Organic Chemistry

Organic Chemistry

Carbon is a tramp - video

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

Practice question

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 –

Practice Question

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

H

CH3

C

H

H

C C C C

H H

H

H H

H

H

H

Step #1 – find the longest parent chain

Step #2 – draw a square around the branches

Step #3 – give numbers to the chain: make sure the branches get the smallest number possible

1 2 3 4 5

3 – methyl pentane

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

Practice Questions

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)

Show video

***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

Video

Practice Question

Practice Question

H. Aromatics hydrocarbons containing one or more

all bonds are the

benzene rings C6H6

OR

same length and strength we draw benzene like this:

Video

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!!!http://www.bing.com/videos/search?q=benzene&mid=013F6F84DA6614E381A6013F6F84DA6614E381A6&FORM=LKVR4#

Practice Question

I. Alcohols

organic compounds with one or more

** OH, its an Alcohol!!!

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)

** o – oh, its an acid!!! – mnemonic device1. 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

Read pg 438 - 441

Read pg 438 – 441 on esters

L. Esters

where can be a carbon chain or hydrogen and can be a carbon chain

combination of a and an** Ester is a cow that likes to eat OATES1. 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

Video

Practice Question

Practice Questions

Practice Questions

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

Practice Question

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 +

Practice Question

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

Catalyst video

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

… …

Practice Question

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

Organic Chemistry

Song

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

Video

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

Fractional Distillation

1. http://www.learnalberta.ca/content/t4tes/courses/senior/chemistry_30/mm/m5/Fractional/main.html

http://resources.schoolscience.co.uk/spe/knowl/4/flash/cracking.htm (animation of fractioning tower and cracking)

2. Animated tour - http://sciencenetlinks.com/interactives/energy/interactive/api_treat_012810.swf

3. Animated tour - http://irvingoil.com/resource/flash/RefineryTour.swf

Fractioning Tower

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

Extraction of Bitumen in Oil sands lab http://

www.learnalberta.ca/content/t4tes/courses/senior/chemistry_30/mm/m5/c30_m5_l05_mm006/c30_m5_l05_mm006.html

Best song in the world

Family song