1. (12 pt) Name following compounds:
NO2
OH
Cl
Br
2. (9 pt) Draw the following compounds.
a. benzyl bromide
b. 3,5-dimethylaniline
c. (S)-2-chlorobutane
3. (8 pt) Draw all possible molecular orbital combinations in benzene. Indicate which
combinations are bonding and antibonding. Circle the degenerate orbitals.
4. (5 pt) Reacting bromine with a benzene ring produces the substitution product rather
than the addition product. Which one of these products is more stable? Why is the
substitution product favored over the addition product?
Br
Br
Br
Addition
Product
Substitution
Product
5. (6pt) Circle the compounds that are aromatic according to the Hückle Rule.
N
N
S
N
N
6. (8 pt) Explain why the following compounds are aromatic or not. Include Frost circles
in your explanation.
cyclobuta-1,3-diene
anti-aromatic
cyclohepta-2,4,6-trien-1-ylium
aromatic
7. (5 pt) Would dibenzo-p-dioxin be aromatic, antiaromatic, or non-aromatic. Based on
this, what would you expect the hybridization of the oxygens to be?
O
O
8. (8 pt) Give the reaction conditions for the following transformations:
?
NO2
?
SO3H
NO2
?
Br
?
NH2
9. (8 pt) Identify the following as activating or deactivating groups. Indicate if they are
meta or ortho-para directing groups.
O
Cl
:
OH
10. (8 pt) Give the products (some have more than 1) of the following reactions
NO2
I2, 2 Cu2+
I2, 2 Cu2+
NH2
O
I2, 2 Cu2+
I2, 2 Cu2+
O
11. (7 pt) Draw the reaction mechanism for the following reaction. Include the formation
of the electrophile. Explain why the acyl electrophile is so stable.
O
Cl
.
AlCl3
O
12. (6 pt) Explain what is wrong with the following reactions:
OH
OH
Cl
AlCl3
NO2
HNO3, H2SO4
Cl
Cl
13. (8 pt) Use retrosynthesis to propose a route to synthesize m-chlorobenzoic acid from
benzene (3 steps are required).
O
Cl
OH
14. (8 pt.) Circle the chiral centers on the following molecules
N
Cl
S
Br
15. (6 pt) Assign the following as R or S
Cl
H
O
P
16. (6 pt) Calculate the specific rotation for the following and indicate which direction
(clockwise / counterclockwise) the light is being rotated:
a. A 3.0 g sample of morphine dissolved in 10 mL of methanol in a 5 dm
polarimeter which gives a observed rotation of -198º.
b. A 1.0 g sample of sucrose dissolved in 8 mL of water in a 10 dm polarimeter
which gives a observed rotation of 83.0º.
17. (8 pt) Identify the following pairs of molecules as constitutional isomers,
enantiomers, diasteriomers, meso, or not isomers.
H
Br
H3C
H
Br
CH3
Cl
Cl
Cl
H
Br
H3C
H
Br
H3C
NH
NH
HO
Cl
O
HO
O
O
18. (8 pt) Label the pictured molecules as either the Re or the Si face.
O
O
O
Br
Cl
O
O
H
19. (4 pt) Hydrogen addition into the Si face of acetophenone (pictured) produces the R
enantiomer, however propyl magnesium bromide addition forms the S enantiomer.
Explain why.
HO
O
H
BrMg
H2
(R)-1-phenylethanol
acetophenone
HO
(S)-2-phenylpentan-2-ol
20. (6 pt) Label the indicated H’s as pro-R or pro-S.
Ha
Hb
Ha
Hb
O
Ha
Hb
Bonus (9 pt) Match the following structures with their uses and circle the chiral
compounds:
A) TNT, an explosive
B) Coniine, a poisonous alkaloid found in hemlock
C) Tryptophan, an essential amino acid required for serotonin production
D) TCDD, a toxic dioxane contaminant in Agent Orange
E) Oseltamivir, an antiviral sold under the name Tamiflu
F) Peonindin, a plant pigment found in roses and cranberries
N
H
Cl
O
Cl
Cl
O
Cl
HN
H2N
OH
OCH3
NO2
O
O
O2N
O
NO2
OH
O
O
HO
HN
O
OH
NH2
OH
Bonus (3 pt) Azo dyes are brightly colored synthetic dyes. What about the structure of
these organic compounds produces such vivid colors?
O
O
O
S
N
OH
OH
O
S
N
N
O
OH
N
N
OH
HO
O
S
N
OH