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Transcript
Chemistry 30
Organic Chemistry Notes
A. Carbon Compounds
30-C1.1k  define organic compounds as compounds containing carbon, recognizing inorganic
exceptions such as carbonates, cyanides, carbides and oxides of carbon

organic compounds are those in which _______________ atoms are almost always
bonded to each other, to __________________ atoms and a few other atoms
(___________________)

inorganic exceptions are the ___________________________________
__________________________________________________________ (no C-C
bonds or C-H bonds)
eg) _____________________________________________________

there are ________________ of organic compounds and all contain
___________________________________

carbon is unique for two reasons:
a) it can bond with ________________________ atoms to form
_________________________________________________
b) it can form combinations of ___________________________
____________________________ (no other element does this!!!!)

recall polarity and intermolecular forces from the chemical bonding unit

polar bonds are formed when there is an ________________ pull on e

_____________ compounds are formed when the polar bonds within a molecule
______________________________________ each other out

the presence of _______________________________ forces and
________________________________________ will allow polar compounds to
________________________________, since it is also polar

_________________________ compounds only have LD forces between molecules
and _______________________ dissolve in water
30-C1.2s  perform an experiment to compare the properties of organic compounds with
inorganic compounds, considering properties such as solubility, viscosity, density,
conductivity and reactivity
Chemistry 30 Organic Chemistry
1
Jill Agnew
B. Structural Isomers
30-C1.5k  define structural isomerism as compounds having the same empirical formulas, but
with different structural formulas, and relate the structures to variations in the
properties of the isomers

isomers are compounds with the _______________________________ but a
___________________________________
Example 1
Draw the three structural isomers for C5H12.
1.
2.
3.
Example 2
Draw three structural isomers for C4H8F2.
1.
2.
3.
30-C1.3s  compile and organize data to compare the properties of structural isomers

different structures result in different ____________________

the arrangement of the atoms determines the types of intermolecular attractions
which then determines properties such as _______________ and
___________________ in water
Example
Draw two isomers of C3H8O. Which one would have a boiling point of 7.4C and which
would have a boiling point of 82.5C? Explain why the boiling points are so different.
Chemistry 30 Organic Chemistry
2
Jill Agnew
C. Formulas and Structural Diagrams
 organic molecules can be drawn in three different ways:
1. complete structural diagram – shows _____________________
eg)
C3H8
C3H7F
2. condensed structural diagrams – shows ___________________
_______________________ but includes the ______________ etc.
attached to each carbon
eg)
C3H8
C3H7F
3. line structural diagrams – shows only ____________________
______________________________ bonds
eg)
C3H8
C5H12
C4H8
Chemistry 30 Organic Chemistry
3
Jill Agnew
30-C1.2s  build molecular models depicting the structures of selected organic and inorganic
compounds
Your Assignment: pg 1
D. Prefixes
1. Number of Functional Groups
6 = hexa
2 = di
7 = hepta
3 = tri
8 = octa
4 = tetra
9 = nona
5 = penta
10 = deca
2. Number of Carbons
1 = __________
6 = __________
2 = __________
7 = __________
3 = __________
8 = __________
4 = __________
9 = __________
5 = __________
10 = __________
30-C1.2k  identify and describe significant organic compounds in daily life, demonstrating
generalized knowledge of their origins and applications
30-C1.3k  name and draw structural, condensed structural and line diagrams and formulas,
using IUPAC nomenclature guidelines, for saturated and unsaturated aliphatic
(including cyclic) and aromatic carbon compounds
30-C1.1sts  explain how science and technology are developed to meet societal needs and
expand human capability
30-C1.2sts  explain that science and technology have influenced, and been influenced by,
historical development and societal needs
30-C1.3s  follow appropriated IUPAC guidelines when writing the names and formulas of
organic compounds
Chemistry 30 Organic Chemistry
4
Jill Agnew
E. Alkanes
eg) ________________________________________

hydrocarbons containing _____________________________________ between the
carbons ie) they are __________________________

can be _____________ continuous chains, _________________ chains,
___________ structures __________________________
1. Properties
 ___________________________________________ in water

can be ___________________________________________ depending on number
of carbon atoms

relatively ______________________ because the ____________ bonds are
___________________________
2. Uses
 natural gas, BBQ’s, lighter fluid, gasoline etc

good for making plastics, lubricants
3. Naming
 IUPAC = International Union of Pure and Applied Chemistry
i. Continuous Chains
 __________________________________
eg)
H
H
H
H
H
C
C
C
C
H
H
H
H
H
ii. Branched Chains
 branches are called ____________ functional group

1 C = __________; 2C = _________; 3 C = __________ etc

find the ___________________________________________ and
____________________________ so the branches get the __________
possible numbers
Chemistry 30 Organic Chemistry
5
Jill Agnew

to name: name the ____________ first (in _______________________ order),
including the ________________________________________ where each group is
found, then name the ________________________
__________________(parent name)
eg)
H
H
H
H
H
H
H
C
C
C
C
C
H
H
CH3 H
H
H
H
H
H
H
C
C
C
C
C
H
CH3 CH2 H
H
H
H
CH3
H
H
H
H
H
H
C
C
C
C
C
H
H
H
Try These:
H
1.
H
2.
H
CH3 CH3
H
H
H
H
H
H
C
C
C
C
C
C
H
CH3 H
CH3 H
H
H
H
H
H
H
C
C
C
C
C
H
CH2 H
H
H
CH3 H
CH3
Chemistry 30 Organic Chemistry
6
Jill Agnew
CH3
3.
CH3
CH
CH2
CH
CH3
CH2
CH
CH3
CH3
CH3
4.
CH3
C
CH3
CH2
CH3
C
CH3
CH3
Try These
Draw the structure for each of the following compounds:
1. 2,2-dimethylpropane
2. 4-ethyl-2,3-dimethylhexane
3. 4-propyloctane
4. 3,5-diethyl-4-methylheptane
Your Assignment: pgs 2-3 in workbook
Chemistry 30 Organic Chemistry
7
Jill Agnew
iii. Cycloalkanes
 use the ________________________ as the _________________ name

__________ + ____________ + _____________
eg)

if there are branches, number the carbons in the ring so the branches get the
_______________________________________________________
eg)
CH2
CH3
CH3
Try These:
CH3
1.
CH3
2.
CH2
CH2
CH2
CH3
CH3
CH3
CH3
3.
CH2
CH2
CH2
CH3
CH2
Chemistry 30 Organic Chemistry
8
Jill Agnew
4. 1,2-dimethylcyclopropane
5. 1,1,2,2-tetraethylcyclohexane
6. 3-butyl-1,1,2-trimethylcyclopentane
Your Assignment: pg 4 in workbook
C. Alkenes
eg) __________________________________________

hydrocarbons containing _____________________________________ ie) they are
_________________________________

can be _________ continuous chains, ___________________ chains, ___________
structures ______________________________
1. Properties
30-C1.3s  interpret the results of a test to distinguish between a saturated and an unsaturated
aliphatic, using aqueous bromine or potassium permanganate solutions

________________________________________ in water

____________________________________ than corresponding alkane because
they have _______________________ which makes the ______ forces of attraction
_______________________
eg) ethane BP = 88.6C
ethene BP = 103.8C

______________________________ than alkanes

double bond has _________________ in the same area
__________________________________ and __________________
Chemistry 30 Organic Chemistry
9
Jill Agnew
________________________________

diagnostic test: use ________________________________________ ***alkenes
_____________________________________________ with these substances
causing a noticeable ______________________, alkanes will not
Br2(l)
A
B
alkene
KMnO4(l)
alkane
A
B
alkane
alkene
**the alkenes will react causing the colour to disappear as the coloured substance is
used up in the reaction
2. Uses
 plastics (PVC)

steroids

welding torches
3. Naming
i. Continuous Chains
 ________________________________________

number carbons to give the ___________________________ the
_________________________________________

the number where the double bond _________________ is to be given as a “ # ”
between the prefix and the suffix
eg)
H
H
H
H
C
C
C
H
H
‗
Chemistry 30 Organic Chemistry
H
H
C
C
C
H
H
H
H
10
Jill Agnew
H
H
H
C
C
‗
H
H
H
C
C
C
H
H
H
H
C
‗
H
H
H
C
C
C
H
H
H
H
H
ii. Branched Chains
 find the longest carbon chain and number it so the _________________ gets the
___________________ number

to name: name the _____________ first (in ______________________ order),
including the _________________ of the carbon where each is found, then the
_________________________ including the ___________________ of the carbon
where the double bond starts
eg)
CH2
‗
C
CH2
CH2
CH2
CH2
CH
CH
CH
CH3
CH3
CH3
CH2
CH3
CH2
CH3
CH3
CH
‗
CH
CH2
CH3
Your Assignment: pgs 5-6 in workbook
Chemistry 30 Organic Chemistry
11
Jill Agnew
iii. Cycloalkenes
 double bond is always numbered ____________

_______________ get the ____________________ numbering sequence after the
______________________________

__________ + ____________ + _____________

list branches in ______________________________________ with the
______________ of the carbon they are on
eg)
CH2
CH3
CH3
CH2
CH3
CH3
Your Assignment: pg 7 in workbook
Chemistry 30 Organic Chemistry
12
Jill Agnew
D. Alkynes
eg) ___________________________________

hydrocarbons containing _____________________________________ ie) they are
also _________________________________

can be ___________ continuous chains, _________________ chains

not plentiful in nature
1. Properties
 ________________

___________________________ (more than alkanes and alkenes)

____________ bond has ________ in the same area _________ force of repulsion

boiling points are ________________ than corresponding alkanes and alkenes
because of their ________________________________ and the ______________
of triple bonds
2. Uses
 welding torches
3. Naming
i. Continuous Chains
 _______________________________

number carbons to give the _____________________________ the
__________________________________________

the number where the triple bond ________________ is to be given as a “ # ”
between the prefix and the suffix
eg)
H
H
H
C
C
H
H
C
≡
H
H
C
C
≡ C
H
Chemistry 30 Organic Chemistry
C
H
H
C
C
H
H
H
H
C
C
H
H
H
H
13
Jill Agnew
ii. Branched Chains
 find the __________________________________________ and number it so the
_________________________ gets the lowest number

to name: name the ______________ first (in _____________________ order),
including the _______________ of the carbon where each is found, then the
___________________________ including the _________________ of the carbon
where the triple bond starts
eg)
CH
CH3
CH
≡
C
C
≡
CH
CH2
CH2
CH2
CH2
CH2
C
CH
CH
CH3
CH2
CH3
CH2
CH2
CH3
CH3
CH3
Your Assignment: pg 8 in workbook
Review
 alkanes – branches, rings – least reactive

alkenes – branches, rings

alkynes – branches – most reactive

all called ___________________________

all ________________ and ___________________________ in water

major intermolecular forces are _______ boiling points are _______
E. Aromatics
 hydrocarbons containing one or more ___________________________
OR

all bonds are the __________________________________________ we draw
benzene like this:
Chemistry 30 Organic Chemistry
14
Jill Agnew
1. Properties
 _______________________

the benzene ring structure is ________________________

aromatics are characterized by strong aromas
2. Uses
 ASA, amphetamines, adrenaline, benzocaine (anesthetic)

moth balls, TNT

wintergreen, menthol, vanilla, cinnamon

SPF in sunscreen
3. Naming
i. Benzene as a Branch
 if you have a really long carbon chain, it is easier to call the benzene ring a
____________________________________
eg)
CH3
CH2
‗
CH
CH2
CH
CH2
CH2
CH
C
CH2
CH2
CH2
CH2
CH3
CH3
CH3
ii. Benzene as the Main Compound
 if only one group is attached, give the ___________________________ attached to
________________________________________________
eg)
CH3
Chemistry 30 Organic Chemistry
15
Jill Agnew

if there is more than one branch, number them so they get the
_________________________________________ and name
___________________________________________________
eg)
CH3
CH2
CH3
CH3
CH3
CH3
CH2
CH2
***watch out for this!
C2H5
CH3
Your Assignment: pgs 9-10 in workbook
30-C1.4k  identify types of compounds from the hydroxyl, carboxyl, ester linkage and halogen
functional groups, given the structural formula
Chemistry 30 Organic Chemistry
16
Jill Agnew
F. Alcohols

organic compounds with one or more ____________________
__________________________________
1. Properties
 have much ___________________________________________ than
corresponding aliphatics because of ___________________________
eg)
methane (CH4) BP = _____________
methanol (CH3OH) BP = ______________

_____________

the __________ end of the alcohol is ______________ while the
_________________________ end _____________  small alcohols are
________________ in water and large alcohols are _________
2. Uses
 antifreeze, rubbing alcohol, beverages, moistening agent
3. Naming
 number the longest carbon chain containing the __________________ so the
___________ group gets the ____________________________

__________________ name (_________________ at end) + _______

give the __________________________________________ where the
_______________________________ is found between the parent name and the
suffix

if there is _____________________________________ hydroxyl group, use a
prefix (_________________________________) to indicate the
___________________ of OH groups and place the numbers between the parent
name and the suffix
***Note, if the suffix starts with a vowel, drop the “e” on the parent name; if the
suffix starts with a consonant, keep the “e” on the parent name
eg)
H
H
H
H
H
C
C
C
C
H
H
OH
H
Chemistry 30 Organic Chemistry
H
17
Jill Agnew
H
H

H
CH3 H
H
C
C
C
C
H
H
OH
H
H
CH3 H
H
C
C
C
C
H
OH
OH
H
an unusual case:
H
H
OH
Your Assignment: pg 11 in workbook
G. Organic Halides

where ______ is __________________ and ______ is a ___________

organic compounds where ________________ has been replaced by
_______________________________________________________

do not readily occur in nature
1. Properties
 can be ____________ or _______________________, depending on the
placement of the halogen groups

many are ________________________________________________
2. Uses
 manufactured for human use eg) DDT, PCB, CFC

anesthetics

dry cleaning fluid

plastics, polymers (Teflon)
Chemistry 30 Organic Chemistry
18
Jill Agnew
3. Naming
 same rules as before…name branches (__________________ included now)
___________________________________
F = _____________
Cl = ____________
Br = ____________
I = ____________
eg)
H
H
Cl
Cl
H
C
C
C
C
H
H
H
H
I
H
F
CH3
Your Assignment: pg 12 in workbook
H. Carboxylic Acids

where _______ is _______________________

organic compounds containing the ____________________________
_____________________________________

considered __________________ since double bonds in functional groups are not
taken into account
1. Properties
 _____________________________________________________

________ boiling points due to _____________________________

__________________________________

diagnostic test: use _______________________________ (will turn _________),
readily react with ______________________,
_________________________________________
2. Uses
 recycling rubber – methanoic acid

vinegar – ethanoic (acetic) acid

rust remover – oxalic acid

fruits – citric acid
Chemistry 30 Organic Chemistry
19
Jill Agnew
3. Naming
 count the longest carbon chain including the ______________ in the
__________________________

the carbon in the carboxyl group is always number ________

drop ______ and add _________________________
eg)
O
║
H
C
OH
O
H
H
║
C
C
OH
H
O
║
C
OH
O
I
H
H
H
C
C
C
H
H
H
║
C
OH
Your Assignment: pg 13 in workbook
I. Esters

where _______ can be a carbon chain or hydrogen and ________ can be a carbon
chain
Chemistry 30 Organic Chemistry
20
Jill Agnew

combination of a ______________________________ and an
______________________

considered _____________________ since double bonds in functional groups are
not taken into account
1. Properties
 ________________

_____________ esters ______________________ in water, ____________ esters
_________

boiling points slightly lower than corresponding carboxylic acids and alcohols due
to lack of hydrogen bonding

very _____________ which allows them to generate ____________
2. Uses
 flavouring agents
3. Naming
 identify the _________________ used to make the ester

change the alcohol name to the corresponding ___________ name
eg) methanol would become _________________

identify the __________________________ the ester was made from

drop the “oic acid” and replace with _________________
eg) butanoic acid would become __________________________

put the ______________________ together with a ______________ in between
eg) ______________________________________

you can have __________________ on esters…they follow the alphabetical rule,
numbering begins at the _________________ of the alcohol and the C=O end of
the carboxylic acid
eg)
O
H
H
H
H
C
C
C
H
H
H
H
H
C
C
║
C
O
H
H
C
C
H
H
H
O
H
║
C
H
HChemistry
Chemistry 30 Organic
O
H
CH3
C
C
H
H21
H
Jill Agnew
O
H
H
H
C
C
║
C
O
CH3 CH3
H
H
C
C
H
H
H
Your Assignment: pg 14 in workbook
J. Boiling Points and Solubility
30-C1.6k  compare, both within a homologous series and among compounds with different
functional groups, the boiling points and solubility of examples of aliphatics,
aromatics, alcohols and carboxylic acids

we can compare the boiling points of various organic compounds using their
_________________ and the _______________________
______________________________ between the molecules
Example 1
Put the following organic compounds in order from highest boiling point to lowest
boiling point.
alcohol, alkane, alkene, aromatic, carboxylic acid
Example 2
Put the following homologous series of organic compounds in order from highest
boiling point to lowest boiling point.
C2H6, C2H5OH, CH3COOH, C2H4
Chemistry 30 Organic Chemistry
22
Jill Agnew

we can also compare the ____________________ of various organic compounds
using their polarity
Insoluble Organic Compounds
Soluble Organic Compounds
K. Organic Reactions
30-C2.1k  define, illustrate and provide examples of simple addition, substitution, elimination,
esterification and combustion reactions
30-C2.2k  predict products and write and interpret balanced equations for the above reactions
30-C2.4k  relate the reactions described above to major reactions that produce thermal energy
and economically important compounds from fossil fuels
30-C2.3s  use IUPAC conventions when writing organic chemical reactions
1. Combustion Reactions
 occurs when a _______________________ reacts with ___________

products are always ________________________________________
________________________________________________

these are economically important reactions for they are the major reactions that
produce __________________________________ required for fuelling our
vehicles, heating our homes, and producing electricity
___ C5H12(l) + ___ O2(g) 
eg)
H
H
H
H
H
C
C
C
C
H
H
H
H
H
Chemistry 30 Organic Chemistry
+ ____ O2(g) 
23
Jill Agnew
2. Addition Reactions
 a ____________ or _____________ bond in an alkene or alkyne is
___________________ and a group or element is ___________
eg)
H
H
‗
C
H
H
H
H
‗
C
H
H
H
H
‗
H
H
H
H
‗
C
H

+
H
OH

+
H
H

+
H
Br

+
1 Cl2
cat
C
H
H
Cl
cat
C
C
Cl
cat
C
C
+
cat
C
H
C

cat
≡
C
≡
H

cat
C
H
+
2 Cl2
Try These:
1.
H
C
H
‗
H
H
H
C
C
C

cat
H
+
ChemistryH30 Organic
Chemistry
H
Br2
24
Jill Agnew
2.
H
H
H
C
C
‗
H
H
H
C
C
C
H
H
H
H
+

cat
HCl
3.
H
H
C
H
C
≡
C
C
H
H
+

cat
1 Cl2
H
Your Assignment: pg 15
3. Substitution Reactions
 the replacement (_____________________) of a hydrogen on an alkane or
aromatic with __________________________________ (eg. F, Cl etc)

commonly used to make ____________________________________
Examples:
H
1.
+
H
C

Cl – Cl
cat
H
H
2.
3.
Br – Br
+
+
Chemistry 30 Organic Chemistry
I–I

cat

cat
25
Jill Agnew
4.
H
H
H
H
H
C
C
C
C
H
H
H
H
+
H

cat
Br2
4. Esterification Reactions
 the reaction of a ________________________________ with an
________________________

the catalyst is ____________________________________
Examples:
1.
O
H
║
H

H2SO4(aq)
C
OH
+
HO
C
H
H
2.
O
H
H
H
C
C
H
H
║
C
H
H
C
C
H
H

H2SO4(aq)
OH
+
HO
H
5. Elimination Reactions
 an ______________ has water removed, forming and ___________ plus the
_______________

_________________________________ can react with a
_________________________________________ to produce an
_______________, a ________________________ and ___________
Examples:
1.
H
H
C
C

cat
H
OH
H
H
Chemistry 30 Organic
Chemistry
26
Jill Agnew
2.
H
H
H
H
C
C
C
C
OH
H
H
H
H
H
C
C
H
H

cat
H
3.
H
H
Cl
+
OH 

cat
Your Assignment: pgs 16-17
6. Polymerization Reactions
30-C1.2sts  explain that science and technology have influenced, and been influenced by,
historical development and societal needs
30-C2.3k  define, illustrate and provide examples of monomers, polymers and polymerization
in living systems and nonliving systems
30-C2.3s  draw or use models to illustrate polymers

a ___________________ is a ______________________________ that forms the
_____________________ for a polymer

a ______________________ is a _____________________________ formed by
the _______________________________________ of
___________________________________________________

depending on the polymer, the monomers that make it up can be
_________________________ or _____________________

polymers can be _______________________
eg) _____________________________________________________

polymers can be ____________________
eg) _____________________________________________________

polymers that can be heated and molded into specific shapes are commonly called
_____________________
Chemistry 30 Organic Chemistry
27
Jill Agnew

plastics are one type of synthetic compound that has been of great benefit to
society (although there are also problems associated with then)

the names of polymers are the monomer name with _____________ in front

many have classical names instead of IUPAC names
Addition Polymers
 formed when the electrons in double or triple bonds in the monomer units are
rearranged

the polymer is the _________________________________ formed
Examples:
1.
H
H
C
H
‗
C
H
+
C
‗

cat
C
H
H
H
H
F
F
F
F
2.
C
‗
C
+
C
‗

cat
C
F
F
F
F
H
Cl
H
Cl
3.
C
4.
‗
C
+
H
C
H
H

cat
C
H
H
C
‗
‗
C
H
H
+
H
H
C
‗

cat
C
H
Condensation Polymers
 polymerization reactions that involve the formation of a ___________
Chemistry 30 Organic Chemistry
28
Jill Agnew
___________________ (commonly ____________) as well as the
____________________

each monomer must have ________ functional groups

two common linkages formed:
1. _____________ linkage – between carboxyl group (COOH) and hydroxyl
group (OH)
2. ______________ linkage – between amino group (NH2) and carboxyl group
(COOH)
Examples:
1.
HO
O
O
║
║
C
C
H
H
C
C
H
H
O
H
H
║
C
C
N

cat
OH
+ HO
OH
2.
HO
O
H
H
║
C
C
N
H
+
HO
H
Chemistry 30 Organic Chemistry

cat
H
H
29
Jill Agnew
K. Petroleum Refining
30-C1.7k  describe, in general terms, the physical, chemical and technological processes used
to separate organic compounds from natural mixtures or solutions
30-C2.1sts  explain how science and technology are developed to meet societal needs and
expand human capability

Alberta has vast reserves of petroleum in the form of natural gas, crude oil and oil
sand deposits

most of this petroleum is refined and then burned as _________

petrochemicals, basic hydrocarbon raw materials such as ethane and propene, are
also used in the production of ______________

refining of petroleum separates the crude mixture into purified components

________________________________________________ is used to separate
the components

distillation works because of the different ______________________ of the
components of petroleum

the ________________ the molecule and the _______________ the boiling point,
the ____________________ it rises in the tower (asphalt, fuel oil, wax at bottom;
gasoline at top)

there are two types of reactions in petroleum refining:
1. Cracking
 __________ long chain hydrocarbons into ______________________

cracking requires heat and pressure

there are many different types of cracking reactions, forming different products
(alkanes, alkenes)
eg) catalytic cracking, steam cracking, hydrocracking

hydrocracking requires ________
Examples:
1.

cat
C9H20 + C8H18
2.

cat
Chemistry 30 Organic Chemistry
30
CH3
CH2
CH2
CH3
+
CH3
Jill Agnew
CH2
CH3
O
║H
2. Reforming
 small hydrocarbons are _______________ to make
_____________________________________

requires heat and pressure

there are several types of reforming reactions
eg) alkylation to produce “high octane” gasoline

all reforming reactions produce _________
Examples:
1. C7H16 + C12H26
2. ethane + octane

cat

cat
30-C1.1s  design a procedure to separate a mixture of organic compounds, based on boiling
point differences
Your Assignment: pgs 18-19
Separate an Organic Mixture – pg 581
Organic Reactions and the Environment Assignment
Chemistry 30 Organic Chemistry
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Jill Agnew