Organic Unit Quiz Assignment 2020
Organic Unit Quiz Assignment 2020
1. Choose a number between 1 and 10. State this number. Draw and name an alkane and an alcohol
with this number of carbon atoms. Compare the molecular polarity and intermolecular forces for each
compound and use these concepts to explain which compound would have the highest boiling point.
(5, C)
Butane
H2
C CH3
H3C C
H2
Butanol
H2 H2
C C
H3C C OH
H2
Butanol is much more polar because it has a hydroxyl group and not only the nonpolar hydrocarbon
chain. There can be hydrogen bonding between OH groups of two butanol molecules. Thus, Butanol
will have stronger intermolecular forces then nonpolar butane. We would have to invest more energy
to break intermolecular forces between Butanol molecules in order to create a gaseous state - Butanol
will have a higher boiling point. interaction between nonpolar
interaction between nonpolar hydrocarbon chains
hydrocarbon chains
H2 H2
H2 C C H
C CH3 H3C C O
H2
H3C C
H2 H2 H2 hydrogen bond
H2 C C H
C CH3
H3C C O
H3C C H2
H2
2. Explain why aldehydes and ketones may act as both polar solvents and non-polar solvents. Include
examples in your answer. (4, T/I)
nonpolar nonpolar
H3C
hydrocarbon chain hydrocarbon chain
H2 H H3C C
C C + O polar
C
H3C C + O H2 - carbonyl group
H2 -
butanal
polar 2-butanone
carbonyl group
Both aldehydes and ketones have nonpolar hydrocarbon chain (so, they can be used as polar solvents), and a
polar carbonyl group (which is the reason why they can be used as polar solvents).
3. Aromatic hydrocarbons are a unique group of unsaturated organic compounds that contain benzene,
C6H6. Explain why these compounds undergo substitution reactions but not addition reactions (like
other unsaturated hydrocarbons). Include in your answer the bonding in benzene. (4, T/I)
The aromaticity brings additional stabilization and they would lose the aromaticity in addition
reactions.
Bonding in benzene:
4. A chemist needs to synthesize ethoxypropane. He has the following substances available: ethene,
propene and water. Using structural diagrams, write a series of chemical reactions to show how the
chemist could synthesize ethoxypropane. (Assume that the chemist can use reaction conditions that
allow him to overcome Markovnikov’s rule.) (5, C)
starting materials:
H2O
+ H 2O OH
reacts slowly, Br
demands light
+ Br2 + HBr
to initiate radical
colorless orange-brown substitution colorless
Doesn't happen
in dark
Br
Br
+ Br2 This reaction is much faster
than the one above.
colorless orange-brown It can happen both in light and dark
colorless
6. Refer to Chapter 2: Polymers in your textbook (Section 2.1-2.5 p 78-100). Choose a polymer. What
type of polymer is it? Describe how this type of polymer is formed, identifying the monomer(s) for
this polymer. What is this polymer used for OR what is a physical property for this type of polymer?
(3, K/U)
This polymer has high durability and is unreactive with almost everything due to strong C-F bonds.
It is also very unipolar and is used to cover surfaces, like pans and cooking dishes, because food
won’t stick to it.