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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
)
Alkynes (
-yne
)
Recap: Alkanes are sp
3
orbital hybridized tetrahedral carbons with single bonds, while alkenes are sp
2
trigonal planar
carbons with one or more double bonds. Alkynes are sp linear carbons with one or more triple bonds.
ethane C
2
H
6
ethene C
2
H
4
ethyne C
2
H
2
Exercise 1.
What is the chemical formula of pent-2-yne? Name 2 isomers.
C
5
H
8
, pent-1-yne, (3Z) penta-1,3-diene
Cyclic alkanes (
cyclo-
+
-ane
)
Normally, sp
3
alkanes have a bond angle of 109.5º. But while the carbon chain wraps around to form a ring, the
structural constraints will bend this angle. In cyclopropane (C
3
H
6
), the bond angle shrinks to merely 60º. The crowded
electron clouds of small cycloalkanes make them very unstable. The larger cycloalkanes, such as cyclohexane (C
6
H
12
),
are more stable as the bond angles approach normal. (The hexagonal line diagram of cyclohexane is misleading - each
carbon is still bonded to 2H and 2C in sp
3
hybridization.) If you have a molecular model kit, build a cyclohexane
following the example on Pubchem:
https://pubchem.ncbi.nlm.nih.gov/compound/Cyclohexane#section=3D-Conformer
Exercise 2.
What is the molecular formula of cyclopentane? Name two isomers of cyclopentane.
C
5
H
10
, (E) pent-2-ene, 2-methylbut-1-ene
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
)
The benzene ring and aromatic compounds
Many students confuse cyclohexane with a critically important cyclic alk
ene
, cyclohexa-1,3,5-
tri
e
ne (C
6
H
6
). There are
three double bonds in this 6-carbon ring, originating from the #1, #3, and #5 C. The six-carbon ring is flat while all six
C are sp
2
hybridized. Six unpaired carbon 2p orbitals float both above and below the plane, forming
three π bonds in two possible ways (1-2, 3-4, 5-6 or 2-3, 4-5, 6-1). These two arrangements of π
bonds “resonate” (average out), so essentially there is a donut-shaped electron cloud both above and
below the six-carbon ring. The C
6
H
6
molecule is called
benzene
. Structurally, benzene is a one-ring
graphene
(a layer of sp
2
carbon atoms with three resonating triple bonds in each ring). But they have very different properties.
Exercise 3.
Draw a Venn diagram to compare and contrast cyclohexane and benzene
Answer:
https://docs.google.com/presentation/d/1HoLRrlCGU5k-OcGFjVr5cMPsshc5ag6j48uNzueUujU/edit?usp=sharing
The benzene ring may be found in a wide variety of organic compounds. Many bind to our olfactory (nose smelling)
receptor proteins, giving us a pleasant smell. Therefore, organic compounds that contain benzene rings are also called
aromatic compounds
(aroma = good smell.) When molecules “bind” together, there is a good structural fitting so
that oppositely charged regions get close enough to attract each other (dp-dp). The non-polar regions also appear to
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
)
unite.
Many colourful pigments contain benzene rings or a similar co-planar structure. Such configuration allows the
compound to absorb certain wavelengths of visible light so that we see vivid colours (the visible wavelengths that are
not absorbed).
Guess what is the compound below (acid = red, alkaline = blue)?
Senior chemistry favourite titration pH indicator, phenolphthalein:
Benzene by itself is quite toxic and may be found in gasoline. Compounds that consist
of multiple benzene rings (only) are called
polyaromatic hydrocarbons (PAHs)
.
PAH may be produced by burning organic compounds such as fossil fuels, tobacco,
even overcooked barbeque. PAHs are carcinogenic - some scientists theorize that
PAH mimics DNA nitrogenous bases and disrupts DNA replication.
Exercise 4
. Compare and contrast the structures of cyclohexane and benzene.
Answer (slide 9):
https://docs.google.com/presentation/d/1HoLRrlCGU5k-OcGFjVr5cMPsshc5ag6j48uNzueUujU/edit?usp=sharing
Exercise 5
. What is the similarity between graphene and benzene?
resonating π bonds above and below the sp
2
plane
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
)
Exercise 6
. What are aromatic compounds?
compounds that contain benzene rings (high school definition)
Exercise 7
. Describe three frequently seen properties of benzene-containing compounds.
Smells good, have colours (2-4 coplanar rings), toxic (if multiple benzene rings are connected together)
Extended topic
Polycyclic Aromatic Hydrocarbons: What Are They and Why Do They Matter?
https://www.youtube.com/watch?v=fjgvmL61e5k
Many functional groups can be attached to a benzene ring. For this course and entry-level university chemistry, please
be familiar with
toluene
(methylbenzene),
phenol
(hydroxybenzene), as well as “o
rtho (1,2) /m
eta (1,3) /p
ara (1,4)”
arrangements.
TNT
The dynamite TNT stands for
tri
nitro
toluene
while its IUPAC name is 2-
methyl
-1,3,5-
tri
nitro
benzene
. (
Toluene
= methylbenzene) Every few years there is news about explosions
caused by nitro group (-NO
2
) / nitrate (NO
3
-
) compounds. The most recent two tragedies
happened in Tianjin, China (2015) and Beirut, Lebanon (2020), each claiming hundreds of
lives.
Why is nitro group/nitrate dangerous? The burning of fuels requires oxygen, but nitro/nitrate compounds supply their
own oxygen. The included O are bonded with the also quite electronegative N. For the same reason that O=O splits
under heat, once there is kinetic energy, the O atoms packed in nitro/nitrate solids are released to grab electrons
from more electronegative atoms, such as C. If there are suitable fuels nearby, this will release more heat, causing
more oxygen to be released... The chain reaction leads to a devastating explosion. Chemicals containing -NO
2
/ NO
3
-
,
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
)
such as fertilizers, should be stored away from potential heat sources and flammable materials, such as wood dust.
Fertilizer-grade ammonium nitrate (NH
4
NO
3
) is banned in many countries under the fear of terrorist bombing.
Exercise 8
. Explain to a family member why lawn fertilizer should be stored away from flammables and heat sources.
Extended topic
Why was the Beirut blast so massive? Ammonium Nitrate explosion explained
https://www.youtube.com/watch?v=MEpFyE_ED7M
Bisphenol A (BPA)
Phenol
is a -OH group attached to benzene. About a decade ago, there was a
widespread fear of bis
phenol
-A (BPA, containing two phenol groups in “bis”
arrangement) added to the inner lining of metal cans and plastic containers. The fear
stems from the suspicion that BPA mimics human female hormone so that ingesting BPA
increases the risk of breast cancer. Back in 2009 Mr. Lee taught a four-year university
course, where we tried to virtually dock a BPA molecule into the model of estradiol protein
receptor. It was not particularly a good fit, so we did not find evidence to support the fear.
The functional group phenol is often confused with “phenyl,” which means a benzene ring
used as a side chain, just like “methyl” is a methane side chain.
Extended topic
Scishow: Is BPA bad?
https://www.youtube.com/watch?v=8mXosTkwtYs
Exercise 9
: Draw the following aromatic compounds:
A.
benzene
B.
ortho-dichlorobenzene (1, 2)
C.
meta-difluorobenzene (1, 3)
D.
para-diethylbenzene (1, 4)
E.
toluene
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
)
F.
phenol
G.
2-methyl-1,3,5-trinitrobenzene
Exercise 10:
Draw the following hydrocarbons:
A.
cyclohexane
B.
cyclopentane
C.
n-hexane
D.
3-ethyl-2-methylpentane
E.
trans
-pent-2-ene
F.
(2Z)-but-2-ene
1
End of Quiz #4 Coverage (2.1-2.2)
Quiz #4 from SCH4U-06
https://docs.google.com/presentation/d/1fAheidUWcJxr7OyXuHqBf9vFqXtZ41gh7wUreQyksvI/edit?usp=sharing
1
D. C. Lee (2020). SCH4U course notes.
(sample citation)
https://docs.google.com/document/d/1tgDCDB87hVyQRt_NJksCQrP6h5zPsedP8Z1ZcyYqFJo/edit?usp=sharing
Accessed on: November 27, 2020
6
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Related Questions
4:30 PM Wed Apr 27
* 74%
O O Q E
HW 12
Home
Insert
Draw
Layout
Review
View
I| Select Objects
Draw with Touch
40. There are five compounds with the formula C6H14 (one of them is linear and the others are branched).
Draw structural formulas for any two of those branched isomers. See Example 6.3 on page 152.
H3C
CH3
CH3
44. Name the following alkanes.
CH¿CH3
CH,CH3
CH3
CH;CH2CHCH2CH¿CH3
CH;CHCHCH,CH;CH3
CH;CHCHCH3
CH3
CH3
a
C
3-CHhylheypare
ethyl-2 methyllnexano
а.
7+3
dimethibulane
С.
46. Name the following alkenes.
CH2=CHCH,CHCH;CHCH3
CH2CH3
CH2=CHCH2CH3
CH3
CH3
CH2=CHCH2CHCH3
a
b
C
|burene
а.
b.
C.
48. Name the following alkynes.
CH,CH3
GH=CH
CH3 C=CCH2CH3
CH;C=CCHCH,CH3
a
b
C
arrow_forward
please answer #6
arrow_forward
Write the name/structural formula of the following compounds:
arrow_forward
09:49
< Back CHE_3100_WS3.1.pdf
Organic Chemistry I
Dashboard
a) C6H10
b. Skeletal Isomers: Isomers that result from the reorganization of the carbon
backbone are called structural isomers. Usually, these are easy to spot using
IUPAC nomenclature; if the name of the parent compound of one molecule is
different from the other molecule that it is being compared to, then the
carbon skeleton has been reorganized and thus they are skeletal isomers of
each other.
WS-3.2: Draw skeletal isomers for the following molecules and provide an IUPAC name
for each structure. Two isomers per compound are sufficient for this exercise.
b) C4H8
c) CsH100
Dk
d)
بلوه
Organic Chemistry I
B
goo
Calendar
2
Shailesh Ambre
To Do
c. Positional Isomers: Positional isomers have the same parent compound (root
name), but the position of the substituents differ. To identify molecules that
share a positional isomer relationship-
i. First, check if the root name is the same.
ii. Second, check all substituents and…
arrow_forward
III. Draw two isomers for the following compounds, in line structural formula only and name
them.
1. Alkane with molecular formula C6H14
2.
●
●
.
●
Cis isomer (Line structure)
● IUPAC name of cis isomer
● Trans isomer (Line structure)
IUPAC name of trans isomer
Isomer 1 (Line structure)
IUPAC name of Isomer 1
Isomer 2 (Line structure)
IUPAC name of Isomer 2
.
arrow_forward
12. Write bond-line structural formulas for (a.) two primary alcohols, (b.) a secondary alcohol, and (c.) a
tertiary alcohol-all having the molecular formula CaH100.
arrow_forward
+ Complete the table
Molecular Formula
Structural Formula
Condensed Formula
Skeletal Formula
Types of Hydrocarbon (Alkane,
Alkene, Alkyne)
CH;CH;CHCHCH3
CH;CH=CHCH3
CH6
Note:
General Formula of Alkane (C,H2n-2), Alkene (C,H2), Alkyne (C,H2n-2). Where n is the number of C atom in the formula.
Alkane (C-C), Alkene (C=C) and Alkyne (C=C)
arrow_forward
CO
Ch
app.101edu.co
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Maps
SC
Bb Bl
!
1
H3C-CH₂
H3C
F1
Q
A
1
option
CH
N
@ 2
2
Ac
Be
G dc
B H
[S
Question 37 of 48
The molecule shown here is classified as what type of organic compound?
A) alkane
B) alkene
CH3
C=C
C) alkyne
D) aromatic compound
E) aldehyde
DII
F8
F2
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command
#3
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arrow_forward
only part 8 please
arrow_forward
In the given items, name the follow alkynes and alkenes
arrow_forward
N|ON|OU|G fic
app.101edu.co
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YouTube
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Question 7 of 31
The molecule shown here is classified as what type of organic compound?
A) alkane
CH3
B) alkene
C) alkyne
CH₂-CH3
D) aromatic compound
E) aldehyde
V
Aa v
>
#3
II
>
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F3
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F4
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BAX G d
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MacBook Air
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F8
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S|G1|CS UONEE
F9
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L
7
F10
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P
F11
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←
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x
Gra
+ 11
KR
☐
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+
arrow_forward
Which of the following compounds is a valid Lewis structure of a hydrocarbon?
H
H-C-Ö-H
H
HH
H-C-N-H
H
I
II
H
H-C-C-H
H
III
HH
H-C-C-H
I
НН
IV
I, II, and IV are valid structures of hydrocarbons.
Only III is a valid structure of hydrocarbons.
All of these compounds are valid structures of hydrocarbons.
Only IV is a valid structure of hydrocarbons.
III and IV are valid structures of hydrocarbons.
arrow_forward
Please classify each compound as saturated or unsaturated. Identify each as alkane, an alkene, or an alkyne.
arrow_forward
Which of the following compounds is not an alkane?
A or B or C
arrow_forward
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- 4:30 PM Wed Apr 27 * 74% O O Q E HW 12 Home Insert Draw Layout Review View I| Select Objects Draw with Touch 40. There are five compounds with the formula C6H14 (one of them is linear and the others are branched). Draw structural formulas for any two of those branched isomers. See Example 6.3 on page 152. H3C CH3 CH3 44. Name the following alkanes. CH¿CH3 CH,CH3 CH3 CH;CH2CHCH2CH¿CH3 CH;CHCHCH,CH;CH3 CH;CHCHCH3 CH3 CH3 a C 3-CHhylheypare ethyl-2 methyllnexano а. 7+3 dimethibulane С. 46. Name the following alkenes. CH2=CHCH,CHCH;CHCH3 CH2CH3 CH2=CHCH2CH3 CH3 CH3 CH2=CHCH2CHCH3 a b C |burene а. b. C. 48. Name the following alkynes. CH,CH3 GH=CH CH3 C=CCH2CH3 CH;C=CCHCH,CH3 a b Carrow_forwardplease answer #6arrow_forwardWrite the name/structural formula of the following compounds:arrow_forward
- 09:49 < Back CHE_3100_WS3.1.pdf Organic Chemistry I Dashboard a) C6H10 b. Skeletal Isomers: Isomers that result from the reorganization of the carbon backbone are called structural isomers. Usually, these are easy to spot using IUPAC nomenclature; if the name of the parent compound of one molecule is different from the other molecule that it is being compared to, then the carbon skeleton has been reorganized and thus they are skeletal isomers of each other. WS-3.2: Draw skeletal isomers for the following molecules and provide an IUPAC name for each structure. Two isomers per compound are sufficient for this exercise. b) C4H8 c) CsH100 Dk d) بلوه Organic Chemistry I B goo Calendar 2 Shailesh Ambre To Do c. Positional Isomers: Positional isomers have the same parent compound (root name), but the position of the substituents differ. To identify molecules that share a positional isomer relationship- i. First, check if the root name is the same. ii. Second, check all substituents and…arrow_forwardIII. Draw two isomers for the following compounds, in line structural formula only and name them. 1. Alkane with molecular formula C6H14 2. ● ● . ● Cis isomer (Line structure) ● IUPAC name of cis isomer ● Trans isomer (Line structure) IUPAC name of trans isomer Isomer 1 (Line structure) IUPAC name of Isomer 1 Isomer 2 (Line structure) IUPAC name of Isomer 2 .arrow_forward12. Write bond-line structural formulas for (a.) two primary alcohols, (b.) a secondary alcohol, and (c.) a tertiary alcohol-all having the molecular formula CaH100.arrow_forward
- + Complete the table Molecular Formula Structural Formula Condensed Formula Skeletal Formula Types of Hydrocarbon (Alkane, Alkene, Alkyne) CH;CH;CHCHCH3 CH;CH=CHCH3 CH6 Note: General Formula of Alkane (C,H2n-2), Alkene (C,H2), Alkyne (C,H2n-2). Where n is the number of C atom in the formula. Alkane (C-C), Alkene (C=C) and Alkyne (C=C)arrow_forwardCO Ch app.101edu.co be Maps SC Bb Bl ! 1 H3C-CH₂ H3C F1 Q A 1 option CH N @ 2 2 Ac Be G dc B H [S Question 37 of 48 The molecule shown here is classified as what type of organic compound? A) alkane B) alkene CH3 C=C C) alkyne D) aromatic compound E) aldehyde DII F8 F2 T W S X дв command #3 80 F3 E D CH₂-CH3 F4 с $ 4 R F % 5 V F5 T X G 6 B F6 Y H & 7 F7 U N 8 J w Mb Hc G 17 CS UO NE Et | | M ( 9 K F9 O H ) O L F10 P F11 WE { + 11 [ t command option Ba Gra C F12 } 1 + dearrow_forwardonly part 8 pleasearrow_forward
- In the given items, name the follow alkynes and alkenesarrow_forwardN|ON|OU|G fic app.101edu.co Maps YouTube 1 N L H3C-CH₂ H3C Q A N G A © 2 - F2 W S C= X H Gb| CCC |2bA|QQ Question 7 of 31 The molecule shown here is classified as what type of organic compound? A) alkane CH3 B) alkene C) alkyne CH₂-CH3 D) aromatic compound E) aldehyde V Aa v > #3 II > 80 F3 E D C $ 4 Q F4 R F D, 67 dº % 5 V F5 T BAX G d G MacBook Air F6 B Y & 7 H F7 U N * 8 J DII F8 M ( 9 K S|G1|CS UONEE F9 O ) H L 7 F10 Done P F11 B ← L x Gra + 11 KR ☐ F12 +arrow_forwardWhich of the following compounds is a valid Lewis structure of a hydrocarbon? H H-C-Ö-H H HH H-C-N-H H I II H H-C-C-H H III HH H-C-C-H I НН IV I, II, and IV are valid structures of hydrocarbons. Only III is a valid structure of hydrocarbons. All of these compounds are valid structures of hydrocarbons. Only IV is a valid structure of hydrocarbons. III and IV are valid structures of hydrocarbons.arrow_forward
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