organic notes 2009

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 carbides

cyanides carbonates,

eg) CO₂, CaCO₃, NaCN, SiC

(O, N, S, P)

(no C-C bonds or C-H 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!!!!)

 _{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}

B. Structural Isomers

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

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

_{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

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.

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

C. Formulas and Structural Diagrams

different ways:

1. complete structural diagram – shows all

bonds

eg) C₃H_{8 H}

H

C C C H H

H

H

H H

eg) C₃H₇F H

H

C C C F 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

3. line structural diagrams – shows only bonds

carbon to carbon

eg) C₃H₈

eg) C₅H₁₂

D. Prefixes

1. Number of Functional Groups

6 =

2 = 7 =

3 = 8 =

4 = 9 =

5 = 10 =

di tri

tetra penta

hexa hepta octa nona

2. Number of Carbons

1 = 6 =

2 = 7 =

3 = 8 =

4 = 9 =

5 = 10 =

meth eth prop but pent

hex hept oct non

E. Alkanes

 _{hydrocarbons containing}

C_nH_2n+2

eg) C₅H₁₂, C₂₀H₄₂, etc.

 _{can be continuous chains,}

chains, structures

only single bonds SATURATED

ring

ie) they are

long branched

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

2. Uses 



natural gas, BBQ’s, lighter fluid, gasoline etc

good for making plastics, lubricants

3. Naming

_{IUPAC =} International Union of Pure and

i. Continuous Chains

 prefix + “ANE” (suffix)

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

alkyl

methy l

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 alphabetical number of the carbon

longest chain

possible numbers

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

eg)

2,3-dimethylpentane H

CH₃

C

CH₃ H

C C C C H

H

H

H H

H

H

H 1 2

3 4

5

iii. Cycloalkanes

_{use the as the}

name

 _{+ +}

eg)

ring structure “parent” prefix

“cyclo” ANE

cyclobutane

_{if there are branches, number the carbons in}

the ring so the branches get the lowest possible number sequence

CH₃

CH₃ CH₂

eg)

1 2 3

4 5

ethyl

methyl

F. Alkenes

 _{hydrocarbons containing} C_nH_2n

eg) C₅H₁₀, C₂₀H₄₀, etc.

one or more double bonds

ie) they are

 _{can be continuous chains,}

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 = 88.6C ethene BP =

103.8C

lower boiling point

fewer e _LD

weaker

more e

-greater repulsion bond less stable _{more reactive than alkanes}

A B A B

Br_2(l) KMnO_4(l)

alkene alkane alkane alkene

*** 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 react

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

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

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 _alphabetical number

CH₂ CH₂ C CH₂ CH₂ CH₂ ‗ CH₂ CH₃ CH₃ eg) CH CH₃

CH CH

CH₂ CH

‗ _CH

iii. Cycloalkenes

_{double bond is always}

numbered

 _{+ +“cyclo” prefix ENE}

1, 2

 _{get the}

after the branches_{double bond}lowest numbering _sequence

_{list branches in with}

the

number

alphabetical order

CH₂ CH₃

CH₂ CH₃ CH₃

CH₃

3-ethylcyclobutene

3-ethyl-1,3-dimethylcyclobutene 1

1

2 2

3 3

4 4

eg) cyclohexene

G. Alkynes

 _{hydrocarbons containing} C_nH_2n-2

eg) C₅H₈, C₂₀H₃₈, etc.

 _{can be continuous chains,} chains

one or more triple bonds

ie) they are also

 _{not plentiful in nature}

UNSATURATED

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)

higher

linear structure nature

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

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

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 bond

longest carbon chain

groups alphabetical number

eg) CH₂ CH C CH

CH₂

CH₂

≡

CH_{2 CH3} CH₂ CH₃ CH₂ 3-propyloct-1-yne C CH₃

CH C

CH₂ CH

Review

 

  

alkanes – branches, rings – least reactive alkenes – branches, rings

alkynes – branches – most reactive all called

major intermolecular forces are boiling points are

aliphatics

LD low

H. Aromatics

 _{hydrocarbons containing one or more}

 _{all bonds are the}

benzene rings C₆H₆

OR

1. Properties

 _{the benzene ring structure is}

_{aromatics are characterized by strong aromas} very stable

2. Uses 



ASA, amphetamines, adrenaline, benzocaine (anesthetic)

moth balls, TNT

 _{wintergreen, menthol, vanilla,}

cinnamon

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

CH₂

CH₂

CH CH C

‗

CH₂ CH₂

CH₃

CH₃

4-phenylheptane

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)

 _{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

CH₃

C₂H₅

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 = -162C

65C

higher boiling points

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 polar

carbon chain is not

soluble not

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

_{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 one

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

H

OH

H

H H

C C C C CH₃

H

H

OH H

 _{an unusual case:} OH

2-methylbutane-2,3-diol

J. Organic Halides

 _{where is}

and is a

R - X

R carbon chain or ring X halogen

 _{organic compounds where}

has been replaced byone or more halogens (F, Cl, Br,

I)

 _{do not readily occur in nature}

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

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

F CH₃

I

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

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

OH ║

O

C H

OH ║

O

C C

H

H H

eg)

methanoic acid

benzoic acid

4-iodobutanoic acid OH

║ O

C

OH ║

O

C C

H

H C C

H

H H

H

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 large

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

_{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”

eg)

O ║

O

C C

H

CH₃ C H

CH₃

H C

H C H

H H

H

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

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

_{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

N. Organic Reactions

 _{occurs when a reacts with} 1. Combustion Reactions

hydrocarbon oxygen

 _{products are always carbon dioxide and} water

_{these 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) C₅H_12(l) + O_2(g)  +_{CO2(g) H} 2O(g)

5 ₆

eg) 1 C₅H_12(l) + 8 O_2(g)  5 CO_2(g) + 6 H₂O_(g)

H

H

H

H H

C C C C H

H

H

H H

+ 6.5 O_2(g)  4 CO_2(g) + 5

H₂O_(g)

_{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 triple

broke n

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

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

_{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 H C

H

Cl

H + H - Cl 1.

substitution

Br – Br

+ cat + H - Br

Br 2.

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

_{the reaction of a with an} 4. Esterification Reactions

Examples

carboxylic acid _alcohol

1.

OH ║

O

C

H H

H H HO C

+ H



O ║

O

C

H H

H H



H₂SO₄(aq) OH ║ O C C H C H H H H

+ C

H H

HO C

H H

H

2.

_{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 alkene

water

organic halides base (hydroxide) alkene

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

_{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 molecule base unit

polymer very, very long molecule covalent

bonding

the same different

_{polymers can be}

eg)

natural

_{polymers can be}

eg)

synthetic

_{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

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 water

polymer

two

ester

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

cat 2.

C

C H O H

HO N ║

H H

C

C H O H

HO N ║ H H + n ∙∙∙

∙∙∙ _{+ H}

2O C

C O H

║ N

H

H

C C

O H

_{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

_{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 lower

 _{two types of reactions in petroleum refining:}

 _{long chain hydrocarbons into} _{cracking 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}

Examples

1. C₁₇H₃₆ + H_2(g)  C₉HC_{208 18} +H

CH₃ CH₂ CH₂ CH₂ CH₃ CH₂ CH₂ cat

+ H_2(g) cat

2.

_{small hydrocarbons are to make} 2. Reforming

Example

_{requires heat and pressure}

C₇H₁₆ + C₁₂H₂₆ C H  +

H₂

19 40

_{there are several types of reforming reactions}

eg) alkylation to produce “high octane” gasoline

_{all reforming reactions produce} joined

larger molecules

Examples

C₇H₁₆ + C₁₂H₂₆ C H  +

H₂

19 40

1.

2.