TV Ontario: Organic Chemistry
Please Answer the following question while you watch the video
1. How many bonds does a Carbon atom make?
2. Draw the structure of:
A. Methane
B. Ethane
3. How many types of butane are there?
4. How does Lithium become stable? How does Fluorine become stable?
5. Why does Carbon share electrons?
6. When Carbon forms four bonds with Hydrogen, what must happen to the orbitals?
7. What shape does the CH4 molecule make?
8. What is the angle between the hybridized orbitals in CH4?
9. What types of bonds form between Carbon and hydrogen?
10. When Carbon forms a double bond, what type of hybrid orbitals are formed? What is the angle
between the hybrid orbitals? Where is the remaining p orbital?
11. What type of bond is formed by the p orbitals for the second bond of a double bond?
12. What is a double bond composed of?
13. Why is the pi bond more vulnerable to chemical attack?
Covalent Bonds Review
Completion - Use this completion exercise to check your understanding of the concepts
and terms introduced during the lessons on covalent bonds. Each blank can be completed
with a term, short phrase or number.
When like atoms are joined by a covalent bond, the bonding electrons are shared ___________, and
the bond is _____-_________. When atoms in a bond are not the same, the bonding electrons are shared
___________, and the bond can be ___________. The degree of polarity between any two atoms is
determined by consulting a table of _____________________. Some molecules are ___________
because they contain polar covalent bonds. The attractions between opposite poles of polar molecules
constitute ________-________ _______________. The dipole-dipole interaction is one of several weak
attractions between molecules. Another weak force that involves hydrogen atoms is the __________ –
______.
As a general rule, molecules adjust their three-dimensional shapes so that valence-electron pairs
around a central atom are as far apart as possible. This is the guiding principle in the valence-shell
electron-pair repulsion, or ___________ theory of molecular geometries.
Molecular Shape – Bond Angles
For each structural formula, write the letter of the molecular shape that best applies to it.
Then label the bond angles on the structural formula.
________ 1.
_________ 2.
________ 3.
________ 4.
________ 5.
Complete the following table by filling in the molecular shape and bond angles around the
central atom for each of the molecules listed
Molecule
Molecular Shape
H2 O
CF4
NH3
CO2
HCN
H2 S
NF3
OF2
CHCl3
SiO2
C2H4
C2H2
BF3
BeCl2
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Bond Angle
The Shape of Small Molecules
On the line at the left, write the term from the list that matches each description below.
ball and stick model
2
sp orbital
bond angle
fullerenes
hybrid orbital
sp orbital
symmetry
trigonal planer
unshared pair
VSEPR theory
____________________ 1. a visual model of molecular geometry
____________________ 2. combination of one s with one p orbital
____________________ 3. the geometric angle between two adjacent bonds
____________________ 4. a pair of valence electrons not involved in a bond
____________________ 5. the theory that states that the pairs of valence electrons are arranged as far
apart as possible in small molecules.
____________________ 6. name for triangular flat molecule
____________________ 7. the type of hybrid orbital in a triangular flat molecule
Draw Lewis dot structures for each of the following molecules and then label the bond
angle around each central atom. Then identify the hybrid orbital for each central atom.
Finally state whether the compound is polar or non-polar.
8. PCl3
9. H2S
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10. CBr4
11. C2H6
12. C2F2
13. NH4
14. OF2
15. NI3
16. BeCl2
17. BF3
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+
Hydrocarbons Practice Problems
Give the IUPAC name for the following molecules:
1. CH3–CH–CH2–CH2–CH2–CH2–CH2–CH3
|
CH3
2. CH3–CH2–CH2–CH–CH2–CH2–CH2–CH2–CH3
|
CH2–CH3
3. CH3–CH2–CH–CH2–CH2–CH3
|
CH3
4. CH3–CH2–CH2–CH2–CH–CH2–CH3
|
CH3
5. CH3–CH2–CH2–CH2–CH–CH2–CH2–CH2–CH2–CH3
|
CH2–CH3
6. CH3–CH2–CH–CH2–CH2–CH2–CH2–CH3
|
CH2–CH3
7. CH3–CH2–CH–CH2–CH2–CH2–CH3
|
CH2–CH2–CH2–CH3
8. CH3–CH–CH2–CH3
|
CH2–CH3
9. CH3–CH2–CH2–CH–CH2–CH2–CH–CH3
|
|
CH3
CH3
10. CH3–CH2–CH2–CH2–CH–CH–CH2–CH2
|
|
|
CH3 CH3
CH3
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Draw the carbon skeleton for the following:
11. 4-methyloctane
12. 4-ethyldecane
13. 3-ethylpentane
14. 3-ethylhexane
15. 5-butyldecane
16. 4-ethylheptane
17. 3-methylnonane
18. 2-methylheptane
19. 4-propylheptane
20. 5-butylnonane
21. Draw the complete structural formula for the 22. Draw the complete structural formula for
one other structural isomer of butane and
one structural isomer of pentane and name
name it.
it.
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23. Draw carbon skeletons for two structural
24. The molecule 2-methylheptane is a
isomers of heptane that have only one branch.
structural isomer of which straight chain
Name the isomers.
alkane?
25. The molecule 2-methylbutane is a structural
isomer of which straight chain alkane?
26. The molecule 3-methyloctane is a structural
isomer of which straight chain alkane?
27. The molecule 3-ethylhexane is a structural
isomer of which straight chain alkane?
28. The molecule 3-methylpentane is a
structural isomer of which straight chain
alkane?
29. The molecule 4-propylheptane is a structural 30. The molecule 3-methylhexane is a
isomer of which straight chain alkane?
structural isomer of which straight chain
alkane?
31. Draw the complete structural formula for:
HC=CCH2CH3
32. Give the name of the compound in problem
31 and explain the meaning of its stem and
ending.
Molecular Arrangements
Match each suffix with its correct description of the bonding of the carbon atoms in a
hydrocarbon
_____ 1. –yne
a. saturated compound (single bonds only)
_____ 2. –ane
b. unsaturated compound with double bonds
_____ 3. –ene
c. unsaturated compound with triple bonds
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Complete the sentence or answer the question.
4. In saturated organic compounds, all the bonds between carbon atoms are _________ _________.
5. The existence of two or more substances with the same molecular formula but different structural
formulas is known as __________________.
6. Compounds with the same atoms bonded in the same order but with a different arrangement of atoms
around a double bond are examples of _____________ _____________.
7. What type of hybridization would be expected in an atom with three outer electrons? __________
What would be the shape and bond angles of the molecule it forms? ______________________
Saturated and Unsaturated Hydrocarbons
Complete each of the following sentences by filling in the appropriate word or phrase from
the list below.
branch carbon
cyclic hydrocarbon
straight-chain alkane
branched alkane
general formula
structural isomer
conformation
parent chain
unsaturated hydrocarbon
8. A(n) __________________________ is a carbon atom bonded to more than two other carbons.
9. A(n) __________________________ shares its molecular formula with another compound but has a
different chemical structure.
10. The __________________________ for an alkane is CnH2n+2.
11. A(n) ______________________ contains at least one double or triple bond between carbon atoms.
12. The longest continuous chain of carbon atoms in a compound is called the _________________.
13. A hydrocarbon with a carbon ring is called a(n) _______________________.
14. A hydrocarbon with a single line of bonds connecting its carbon atoms is a(n) ________________.
Write the letter of the structure that matches each name
_____ 15. cyclohexane
_____ 16. cyclopropane
_____ 17. cycloctane
_____ 18. cyclopentane
_____ 19. cycloheptane
_____ 20. cyclobutane
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If the statement is true write “true”. If it is false, change the underlined word(s) to make
the statement true.
______________ 21. An alkane with 22 carbon atoms has the molecular formula C22H44.
______________ 22. An alkane contains double bonds.
______________ 23. A branched alkane contains carbons atoms bonded to more than two other carbon
atoms.
______________ 24. A branched alkane has a lower boiling point than a straight chain alkane.
______________ 25. When two structures differ only by one or more bond rotations, they are said to be
structural isomers of one another.
______________ 26. A cycloalkane is a cyclic hydrocarbon with one double bond.
______________ 27. Alkenes are unsaturated hydrocarbons.
______________ 28. Hydrocarbons with triple bonds are alkenes.
______________ 29. Benzene is a cyclic arrangement of 6 carbon atoms and 6 hydrogen atoms.
Answer the following questions in the space provided
30. Write the molecular formulas for each of the following hydrocarbons:
a. butane ____________________________
d. propane ___________________________
b. hexane ___________________________
e. octyne ____________________________
c. ethyne ____________________________
f. 2-methylpentane _____________________
31. What are the IUPAC names of the following hydrocarbons:
a. CH3–CH2–CH2–CH–CH3
|
b. CH3–CH2–CH–CH3
|
CH2–CH3
CH3
32. Draw the condensed structural formulas of the following hydrocarbons:
a. 2–methylpropane
b. 3–ethylhexane
c. 4-propyloctane
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33. Draw the carbon skeleton for the three structural isomers of pentane
34. Draw the structure of benzene. What is the significance of resonance with respect to benzene?
35. Draw complete structural formula for each of the following:
a. 1,1–dibromopropane
b. 1,4–hexadiene
c. chloroethane
d. 1,2–dibromopropane
e. 3–methyl–1–pentene
f. 1–chloro–4–ethylhexane
Vocabulary Review
On the line at the left, write the term from the list that correctly completes each statement.
conjugated system
geometric isomer
isomerism
sigma bond
unshaired pair
delocalization
hybridization
pi bond
structural isomer
double bond
hybrid orbital
saturated compound
triple bond
functional group
isomer
shared pair
unsaturated compound
______________ 1. A substance with the same molecular formula as another but a different structure, is
called a(n) ___________.
______________ 2. A(n) _________ is formed when two p orbitals overlap sideways with their axes
parallel.
______________ 3. A pair of outer electrons that bond two atoms is called a(n) ____________
______________ 4. Three pairs of outer electrons that bond two atoms form a(n) ___________
______________ 5. The merging of s and p orbitals to form identical orbitals is called ________
______________ 6. An organic compound with at least one double or triple bond between carbon atoms
is called a(n) _____________.
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____________________ 7. Methylpropane is an isomer of butane called a(n) __________ because it has
a different arrangement of the carbon chain.
____________________ 8. A part of an organic compound that includes an atom other than carbon or
hydrogen is called a(n) _____________.
____________________ 9. A(n) _____________ is formed by the direct overlap of two orbitals.
____________________ 10. Two pairs of orbitals binding two atoms forms a(n) __________ ________.
____________________ 11. The merging of an s and a p orbital form a(n) _________ _________.
____________________ 12. The existence of two or more compounds with the same molecular formula,
but different structures is called _____________.
____________________ 13. Two electrons in a nonbonding orbital are called a(n) ___________
_______.
____________________ 14. The overlap of unhybridized p orbitals throughout a molecule produces a(n)
___________ __________.
____________________ 15. An isomer in which the same groups are arranged differently around a
double bond is called a(n) __________ __________.
____________________ 16. An organic compound in which all the carbon atoms are joined by single
bonds is called a(n) ___________ _____________.
____________________ 17. The equal sharing of p electrons by all the carbon atoms of a molecule is
called _____________.
Hydrocarbon Compounds - Review Sheet
Use this completion exercise to check your knowledge of the terms and your
understanding of the concepts introduced in this chapter. Each blank can be completed
with a term, short phrase, or number.
The branch of chemistry that deals with ____________ compounds is called ____________
chemistry. Carbon makes stable ____________ bonds with other carbons to form chain and ring
compounds. ______________ are compounds containing only carbon and hydrogen. Many
hydrocarbons exhibit ____________ isomerism. Structural isomers have the same ____________
formula but different ____________.
Alkanes contain only carbon–carbon ____________ bonds. The groups attached to single bonds in
continuous–chain alkanes rotate freely about the bonds at room temperature. Alkenes are ___________
hydrocarbons. That is, they contain one or more carbon–carbon ____________ bonds. Alkynes are also
unsaturated compounds. They contain one or more carbon–carbon ____________ bonds.
Aromatic hydrocarbons, or ____________, are related to the hydrocarbon ____________. Benzene
is rather unusual among hydrocarbons. As a result of ___________________, the interior bonds of the
benzene ring are somewhere between ordinary single and double bonds.
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Covalent Bonding and Hydrocarbons - Challenge Problems
#1. Draw the structure of 2-methyl-3,4,5-trioctene. How many sigma bonds are present in this
compound? What is the hybridization of the bonding of each carbon and the angle of the bonds
around each carbon?
#2. There are some compounds in which one atom has more electrons than the corresponding noble gas.
Examples are PCl5, SF6, and IF7. Looking at the outer shell configurations of P, S and I, can you
develop an orbital hybridization scheme to explain the existence of these compounds.
#3. Ethyl Alcohol (CH3CH2OH) and Dimethyl ether (CH3 – O – CH3) each have the same molecular
formula (C2H6O). Yet, ethyl alcohol has a much higher boiling point (78°C) than dimethyl ether
(–25°C). Explain at a molcular level what causes this difference.
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Transitioning into the New year
In the puzzle below find the full name of every transition metal. Each name is in a straight-line
segment. The first one, SCANDIUM, is in bold to help you get started. Letters may be used more than
once. The unused letters spell out a message.
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