Organic Chemistry UNITTest

Organic Chemistry UNITTest
Multiple Choice - 10 Marks (1 each)
Identify the letter of the choice that best completes the statement or answers the question.
1. When two alcohols undergo a self condensation, what is formed?
a. liquid alcohol
d. an aldehyde
b. a ketone
e. an ether
c. an ester
What is the correct name for the above compound?
a. 2-methyl-3-butanol
d. 3-methyl-2-butanol
b. 2-pentanol
e. none of these
c. isobutanol
3. What results when a secondary alcohol is oxidized?
a. a ketone
d. an acid
b. an amine
e. no reaction
c. an aldehyde
The correct name for the compound given above is which of the following?
a. 2-cycloproproxylcyclobutane
c. 2-cyclobutoxycyclopropane
b. cyclobutylpropoxy ether
d. cyclopropoxycyclobutane
5. Which of the following classes of organic compounds does not contain oxygen?
a. aldehydes
d. ethers
b. amines
e. amides
c. amino acids
6. When excess hydrogen bromide is added to pentyne, the possible product is which of the following?
a. 1,1-dibromopentane
c. 1,1,2,2-tetrabromopentane
b. 1,2-dibromopentane
d. 2,2-dibromopentane
7. Butane and fluorine gas would react by which of the following?
a. addition
c. substitution
b. combustion
d. single displacement
The molecule above is which of the following?
a. a saturated fatty acid
d. palmitin
b. a triglyceride
e. a natural oil found in grain
c. an unsaturated fatty acid
9. The chemical bond between glycerin and a fatty acid is which of the following?
a. an ester bond
d. an ether bond
b. a double bond
e. a hydrogen bond
c. a peptide bond
____ 10. The polymer formed from lactic acid (structure shown below) is used for surgical sutures. The polymer
structure is best represented by which of the following?
(lactic acid)
Short Answer 3 marks each - Choose 5 of the 6 questions! (15 marks)
1. A chemist is required to make the compound below for her company. Propose a one step synthesis that will
save the company time and money.
2. A world shortage of ethylene glycol in the late 1990s caused many Canadian companies to manufacture their
own. Using the readily available petrochemical ethene (and any inorganic reagents), describe a possible
synthesis whereby this was done.
3. Aspartame, marketed under the trade name Nutra-Sweet, has the following structure:
It is made from 2 compounds known as amino acids by the production of an amide bond. What are the
structures of these 2 amino acids?
4. In your own words state Markovnikov’s rule. Show an example that illustrates the rule.
5. Describe what a micelle is in words and with the aid of a diagram.
6. As a chemist in a plastics company, you are required to produce a waterproof polymer as shown below. Draw
and name the monomer for this reaction.
Problem - 5 marks each, answer both of the following - 10 marks
1. In your lab you have ethanol, 1-butanol, 2-propanol and all the inorganic acids you need. Describe how you would
prepare ethyl butanoate and then use saponification to prepare soap molecules with 4-carbon chains. Remember to show
names and structures for all organic molecules and indicate all catalysts. Don’t forget the saponification reaction.
2. Proteins are naturally occuring polyamides while Nylon is a synthetic polyamide.
a) Draw a synthesis pathway for a di-peptide (2 amino acids - just use “R” to indicate the side chain) and a
pathway for Nylon 4,6.
b)In nature there are 20 commonly used amino acids, explain briefly how the different side chains (“R”
groups) can alter a protein’s properties and how this could be achieved synthetically with Nylon
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