Practice Exam 5 – Organic Chemistry and Spectroscopy - This is a partial exam
Use the NMR and IR tables in your lab manual as reference material for the exam.
Multiple Choice (2 points each)
_____1. Select the correct name for the following compound.
A) 3-ethyl-2,3-dimethyl-1-propanol
B) 2,3,4-trimethyl-1-butanol
C) 2,3-dimethyl-1-pentanol
D) 3,4-dimethyl-5-pentanol
E) 3-ethyl-2-methyl-1-butanol
_____2. Select the correct reaction type for the following process.
A) addition
B) elimination
C) substitution
D) condensation
_____3. Anethole, a derivative of anise, is used in flavoring and as perfume in soap and
toothpaste. Identify the functional group circled.
A) aldehyde
B) ketone
C) ester
D) ether
E) alcohol
_____4. One characteristic of the monomers that form condensation polymers that is not
common in monomers which form addition polymers is
A) pi bonds
B) the presence of two functional groups
C) alkyl side chains
D) ability to form free radicals
_____5. Benzocaine is from a family of chemicals that are good local anesthetics.
Identify the
functional group circled.
A) aldehyde
B) ketone
C) ester
D) carboxylic acid
E) ether
_____6. Identify the products of the reaction of 3-octene with chlorine.
A)
B)
C)
D)
_____7. A four-carbon alcohol was oxidized with acidified potassium dichromate to form
a ketone. Which structure represents the original alcohol?
8. (3 pts) In one sentence, what is the general requirement for a molecule to be optically
active?
9. (4 pts) Name the compounds with the molecular structure shown.
A) ____________________________________
B) ____________________________________
10. (4 pts) Draw a structural formula for the following compounds:
A) 1-bromopropanone
B) butanoic acid
11. (6 pts) A) Draw two geometric isomers with the molecular formula C2H6O.
Structure 1
Structure 2
B) Which one will have the higher boiling point, and why?
12. (4 pts) Match the letters A and B with the statements below.
A. Infrared Spectroscopy
B. NMR Spectroscopy
_____ Absoptions result from the changes in the nuclear spin of protons in a molecule.
_____ Used to determine the functional groups present in a molecule.
_____ Absorptions result in increased vibrational motion between atoms in a molecule.
_____ Can give information about the number of equivalent protons in a molecule.
13. (16 pts) Sketch an NMR spectrum for each of the following. TMS is shown on each
axis.
i) Show the relative location of the proton peaks by writing the correct on the
axis below each peak.
ii) Label the molecule’s protons responsible for each peak.
iii) Show spin spin splitting for each peak.
iv) State the relative area for each peak.
A) CH3CH2OCH3
__________________________________________________

TMS
B) methylbenzene
__________________________________________________

TMS
C) methyl propanoate, CH3CH2COOCH3
__________________________________________________

TMS
14. (4 pts) Write products for the following reactions. [O] means oxidized.
[O]
A) CH3CH2CH2OH 
B) CH3CH2COOH + CH3CH2OH 
15. (6 pts) Use the infrared spectra labeled A and B to answer this question.
Spectrum A
Spectrum B
A) The most intense absorption in both of the spectra is caused by absorption of
_________.
B) Which is the spectrum of butanal? _________________.
Explain.
C) Explain how you know that the above spectra do not contain a benzene ring.