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UNIVERSITY OF MEMPHIS
Department of Chemistry
CHEM 3311 Unit I Examination, Fall 2003
Dr. Abby Parrill
- Fill in the blanks in the following table (2% each blank=16%).
Condensed Line Structure Name Functional Group | Expected IR Peak
Structure Names Positions
cd ff, E- 4 pentene alkene we te SOtmn
fs H=cHe =
inat thcthsy abhe ag A FAQ can,
ailehal ” 32000 |
(38]-3-heptanol allame acuopaciae
cHyttzctlord CHy Lif, 7 vj0d0
fe, Sol
. Order the following structures based on increasing boiling points. Provide a brief explanation for your order
(5% order, 6% expl
A
janation=11%).
ge ee
Lowest
B
gy
LOSE
An te
co ithaca f sie ene
cad
Highest
Pot "
a mybeulg wot Ceo hin & bracohe v6 clo bf“
. Explain the Mien acd! tween one uch acute toxicity. Also indicate what LDs9 means and whether it
AD hae
phages. a
relates to acute or chronic toxicity. be.
pmed 4
stnge"
ZDsp wueaetues acut
502 of He py
tog feel hoe Seagooies MLA
oil x ental tp”
&
Chg RCLCAL
gos ead wth y ell!
Lesher LK pf
a. Draw the structures of the two lowest energy conformations of cis-1,3-dimethyleyclohexane,
a. Are these two conformations you drew identical, enantiomers, or diastereomers?
b. Identify the relative energies of the two structures (cither same, or indicate the higher and lower energy
conformation),
¢. Briefly explain your relative energies.
im Conformation 1 Conformation 2
Structures (a) q
(436) |
_
CH
i ety S- 4
Cis cH, C3
Relationship (b) :
(2%) deat Atginning
Relative
Energies (c) ‘ &
2%) Lorks a
Energy = ‘ ‘
Explanation (d) zh ont Capeupoa “~ conf 2 ahe close * sack Ste
(2%) art dL, etl ee at fin 5, sibte.
ane ig gta’, Lf 4c fu cn,
re, 2 Bo, Gea A” higher ter :
Identify the hybridizatién and geometry 6f the underlined ¢arbon atom in the’ lowing structures. (3% per
structure = 9%)
Hybridizatioi Geometry :
a. CHSCCH, 52 2 thakedral
b. CH=C=CH 3 Lirmcas
e. CHy=C=CH; Sf —Litgersel Gag 7
Order the carbocations below from least stable to most stable. Provide a brief explanation for the most and
least stable. (5% order, 6% explanation=11%)
° CH,
Hoe CH; Ho NO2 CHs
Least
o Z a 2 iy ow cf
tN guts due pokes be
| hangto ing clot A
C vy a
“punk mith ALO ALES Stebel ipod
