Chemistry 331 Organic Chemistry I Exam 1

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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:

5. For the following compound:

CH3 CH3 CH2 CH CH C CH3

e a c d 3 2 What is the hybridization (sp , sp , sp, etc.) at each of the carbon atoms indicated? (10 points)

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)

7. Arrange the following compounds in order of increasing acidity (5 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

CH 331, Exam 1 Page 3

9. Give each atom the appropriate formal charge. (5 points)

CH3 H3C N
+

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 H3C H3C CH3

CH3 H3C

CH3

CH3

CH3

CH3 CH3

CH 331, Exam 1 Page 4

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 H C H 3C O OH HO H5C 6 O O O O CH 3 CH 3 O CH3 O CH3 OH

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