Download Organic Chemistry Notes

Organic chemistry:
GO 1: You will explore organic compounds as a common form of matter
GO 2: You will describe chemical reactions of organic compounds
Lesson 1: Intro

You will define organic compounds as compounds containing carbon, recognizing inorganic
exceptions such as carbonates, cyanides, carbides and oxides of carbon

You will identify and describe significant organic compounds in daily life, demonstrating
generalized knowledge of their origins and applications; e.g., methane, methanol, ethane,
ethanol, ethanoic acid, propane, benzene, octane, glucose, polyethylene
Organic compound include all compounds of carbon except:
a)
b)
c)
d)
Oxides (CO2, CO)
Carbonates (Na2CO3)
Carbides (K4C)
Cyanides (LiCN)
no hydrogen
Ionic
They have to consist of primarily carbon and hydrogen (hydrocarbon).
The carbon molecule has 4 valence electrons.
It does not generally form ionic bonds because of its number of valence electrons. It forms
covalent bonds to non-metal atoms like hydrogen, oxygen and halogens.
Organics are derived from:
a) Living organisms
a. Food (protein, fats, carbohydrates)
b. Fuels (methane, ethane)
c. Fabrics (cotton, wool, rayon)
d. Wood and paper products
e. Antibiotics and vitamins
f. Flavours and perfumes
g. Explosives
b) Synthetics
a. Paint, varnish
b. Plastics
c. Soap/detergent
d. Chemical additives (pesticide, insecticide, fertilizer)
Hydrocarbons
Aliphatics
Alkanes Alkenes Alkynes
Nelson Read pg 356-358
Do pg 361#1,2
Cyclics
Aromatics
(Benzene parent)

You will name and draw structural, condensed structural and line diagrams and formulas, using
International Union of Pure and Applied Chemistry (IUPAC) nomenclature guidelines, for
saturated and unsaturated aliphatic (including cyclic) and aromatic carbon compounds
containing up to 10 carbon atoms in the parent chain (e.g., pentane; 3-ethyl-2,4dimethylpentane) or cyclic structure (e.g., cyclopentane)
Lesson 2: Alkanes
CnH2n+2
(empirical/molecular formula)
-simplest organic molecule
-saturated – contain only single covalent bonds which means each carbon has 4 bonds
making a tetrahedral shape around it.
A continuous chain alkane has the carbon atoms all in a straight chain. They are named
according to the root words below with the ending ‘ane’. (IUPAC naming system)
-root words
# carbon
1
2
3
4
5
6
7
8
9
10
Eg.
Root name
meth
eth
prop
but
pent
hex
hept
oct
non
dec
-naming branched chain alkanes:
Alkanes can have hydrocarbon branches called alkyl groups. The alkyl groups are named first
and use the same root name but with a ‘yl’ ending. Eg. Methyl, ethyl, propyl, butyl, etc.
Use the following steps to name branched chain alkanes:
1. Find the longest continuous chain of carbons in the molecule.
2. Number the carbons in the main chain in sequence.
Start at the end that will give the alkyl groups the smallest numbers. The
numbers will be the ‘address’ of the alkyl group.
3. Prefixes are used to indicate how often an alkyl group appears (if it appears more
than once). Prefixes: di, tri, tetra, penta are used.
4. Alkyl groups are listed in alphabetical order (ignoring the prefixes)
5. Start the name with the address of the alkyl group and then the name of it, continue
this with the next alkyl group, lastly the main chain is named as per usual.
-commas separate numbers
-hyphens separate a number from a word
The name is considered one word with no upper-case letters.
Nelson summary pg 368
Questions pg 373 #6,7ab
-writing structural formula
1. Find the parent carbon chain (main chain) at the end of the name and draw its structure
leaving the hydrogen’s off.
2. Number the carbons in this parent chain.
3. Identify the substituent (branch, or also called alkyl) groups and draw them attached to the
proper parent carbon (by address).
4. Add hydrogen’s to fill in the rest of the bonding sites.
Nelson summary pg 369
Questions page 370 #7, 9-11 pg 373 #5,8
-other types of structural formulas
Condensed Structural Formulas: Leave out some of the bonds (C-H) from the structural
formula.
Eg.
Butane
CH3-CH2-CH2-CH3
Line Structural Formulas: the most condensed type of formula. A change in direction of the
line indicates a carbon position. Each line therefore indicates a carbon-carbon bond. No other
bonds or atoms are shown unless they are something other than carbon and hydrogen.
pg 373 #7c
-Properties of Alkanes:
Alkanes contain only covalent bonding without any major difference in polarity (no dipoles).
Therefore the only type of intermolecular bonding that exists is London dispersion. The larger
the molecule the more London dispersion force and therefore the more likely it will be a
condensed state (liquid or solid). Since there is very little intermolecular bonding (compared to
some other molecules) the smaller alkanes are gases at SATP.
Size
Boiling point
(#of carbon ) range(oC)
below 0
1-4
Examples of uses
Gases: used for fuels to cook and heat
homes
5-16
30-275
Liquids: used for automotive, diesel, and
jet engine fuels: also used as raw material
for the petrochemical industry
16-22
over 250
Heavy liquids: used for oil furnaces and
lubricating oils; also used as raw materials
to break down into smaller molecules
Over 18
Over 400
Semi-solids: used for lubricating
greases and paraffin waxes to make
candles, waxed paper, and cosmetics
Over 26
Over 500
Solid residues: used for asphalts and
tars in the paving and roofing industries
Pg 375 table 5
Another result of being non-polar is that they are insoluble in water. Water is very polar and
‘like dissolves like’ therefore alkanes are soluble in other organic (or non-polar) solvents but
NOT polar substances like water.
Homologous series- same functional group (general structure) but differ in their length.
You need to be able to describe how properties change within a homologous series.
Nelson q pg 373 #6,7,10
Lesson 3: Cycloalkanes, Alkenes and Alkynes
Cycloalkanes and Alkenes CnH2n
Cycloalkanes: If a hydrogen is removed off of each end of an alkane, the ends can be joined to
make a cycloalkane. It consists of all single bonded carbons in a ring. (saturated!!) These too
can be branched.
Naming them is similar to alkanes except the root name has the prefix ‘cyclo’ in front of
it. The branches still have the lowest ‘address’ or number to them, and with a ring format, one
of the branches will always have the number ‘1’.
Eg.
Properties: - higher b.p. and density than corresponding alkane (more compact)
-small ones are more reactive because of restrictive bond angles (C3-5)
Nelsonpg373#8
Alkenes: -have at least one double bond in them - unsaturated
This spot with the double bond is inflexible (rigid) and also unstable. This makes it more
reactive (less stable) than its corresponding alkane.
Naming them is similar to alkanes except
-the longest (parent) chain MUST have the double bond(s) in it.
-the double bond also has to have an ‘address’ and takes priority over the branches therefore
the double bond MUST have the lowest possible number when numbering the chain.
-the parent chain ends in the address-‘ene’.
-multiple double bonds need addresses and prefixes before the ‘ene’. Eg. but-1,3-diene
Exception: ethylene
The properties of alkenes are very similar to their corresponding alkane except that their
boiling points are even slightly lower because of less atoms (electrons) and therefore less
London dispersion than the alkane with the same # of carbons.
Eg.
*for each double bond or ring structure their empirical formula drops by two hydrogen
Alkynes
CnH2n-2
-Organic compounds containing carbon-carbon triple bonds (unsaturated)
-Named with the same rules as alkenes but ending in ‘yne’.
Exception is also the two carbon structure which is called ‘acetylene’ instead of ethyne
Properties are similar to their corresponding alkanes and alkenes except that their boiling
points are actually higher than their corresponding alkane. They have fewer electrons (less LD)
but their rigid linear structure and nature of the triple bond cause them to attract one another
more and therefore a tighter structure and higher boiling point are a result.
Nelson pg 377#1-7 (omit 6)
Lesson 4: Structural Isomers

You will define structural isomerism as compounds having the same molecular formulas, but
with different structural formulas, and relate the structures to variations in the properties of the
isomers

You will build molecular models depicting the structures of selected organic and inorganic
compounds
A structural isomer has the same empirical chemical formula but a different structure (shape).
It would therefore be named differently! The name and structure identifies the isomer.
The physical properties of structural isomers are different. The more highly branched the
hydrocarbon is, the lower its boiling point compared with its structural isomers.
CnH2n+2(aliphatic alkane)
CnH2n (alkene or cyclic alkane)
CnH2n-2 (alkyne, double alkene, or combination of cyclic and alkene)
Eg. Draw structural isomers of C5H8.
Nelson pg 377#6, 380 #1-11
Assignment
Lesson 5: Aromatics
A special group of hydrocarbons compounds that are uniquely stable and flat in shape.
They are unsaturated and cyclic.
They are often made up of benzene or benzene derivatives.
They have pleasant odours (hence the name)
Benzene (C6H6); A six member carbon ring with a hydrogen attached to each carbon. (3
double bonds6x 1.5 bonds)
Derivatives of Benzene: Compounds containing substituents (branches) attached to the
benzene ring. The benzene ring may be named as a branch or as the parent molecule
depending on the amount of branching of each part of the molecule.
Nomenclature:
-benzene as a branch is called ‘phenyl’.
-benzene as the parent chain: one branch does not require an ‘address’ since it is always ‘one’
(as per cyclos).
-two branches – use numbers or an older system of ‘ortho’(1,2), ‘meta’(1,3), ‘para’(1,4)
to show the branch positions.
eg.
Hydrocarbon Derivatives: contain a ‘functional group’ which is a chemically reactive
part (this can include the double and triple bonds). The functional group gives specific
characteristics to chemical reactions. Organic compounds are classified by functional groups.



You will name and draw structural, condensed structural and line diagrams and formulas, using
International Union of Pure and Applied Chemistry (IUPAC) nomenclature guidelines, for
saturated and unsaturated aliphatic (including cyclic) and aromatic carbon compounds
containing only one type of a functional group (with multiple bonds categorized as a functional
group; e.g., pent-2-ene), including simple halogenated hydrocarbons (e.g., 2- chloropentane),
alcohols (e.g., pentan-2-ol), carboxylic acids (e.g., pentanoic acid) and esters (e.g., methyl
pentanoate), and with multiple occurrences of the functional group limited to halogens (e.g., 2bromo-1-chloropentane) and alcohols (e.g., pentane-2,3-diol)
You will identify types of compounds from the hydroxyl, carboxyl, ester linkage and halogen
functional groups, given the structural formula
You will 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
Here are some examples (the ones that we will study), but there are others.
Compound Type-category
Halocarbon
Alcohol
Carboxylic Acid
Compound Structure
R-X (X = F,Cl,Br,I)
R-OH
O
R-C-OH
Ester
O
R-C-O-R
*R represents any hydrocarbon chain/ring
Functional Group Name
Halogen
Hydroxyl
Carboxyl
Ester
Lesson 6: Halocarbons/Alkyl and Aryl(Aromatics) Halides
-result from the substitution of a halogen for hydrogen in a hydrocarbon. {If the
hydrocarbon is an aliphatic chain, it may also be called an alkyl halide. If the hydrocarbon is
attached to a benzene ring, it is called an aryl halide.}
Nomenclature:
-The halogen is treated just like a branch using the names
Fluoro for Fluorine
Chloro for Chlorine
Bromo for Bromine
Iodo for Iodine
Eg.
Properties:
-they have a dipole because the halogen is very electronegative compared to the
carbon. This means that the electrons sit closer to the halogen creating a partial separation of
charge – dipole.
-the dipole in the molecule causes stronger intermolecular bonding (now has dipoledipole in ADDITION to LD forces). This raises the boiling point compared to the molecule
without the halogen.
- the dipole also makes the molecule more likely to react. (easier to remove the halogen
than if it was a hydrogen).
-depending on the amount of the molecule that is polar (dipoles) compared to the
amount that is non-polar, the molecule may or may not dissolve in polar solvents like water.
(like dissolves like)
-many are toxic!!! Eg. CFC’s (chloro-fluoro- carbons) and PCB’s
1. addition reaction; halogenations
Halogenation is the ADDITION of a halogen to an alkene or alkyne. When a halogen reagent
like chlorine (Cl2) or bromine (Br2) is added, the product is a disubstituted halocarbon.
Eg.
*Bromine is used as a saturation test for organic molecules. Bromine has a brown-orange
color, but most organic compounds of bromine are colorless. Loss of the orange color when
added to the organic molecule is a positive test for unsaturation (alkene or alkyne).
Also a hydrogen halide like hydrogen chloride or hydrogen bromide can be added to produce a
monosubstituted halocarbon.
Eg. Addition of hydrogen chloride to ethene
2. substitution reaction(reactions of alkanes and aromatics)
Uses halogens like Cl2 or Br2 (slow process and is unpredictable as to where the halogen will
end up or how many will end up on the molecule)
Eg.
Lesson 7: alcohols
Are organic compounds with a hydroxyl (-OH) group attached.
The oxygen atom is held tightly to the carbon atom, and the hydrogen atom is held tightly to
the oxygen atom so the alcohol does not display acidic or basic properties even though an –OH
group is present. These alcohols are non-ionic; the oxygen is covalently bonded to the carbon.
Generally most alcohols are saturated.
Primary alcohol: The carbon with the alcohol has only one other carbon attached to it (end
carbon).
Secondary alcohol: The carbon with the alcohol has two other carbons attached to it. (middle
carbon)
Tertiary alcohol: The carbon with the alcohol is completely branched (3 other carbons attached
to it.(middle and branched as well)
Nomenclature
IUPAC: (the hydroxyl is treated much like a double or triple bond)
-for continuous straight chain and substituted alcohols, drop the ‘e’ ending of the parent alkane
name and add the ‘ol’ ending for the alcohol. The parent alkane is the longest continuous chain
of carbons that includes the carbon with the hydroxyl group attached.
-number the longest chain giving the position of the hydroxyl group the lowest possible
number.
-alcohols containing two, three and four hydroxyl branches are called diols, triols, and tetrols.
(Don’t drop the ‘e’ on the parent name. Parent-addresses-prefix‘ol’)
Eg.
-compounds with more than one hydroxyl group are commonly called ‘glycols’.
Eg. Ethylene glycol
-hydroxyl named as a branch is ‘hydroxy’
Properties:
-have strong hydrogen bonding (makes alcohols a liquid)
-high boiling points
-low freezing points
-polar molecules – more soluble in water than other hydrocarbons we have seen yet.
Preparation of alcohols:
1. Hydration Reaction (Addition)
-add water to alkene or alkyne
2. Fermentation-the production of ethanol from sugars by the action of yeast or bacteria
GlucoseEthanol + carbon dioxide (do chemical formulas)
Ethanol is the intoxicating substance in alcoholic beverages. Fermentation can take place by
distilling (removing water) to make hard alcohols or without distillation to form beer. Wine is
higher alcohol content than beer because additional alcohol is added
Lesson 8:Carboxylic Acids (organic acids)
-compounds with a carboxyl group COOH
-they are weak acids since the H on the hydroxyl group slightly ionizes in solution to give
an
Having two oxygen on the carbon makes the H in the carboxyl acidic even though the H
in the hydroxyl of an alcohol is not.
H+.
Nomenclature:
-the ‘e’ ending of the parent alkane is replaced by the ending ‘oic acid’. An address is not
necessary as it is always on the end (carbon 1) of the parent chain.
Eg.
Methanoic acid
Ethanoic acid
Propanoic acid
Oxalic acid
*Benzoic acid
2-hydroxybenzoic acid
Naming branches:
Eg.
Properties of Carboxylic acids:
-they have higher melting and boiling points than similar alkanes. This is due to their hydrogen
bonding. Aromatic carboxylic acids are crystalline solids at room temperature
-small chain (1-4 carbons) are miscible with water (mix) since they are polar. The solubility
drops with higher carboxylic acids as more of the molecule is non-polar than polar. (like
alcohols). Most will still dissolve in organic polar solvents like acetone or ethanol
-smaller ones are colorless, volatile and have a sharp unpleasant odour
-higher mass aliphatic ones are non-volatile, have a low melting point and are waxy solids.
A fatty acid is a continuous chain carboxylic acid that was first isolated from fats.
Eg. Stearic acid is obtained from beef fat (C18). It is also used to make wax candles
-Reactions of carboxylic acids:
1. esterification (to form an ester)
alcohol + carboxylic acid - ester + H2O

You will predict the ester formed from an alcohol and an organic acid
2. Neutralize a base
3. react with active metals (group 1 and 2) to form hydrogen gas. (acid reaction)
eg. Pg 438 Nelson
Lesson 9: Esters
-derivatives of carboxylic acids in which the OH of the carboxyl group has been replaced
by an –O-R from an alcohol. (esterification)
The R group can be short or long chains, aliphatic (alkyl) or aromatic (aryl), saturated or
unsaturated.
Nomenclature:
-the side of the ester that was originally the alcohol part is named first (single bonded
oxygen) as though it is a branch.
-the side of the ester that was originally the acid part (with double bonded oxygen) is
named last and has the ending ‘oate’ to indicate the ester group.
-the two parts of the name are two separate words.
Eg.
Properties of Esters:
1.
2.
3.
4.
Insoluble in water (hidden polar region and no hydrogen bonding)
Liquids (used as solvents, artificial flavours)
Adding water can change it back to the alcohol and acid (requires H+ for catalyst)
Relatively stable (not too reactive) since they have weak attractions (no hydrogen
bonds)
5. Have very pleasant fragrances of fruits, flowers. Often used to make perfumes or
artificial extracts for baking.
Lesson 10: Summarize reactions





You will design a procedure to identify types of organic compounds
You will define, illustrate and provide examples of simple addition, substitution, elimination,
esterification and combustion reactions
You will predict products and write and interpret balanced equations for the above reactions
You will relate the reactions to major reactions that produce thermal energy and economically
important compounds from fossil fuels
You will perform an experiment to investigate the reactions of organic compounds; eg.
polymers, esters
1. Addition Reactions: (alkene, alkyne, and cyclo alkene reactions excluding benzene) can also
break the ring of a cycloalkane
a. Hydration-addition of water to an unsaturated molecule to form an alcohol (isomers are
possible)
b.
Halogenation – addition of a halogen to an unsaturated molecule to form a halocarbon
product is a disubstituted halocarbon
-When a hydrogen halide like Hydrogen chloride or hydrogen bromide is added
then the product is a monosubstitued halocarbon. (isomers are possible)
c.
Hydrogenation – Hydrogen is added to a carbon-carbon double bond to give an alkane.
-catalyst: platinum or palladium
-used to saturate or partially saturate unsaturated oils to make margarine
Eg. Addition of hydrogen to ethene
Read pg 374,419
2.
Substitution Reactions: reactions of alkanes (UV catalyst)and benzene(FeBr3 catalyst)
Halogens (can put halogens anywhere in different quantities)
Halocarbons +hydroxide  alcohol + halide ion
Read pg 421
3. Elimination Reaction:(alkane reaction)
-to make ‘enes’ (dehydrogenation)
-when ethane is ‘cracked’ it is not kept as ethene. It is allowed to react with itself to form
polyethylene. Polyethylene is a starting point in almost all plastics and synthetic fibers.
-requires heat!
Saturated alcohol (acid catalyst) alkene + water
Alkyl halide + OH-  alkene + water +halide ion
** double bond will form mostly on the more interior side of the molecule from the halide or
alcohol. (isomers are present though)
Read pg 431-432,434
4.
Combustion
Incomplete combustion Nelson pg 399 #2, pg 400 #4,5
***and of course ESTERIFICATION
http://www.flixxy.com/convert-plastic-to-oil.htm
Petroleum seperation -Refining and using organic compounds


You will describe, in general terms, the physical, chemical and technological processes
(fractional distillation and solvent extraction) used to separate organic compounds from natural
mixtures or solutions; e.g., petroleum refining, bitumen recovery
You will design a procedure to separate a mixture of organic compounds, based on boiling point
differences
Nelson read pg 386-391
Fractional Distillation (distillation tower)pg386,389
-used to separate crude oil into its components based on boiling points. Heat is applied
to the bottom of the tower. The temperature decreases as you move up away from the heat
source. The molecules boil at the bottom and condense further up the tower at different levels
depending on their boiling points.
Chemical ways of refining oil: (used to create more of the type of oil wanted/used)
1. Fractioning –‘cracking’
-uses severe heat (thermal cracking) or an appropriate catalyst (catalytic cracking) to break a
long chain hydrocarbon into shorter chain molecules. Pure carbon ‘coke’ is produced. Pg 389
rxn
Hydrocracking is a combination of catalytic cracking and hydrogenation. It prevents the
production of ‘coke’ (pure carbon). Pg390 rxn (top)
2. Reforming – converting larger molecules into other molecules (rearranging). Most of it is done
with a catalyst and so it is called catalytic reforming. Hydrogen is a byproduct! For better
burning in gasoline, aromatics are often made from aliphatics by catalytic reforming.
- converting straight chain hydrocarbons into branched-chain alkanes is a type of reforming
called alkylation.
q. pg 388 #4 and 391 #10,12,13,15
Polymerization Reactions – Monomers and Polymers (pg 445) - VIDEO

You will define, illustrate and provide examples of monomers (e.g., ethylene), polymers (e.g.,
polyethylene) and polymerization in living systems (e.g., carbohydrates, proteins) and nonliving
systems (e.g., nylon, polyester, plastics)
Plastics are all around us. They belong to a group of substances called POLYMERS: large molecules
made by linking together many smaller molecules (MONOMERS). Plastics are synthetic polymers, but
many natural polymers exist as well such as amber from tree sap, a tortoise shell, rubber and cotton
plant polymers, wool and silk animal polymers, and polymers made within our cells such as protein and
carbohydrates
Different types of monomers form their links in different ways, by either ADDITION or CONDENSATION
reactions.
1. Addition Polymers:
Eg. Many plastics:
- polypropylene (polypropene)-in ropes and carpet
- polyvinyl chloride (PVC) – for pipes and wire insulation and waterproof coating on raincoats or
upholstery
- Plexiglas
- polystyrene (Styrofoam)
- natural rubber
- insulated cups
- Teflon (tetrafluoroethene monomer)
They are formed when monomer units with double or triple bonds join each other by the
breaking of the multiple bond.
****The polymer is the ONLY product formed!!
Eg. From pg 445-447
The monomers form dimers and trimers that continue to react to form polymers (many).
Do pg 448 questions #1,2,3,7
2. Condensation Polymers:
Eg. Synthetic fibers like nylon and polyester
Natural polymers like proteins and DNA
They are formed when two different monomer units bond at their functional group sites
(reactive points) and a small molecule is said to be ‘condensed out’ of the reaction.
***These reactions, therefore, involve the formation of the polymer PLUS an additional small
molecule formed from the removal of some atoms on the functional groups. (to allow for
bonding)
*** To form a condensation polymer, the monomer molecules must EACH have at least two
functional groups, one on each end, to allow for continuous bonding –-> polymer formation.
Synthetic polymers:
Usually similar to a naturally occurring substance and therefore called a structural analog.
Eg. Nylon is a structural analog to protein. (however a very different function – NOT a functional
analog!)
Functional analogs are synthetic compounds that perform the same function as a naturally
occurring substance but do not necessarily have similarities in chemical structure.
eg. Synthetic sweeteners
(copy natural /structural analog on pg 449)
Polyesters: A carboxylic acid reacts with an alcohol in an esterification reaction. Water is
eliminated and an ester if produced. It can be repeated to form many esters joined in a long
chain – polyester – if there are two carboxylic acids on the one molecule and two alcohols (one
on each end) of the other molecule.
 Synthetic:
Pg451 eg. (Dacron)

Natural:
Lipids: (fats and oils) made from the esterification reactions between glycerol (propane1,2,3-triol) and fatty acids (long-chain carboxylic acids). Since there are 3 hydroxyl
groups, three molecules of fatty acid can react with each glycerol to form a tri-ester.
This is a condensation reaction but not specifically a polymerization reaction (most you
can have is 3 esters)
http://www.youtube.com/watch?NR=1&feature=endscreen&v=Hr6dZ6aWpF4
Read last paragraph on pg 450
Do #9-11 pg 451.
Do pg 452 #12-14
Polyamides:
 Natural – proteins; polypeptides
 Synthetic – nylon 6,6
Read pg 452-454 – other eg.
Polysaccharides:
 Natural – starch
 Synthetic – cellulose triacetate used in fabrics
Read pg 456-458
q. pg 458 #18,20,23
***Summary pg 469