Practice Exam #1

I. Identify the appropriate hybridization for each of the carbon atoms that have an arrow
pointing to it in the compound shown below. Note: Place it on the blank beside the
letter.

NH2
a) O
H
O
O O
N N
P
N
O O N
N
HO
OH

b)
c)

II. Write the charge state of the in bold of each of the compounds below. Descriptors
are: positive, negative, or neutral. Assume full octet for each molecule.

a) b) c) H d) O
O
O Al O
N
N H
III. Of the reactions below select the one curved arrow notation is correct.

A + H Br + Br

B + H Br + Br

C + H Br + Br

B + H Br + Br

IV. a) Circle the most stable conformation below. If more than one Newman projection
is tied for the most stable, circle them all.
b) Draw a box around the least stable conformation. If more than one Newman
projection is tied for the least stable, draw a box around all of them.

CH3
CH3
H H H 3C
CH3 H
H H 3C H CH3
CH3
H 3C
H 3C CH3 H 3C CH3 H 3C CH3
CH3
H
H 3C CH3
CH3

A B C
V. a) Draw the Newman projection of the compound shown below looking through
C3 – C4. Use the line structure depicted.

C4
C3

b) Draw the Newman projection of the most stable conformation of the compound
shown above.

c) Draw the Newman projection that shows the transition state between the
conformations that you provided in answers a) and b) .
 VI. Arrange the compounds shown below from the lowest pKa to the highest pKa.
Example for formatting: “highest pKa A > B > C > D > E >F lowest pKa”

NH3
NH2 NH3

Br
A B C

NH3 OH2 OH

F3C

D E F
 VII. a) Arrange the following compounds from the least basic to the most basic.
Example for formatting: “least basic A < B < C < D < E <F most basic”

OH Cl
NH2

A B C D E

b) From the compounds shown above circle the letter corresponding to the
compound(s) that would undergo a product favored Brønstead-Lowry acid/base
reaction with water (H2O).

VIII. Which reaction coordinate diagram correctly depicts the following transformation?

HBr Br

a) b) c) d)
 IX. In each box draw the structure of the expected product or product in each of the
following reactions. In the case of more than one expected product clearly identify
which would be the major and minor products. In the case of multiple products
having the same extent also clearly indicate.
Note: Be careful not to draw the same compound twice.

a)

HBr

b) F3C

HBr

c)

H2
Pd (C)
 X. a) Provide the curve-arrow notation for the following transformation.

CH3 CH3

H
CH3 CH3
H 3C H 3C

b) Draw a reaction coordinate diagram that depicts the transformation. Clearly label
the position of each carbocation as well as the transition state.
XI. Draw a curved-arrow mechanism for the transformation shown below.

HCl
Cl

XII. Provide a brief explanation for the occurrence shown below.

HBr Br

NH2 NH2

NOT formed