missing information! Person on your left (or empty or aisle) Person on your right (or empty or aisle) Class you are registered for (onground or hybrid) The room where most students will take the test for your class, i. e. ls a-191 for onground and ps h-152 for hybrid) **you are not allowed to take spare copies of this exam from the testing room*: print your name on each page! 2____________/22: use blank pages as scratch paper work on blank pages will not be graded, write clearly, molecular models are allowed, do not use red ink. Extra credit_____/5: don"t cheat, use common sense! Li be b c n o f ne. Na mg al si p s cl ar. K ca sc ti v cr mn fe co ni cu zn ga ge as se br kr.