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CH 331, Exam 1 Page 1 1. Expand the condensed structures to show the covalent bonds and nonbonding pairs of electrons (5 points). a.) CH3CH2NHCH3 b) ClCH(CH3)2 c) (CH3)2CHCH2CHCOOH d) Cl(CH2)5CN e) CH3CH2CH2NO2 2. Draw the Lewis dot structure of propionic acid, CH3CH2COOH. (5 points)
3. Which of the following molecules would you expect to have a dipole moment of 0? (5 points) a)CH3CH3 b) CHCl3 c) N(CH3)3 d) HCOOH e)H2C=CH2
4. Predict the bond angles for the following molecules (5 points). a) C-N-H in (CH3)2NH angle: b) C-N-C in (CH3)2NH angle: c) C-O-C in CH3CH2OCH3 angle: d) H-C-H in H2C=O angle:
CH
a)
b)
c)
d)
e)
CH 331, Exam 1 Page 2 6. Draw and discuss the bonding scheme for ethene (H2C=CH2) using valence bond theory. Be sure to include hybridization, bond angles, s- and p-bonding as well as molecular geometry. (10 points)
CH3CH2CH2CO2H
CH3CH2CHCO2H Cl
ClCH2CH2CH2CO2H
CH3CHCH2CO2H Cl
8. Isooctane (C8H18) is a major constituent of commercial gasoline. What is the IUPAC name for isooctane? (5 points)
CH 3 CH 3 C CH 2 CH 3
CH 3 CH CH3
CH3
H3C O
+
CH3
CH3 H H C H
H3C N
+ -
10. Give the IUPAC name of the following compounds. (10 points)
H3C CH3 CH3
CH3 H3C
CH3
CH3
CH3
CH3 CH3
11. The compound below, paclitaxel (TAXOL, isolated from the Pacific yew tree, Taxus brevifolia), is clinically useful in the treatment of ovarian cancer. Identify the functional groups indicated in TAXOL. (10 points).
O H5C 6 NH
C 6H5 O
12. Dr aw the chai r thr ee-di mens i onal confor mati on of cycl ohex ane and label one of the axial hydr ogens and one of the equatorial hydr ogens . (5 poi nts )
CH 331, Exam 1 Page 5 13. Draw the most stable conformation for cis-1-t-butyl-4-methylcyclohexane. (5 points)
H3C H3C H3C CH3
14. Assign the different conformations of butane to the potential energy diagram. (5 points)
A C C A
E E
B D
0 0
60 60
240 120 180 180 120 240 Degrees ofof Rotation Degrees Rotation q
300
300
360 360
CH3 H H
CH3 H H
CH3CH3 H H H H H
H CH3 H HH H CH3 H
CH3
H H H
CH3 H H
H H CH3
CH3 H H
B Gauche
A Eclipsed
C Eclipsed
E Gauche
D Anti
15. Draw an example of a compound of your own choice for each entry, which has the following functional group:(10 points) a.) alcohol b.) aldehyde c.) ester d.) amin e.) carboxylic acid