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OCV Chemistry, Grade 12 University Preparation (SCH4U-04/05)
Ottawa-Carleton Virtual Secondary School 2020-2021
Mr. Daniel Cho-En Lee (
daniel.cho-en.lee@ocdsb.ca
)
Oxidation reaction of alcohols
Alcohols may undergo an oxidation reaction
to become another functional group. Oxidation (the removal of electrons, Unit 5) happens on the hydroxyl C
atom. Among its 4 bonds, there is one C-O, and a total of 3 C-H and C-C. If more bonds become C-O, this C becomes more δ
+
, which is equivalent to losing e
-
.
❏
A primary (1º) alcohol, such as butan-1-ol, is first oxidized to aldehyde
, where the hydroxyl -OH group becomes a carbonyl =O group. The C
=O group is at the beginning of the chain. The aldehyde may be oxidized further to become a carboxyl -COOH group. The organic compound is now a carboxylic acid
, as the H on -
COOH has a small chance to join water (to become H
3
O
+
).
❏
A secondary alcohol (2º), such as pentan-2-ol, is oxidized to a ketone
. Like the primary alcohol, the -OH group is converted to a =O group, but the C
=O is in the middle of the chain. A ketone cannot be oxidized further.
❏
A tertiary alcohol (3º), such as 2-methylpentan-2-ol, cannot
undergo an oxidation reaction.
Skipped lab #2 - Alcohol oxidation
KMnO
4
(MnO
4
-
is permanganate) is used to take electrons from the
alcohols. MnO
4
-
(aq)
is violet (
purple when more concentrated). If the
alcohol loses electrons (becomes oxidized), the electron is transferred
to the “Mn
+7
” in MnO
4
-
to produce a black precipitate MnO
2(s)
(which
contains Mn
+4
) or Mn
2+
(aq)
, which is light pink. A colour change indicates
the reaction has happened.
Pre-lab: Predict the product of each oxidation reaction below, or write “no reaction.” Include any possible 1
OCV Chemistry, Grade 12 University Preparation (SCH4U-04/05)
Ottawa-Carleton Virtual Secondary School 2020-2021
Mr. Daniel Cho-En Lee (
daniel.cho-en.lee@ocdsb.ca
)
intermediate product.
❏
butan-1-ol → [O] (means oxidation)
→ ❏
butan-2-ol → [O]
❏
2-methylpropan-2-ol → [O]
No reaction
❏
propan-1-ol → [O]
❏
propan-2-ol → [O]
Discussion questions
(besides comparing results to hypotheses)
❏
The organic carbon compound is oxidized - it loses electrons. Where did the electrons go in this experiment? MnO
4
-
How does the transfer of electrons reflected on the colour change of the solution? From dark purple (MnO
4
-
) to light pink (Mn
2+
) with black precipitates (MnO
2
).
Drinking problem
If ethanol were classified as a drug, it would be the no.1 harmful drug in the society. While in terms of lethal-
dosage it is less deadly than heroin, cocaine and fentanyl (which is a rapidly growing crisis), ethanol is widely available and often culturally encouraged. Watch: Alcohol on the Brain - Acute effects
2
OCV Chemistry, Grade 12 University Preparation (SCH4U-04/05)
Ottawa-Carleton Virtual Secondary School 2020-2021
Mr. Daniel Cho-En Lee (
daniel.cho-en.lee@ocdsb.ca
)
https://youtu.be/zdCUZctmCqs
We already understand the principles of intermolecular reactions. If ethanol binds to a protein receptor/channel on the brain cell synapse, that means the δ
+
and δ
-
regions of ethanol are likely attracted to the oppositely charged regions on the protein, while its non-polar hydrocarbon regions are also aligned with a non-
polar region on the protein.
Exercise 1
. Intermolecular binding
(a)
Go to Pubchem and find a 3D model of “ethylene glycol.”
(b)
Rotate to your favourite “space filling” view.
(c)
Take a screenshot and then paste it on a Google slide. Crop the image to focus on the molecule.
(d)
Use multiple text boxes to label the surface of this molecule with either δ
+
, δ
-
, or nothing (meaning there is no
dipole there). Tips:
❏
O is δ
- if bonded to more electropositive atoms (e.g. C, H)
❏
H is δ
+
if bonded to more electronegative atoms (e.g. O)
❏
a hydrocarbon region is quite non-polar
You may also change the font size to reflect the relative strength of each dipole.
(e)
Finally, draw an imaginary protein binding site engulfing this ethanol molecule. Assign the complimentary δ
+
, δ
-
, and nothing inside the binding site. (What goes with what?)
Example (page 11)
https://docs.google.com/presentation/d/1HoLRrlCGU5k-OcGFjVr5cMPsshc5ag6j48uNzueUujU/edit?usp=sharing
Short-term intoxication
After ethanol binds to a protein receptor/channel in the brain, the protein channel opens and ushers in another chemical, which reduces the neurons’ activity and cognitive function. The neurons with this particular type of receptor are especially responsible for the self-inhibitory thinking (e.g. Hm… I really should not swear in front of my students.) So drinking alcohol suppresses inhibition. As a result, ethanol intoxicated individuals would typically behave wildly and cause damage. 3
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OCV Chemistry, Grade 12 University Preparation (SCH4U-04/05)
Ottawa-Carleton Virtual Secondary School 2020-2021
Mr. Daniel Cho-En Lee (
daniel.cho-en.lee@ocdsb.ca
)
Long-term cancer risk of ethanol
Chronic drinkers also have elevated risk of developing cancer. As ethanol is
metabolized in the liver, it is first oxidized to form ethanal (old:
acetaldehyde), an aldehyde with the help of an enzyme (a protein catalyst).
Then, there is a second enzyme to catalyze a second oxidation reaction of
ethanal to form ethanoic acid (old: acetic acid). The acid is then excreted.
The second step of the ethanol oxidation happens more slowly than the
first. Heavy drinking causes a build-up of ethanal
, which causes the person’s
face to turn red. Worse, ethanal also causes DNA damage and increases the
risk of cancer. Group 1 carcinogens (clear evidence of increasing cancer risk)
https://www.cancer.org/cancer/cancer-causes/general-info/known-and-probable-human-carcinogens.html
Exercise 2. List a few compounds that you have learned in this unit that is a group-1 carcinogen.
In East Asia, the majority of people have a potent first enzyme, so that ethanol is quickly oxidized to ethanal. Their ethanol intoxication is less severe. However, about half of East Asians also have a weakened second enzyme, so that the build up of ethanal is much worse.
Exercise 3. Big D is diagnosed with Covid-19. Knowing that alcohol can kill viruses quickly, Big D is planning to quaff
a full bottle of hand sanitizer, which contains 70% ethanol. What are the immediate effects of a flood of ethanol/propan-2-ol on the epithelial (upper skin) cells inside Big D’s mouth and esophagus? What are you going to observe on Big D’s face? What are the long-term effects of drinking a lot of ethanol (if Big D survived)? Explain each briefly.
Immediate effect
Face
Long-term effect
Ethanol molecules penetrate lipid membrane and disrupts intermolecular interactions in the cell;
Face will turn red as ethanol is oxidized to ethanal
Increased cancer risk due to ethanal build up (before it is further oxidized to ethanoic acid)
4
OCV Chemistry, Grade 12 University Preparation (SCH4U-04/05)
Ottawa-Carleton Virtual Secondary School 2020-2021
Mr. Daniel Cho-En Lee (
daniel.cho-en.lee@ocdsb.ca
)
Ethanol bind to protein receptor in the brain and slows down thoughts
Exercise 4. Maybe you have an unfortunate family member who suffers/suffered from alcoholism. Given that the immediate effect of ethanol drinking is “dumbing down the minds”, what do you think is the reason behind alcohol consumption? Propose some strategies to reduce excessive alcohol consumption. (research and quiz #6 question)
Methanol poisoning
Chubbyemu: A Man Drank 2 Liters Moonshine In 2 Hours...
https://youtu.be/4DQUrg0Yhu4
Being cheaper to produce than ethanol but having similar properties, methanol
is involved in a number of industrial processes. It could be mixed in alcohol
drinks intentionally or accidentally (as the methanol was not removed before
ethanol started to boil in the distiller). Just like ethanol, methanol can be broken down by the same two enzymes first
to an aldehyde (methanal, old: formaldehyde) and then a carboxylic acid
(methanoic acid, old: formic acid). As an acid, methanoic acid is 10 times more acidic (unit 4) than ethanoic acid. It acidifies the blood and disrupts various physiological functions. Besides, methanoic acid binds to an important protein that is involved in the electron transport chain on the inner membrane of mitochondria (we will see this again in 2.9 with more details). This binding shuts off the mitochondria to utilize oxygen to produce chemical energy, ATP. Methanoic acid poisoning causes blindness, as the optic nerves suffer from a lack of oxygen, and even death.
While the methanol-poisoned patient’s life is in danger, doctors would inject the patient with a large amount of ethanol. Ethanol and its oxidation reaction product, ethanal, competes with methanol and methanal for the same two enzymes
. In the meantime, a weak base, such as baking soda, is introduced to neutralize the excessive acid.
Exercise 5. A friend holds a moonshine party. After a while guests start to feel dizzy and their visions blur. Some yell
“I can’t see!” What is happening to them and why? What do you expect their immediate treatments to be? Explain why.
5
OCV Chemistry, Grade 12 University Preparation (SCH4U-04/05)
Ottawa-Carleton Virtual Secondary School 2020-2021
Mr. Daniel Cho-En Lee (
daniel.cho-en.lee@ocdsb.ca
)
Methanol is oxidized eventually to methanoic acid, which is acidic enough to lower the blood pH and disrupts physiological functions. Methanoic acid also blocks oxygen uptake in the mitochondria. Immediate treatment: introduce ethanol to compete with the oxidation pathways and reduce methanoic acid production. Also a weak acid such as baking soda is introduced to neutralize the existing acid.
Exercise 5.5
. Big D’s face stays red for a long time
even after just a little sip of beer. Is Big D more or less prone to methanol poisoning?
Less, because the second step of oxidation (methanal → methanoic acid) is slowed.
Ether (...
oxy-
, as side chain only)
An ether has an oxygen atom linking two hydrocarbon chains. In the current IUPAC rules,
ether is always named as a side chain
, never a main chain. The longer hydrocarbon chain
is the main chain. The shorter carbon chain becomes the ether side chain.
Because ether is named like a side chain, it may be arranged alphabetically with other side chains. For example, meth
o
xy comes before meth
y
l, because the “o” in methoxy comes before the “y” in methyl.
Since there is no hydrogen attached to the central oxygen, ether makes no hydrogen bonds with each other. The boiling point of ether is therefore much lower than that of alcohol. Since ethers are very volatile, they should be kept away from heat sources and especially an open flame.
Watch
: A high-school teacher sends a fireball at students:
https://youtu.be/fqY5ksPYx7U
Ether can be an isomer of alcohol, but they have very different properties.
Exercise 6.
Compare the following chemicals and explain their properties
meth
oxy
meth
ane
eth
anol
molecular formula
C
2
H
6
O
C
2
H
5
OH (C
2
H
6
O)
average # of hydrogen bonds
0 (no strong δ
+
H)
2
boiling point (look it up)
-24ºC
78ºC
which is more dangerous this
6
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(reactive/explosive) as a fuel?
Ethoxyethane is a useful sedative for small insects, which are typically overdosed to death in university labs. Contrary to the portrayals in TV and movies, it takes a large dose and many minutes to sedate huaman with this ether. There are better alternatives.
When tetraethyl lead was first banned, the above ether (old name: methyl t-butyl ether, MTBE) was used to raise octane number in gasoline. Due to its polar oxygen, MTBE is more soluble in water than the hydrocarbons in gasoline. It did not take long before MTBE was found in the groundwater and water wells near gas stations. There has been suspicion that MTBE consumption leads to cancer. Fortunately MTBE is no longer in use since early this century, as currently ethanol is the favourite additive to raise octane number.
Exercise 7. A grade 10 science teacher opens a bottle of “diethyl ether” in the chemical room, and is about to pour it
on a “rainbow” flame demonstration in order to keep the colourful fire going. Is this a good idea? Explain why or why not.
No, ethoxyethane (diethyl ether) has poor intermolecular attractions (bp = 35ºC). The bottle likely contains a large amount of evaporated ether. They will react with oxygen near the hot flame, which may spread into the bottle and cause an explosion, such as sending a fireball toward students.
Kahoot!
7
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- ow.com/ilrn/takeAssignment/takeCovalentActivity.do?locator=assignment-take [References] The combustion of 0.1562 g benzoic acid increases the temperature of a bomb calorimeter by 2.54°C. Calculate the heat capacity of this calorimeter. (The energy released by combustion of benzoic acid is 26.42 kJ/g.) Heat capacity kJ/°C A 0.2186-g sample of vanillin (C8 Hg O3) is then burned in the same calorimeter, and the temperature increases by 3.26°C. What is the energy of combustion per gram of vanillin? Energy kJ/g Per mole of vanillin? Energy kJ/molarrow_forwardBalanced chemical equation for the combustion of ethanol as a reference. C₂H5OH (1)+30₂ (g) → 2 CO₂ (g) + 3 H₂O(g) C-H=410 kJ/mol Selected Bond Energies O-H=463 kJ/mol How much energy is required to break the bonds in ethanol? Show your work. C-O=358 kl/mol C-C= 348 kJ/mol H-Carrow_forwardGive one possibility for the mystery reactant R in this organic reaction: Pd R + H2 CH3-CH2-CH2-CH3 Specifically, in the drawing area below draw the condensed structure of what R might be. There may be more than one correct answer. Note: keep in mind that the equation above states R and H2 are present in a 1:1 mole ratio. No reaction. Click anywhere to draw the first atom of your structure. ☑ G ☐ : ☐ टेarrow_forward
- The name carbohydrate comes from the fact that many simple sugars have chemical formulae that look like water has simply been added to carbon. (The suffix hydrate from the Greek word hydor ("water") means "compound formed by the addition of water.") The actual chemical structure of carbohydrates doesn't look anything like water molecules bonded to carbon atoms (see sketch at right). But it is nevertheless possible to chemically extract all the hydrogen and oxygen from many simple carbohydrates as water, leaving only carbon behind. If you search the Internet for "reaction of sulfuric acid and sugar" you will find some impressive videos of this. Suppose you had (200. g) of ordinary table sugar, which chemists call sucrose, and which has the chemical formula C12H₂2011. Calculate the maximum mass of water you could theoretically extract. Be sure your answer has alunit symbol, and round it to 3 significant digits. 0 HO CH₂OH OH OH OH The actual chemical structure of glucose.arrow_forwardThe name carbohydrate comes from the fact that many simple sugars have chemical formulae that look like water has simply been added to carbon. (The suffix hydrate from the Greek word hydor ("water") means "compound formed by the addition of water.") The actual chemical structure of carbohydrates doesn't look anything like water molecules bonded to carbon atoms (see sketch at right). But it is nevertheless possible to chemically extract all the hydrogen and oxygen from many simple carbohydrates as water, leaving only carbon behind. If you search the Internet for "reaction of sulfuric acid and sugar" you will find some impressive videos of this. Suppose you had 300.g of ordinary table sugar, which chemists call sucrose, and which has the chemical formula C12H22O11 . Calculate the maximum mass of water you could theoretically extract. Be sure your answer has a unit symbol, and round it to the correct number of significant digits.arrow_forward5. Acetone and 2-propanol are chemically interconvertible. Reduction (by the addition of the equivalent of H2) of acetone yields 2-propanol. Conversely, oxidation (by the removal of the equivalent of H2) of 2-propanol yields acetone. Is the evaporation data for these substances the same or different? If different, can you account for why this may be the case from a comparison of the Lewis structures of each substance and the IMFs present in each substance? Explain.arrow_forward
- Consider the acid-base reaction between iodoethane (CH3CH2I) and hydroxide (-OH). CH3CH2I + OH- --> CH3CH2OH + l- Use the table of bond energies to estimate the change in enthalpy (∆H in kJ/mol) for this reaction. Think about the bonds that are broken and that are formed. This reaction is endothermic, exothermic or energy neutral Using your calculation, what can you say about the strengths of the bonds? -The bonds before the reaction are stronger than the bonds after the reaction. -The bonds after the reaction are stronger than the bonds before the reaction. or -The bonds before and after the reaction are equivalent in strength.arrow_forwardNucleotides are molecules that make up the structures of RNA and DNA. Modify the compounds to create adenosine monophosphate (AMP).arrow_forwardUsing bond energies and the energy change of the reaction, calculate the bond energy of the CH single bond. Do not round your answer. C4H10 is butane 2C4H10 + 13O2 → 8CO2 + 10H2O . Bond Energy(kJ/mol) C-C 346 O=O 495 C=O 805 O-H 459 Reaction energy(kJ) -5329arrow_forward
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