a. carbon compounds
DESCRIPTION
Organic Chemistry. A. Carbon Compounds. organic compounds are those in which carbon atoms are almost always bonded to each other, to hydrogen atoms and a few other atoms. (O, N, S, P). inorganic exceptions are the. oxides of carbon,. carbonates,. cyanides. and carbides. - PowerPoint PPT PresentationTRANSCRIPT
A. Carbon Compounds
organic compounds are those in which carbon atoms are almost always bonded to each other, to hydrogen atoms and a few other atoms
there are millions of organic compounds and all contain
Organic Chemistry
inorganic exceptions are theoxides of carbon,
and carbidescyanidescarbonates,
eg) CO2, CaCO3, NaCN, SiC
(O, N, S, P)
(no C-C bonds or C-H bonds)
covalent bonds
carbon is unique for two reasons:
it can bond with atoms to form long chains, rings, spheres, tubes, sheets etc.
a)
b) it can form combinations of single, double and triple bonds
(no other element does this!!!!)
other carbon
recall polarity and intermolecular forces from the chemical bonding unit
polar bonds are formed when there is an uneven pull on e
polar compounds are formed when the polar bonds within a molecule do not cancel each other out
the presence of dipole-dipole forces and hydrogen bonding will allow polar compounds to dissolve in water, since it is also polar non-polar compounds only have LD forces between molecules and will not dissolve in water
B. Structural Isomers
isomers are compounds with the same molecular formulabut adifferent structure
Example 1
Draw the three structural isomers for C5H12.
H
H
C
H
H
C C C C
H H
H
H H
H
H
H
H
H CH3 H
H
C C C C
H H
H
H
H
H
H C H3
C C C
CH3 H
H
H
H
1. 2.
3.
Example 2
Draw three structural isomers for C4H8F2 .
H
F H H
F
C C C C
H H
H
H
H
1. 2.
3. H
H F H
F
C C C C
H H
H
H
H
H
H H F
F
C C C C
H H
H
H
H
different structures result in differentproperties
the arrangement of the atoms determines the types of intermolecular attractions which then determines properties such as and in water
boiling point solubility
Example
Draw two isomers of C3H8O. Which one would have a boiling point of 7.4C and which would have a boiling point of 82.5C? Explain why the boiling points are so different.
H
H
C C C H
H H
H
OH H
H
H H
H
C O C C
H
H
H
H
has HB between molecules which makes the boiling point quite high
does not have HB between molecules therefore the boiling point is significantly lower
82.5C – 7.4C –
C. Formulas and Structural Diagrams organic molecules can be drawn in three
different ways:
1. complete structural diagram – shows all bonds eg) C3H8 H
H
C C C H
H H
H
H H
eg) C3H7F
H
H
C C C F
H H
H
H H
2. condensed structural diagrams – shows but includes the etc. attached to each carbon
eg) C3H8
eg) C3H7F
CH3 CH2 CH3
CH3 CH2 CH2F
hydrogens carbon to carbon bonds
3. line structural diagrams – shows only bonds carbon to carbon
eg) C3H8
eg) C5H12
eg) C4H8
D. Prefixes 1. Number of Functional Groups
6 =
2 = 7 =
3 = 8 =
4 = 9 =
5 = 10 =
di
tri
tetra
penta
hexa
hepta
octa
nona
deca
2. Number of Carbons
1 = 6 =
2 = 7 =
3 = 8 =
4 = 9 =
5 = 10 =
meth
eth
prop
but
pent
hex
hept
oct
non
dec
E. Alkanes
hydrocarbons containing
CnH2n+2
eg) C5H12, C20H42, etc.
can be continuous chains, chains, structures
only single bonds
SATURATED
ring
ie) they are
long branched(cycloalkanes)
1. Properties
can be depending on number of carbon atoms
relatively because the bonds are
nonpolar not soluble
solid, liquid or gas
very stableunreactive single
in water
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
prefix + “ANE” (suffix)
eg) H
H
H
H
H
C C C C
H H
H
H H
butane
ii. Branched Chains
branches are called functional group
1 C = ; 2C = ; 3 C = etc
alkyl
methyl
ethyl propyl
find the and so the branches get the
longest carbon chain number it lowest
to name: name the first (in order), including the where each group is found, then name the
groups alphabeticalnumber of the carbon
longest chain
possible numbers
(parent name)
eg)3-methylpentane
H
CH3
C
H
H
C C C C
H H
H
H H
H
H
H
1 2 3 4 5
methyl
H
CH2
C
H
H
C C C C
H H
H
CH3 H
H
H
H
CH3
1 2 3 4 5
methyl
ethyl
3-ethyl-2-methylpentane
eg)
2,3-dimethylpentane
H
CH3
C
CH3
H
C C C C
H H
H
H H
H
H
H
12345
methylmethyl
iii. Cycloalkanes
use the as the name
+ +
eg)
ring structure “parent”
prefix“cyclo” ANE
cyclobutane
cyclopropane
if there are branches, number the carbons in the ring so the branches get the lowest possible number sequence
CH3
CH3 CH2
eg)
1
23
45
ethyl
methyl
1-ethyl-3-methylcyclopentane
F. Alkenes
hydrocarbons containing
CnH2n
eg) C5H10, C20H40, etc.
one or more double bonds
ie) they are
can be continuous chains, chains, structures
branched
longring (cycloalkenes)
UNSATURATED
1. Properties
double bond has in the same area and
nonpolar not soluble
than corresponding alkane because they have which makes the forces of attraction
eg) ethane BP = 88.6C ethene BP = 103.8C
lower boiling pointfewer e LDweaker
more e-
greater repulsion bond less stable
than alkanesmore reactive
in water
A B A BBr2(l) KMnO4(l)
alkene alkenealkane alkane
*** the alkenes will react causing the colour to disappear as the coloured substance is used up in the reaction
diagnostic test: use KMnO4(aq) or Br2(l)
***alkenes with these substances causing a noticeable alkanes will not
(double bond) will reactcolour change,
2. Uses
plastics (PVC)
steroids
3. Naming
welding torches
i. Continuous Chains prefix + “ENE” (suffix)
number carbons to give the the
double bond lowest number
the number where the double bond is to be given as a “ # ” between the prefix and the suffix
starts
eg) H
C
H
C C C C
H H
H
H H
H
C
H H
H
H ‗
H
C
H
C C C
H
H
H
H
C
H H
H
H ‗
H
C
H
C C
H
H
C
H H
H
H ‗
hex-3-ene
pent-2-ene
but-1-ene
ii. Branched Chains find the longest carbon chain and number it so
the gets the lowest possible 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
double bond
groups alphabeticalnumber
parent namenumber
CH2
CH2
C CH2
CH2
CH2
‗ CH2
CH3
CH3
eg)
CH CH3
CH CH
CH2
CH ‗ CH CH3
CH2 CH3
CH3
CH3
2-ethylhept-1-ene
4,5,6-trimethylnon-2-ene
iii. Cycloalkenes
double bond is always numbered
+ +prefix“cyclo” ENE
1, 2
get the after the branches lowest numbering
sequencedouble bond
list branches in with thenumber
alphabetical order
of the carbon they are on
CH2 CH3
CH2 CH3
CH3
CH3
3-ethylcyclobutene
3-ethyl-1,3-dimethylcyclobutene
1
1
2
2
3
3
4
4
eg) cyclohexene
cyclopropene
G. Alkynes
hydrocarbons containing
CnH2n-2
eg) C5H8, C20H38, etc.
can be continuous chains, chains
one or more triple bonds ie) they are also
not plentiful in nature
UNSATURATED
long branched
1. Properties
bond has in the same area force of repulsion
very reactive
boiling points are than corresponding alkanes and alkenes because of their and the of triple bonds
2. Uses
welding torches
nonpolar
(more than alkanes and alkenes)
higherlinear structure
nature
triple 6 e- high
i. Continuous Chains prefix + “YNE”
number carbons to give the the
triple bond lowest number
3. Naming
the number where the triple bond is to be given as a “ # ” between the prefix and the suffix
starts
eg)
hex-3-yne C C C C C
H H
H
H H
H
C
H H
H
H ≡
C C C C
H
H
H
H
C
H H
H
H ≡ pent-2-yne
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
triple bondlongest carbon chain
groups alphabeticalnumber
parent namenumber
eg) CH2
CH C CH
CH2
CH2
≡ CH2
CH3
CH2
CH3
CH2
3-propyloct-1-yne
C CH3
CH C
CH2
CH ≡ CH CH3
CH3
CH3
CH3
2,5,6-trimethyloct-3-yne
Review
alkanes – branches, rings – least reactive
alkenes – branches, rings
alkynes – branches – most reactive
all called
major intermolecular forces are boiling points are
aliphatics
LDlow
all and in water nonpolar not soluble
H. Aromatics hydrocarbons containing one or more
all bonds are the
benzene rings C6H6
OR
same length and strength we draw benzene like this:
1. Properties
the benzene ring structure is
aromatics are characterized by strong aromas
very stable
nonpolar
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 “phenyl” group
eg)
CH3
CH2 CH2 CH CH2 CH3 CH2
CH2
CH2
CH CH C ‗ CH2
CH2
CH3
CH3
4-phenylheptane
3-methyl-5,5-diphenyloct-1-ene
ii. Benzene as a the Main Compound if only one group is attached, give the
attached to alkyl name “benzene”
(no number is necessary)
eg)
CH3 methylbenzene
if there is more than one branch, number them so they get the and name
eg) 1-ethyl-3-methylbenzene
1,3-dimethyl-5-propylbenzene
lowest sequence alphabetically
CH3
CH3
CH2
CH3
CH3
CH3
CH2
CH2
CH3
C2H5
1-ethyl-3-methylcyclohexane
***Watch out for this!!!
I. Alcohols
organic compounds with one or more
R - OH
OH (hydroxyl) groups
1. Properties have much
than corresponding aliphatics because of
eg) methane (CH4) BP =
methanol (CH3OH) BP =
-162C
65C
higher boiling points hydrogen bonding!
2. Uses
antifreeze, rubbing alcohol, beverages, moistening agent
the end of the alcohol is while the end small alcohols are in water and large alcohols are
–OH polarcarbon chain is notsoluble not
polar
3. Naming number the longest carbon chain containing
the so the group gets thehydroxyl group
name at end
give the where the is found between the parent name and the suffix
number for the carbon –OH group
–OH
lowest number
+ “OL”aliphatic (without “e” )
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
more than onedi, tri, tetra number
H
OH
H
H
H
C C C C
H H
H
H H
eg)
H
OH
H
H
H
C C C C
CH3 H
H
H H
butan-2-ol
3-methylbutan-2-ol
H
OH
H
H
H
C C C C
CH3 H
H
OH H
an unusual case: OH
2-methylbutane-2,3-diol
phenol
J. Organic Halides
where is and is a
R - X
R carbon chain or ring Xhalogen
organic compounds where has been replaced byone or more halogens (F, Cl, Br,
I) do not readily occur in nature
hydrogen
1. Properties
can be or , depending on the placement of the halogen groups
many are
2. Uses
toxic and dangerous
anesthetics
dry cleaning fluid
plastics, polymers (Teflon)
manufactured for human use eg) DDT, PCB, CFC
polar nonpolar
3. Naming
same rules as before… name branches ( included now)
F = fluoro Cl = chloro
Br = bromo
I = iodo
eg) Cl
H
H
H
H
C C C C
Cl H
H
H H
2,3-dichlorobutane
halogensalphabetically
F CH3
I
2-fluoro-4-iodo-1-methylbenzene
K. Carboxylic Acids
where is R carbon chain or ring organic compounds containing the
OH║O
R C
carboxyl functional group (-COOH)
1. Properties
polar dissolve in water
boiling points due to
weakly acidic
diagnostic test: use (will turn ), metals, neutralize
bases
high hydrogen bonding
litmus paper red
readily react with
2. Uses
vinegar – ethanoic (acetic) acid
rust remover – oxalic acid
fruits – citric acid
recycling rubber – methanoic acid
3. Naming count the longest carbon chain including the
drop and add
carbon in the carboxyl group
the carbon in the carboxyl group is always number
1
“e” “OIC ACID”
OH
║
O
CH
OH
║
O
CC
H
H
H
eg)
methanoic acid
ethanoic acid
benzoic acid
4-iodobutanoic acid
OH
║
O
C
OH
║
O
CC
H
H
CC
H
H H
H
I
L. Esters
where can be a carbon chain or hydrogen and can be a carbon chain
combination of a and an
1. Properties
esters in water, esters
boiling points slightly lower than corresponding carboxylic acids and alcohols due to lack of hydrogen bonding
O ║O
R C R’
R R’
carboxylic acid alcohol
small dissolve largedo not
polar
2. Uses
flavouring agents
3. Naming identify the used to make the
ester
identify the the ester was made from
change the alcohol name to the corresponding name eg) methanol would become
alcohol
alkyl
methyl
carboxylic acid
very which allows them to generate
volatilearomas
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
two names space
methyl butanoate
branches
O end
drop the “oic acid” and replace with
eg) butanoic acid would become
“oate”
“butanoate”
eg)
O ║O
CC
H
H
CC
H
H H
H
H C
H
C
H
H
H
H
O ║O
CC
H
H
C
H
H
H C
H
C
CH3
H
H
H
ethyl butanoate
propyl propanoate
eg)
O
║
O
CC
H
CH3
C
H
CH3
H C
H
C
H
H
H
H
ethyl 2-methylbutanoate
M. Boiling Points and Solubility
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 alkene carboxylic acid alcohol aromatic alkane
highest lowest
polarityintermolecular attractions
Example 2
Put the following homologous series of organic compounds in order from highest boiling point to lowest boiling point.
C2H6, C2H5OH, CH3COOH, C2H4
highest lowest
CH3COOH C2H4C2H6C2H5OH
we can also compare the of various organic compounds using their polarity
solubility
Insoluble Organic Compounds
Soluble Organic Compounds
organic halides
aliphatics – alkanes, alkenes, alkynes
aromatics
alcohols – large (7 or more carbons)
esters – large
carboxylic acids
alcohols – small (less than 7 carbons)
esters – small
organic halides
N. Organic Reactions
occurs when a reacts with 1. Combustion Reactions
hydrocarbon oxygen
products are always carbon dioxide and waterthese are economically important reactions for
they are the major reactions that produce required for fuelling our vehicles, heating our homes, and producing electricity
thermal energy
eg) C5H12(l) + O2(g) +CO2(g) H2O(g)5 681
eg) 1 C5H12(l) + 8 O2(g) 5 CO2(g) + 6 H2O(g)
H
H
H
H
H
C C C C
H H
H
H H
+ 6.5 O2(g) 4 CO2(g) + 5 H2O(g)
***balance these reactions
a or bond in an alkene or alkyne is and a group or element is (a catalyst is present)
2. Addition Reactions
eg)
H H
C C
H H
‗ Cl Cl +
Cl
H
H
C C
H
H
Cl
double triplebroken
added
H
OH
H
C C
H
H
H
H
H
H
C C
H
H
H
H H
C C
H H
‗ H OH +
H H
C C
H H
‗ H H +
H
H
Br C C
H
H
H
H H
C C
H H
‗ H Br +
C C H H ≡ 1 Cl2 +
C C H H ≡ 2 Cl2 +
H H
C C
Cl Cl
‗
Cl
Cl
H C C H
Cl
Cl
the replacement ( ) of a hydrogen on an alkane or aromatic with (eg. F, Cl etc)
3. Substitution Reactions
commonly used to make
Examples
organic halides
C H
H
H
H Cl – Cl + cat
C H
H
Cl
H H - Cl +
1.
substitutionanother atom
Br – Br + cat
H - Br +
Br2.
I – I + cat
H - I +
I
3.
4.
H
H
H
C C C
H
H
H
H
C
H
H
H H
Br
H
H C C C
H
H
H
H
C
H
H
Br2 + cat
H - Br +
the reaction of a with an4. Esterification Reactions
Examples
carboxylic acid alcohol
1.
OH║O
CH H
H
H
HO C + H2SO4(aq)
O║O
CH H
H
H
C + H – OH
the catalyst issulphuric acid
H2SO4(aq)
OH║O
CCH C
H
H
H
H
+ C
H
H
HO C
H
H
H
2.
+ H – OH
C
H
H
C
H
H
H O║O
CCH C
H
H
H
H
an has water removed, forming an plus the
5. Elimination Reactions
Examples
H
H
OH
H
H
H C C
1. cat
H H
C C H H
‗ + H – OH
can react with a to produce an , a and
alcohol alkenewater
organic halides base (hydroxide) alkenehalide ion water
H
H
H
H
H
C C C C
H H
H
H OH
cat
2.
H – OH
H
C
H
C C H
H
C
H H
H
H ‗ +
3. H
H
Cl
H
H
H C C + OH cat
H H
C C H H
‗ + H – OH + Cl
a is a that forms the for a polymer
6. Polymerization Reactions
a is a formed by the of
depending on the polymer, the monomers that make it up can be or
monomer simple moleculebase unit
polymer very, very long moleculecovalent bonding
the samedifferent
bazillions of monomers
polymers can be
eg)
natural
carbohydrates, proteins, DNA
polymers can be
eg)
synthetic
nylon, PVC, Teflon, polyester
polymers that can be heated and molded into specific shapes are commonly called
the names of polymers are the monomer name with in front
many have classical names instead of IUPAC names
plastics
“poly”
plastics are one type of synthetic compound that has been of great benefit to society (although there are also problems associated with then)
Addition Polymers formed when the electrons in double or triple
bonds in the monomer units are rearranged
the polymer is the formed only product
Examples
H H
C C
H H
‗ +
H H
C C
H H
‗
cat
1. H
H H
H
C C C C
H H
H H n
polyethene
… …
F F
C C
F F
‗ +
F F
C C
F F
‗
cat
2.
Teflon
H Cl
C C
H H
‗ +
H Cl
C C
H H
‗
cat
3.
polyvinyl chloride (PVC)
F
F F
F
C C C C
F F
F F n
… …
H
H H
Cl
C C C C
Cl H
H H n
… …
H
C C
H H
‗ +
H
C C
H H
‗
cat
4.
polystyrene (styrofoam)
H
H H
C C C C
H
H H n
… …
Condensation Polymers polymerization reactions that involve the
formation of a (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)
small molecule waterpolymer
two
ester
amide
Examples
1.
polyethylene terephthalate PET
C C cat
C C OH
O O
HO ║
OH HO
H H
H H
+ ║
n
∙∙∙∙∙∙ C C O
O ║
O
O ║
C C
H H
H H
+ H2O
ester linkage
cat
2.
C C H
O H
HO N ║
H
H
C C H
O H
HO N ║
H
H
+
n
∙∙∙∙∙∙ + H2O C C
O H
N ║
H
H
C C
O H
N ║
H
H
protein
amide linkage
Alberta has vast reserves of petroleum in the form of natural gas, crude oil and oil sand deposits
O. Petroleum Refining
most of this petroleum is refined and then burned as
petrochemicals are also used in the production of
fuel
plastics
refining of petroleum separates the crude mixture into purified components
is used to separate the components fractional distillation
http://home.att.net/~cat6a/fuels-IV.htm
distillation works because of the different of the components of crude oil boiling points
the the molecule and the the boiling point, the it rises in the tower (asphalt, fuel oil, wax at bottom; gasoline at top) distillation tower:
lighter lowerhigher
two types of reactions in petroleum refining:
long chain hydrocarbons intocracking requires heat and pressure
1. Cracking
there are many different types of cracking reactions, forming different products (alkanes, alkenes) eg) catalytic cracking, steam cracking, hydrocracking hydrocracking requires
breaks smaller units
H2(g)
Examples
1. C17H36 + C9H20 +H2(g) C H8 18
CH3 CH2 CH2 CH2 CH3 CH2 CH2
cat
+ H2(g) cat
2.
CH3 CH2 CH2 CH3 + CH3 CH2 CH3
small hydrocarbons are to make
2. Reforming
Example
requires heat and pressure
C7H16 + C12H26 +C H
H219 40
there are several types of reforming reactions
eg) alkylation to produce “high octane” gasoline
all reforming reactions produce
joinedlarger molecules
H2(g)
Examples
C7H16 + C12H26 +C H
H219 40
1.
2.
ethane + octane decane + hydrogen gas