Organic Chemistry, CHM 212 NAME:______________________________

Test 1, 2016

Part 1: Multiple Choice

1. How many different proton and carbon NMR signals would the following structure have?

# Proton signals # Carbon signals

a. 4 6
b. 5 6
c. 4 7
d. 12 7

2. Predict the coupling pattern for the protons labeled in the compound below.

3. Which of the following molecules would give more than one signal in the 1H-NMR spectra? (Hint:
symmetry simplifies the spectra)

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4. A compound with the molecular formula C5H11Cl exhibits the following 1H NMR spectrum. What
is the correct structure of this compound?

5. Based on the 13C-NMR spectrum, select the correct structure of the compound.

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6. The 1H-NMR and 13C-NMR of an unknown compound with molecular formula of C9H12O are
shown below. What is the structure of the compound?

O
a. b. c. d.
OH O O

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7. The 1H-NMR, 13C-NMR and IR of an unknown compound with molecular formula of C9H12O2 are
shown below. Integrations are shown below each 1H-NMR signal. What is the structure of the
compound?

d
t

1H 2H 6H 3H

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8. Provide the correct IUPAC name for the following compound.

a. m-bromobenzaldehyde
b. m-bromocarbonylbenzene
c. o-bromobenzaldehyde
d. o-bromocarbonylbenzene

9. Which of the compounds below is 3-bromo-4-nitroaniline?

10. In the molecule below, in what type of orbital is each lone pair found?

a. A is in an sp2 orbital and B is in a p orbital

b. A is in a p orbital and B is in an sp2 orbital
c. A is in an sp2 and B is in an sp3 orbitals
d. A and B are both in sp2 orbitals

11. Which of the compounds below is aromatic?

12. Which of the following is the correct molecular orbital diagram for pyridine?

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13. What substituent Y would result in the formation of the product shown?

a. Y = Br
b. Y = NO2
c. Y = CH3
d. None of the above

14. Only one of the products shown cannot be formed in the FriedelCrafts alkylation reaction given
below. Which one?

Cl

product
AlCl3

a. b. c. d.

15. What is the product of the following reaction?

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16. Choose the major product(s) of the following electrophilic aromatic substitution.

CO2H

HNO3

H2SO4
?

CO2H
CO2H CO2H CO2H
O2N NO2

O2N
NO2

I II III IV

a. I only
b. II only
c. I and III
d. II and IV

17. Rank the following reactions from the fastest to the slowest:

a. II > I > III > IV

b. I > II > III > IV
c. IV > II > III > I
d. I > III > II > IV

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18. Four structures are shown below to represent the resonance effect of the OH group attached to a
benzene ring in order to explain why OH activates the ring towards electrophilic aromatic substitu-
tion reactions. One of the structures is not correct which one?

19. Choose the three-step sequence below that would lead to the formation of the product shown. Only
one sequence is correct.

Br2 Cl Pd, H2
a.
FeBr3 AlCl3

Br
O

Cl Br2 Pd, H2
b.
AlCl3 FeBr3

Br

Cl Br2 Pd, H2
c.
AlCl3 FeBr3

Br

Br2 Pd, H2 Cl
d.
FeBr3 AlCl3

Br

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20. The following three-step synthetic sequence has been devised. What is the correct final product?

Cl HNO3 1. Fe, H3O+

AlCl3 H2SO4 2. -OH

O O

H2N O2N
NH2 NH2

a. b. c. d.

Part 2: Write-In

21. (6 pts) Write a complete mechanism (including charges and arrows) for the Friedel-Crafts
alkylation reaction shown below. Show the structure and mechanistic arrows for generation of the
active electrophile. It is not necessary to show all intermediate resonance structures, only one is
required.

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22. (4 pts) An arene A undergoes bromination to produce a new arene B. The 1H NMR and 13C NMR
are given below. Draw the structure of arene B in the box given.

s t
dd

1H each 2H 3H

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23. (6 pts) Toluene undergoes chlorination to primarily produce the ortho/para chloro products while
the meta chloro product is a minor product (only the ortho and meta pathways are shown below).
The initially-formed carbocation intermediates A and D are given.

a. Draw two other resonance structures for each intermediate in the boxes shown (B-C and E-F),
including curved arrows to demonstrate electron movement.

b. Using intermediates A-C and D-F, explain why the ortho substitution pathway is favored over
the meta substitution pathway.

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24. (4 pts) Devise a valid synthesis for converting benzene to the product given below. Show all
reagents required for the synthesis in the correct order AND show the products of each reaction.
Mechanistic arrows are NOT required. (Hint: This synthesis requires 4 steps).

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