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Organic Unit Quiz Assignment 2020

The document contains instructions for an Organic Unit Quiz Assignment with 6 short answer questions. Question 1 asks students to choose a number between 1 and 10, draw the corresponding alkane and alcohol, compare their molecular polarity and intermolecular forces, and explain which would have the higher boiling point. Question 2 explains why aldehydes and ketones can act as both polar and nonpolar solvents. Question 3 discusses aromatic hydrocarbon substitution versus addition reactions and benzene bonding. Question 4 provides a multi-step reaction to synthesize ethoxypropane from given starting materials. Question 5 asks how a student would identify cyclohexane versus cyclohexene using bromine water. Question 6 requires students to choose

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0% found this document useful (0 votes)
41 views6 pages

Organic Unit Quiz Assignment 2020

The document contains instructions for an Organic Unit Quiz Assignment with 6 short answer questions. Question 1 asks students to choose a number between 1 and 10, draw the corresponding alkane and alcohol, compare their molecular polarity and intermolecular forces, and explain which would have the higher boiling point. Question 2 explains why aldehydes and ketones can act as both polar and nonpolar solvents. Question 3 discusses aromatic hydrocarbon substitution versus addition reactions and benzene bonding. Question 4 provides a multi-step reaction to synthesize ethoxypropane from given starting materials. Question 5 asks how a student would identify cyclohexane versus cyclohexene using bromine water. Question 6 requires students to choose

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Organic Unit Quiz Assignment Total /30

Part 1 - Multiple Choice (5, K/U)


Complete the Organic Unit Quiz Assignment Multiple Choice form and submit.

Part 2 – Short Answer (25)


Answer the questions individually. All work must be shown for full marks. Only handwritten answers will
be accepted. Take pictures of your work and submit. Marks for each question are shown after the question.

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:

Figure is taken from the internet.

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

+ *this reaction is against Markovnikov rule,


OH O but we suppose that appropriate conditions
can be found to overcome Markovnikov selectivity
1-ethoxypropane
5. In a laboratory experiment your lab partner forgot to label two test tubes, both of which contain
colourless, transparent liquids. You know one contains cyclohexane and the other contains
cyclohexene. You discover bromine water (Br2) in the lab and decide to add it to both hydrocarbons to
determine their identity. Explain how you would know the identity of the hydrocarbons in each test
tube referring to the structure of each hydrocarbon in your answer. (4, A)

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.

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