Practice

Exam Questions


1. Atorvastatin is a drug used in the treatment of high blood cholesterol. It
binds and inhibits an enzyme that is part of the pathway to cholesterol
synthesis in the liver.

O
OH OH O

N
N OH
H

F

a) Draw all non-bonding electrons in the structure.

b) It is known that atorvastatin’s main bonding force to the enzyme is
hydrogen-bonding. It can have as many as 9 hydrogen bonds to the
enzyme’s active site. Circle all the atoms that can produce hydrogen
bonding with the enzyme.

c) The enzyme-binding site has cationic properties. Place a box around the
functional group that gives atorvastatin anionic properties.

d) Place a star next to the sp2 hybridized oxygen atoms.


2. Arrange the following compounds in decreasing order of acidity; from the
most acidic =1 to the least acidic = 5. Note: Use the arrows to compare
hydrogen atoms.

H

O
H
O
H H H
O

MeO Me OMe Cl



O

O
H H
O

Cl Cl
F

3. Albuterol, shown below, is a medication used in the treatment of asthma. It
relaxes the smooth muscle of the bronchi.

OH

H
N

HO



HO


albuterol

a) Clearly draw in all non-bonding electrons.


b) Draw a box around the most acidic hydrogen in albuterol.


c) What is the standard pKa of the hydrogen atom in albuterol that you drew
a box around?




d) The oral medication of albuterol is sold as the conjugate acid. Clearly
draw a circle around the atom that will make albuterol, shown above, into its
conjugate acid.




4. Circle the compound, from the list below, that reacts with EtOH and H2SO4 as
a catalyst and will produce the lowest yield of the major product(s)?

 5. For the following reaction answer the questions below.




+ OCH3

A B

a) Circle the compound that represents the Lewis base (letter A or B).


b) Use the curved-arrow notation to depict product formation.


c) Draw the product of the reaction in the box.


d) If a fluorine were placed on one of the benzene rings of compound A,
would it make the compound

MORE or LESS

reactive? (Circle one)


6. In each of the following reactions provide curved arrows to show electron
flow and draw the structure of the products formed.

a) O
O H
+ OH
H
O
F F

O

b)
H
+
OC(CH3)3
H
N

H

 7. In the following reaction there are several starting materials that can
potentially provide the product shown below. Propose starting reagents that
fulfill the requirements. More than one structure can fulfill the requirements.


H2 / Pd (C)


?
C6H10














8. Shown below is the arrow-pushing mechanism for two reactions. Draw the
structure of the product(s) in each case.

H 3C OH
a)
O Ph
O

O
H


O
b)


H











9. Draw the structure of the major product(s) of each reaction shown below.
Consider all possibilities. You do not need to provide a mechanism.


a)
H 2O
H2SO4 cat




b) HBr







c)
CH3OH

H2SO4 cat






d) HCl



















10. Shown below is the structure of one stereoisomer of 3-bromo-2,4,5-
trimethylhexane.

H




Br H


a) Looking through carbon atoms 3 and 4 of the structure draw all Newman
staggered and eclipsed conformations around this bond using the
templates provided.























b) Circle the most stable conformation and draw a box around the least
stable conformation.










11. Hydrofluorination (addition of HF to an alkene) can be accomplished under
certain conditions. It requires a complex (KHSO4 Ÿ 13 HF dissolved in
CH2Cl2). The addition reaction below, using “HF” as abbreviation for the
complex, shows two products (A: major product and B: minor product. Draw
each corresponding product over the letters provided.





“HF”




A B

a) Draw a curved-arrow mechanism that accounts for the formation of
compound A. Show all intermediates and formal charges.















b) Provide a brief explanation for product A being the major product.












12. Look closely at the transformation shown below.


CH3OH / H3PO4 (cat) OCH3




a) Draw, in the blank below, the structure of the first intermediate formed in
the reaction as this diene reacts with one equivalent of CH3OH2+.









b) In the structure drawn on part (a) circle the section of the molecule that is
most electrophilic, i.e. Lewis acid.

























13. Below is the reaction coordinate diagram for the addition of HCl to 3-methyl-
1-butene.

+ HCl

a) Provide an arrow-pushing mechanism for the reaction showing all

intermediates and products.

b) Explain the formation of each intermediate.