SCH4U Lee 2.4
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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
)
Functional groups
IUPAC Functional Groups Naming Priorities
You should be familiar with the naming of red
starred suffixes and prefixes
*
. When there are
more than two functional groups,
the highest-
priority group becomes the
suffix
. For all lower-
priority groups, use their
prefix
, like methyl is the
prefix of a one-carbon alkane side chain.
❏
If there is a carboxyl group (highest
priority), this compound is a carboxylic
acid (e.g. ...ethanoic acid)
❏
Halogens and ethers have lower
priorities than alkanes, so they are always named using prefixes (e.g. fluoro-, ethoxy-).
Review: What does hydrogen bond look like?
https://sketchfab.com/3d-models/ice-lattice-7bacd374b8d849a2bdc92148b840b6ef
Up to how many hydrogen bonds can be made in this molecule?
3 maximum, in reality, up to 2 on average
6, 4 (ethane
-1,2-diol)
3, 2
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
)
How about this molecule?
And this?
Which of the above has the highest boiling point?
middle
Alcohols
(
suffix: -ol
) (prefix: hydroxy-) (-OH = a
hydroxyl
group)
Exercise 1.
(a)
What is the chemical (molecular) formula of propan-1-ol? What is the other possible propanol?
Better: C
3
H
7
OH (ok: C
3
H
8
O), propan-2-ol
(b)
Among alcohols, how many isomers of butanols are there? Draw their line diagrams.
See below
(c)
The molecule on the right is
glycerol
. What is its IUPAC name? (hint: it is a …
tri
ol)
propane-1,2,3-triol
With a polar O-H bond like those in water, alcohol makes hydrogen
bonds with each other and polar solvents such as water. The
hydrocarbon region on the alcohol provides only weak intermolecular
attractions. Therefore, the b.p. of small alcohols are lower than that of
water. Small alcohols are miscible with water, as their polar region (-OH)
is relatively large. For bigger alcohols (starting with butan-1-ol), they
become immiscible with water, like oil and water.
Halogenation reactions of primary, secondary, and tertiary alcohol
Remember Markovnikov’s rule? The same C-H dipole analysis can be used to predict the reactions of the halogenation
reaction of alcohols. As the O-H group is bonded to a
C
, we can classify alcohols based on how many additional carbon
atoms this
C
is bonded to. If it is bonded to only 1 C atom, we have a primary (1º) alcohol.
With an alkane mainchain, each carbon makes 4 bonds. Regarding the
C
where the -OH group is attached, there is
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
)
already an -OH bond. The rest of the 3 bonds are either
C
-C or
C
-H.
❏
A primary alcohol has its hydroxyl
C
bonded to 1 C and 2 H, in addition to 1 O.
❏
A secondary alcohol has its hydroxyl
C
bonded to 2 C and 1 H, in addition to 1 O.
❏
A tertiary alcohol has its hydroxyl
C
bonded to 3 C, in addition to 1 O.
Also, we know that with each
C
-H bond, the
C
gains a weak δ
-
. With each
C
-O bond, the
C
gains a δ
+
. There is no
dipole moment generated across a C-C bond.
Exercise 2.
Among primary, secondary, and tertiary alcohol, regarding the
carbon atom
where the -OH group is
attached, which
C
carries, relatively, the strongest partial negative charge? Explain.
Back in the halogenation reaction of alkenes, we know that over a double bond, the carbon with the
smaller δ
-
is the preferred site of halogenation. You may therefore infer that
a tertiary alcohol is the best candidate
to receive a halogen
, such as Cl. But the -OH bonded carbon is already making four bonds. The period-2 carbon is too
small to have an open surface area to make a 5th bond with the halogen. An existing bond has to be removed first.
In the case, the -OH group will leave, and the -X (e.g. -Cl) will take its place.
Exercise 2.5.
With suitable conditions and catalyst, it is possible to add water onto an alkene. This is a type of
addition reaction, or more specifically,
hydration
.
(a)
Using your knowledge in dipole analysis (or simply recite Markonikov’s rule), what should be the major product of
the following reaction?
Propene + HCl
→
2-chloropropane
Propene + H
2
O (H
+
-OH
-
) →
propan-2-ol
(b)
The reverse reaction of hydration is dehydration, which is a type of elimination reaction. For butan-1-ol, name the
product of its elimination/dehydration reaction.
Elimination: butan-1-ol → H
2
O +
but-1-ene
Substitution Reaction
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
)
An
addition
reaction adds a small molecule (e.g. H
2
, X
2
, H-X) to an existing molecule.
A
substitution
reaction replaces a small group with another small group - a “double displacement” in 3U words.
Exercise 3.
What are the products of each of the substitution reactions above (+HCl)?
A.
butan-1-ol + HCl →
1-chlorobutane + H
2
O
B.
2-methylpropan-1-ol + HCl →
1-chloro-2-methylpropane + H
2
O
C.
butan-2-ol + HCl →
2-chlorobutane + H
2
O
D.
2-methylpropan-2-ol + HCl →
2-chloro-2-methylpropane + H
2
O
Exercise 4.
Out of the four reactions above, which one should be the fastest?
D) because the carbon in C-OH is the least δ
-
and it allows for the easiest attachment of Cl
-
.
Exercise 5.
Complete the following reactions with IUPAC names for organic compounds. It might help to draw the
reactant organic compound first. If there are more than one possible products, only show the main product.
(a)
prop-1-ene + HCl →
2-chloropropane
(b)
prop-1-ene + Cl
2
→
1,2-dichloropropane
(c)
1,2-dichloropropane → Cl
2
+
propene
(d)
1-chlorobutane → HCl +
but-1-ene
(e)
propan-1-ol + HCl →
1-chloropropane + H
2
O
(f)
propan-2-ol + HCl →
2-chloropropane + H
2
O
(g)
2-methylbutan-2-ol + HCl →
2-chloro-2-methylbutane + H
2
O
Exercise 6.
Each of pentan-1-ol, pentan-3-ol,
2-methylbutan-2-ol, and 2,2-dimethylpropan-1-ol undergoes a
substitution reaction with HCl. Which reaction should happen the most quickly?
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
)
Skipped lab #1 - Alcohol halogenation
In a typical semester, here students have a half-period lab to verify the
above hypothesis on reaction rate. Here are the pre-lab questions:
(1)
Draw a structural or line diagram of the following:
A.
butan-1-ol
B.
butan-2-ol
C.
2-methylpropan-2-ol
D.
propan-1-ol
E.
propan-2-ol
(2)
Draw the possible halogenation reaction for each of the five alcohols. Name all reactants and products.
(3) Are
1°, 2°, and 3° alcohols all expected to undergo substitution (halogenation) quickly? Explain why in 20
words.
During the lab
Students proceed to mix concentrated HCl with each alcohol. Here are signs that a reaction took place:
❏
There were tiny liquid droplets observed on the inner wall of the glass tube within seconds.
❏
The solution became cloudy.
Some alcohols were immiscible with HCl, and nothing seemed to happen overnight.
Discussion questions
(besides comparing results with hypothesis)
1.
What could be the tiny liquid droplets on the glass tube? Explain.
If a molecule makes weak intermolecular forces, it is more likely to escape into the gas phase (evaporate/boil).
So the tiny liquid droplets on the glass tube are chemicals that had weaker intermolecular forces and escaped the
liquid phase. One way to tell which chemical has the weakest intermolecular force is to look up the boiling points.
Even better, we can discuss the number of hydrogen bonds in each:
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
)
2-methylpropan-2-ol (83ºC) + HCl (dissociated into ions) →
2-chloro-2-
methylpropane (b.p. = 51ºC) + H
2
O (b.p. = 100ºC)
●
2-methylpropan-2-ol: one alcohol group, max. 3 hydrogen bonds (on average,
up to 2
)
●
HCl is a strong acid and has dissociated to H
+
(H
3
O
+
) and Cl
-
.
Ions
are very unlikely to boil off because of the
strong electrostatic attractions in ion-dipoles.
●
2-chloro-2-methylpropane makes
no
hydrogen bonds among themselves. (They do have the mediocre
δ
-
Cl-C attract the δ
+
of H
2
O and -OH, though these are not comparable with the authentic H-bonds among
H
2
O and OH.)
●
You already know that H
2
O makes
up to 4
H-bonds.
2.
How can the cloudiness in some reactions be explained?
2-chloro-2-methylpropane can make a weak hydrogen bond (probably better to say permanent dp-dp) with water or
-OH but the water and alcohol make more and stronger hydrogen bonds among themselves.
3.
Suppose a reaction was expected to take place, but the reactants separated into two layers and no reaction
seemed to happen. Why is there no reaction?
At the liquid interface there are very limited contacts among reactant molecules.
End of Quiz #5 coverage
SCH4U-06 Quiz #5-#6
https://docs.google.com/presentation/d/1mUy2IUFos3TPGw_Q1Bsvs3kg9RA78O3oVLs5rOweq2I/edit?usp=sharing
https://docs.google.com/presentation/d/1S4KWlEi9eFBitfrcWzs7EY9XXTjWD-BK-iCEdeRBZ2w/edit?usp=sharing
Alcohol vs. SARS-CoV-2
Hand sanitizers are commonplace during this COVID-19 pandemic. If
you have ever taken a deep breath from your just-sanitized hand and,
you can smell alcohol. The major and active ingredient of hand
sanitizers is alcohol, either
70% ethanol
(old: ethyl alcohol) or
propan-2-ol
(old: isopropyl alcohol). During our next break, if you have a hand sanitizer bottle, take a look at the
label to see if it contains one of these two alcohols.
6
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Chemistry, Grade 12 University Preparation (SCH4U-04/05)
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Mr. Daniel Cho-En Lee (
daniel.cho-en.lee@ocdsb.ca
)
These two alcohols are able to disrupt the lipid capsule of SARS-CoV-2 (severe acute respiratory symptom -
coronavirus - 2), the virus that causes COVID-19.
Soap and alcohol both work
In high school biology, we typically describe viruses as
“genetic material encapsulated by proteins.” In the case of
SARS-CoV-2, proteins do not cover the virus entirely, but
there is a lipid membrane that protects its RNA. Like fat, lipid
has long hydrocarbon tails, though only 2 tails. (Fat has 3.)
You might have learned the structure of soap, which is part of
a hydrolyzed fat molecule. Soap keeps the long, non-
polar
hydrocarbon tail of fat and now has an even more
polar
head due to hydrolysis. The polar head of soap
establishes hydrogen bonds with water.
When we rub our soapy hands together in the sink, we give the soap’s non-polar tails a chance to establish LDF with
the virus’ protective lipid layer. Since the soap’s tails are not really structurally compatible with the viral lipid, they
will disintegrate the virus’ protective layer. Then the broken virus may be washed away with water.
Watch
: Fighting Coronavirus with Soap
https://youtu.be/s2EVlqql_f8
Ethanol and propanol disable the virus with a
different approach. Pathogens are evolved in nature
to survive in an aqueous (solvent = water)
environment. The lipid layer keeps water and water
soluble chemicals out. By rubbing our hands using a
liquid alcohol, we flood the pathogens with a not-so-
polar solvent. These small alcohols are not polar to diffuse through the lipid membranes and enter the cell. Both polar
and non-polar regions on the macromolecules (e.g. proteins) of the pathogens interact with alcohol, dropping their
existing interactions and establishing new ones. Proteins will change their conformations and often denature and
7
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
)
aggregate, losing their functions.
Note: 95% ethanol/propan-2-ol does not work as well as 70% here. The 95% alcohol causes a big mess of
aggregates near the surface of the pathogens quickly. The big mess becomes a new protective layer!
Exercise 5
. Compare the chemistry behind using soap or 70% ethanol/propan-2-ol as a hand sanitizer. In which
aspects are they similar? In which aspects are they different?
Wash hand with Soap
Hand sanitizer
70% ethanol or 70% ethan-2-ol
Summary
in 20 words
Soap molecule is incorporated into the lipid
membrane and causes leaks
Alcohol molecules penetrate the lipid membrane
and disrupts intermolecular forces of the
interior
Similar
Disables the virus
Different
Soap molecules displaces regular lipid
molecules on the membrane
Alcohol displaces regular water solvent inside
the virus
8
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The structure of the antiviral drug penciclovir is shown below. Which of the
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Examine the following compounds, and answer questions 31-35.
CH3-CH2-CH-CH,
CH-CH-CH,-OH
CH-CH2-OH
CH-CH-OH
CH3-CH2-CH2-CH-OH
CH3-CH2-O-CH2-CH,
Он
CH,
CH.CH,
II
III
IV
V
VI
31 Is
31
arrow_forward
Using family suffixes to name organic compounds
Name these organic compounds:
structure
name
H.
H–C– OH
H.
CH, — СН,— СH,
–C – H
||
Н— С — ОН
Check
Explanation
O 2021 McGraw Hill LLC. AlI Rights Reserved. Tern
||
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(Picture attached)
Functional Groups:
1. Benzene
2. Halogen
3. Carboxyl
4. Hydroxyl
Identify the functional groups that the 2 molecules contain. Note: each functional group can be used more than once. Put in numerical order with no space.
Sucarlose =
Ibuprofen =
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Oo.105.
Subject :- Chemistry
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A. Identify the name of the functional group where the given organic compounds belong
(alcohol, ether, aldehyde, ketone, carboxylic acid, ester, amine)
1.
H
H
Br
H
H -C
C-H
H
H
H
2.
H
H
Н—с
H -5-
H
H
N-
H-
3.
H
H
-нн
I-
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No need to upload any image give me the name with proper explanation will upvote.
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CI
H2C-CH2-CH2-CH2-C-H
Туре of functional group
u.
CI
H2C-CH2-CH2-CH2-C-H
IUPAC
CI
H2C-CH2-CH2-CH2-C-H
Common Name
CH3 O
H.
Туре of functional group
V.
CH, O
Br
IUPAC
CH, O
Br
H.
Common Name
arrow_forward
Acetaminophen, a popular painkiller, has the following structure:
Name the recognizable functional groups in this molecule. Do you think there are other groups of atoms in this molecule that might qualify as functional groups?
arrow_forward
classify the following according to their functional group
arrow_forward
Please help with organic chem hw
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could i get help with questions 1-3 please
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CI
Br-C-CH,-CH-CH3
j.
Туре of functional group
CI
Br-
-C-CH2-CH–CH3
IUPAC
CI
Br-C-CH,-CH-CH3
Common Name
CH3
kk. H3C-CH-Ĉ-CH3
Туре of functional group
CH3 1
H3C-CH-C-CH3
IUPAC
ÇH3
H3C-CH-C-CH3
Derived Name
arrow_forward
CH2-CH2-CH2-CH2-CH3
сс.
Туре of functional group
of
CH2-CH2-CH2-CH2-CH3
Common Name 1
CH2-CH2-CH2–CH,-CH3
Common Name 2 (Derived Name)
dd. H3C-CH2-CH2-CH2-C=N
Туре of functional
group
H3C-CH2-CH2-CH,-CEN
IUPAC
H3C-CH2-CH2-CH2-CEN
Common Name 1
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1-2 please
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Can you please answer the question #2? Thanks
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c) pgs. 413-416 book
i
1.
2. H₂, Ni
NH₂
"
H*
arrow_forward
can you identify functional group?
the molecular formula for this C3H7NO
and DBE value is 1
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H3C-CH2-CH2-CH2-CEN
Common Name 2 (Derived Name)
H3C-CH2-CEN
ee.
Type of functional
group
H3C-CH2-CEN
IUPAC
H3C-CH2-CEN
Common Name 1
H3C-CH2-CN
Common Name 2 (Derived Name)
ff. H3C-CH2-CH2-CEN
Type of functional group
H3C-CH2-CH2-CEN
IUPAC
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O ORGANIC FUNCTIONAL GROUPS
Naming and drawing aldehydes
Write the systematic name of each organic molecule:
OH
I
H-C-CH₂-CH-CH₂-OH
structure
O
||
Explanation
H—C-CH2-CH2–CH3
HỌ—CH2CH2–CH2–CH2−C−H
Check
name
O
0
please answer!! read directions. thank you! | Chegg.com
X
Ⓒ2023 McGraw Hill LLC. All Rights Reserved. Ter
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Identify the functional groups in the following molecules.
(Use names from the table below. List each class of functional group only once. If there are fewer than 3 functional groups, leave an appropriate number of answer boxes
empty.)
a)
b)
s
epibatadine, analgesic from skin of
neotropical frog, 200x potency of morphine
OH
Name Structure
Alkene
Alkyne
Structures of Some Common Functional Groups
Arene
Halide.
Alcohol
-C=C1
X*
(X=F, Cl, Br, 1)
Nitro
Thiol
Name
Aldehyde
Ketone
Carboxylic Acid
Structure
XSH
i
**
OH
W
Previous
Next
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A Moving to another question will save this response.
Question 13
Which of the following would be a correct molecular formula for a 5 carbon alkyne? (I would strongly suggest you draw the structure.)
O CSH10
O C5H14
O CgH8
O CgH5
O C5H12
A Moving to another question will save this response.
MacBook Air
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F2
F3
F4
F5
F6
F7
24
2
4
W
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T.
Y
< CO
# 3
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- N Chrome → C Ol H₂N MARK File Edit View History Aktiv Chemistry esc app.101edu.co -C ! 1 NIC Q IZ @ 2 C-N C- X WYKW W N Bookmarks Profiles Tab Window Help + CH H₂C-CH₂ HO-C H₂ The structure of the antiviral drug penciclovir is shown below. Which of the following functional groups is indicated by the box? 1,503 #3 CH-CH₂ E $ 4 ОН R JUN 30 do 5 % MacBook Pro A 6 121 Y & 7 W U A) amine B) alcohol C) ketone D) amide 8 ( O 25 9 www ú 0 0 O 15% P D - Barrow_forwardExamine the following compounds, and answer questions 31-35. CH3-CH2-CH-CH, CH-CH-CH,-OH CH-CH2-OH CH-CH-OH CH3-CH2-CH2-CH-OH CH3-CH2-O-CH2-CH, Он CH, CH.CH, II III IV V VI 31 Is 31arrow_forwardUsing family suffixes to name organic compounds Name these organic compounds: structure name H. H–C– OH H. CH, — СН,— СH, –C – H || Н— С — ОН Check Explanation O 2021 McGraw Hill LLC. AlI Rights Reserved. Tern ||arrow_forward
- (Picture attached) Functional Groups: 1. Benzene 2. Halogen 3. Carboxyl 4. Hydroxyl Identify the functional groups that the 2 molecules contain. Note: each functional group can be used more than once. Put in numerical order with no space. Sucarlose = Ibuprofen =arrow_forwardOo.105. Subject :- Chemistryarrow_forwardA. Identify the name of the functional group where the given organic compounds belong (alcohol, ether, aldehyde, ketone, carboxylic acid, ester, amine) 1. H H Br H H -C C-H H H H 2. H H Н—с H -5- H H N- H- 3. H H -нн I-arrow_forward
- No need to upload any image give me the name with proper explanation will upvote.arrow_forwardCI H2C-CH2-CH2-CH2-C-H Туре of functional group u. CI H2C-CH2-CH2-CH2-C-H IUPAC CI H2C-CH2-CH2-CH2-C-H Common Name CH3 O H. Туре of functional group V. CH, O Br IUPAC CH, O Br H. Common Namearrow_forwardAcetaminophen, a popular painkiller, has the following structure: Name the recognizable functional groups in this molecule. Do you think there are other groups of atoms in this molecule that might qualify as functional groups?arrow_forward
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