Name: _________KEY__________

Chemistry 343: Summer 2006

Hour Exam I
Instructor: Weaver

1. Draw the best Lewis structure for nitrate ion (NO3). Include all lone pairs and
formal charges for each atom. (6 points)

O
-1

+1
N

O
-1

2. Draw the two best Lewis structures for acetonitrile oxide (CH3CNO). Show how
electron pushing arrows can be used to interconvert these Lewis structures. (6
points)

H
H

H
C

3. Indicate the number of valence electrons expected for the following atoms or ions. (6
points)
Potassium Ion: ___0____

Bromine Atom: ____7___

Hydride Anion: __-1___

Carbon Atom: ____4___

Sulfur Atom:

Iodide Ion:

____6___

____8___

Name: ___________________________
Student ID#: ______________________
4. Consider the structure of Cortisone in answering the following (7 points):
What
is
formula?

cortisones

molecular

OH

C21H28O5

OH
H

How many sp3 hybridized carbons are

in cortisone?
H

16
How many sp2 hybridized carbons are
in cortisone?

O
Cortisone

5
5. Give an example of a compound whose carbon-carbon sigma bonds involve sp2
hybridized orbitals. (5 Points)
Ethene, acetone, acetaldehyde, benzene, etc.

Page 1

________/16

Page 2

________/12

Page 3

________/14

Page 4

________/21

Page 5

________/17

Page 6

________/20

Total

________/100

Name: ___________________________
Student ID#: ______________________
6. Classify the following halides and alcohols as primary (1), secondary (2) or tertiary
(3). (4 points)
OH

Br
HO
Cl
Primary

Secondary

Secondary

Tertiary

7. Provide valid IUPAC (systematic) names for the following compounds (10 points):

Br

OH

Cl

Name: ___________________________
Student ID#: ______________________
8. An unknown compound has molecular formula C8H8O. The IR spectrum contains
an intense absorption at 1686 cm-1 and additional absorptions are observed at 3006
and 2967 cm-1. Calculate the unsaturation number for this compound. What
functional groups/atom types are indicated by the IR absorptions? Finally, propose
a structure for this unknown. (12 points)
r + p = 8 - 8/2 + 1 = 5 (indicates possible benzene ring)
O
1686 cm-1

Carbonyl (ketone)

2967 cm-1

sp3 C-H Stretching

O
CH3

Alkyl (CH3??)

3006 cm-1 sp2 C-H Stretching

(Consistent w/ Benzene Ring)

C8C8O
(also accepted aldehyde variant)

9. Draw the most stable chair conformation and its chair flipped form for the
cyclohexane derivative shown below. Clearly indicate which is the most stable (9
points).
Me

Et

Me

Bu

Me
Et
t

Bu

Me
Most Stable
t
Bu Equatorial

Bu

Et
Me
Me

Name: ___________________________
Student ID#: ______________________
10. Consider the following acids. Rank these in order of decreasing acidity (1 = most
acidic, 4 = least acidic). (4 points)
OH

OH

OH
Cl

Br

Alcohol

Resonance

Inductive
Effect

Alkyl

11. Rank the following in order of decreasing basicity (1 = most basic, 4 = least basic).
(4 points)

NH3

CH3CH2

HCO3

NaNH2

12. Give the hybridization of the central atom for each compounds below. Are the
molecules polar or non polar? (9 points)
Compound

Central Atom Hybridization

Polar? (Y/N)

BF3

sp2

NO

CO32-

sp2

NO

CH2Br2

sp3

YES

Name: ___________________________
Student ID#: ______________________
13. Give a curved arrow mechanism for the following reaction, which is a sequence of
acid/base reactions. (12 points)
Br

OH
HBr

OH
Ph

-Br

Br

H 2O

OH2
Ph

-H2O

Br
Br
Ph

14. Clearly identify and label 6 DIFFERENT functional groups present in the following
molecule. (8 points)

Ketone (Carbonyl -1)

O

Alcohol
OH

Lactam
(amide -1)

Alkene

NH2
Amine
O
Aldehyde (Carbonyl -1)

Ether
OCH2CH3