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 (no C-C bonds or C-H bonds) eg) CO2, CaCO3, NaCN, SiC

Sample Diploma Question Use the following information to answer the next question. Chemical Compounds CO(g) 5 C2H5OH(l) Na2CO3(aq) 6 KCN(g) CH4(g) 7 CoCl2(aq) HOOCCOOH(aq) 8 CH3COOH(aq)

1 2 3 4

The chemical compounds numbered above that represent organic compounds are _______, _______, _______, and _______.

there are millions of organic compounds and all contain covalent bonds carbon is unique for two reasons: a) it can bond with other carbon atoms to form long chains, rings, spheres, tubes, sheets etc.

b) it can form combinations of single, double and triple bonds (no other element does this!!!!)

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 formula but a different structure

Example 1 Draw the three structural isomers for C5H12. 1.

H H C H H C H H C H H C H H C H H

2.
H

H C H

H C

H C

H C H

CH3 H H

3.
H

H C H

CH3 H C C H

C H3 H

Example 2 Draw three structural isomers for C4H8F2 . 1.

H H C H H C H H C F C H

2.
H

H C H

H C H

H C F

F C H H

H F

3.
H

H C H

H C F

H C

F C H

H H

different structures result in different

properties

the arrangement of the atoms determines the types of intermolecular attractions which then determines properties such as boiling point and solubility 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 82.5rC? Explain why the boiling points are so different.
H H C H H C H C H H H C H O H C H H C H H

OH H

82.5rC has HB between molecules which makes the boiling point quite high

7.4rC does not have HB between molecules therefore the boiling point is significantly lower

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 H
H C H C H H H C H C H H C H H C H F H

eg)

C3H7F

2. condensed structural diagrams shows carbon to carbon bonds but includes the hydrogens etc. attached to each carbon eg) C3H8

CH3

CH2

CH3

eg)

C3H7F

CH3

CH2

CH2F

3. line structural diagrams shows only carbon bonds eg) C3H8

carbon to

eg)

C5H12

eg)

C4H8

Sample Diploma Question The structural diagram below that is an isomer of pentane, C5H12, is
A.
H C C H H H H C C C H H H

B.

H H C H H H C C H H H C H H

H C

C.

H C H H H C C H C C H H C H H

D.
H C

H H C H H H C C H H H H

D. Prefixes 1. Number of Functional Groups

6 = hexa 2 = di 3 = tri 4 = tetra 5 = penta 7 = hepta 8 = octa 9 = nona 10 = deca

2. Number of Carbons
1 = meth 2 = eth 3 = prop 4 = but 5 = pent 6 = hex 7 = hept 8 = oct 9 = non 10 = dec

E. Alkanes
eg) C5H12, C20H42, etc.

CnH2n+2

hydrocarbons containing only single bonds ie) they are SATURATED

can be long continuous chains, branched chains, ring structures (cycloalkanes)

1. Properties nonpolar @not soluble in water depending on

can be solid, liquid or gas number of carbon atoms

relatively unreactive because the single bonds are very stable

2. Uses natural gas, BBQs, 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 C H H C H H C H H C H H

butane

ii. Branched Chains branches are called alkyl functional group

1 C = methyl ; 2C = ethyl ; 3 C = propyl etc find the longest carbon chain and number it so the branches get the lowest possible numbers to name: name the groups first (in alphabetical order), including the number of the carbon where each group is found, then name the longest chain (parent name)

eg)
H

H H

1 2 3 4 5 C C C C C H H CH3H H

3-methylpentane

methyl
H 1 C H H 2 C H 3 C H 4 C H 5 C H

3-ethyl-2-methylpentane

CH3 CH2 H

methyl CH3 ethyl

eg)
H

H H

1 2 3 4 5 C C C C C H CH3 CH3 H H

methyl methyl 2,3-dimethylpentane

Sample Diploma Question Which of the following line diagrams represents 2,3-dimethylpentane?
A. B.

C.

D.

iii. Cycloalkanes use the ring structure as the parent name

cyclo+ prefix + ANE eg)

cyclobutane

cyclopropane

if there are branches, number the carbons in the ring so the branches get the lowest number sequence eg)
4 3 CH3 5 2 1 CH2 CH3

ethyl

methyl 1-ethyl-3-methylcyclopentane

F. Alkenes

CnH2n

eg) C5H10, C20H40, etc. hydrocarbons containing one or more double bonds ie) they are UNSATURATED can be long continuous chains, branched chains, ring structures (cycloalkenes)

1. Properties nonpolar @not soluble in water lower boiling point than corresponding alkane because they have fewer e which makes the LD forces of attraction weaker eg) ethane BP = 88.6rC more reactive ethene BP = 103.8rC

than alkanes

double bond has more e- in the same area @ greater repulsion and bond less stable

diagnostic test: use KMnO4(aq) or Br2(l) ***alkenes (double bond) will react with these substances causing a noticeable colour change, alkanes will not

Br2(l)

KMnO4(l)

alkene

alkane

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 prefix + double bond # + ENE (suffix) number carbons to give the double bond the lowest number the number where the double bond starts is to be given as a  #  between the prefix and the suffix

eg)

H H H

H H

H C C C C C C H H H H H H

hex-3-ene

H H H H H H C C C C C H H H C H H H H H H C C C H

pent-2-ene

but-1-ene

H H

ii. Branched Chains find the longest carbon chain and number it so the double bond gets the lowest possible number to name: name the groups first (in alphabetical order), including the number of the carbon where each is found, then the parent name including the number of the carbon where the double bond starts

eg)

CH2

C CH2 CH3

CH2 CH2 CH2 CH2 CH3

2-ethylhept-1-ene

CH3 CH CH

CH CH CH CH3 CH3 CH3 CH2 CH2 CH3

4,5,6-trimethylnon-2-ene

iii. Cycloalkenes double bond is always numbered 1, 2

branches get the lowest numbering sequence after the double bond cyclo+ prefix + ENE list branches in alphabetical order with the number of the carbon they are on

eg)

cyclohexene

cyclopropene
CH2 CH3 3

2 1 CH3 1 2

3-ethylcyclobutene
4 4 3 CH2 CH3 CH3

3-ethyl-1,3-dimethylcyclobutene

G. Alkynes

CnH2n-2

eg) C5H8, C20H38, etc. hydrocarbons containing one or more triple bonds ie) they are also UNSATURATED can be long continuous chains, branched chains not plentiful in nature

1. Properties nonpolar very reactive (more than alkanes and alkenes) triple bond has 6 e- in the same area @ high force of repulsion boiling points are higher than corresponding alkanes and alkenes because of their linear structure and the nature of triple bonds 2. Uses welding torches

3. Naming i. Continuous Chains prefix + triple bond # + YNE number carbons to give the triple bond lowest number the

the number where the triple bond starts is to be given as a  #  between the prefix and the suffix

eg)

H H H C C C C

H H C C H

hex-3-yne

H H

H H

H H

H C C C C C H H H H

pent-2-yne

ii. Branched Chains find the longest carbon chain and number it so the triple bond gets the lowest number to name: name the groups first (in alphabetical order), including the number of the carbon where each is found, then the parent name including the number of the carbon where the triple bond starts

eg)

CH C

CH

CH2 CH2 CH2 CH2 CH3

CH2 CH2 CH3

3-propyloct-1-yne

CH3 CH CH3

CH

CH

CH3

CH3 CH2 CH3

2,5,6-trimethyloct-3-yne

Review alkanes branches, rings least reactive alkenes branches, rings alkynes branches most reactive all called aliphatics all nonpolar and not soluble in water major intermolecular forces are LD @boiling points are low

H. Aromatics hydrocarbons containing one or more benzene rings C6H6 OR

all bonds are the same length and strength @we draw benzene like this:

1. Properties nonpolar the benzene ring structure is very stable 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 phenyl group eg)
CH3 CH2 CH2 CH CH2 CH2 CH3

4-phenylheptane

CH2 CH

CH CH3

CH2 C

CH2 CH2 CH3

3-methyl-5,5-diphenyloct-1-ene

ii. Benzene as a the Main Compound if only one group is attached, give the alkyl name attached to benzene (no number is necessary) eg)
CH3

methylbenzene

if there is more than one branch, number them so they get the lowest sequence and name alphabetically
CH3

eg)
CH2 CH3 CH3

1-ethyl-3-methylbenzene

1,3-dimethyl-5-propylbenzene
CH3

CH3 CH2 CH2

I. Alcohols

R - OH

organic compounds with one or more OH (hydroxyl) groups 1. Properties have much higher boiling points than corresponding aliphatics because of hydrogen bonding! eg) methane (CH4) BP = -162rC methanol (CH3OH) BP = 65rC

polar the OH end of the alcohol is polar while the carbon chain end is not @ small alcohols are soluble in water and large alcohols are not

2. Uses antifreeze, rubbing alcohol, beverages, moistening agent

3. Naming number the longest carbon chain containing the hydroxyl group so the OH group gets the lowest number aliphatic name (without e at end + OL ) give the number for the carbon where the OH group is found between the parent name and the suffix

if there is more than one hydroxyl group, use a prefix ( di, tri, tetra ) to indicate the number 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

H C H

H C

H C H

eg)

C H

butan-2-ol

OH H

H H C H

CH3 H C H C

H C H

3-methylbutan-2-ol

OH H

H H C H

CH3 H C C

H C H

OH OH H

2-methylbutane-2,3-diol

simplest aromatic alcohol:

OH

phenol

J. Organic Halides

R-X and X is a

where R is carbon chain or ring halogen

organic compounds where hydrogen has been replaced by one or more halogens (F, Cl, Br, I) do not readily occur in nature

1. Properties can be polar or nonpolar , 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) toxic and dangerous

3. Naming same rules as before name branches ( halogens included now) alphabetically F = fluoro Cl = chloro eg )
H

Br = bromo

I = iodo

H C H

Cl C H

Cl C H

H C H H

2,3-dichlorobutane

2-fluoro-4-iodo-1-methylbenzene
CH3 F

K. Carboxylic Acids
R

O C OH

where R is carbon chain or ring organic compounds containing the carboxyl functional group (-COOH) considered saturated since double bonds in functional groups are not taken into account 1. Properties polar @ dissolve in water high boiling points due to hydrogen bonding weakly acidic diagnostic test: use litmus paper (will turn red ), readily react with metals, neutralize bases

2. Uses recycling rubber methanoic acid vinegar ethanoic (acetic) acid rust remover oxalic acid fruits citric acid 3. Naming count the longest carbon chain including the carbon in the carboxyl group the carbon in the carboxyl group is always number 1 drop e and add OIC ACID

eg)
H

methanoic acid
C OH

H H C H

O C OH

ethanoic acid

O C OH

benzoic acid

H I C H

H C H

H C H

OH

4-iodobutanoic acid

L. Esters

where R can be a carbon chain or hydrogen and R can be a carbon chain combination of a carboxylic acid and an alcohol considered saturated since double bonds in functional groups are not taken into account 1. Properties polar small esters dissolve in water, large esters do not boiling points slightly lower than corresponding carboxylic acids and alcohols due to lack of hydrogen bonding

very volatile aromas 2. Uses

which allows them to generate

flavouring agents 3. Naming identify the alcohol used to make the ester change the alcohol name to the corresponding alkyl name eg) methanol would become methyl identify the carboxylic acid made from the ester was

drop the oic acid and replace with oate eg) butanoic acid would become butanoate put the two names between together with a space in

eg) methyl butanoate you can have branches on estersthey follow the alphabetical rule, numbering begins at the O end of the alcohol and the C=O end of the carboxylic acid

eg)
H H H H C C C H H H

H H

C O C C H H H

ethyl butanoate

H H H C C H H

H CH3

C O C C H H H

propyl propanoate

eg)

H H H C C

O C

H H O C C H

CH3CH3

H H

ethyl 2-methylbutanoate

Sample Diploma Question

The structural diagrams that represent the aromatic, the carboxylic acid, the unsaturated aliphatic and the halogenated hydrocarbon, respectively, are ________, ________, ________, and ________.

M. Boiling Points and Solubility we can compare the boiling points of various organic compounds using their and polarity the intermolecular attractions 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
carboxylic acid alcohol aromatic alkane alkene
highest lowest

Example 2 Put the following homologous series of organic compounds in order from highest boiling point to lowest boiling point. C2H6, C2H5OH, CH3COOH, C2H4 CH3COOH C2H5OH
highest

C2H6

C2H4
lowest

we can also compare the solubility of various organic compounds using their polarity
Insoluble Organic Compounds aliphatics alkanes, alkenes, alkynes aromatics alcohols large (7 or more carbons) esters large organic halides alcohols small (less than 7 carbons) esters small organic halides Soluble Organic Compounds carboxylic acids

N. Organic Reactions 1. Combustion Reactions occurs when a hydrocarbon reacts with oxygen products are always carbon dioxide and water these are economically important reactions for they are the major reactions that produce thermal energy required for fuelling our vehicles, heating our homes, and producing electricity eg) 1 C5H12(l) + 8 O2(g) p 5 CO2(g) + 6H O 2 (g)

eg) 1 C5H12(l) + 8 O2(g) p 5 CO2(g) + 6 H2O(g)

H H C H H C H H C H H C H H

+ 6.5 O2(g) p 4 CO2(g) + 5 H2O(g) ***balance these reactions

2. Addition Reactions a double or triple bond in an alkene or alkyne is broken and a group or element is added

eg)
H C H C H H + Cl Cl p H H C H C H

Cl Cl

H C H C

H + H H OH p H

H C H

H C OH H

H C H C

H + H H H p H

H C H

H C H H

H C H C

H + H H H Br p H

H C H

H C Br H H

H C C H +

1 Cl2

p Cl

C Cl

Cl Cl H C C H + 2 Cl2 p H C C H

Cl Cl

3. Substitution Reactions the replacement ( substitution ) of a hydrogen on an alkane or aromatic with another atom (eg. F, Cl etc) commonly used to make organic halides Examples
1. H H C H H + cat Cl Cl p H H C Cl H + H - Cl

2. + Br Br

Br cat p + H - Br

3. +

cat II p I

H-I

4. H H C H H C H H H C C H + Br2 cat p H H C H Br C H H C H H C H H + H - Br

H H

4. Esterification Reactions the reaction of a carboxylic acid with an alcohol the catalyst is sulphuric acid Examples
1. O H C OH + H HO C H O H C O H C H H + H OH H H2SO4(aq)

2.
H H C H H C H O C H OH + HO C H H C H O C O H H2SO4(aq)

H H C H

H C H

H C H

H C H H + H OH

5. Elimination Reactions an alcohol has water removed, forming an alkene plus the water organic halides can react with a base (hydroxide) to produce an alkene , a halide ion and water Examples 1.
H H C H H C H OH cat p H C C H H H + H OH

2.
H

H C

H C

H C H

H C H H

cat p

H C H

H C

H C H

H C H H + H OH

OH H

3.
H

H C H

H C H Cl + OH


cat p

H C C H

H + H H OH + Cl 

Sample Diploma Question

Common Organic Reactions 1 C2H4(g) + H2(g) p C2H6(g)

2 C2H5OH(l) p C2H4(g) + H2O(l) 3 C6H6(l) + Br2(l) p C6H5Br(l) + HBr(g) 4 CH3COOH(l) + CH3OH(l) p CH3COOCH3(l) + H2O(l) The esterification, addition, substitution and elimination reactions respectively are ________, ________, ________, and ________.

6. Polymerization Reactions a monomer is a simple molecule the base unit for a polymer

that forms

a polymer is a very, very long molecule formed by the covalent bonding of bazillions of monomers depending on the polymer, the monomers that make it up can be the same or different

polymers can be natural eg) carbohydrates, proteins, DNA

polymers can be synthetic eg) nylon, PVC, Teflon, polyester

polymers that can be heated and molded into specific shapes are commonly called plastics

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 poly 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 only product Examples 1.
H C C H H H + H H C C H H cat p H H C H H C H H C H n

formed

C H

polyethene

2.

F C C F

F + F

F C C F

F F

cat p

F C F

F C F

F C F n

C F

Teflon 3.
H C C H H Cl + H H C C H Cl cat p H C H Cl H C H C H Cl C H n

polyvinyl chloride (PVC) 4.

H C C H H + H H C C H cat p H C H C H H C H C H n

polystyrene (styrofoam)

Condensation Polymers polymerization reactions that involve the formation of a small molecule (commonly water ) as well as the polymer each monomer must have two functional groups two common linkages formed: 1. ester linkage between carboxyl group (COOH) and hydroxyl group (OH) 2. amide linkage between amino group (NH2) and carboxyl group (COOH)

Examples
1. O HO C O C H OH + HO C H H C H ester linkage O OH
cat p

O O C

H H + H2O n

C O C C H H

polyethylene terephthalate PET

2. O H H HO C C N H + HO H O H H C C N H H amide linkage

cat p

O H H O H H C C H N C C H N n + H2O

protein

Sample Diploma Question

Use the following information to answer the next question
F CH2 C F F CH2 C F

The monomer for the polymer in the structural diagram above is ____i____, and it was produced by a _____ii____ polymerization reaction. Row A. B. C. D. i CH2CF2CH2CF2 CH2CF2CH2CF2 CH2!CF2 CH2!CF2 ii addition condensation addition condensation

O. Petroleum Refining 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 fuel petrochemicals are also used in the production of plastics

refining of petroleum separates the crude mixture into purified components fractional distillation is used to separate the components distillation works because of the different boiling points of the components of crude oil the lighter the molecule and the lower the boiling point, the higher it rises in the tower (asphalt, fuel oil, wax at bottom; gasoline at top)

Fractional Distillation Tower

light hydrocarbons low molar mass

heavy hydrocarbons high molar mass

two types of reactions in petroleum refining: 1. Cracking breaks long chain hydrocarbons into smaller units 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 H2(g)

Examples 1.
CH3 (CH2)15 CH3 + H2(g)

cat

CH3 (CH2)6 +

CH3 CH3 (CH2)7 CH3

2.
CH3 CH2 CH2 CH2 CH3 CH2 CH2 + H2(g) CH3 CH2 CH2 CH3 + cat

p
CH3 CH2 CH3

2. Reforming small hydrocarbons are joined to make larger molecules requires heat and pressure there are several types of reforming reactions eg) alkylation to produce high octane gasoline all reforming reactions produce H2(g)

Example C7H16 + C12H26 p C 19H 40 + H2

Examples 1. C7H16 + C12H26 p C 19H 40 + H2

2. ethane + octane decane + hydrogen gas