What is carbon compound ???

- Compound that contains carbon , C combined with other elements .

Carbon compounds

Organic compounds

Inorganic compounds

-a carbon compound -normally found in found in , produced by, mineral and water or derived from living resources organism -eg. CO32-, HCO3Eg. Protein , carbohydrate , cyanide ,CN- , fat , vitamins ,petroleum, carbide,C4-, natural gas , antibiotic , CO2 , CO natural rubber , plastic , detergent , pesticides

Most organic compounds contain the elements C and H. Hence complete combustion of organic compounds produces CO2 + H2O Organic Compounds
Complete combustion

CO2 +

H2O

ACTIVITY 2.1 LATIHAN 2U

Combustion of organic compounds and their product .

WHY IS CARBON UNIQUE ??

1. 2. 3. Forms four covalent bonds Bonds covalently to: H, O, N, P, S, and all other nonmetals (except noble gases) Carbon atoms join to form: Chains and Rings

CH3CH2CH2CH3 CH3CH2CH2CH3

H2 H2 C C H2C CH2 H2C CH2 H2C CH2 H C CH

2 2

WHY IS CARBON UNIQUE ??

4. Carbon can form multiple bonds to itself, oxygen, and nitrogen. Example:

C-C (single bond)

C=C (double bond) C=C (triple bond)

CLASSIFICATION OF ORGANIC COMPOUNDS Organic compounds

Hydrocarbons

Non-hydrocarbons Carboxylic esters Acids

- An organic compound that contains only Alcohols carbon ,C and hydrogen ,H

Aromatic

Aliphatic

Alkanes

Alkenes

Alkynes

HYDROCARBON
-organic compounds that contain only carbon, C and hydrogen ,H

SATURATED HYDROCARBON
-Hydrocarbons that contain only single covalent bonds between the carbon atoms

UNSATURATED HYDROCARBON
-Hydrocarbons that contain double or triple bonds between the carbon atoms

Eg. alkane

Eg. Alkene, Alkyne

The main source of hydrocarbons is natural gas and petroleum

HOMOLOGOUS SERIES

-is a group of organic compounds in which each member differs from the next one in the series by a fixed unit of structure .
-

CH2 unit

-Eg. Alkane , alkene , alkyne , alcohols , carboxylic acids , esters.

CHARACTERISTIC OF HOMOLOGOUS SERIES

1.Members of the series can be represented by a general formula. 2. Successive members differ from each other by CH2 3. Physical properties change regularly with increasing number of carbon atoms per molecule .

4. Members have similar chemical properties because they have the same functional group. 5. Members can be prepared by similar methods

What is a functional group ??

-An atom or group of atoms that is responsible for the similar chemical properties of a homologous series .

Eg. Double bond (C=C) , triple bond (C=C) hydroxyl (-OH) ,carboxyl (COOH) , ester (COOR)

EXAMPLE OF HOMOLOGOUS SERIES

HOMOLOGOUS SERIES GENERAL FORMULA

FUNCTIONAL GROUP

ALKANES CnH2n+2 ,n =1,2,.. ALKENES ALKYNES

-C=C-C=C-OH

CnH2n , n =2,3,..
CnH2n-2 , n =2,3,..

ALCOHOLS CnH2n+1OH , n=1,2,..

CARBOXYLIC C H n 2n+1COOH ,n=0,1,.. -COOH ACIDS CnH2n+1COOCmH2m+1 , ESTERS -COOR n=0,1,.. , m=1,2,

ALKANES
-General formula :

CnH2n+2 ,n =1,2,..

-saturated hydrocarbon
-Naming use IUPAC nomenclature - the name of a straightchain alkanes consist of two components : root & ending(ane) -root :indicates how many atoms in the longest continuous chain -ending ane : indicates the compound is a member of alkane family

NAME OF ALKANES (C1-C10)

Number of C atoms

1
2

Root name methethprop-

IUPAC name

methane
ethane

3 4
5

propane butane
pentane

butpenthex-

6
7

hexane heptane octane nonane decane

8 9
10

heptoctnondec-

No. of C atoms

Nomenclature / Molecular formula

Structural Formula
H H C H H

1 C

Methane

CH4

2 C

Ethane

C2H6

H H C H

H C H H

3 C

H C H

H C H H

Propane

C3H8

C H

No. of C atoms

Nomenclature / Molecular formula

Structural Formula
H H C H H C H H C H H

4 C

Butane

C4H10

C H

6 C

Hexane

C6H14

ISOMERISM OF ALKANES
Isomerism the phenomenon of organic compounds existing as isomers .

Isomers - compounds with the same molecular formulae but different structural formulae

ISOMERISM

Structural isomerism

Stereoisomerism

chain

positional

enantiomer

geometric

Functional group

Isomer have different physical properties but **similar chemical properties

Sometimes isomer have different chemical properties (different functional group)

STRUCTURAL ISOMERISM IN ALKANES

Please draw as many isomer as you can for :

1. C4H10 2. C5H12
3. C6H14

P/s - Give answer

Steps :

IUPAC NOMENCLATURE

1.Find the longest continuous chain of carbon atoms , and use the name of this chain as the base name of the compound.

2.Identify the substituent group

3.Name and give the location of each substituent group(substituent get the lowest no)

4.When two or more substituents are present ,list them in alphabetical order . Use prefix di-(two), tri-(three), tetra-(four). 5.Number and number ( ,) number and alphabet(-)

Substituent group atom or group of atoms which attached to the longest chain . Eg. : alkyl ( a substituent group that is formed by removing an H atom from an alkane)
alkane structure alkyl structure

methane ethane

CH4 CH3CH3

methyl ethyl

-CH3 -CH2CH3

propane CH3CH2CH3

propyl -CH2CH2CH3

iodo Ethyl CH2CH3

Longest chain

H-C-C-C-C-C-C-C-C-C-H
Br CH3
methyl Bromo

Cl Chloro

Examples of substituent group

Example on naming the alkane HHH H

H-C-C-C-C-H
HH H C H H Step 1 longest continuous chain contains 4 C atoms . - base name : butane H

HHH H

H-C-C-C-C-H
HH H C H H Step 2 identify substituent group -substituent group : methyl H

HHH H

H-C-C-C-C-H
HH H C H H

H
Step 3 number the carbon atom in the longest chain . How??? From left- methyl on the second C atom - From right-methyl on the third C atom Name of the alkane : 2-methylbutane

Let us draw the isomers for C4H10 , C5H12 and C6H14 .

Please name all the isomers according to the IUPAC nomenclature .

Physical Properties

a) Melting and Boiling Point

* Low boiling points and melting points because Van der Waals forces between molecules are weak

b) Physical State at Room Temperature

CH4 - C4H10 : gas C5H12 - C17H38 : liquid C18H38 : solid

c) Solubility
* Soluble in non polar solvents (organic solvents), insoluble in water. Why???

d) Density
* The density of the alkanes increases with increasing number of carbon atoms per molecule , BUT is less than water. Hence, alkanes form the upper layer in an alkane-water mixture.

e) Electrical Conductivity

Do not conduct electricity because : alkanes are covalent compounds, do not have free moving ions but are made up of molecules

a) Melting and Boiling Point

a) Melting and Boiling Point

The boiling point increases between 20 -30 C per -CH2 group.

Boiling points and melting points increase as number of carbon atoms per molecule increases. Then, size of molecules increases (molecular mass increases) Forces between molecules (van der Waals forces) are stronger

More heat energy is needed to overcome the forces

CHEMICAL PROPERTIES OF ALKANES Alkanes - non-polar , saturated hydrocarbons, without any functional group. -these make alkanes nonreactive . -they do not react with acids,alkalis, oxidizing agents or reducing agents -but,under right condition,alkanes may undergo substitution or elimination reactions

REACTION 1 : COMBUSTION OF ALKANES

i) Sufficient or excess O2 (complete combustion) Alkanes + O2 CO2 + H2O + heat ii) Not enough O2 (incomplete combustion) Alkanes + O2 CO + H2O
OR

Alkanes + O2 C + H2O

Number of carbon atoms per molecule increase

Percentage of carbon in alkane increase

More sooty flame

Comparison the sootiness of the flame between pentane and octane

Percentage of = 5(12) carbon in pentane 5(12) +12(1) x 100 (C5H12) = 83.33% Percentage of carbon in octane (C8H18)

= 8(12) x 100 8(12) +18(1) = 84%

Because of % of carbon in octane is higher than in pentane , therefore octane burns with a more sooty flame compared to pentane

REACTION 2 : SUBSTITUTION REACTION

( Halogenation ) In this reaction , each hydrogen atom in the alkane molecule is substituted by a halogen atom .
General equation

RH + X2 RX + HX
X=Cl ,Br

Condition : exposed to ultra violet light or heated to high temperature (200-4000C)

Show the animation

Free-radical substitution reaction

-involves initiation , propagation and termination steps uv i) Initiation step Cl2 2 Cl.

ii) propagation CH4 + Cl. step CH3. + Cl2 iii) termination step Cl. + Cl. CH3. + Cl. CH3. + CH3.

CH3. + HCl

CH3Cl + Cl. Cl2 CH3Cl CH3CH3

Chemical equation

CH4 + Cl2
CH4 + 2 Cl2 CH4 + 3 Cl2

CH3Cl

+ HCl

CH2Cl2 + 2 HCl CHCl3 + 3 HCl

CH4 + 4 Cl2

CCl4

+ 4 HCl

What about bromine ??? Any colour changes ???

-General formula :

CnH2n ,n =2,3,..

-functional group : -C=C-unsaturated hydrocarbon -each member of alkenes contains at least one carbon-carbon double bond(-C=C)

-Naming use IUPAC nomenclature - alkenes are named by substituting the ending ane in the name of the corresponding alkane with ene
-ending ene : indicates the compound is a member of alkenes family

NAME OF STRAIGHT CHAIN ALKENES (C2-C10)

Number of C atoms

Root name ethprop-

IUPAC name

ethene/ethylene propene/propylene but-1-ene

pent-1-ene

3 4
5

butpenthex-

6
7 8

heptoctnondec-

hex-1-ene hept-1-ene oct-1-ene non-1-ene dec-1-ene

9
10

Steps :

IUPAC NOMENCLATURE

1.Find the longest continuous carbon chain containing the double bond (main chain). use the name of this chain as the base name of the compound. 2.Identify the substituent group 3.The location of the double bond is shown by a number. The numbering starts from the end of the main chain that gives a lower number to the C=C. (also state the location of substituent)

4.When two or more substituents are present ,list them in alphabetical order . Use prefix di-(two), tri-(three), tetra-(four). 5.Number and number (,) number and alphabet(-) 6.Alkenes containing two and three double bonds are known as alkadienes and alkatrienes respectively .(replace the ending ne from the name of the corresponding alkanes with diene and triene respectively .

EXAMPLE ON NAMING THE ALKENES

H HCH H H H

H-C-C-C-C=C-C-H
H HH H H H C H

H
Step 1 longest continuous chain contains -C=C- , 7 C atoms . - base name : heptene

H HCH H H

methyl
H

H-C-C-C-C=C-C-H
H HH H H H C H H Step 2 identify substituent group -substituent group : methyl

H HCH H H H

methyl

H-C-C-C-C=C-C-H
H HH H H H C H H Step 3 number the carbon atom in the main chain . How??? From right - double bond on second C , methyl on the fourth C atom .

H HCH H H H

methyl

H-C-C-C-C=C-C-H
H HH H H H C H H From left- double bond on fifth C , methyl on the fourth C atom . Which one is the correct way ?? .

Name of the alkene : 4-methylhept-2-ene

Did alkenes shows isomerism ???

Let us draw the isomers for C4H8 and C5H10.

Please name all the isomers according to the IUPAC nomenclature .

PHYSICAL PROPERTIES

What do you think of the physical properties of alkenes?? Are they similar to alkanes??
Discuss in your groups and comes out with conclusion on : i) Physical state at room temperature ii)Melting and boiling point iii)Density iv)Solubility in water and organic solvent v)Electrical conductivity

CHEMICAL PROPERTIES OF ALKENES

Alkenes
-unsaturated hydrocarbons with -C=C- as functional group. -these make alkenes more reactive than alkanes. -Reactions of alkenes are mainly addition reactions to the double bond

REACTION 1 : COMBUSTION OF ALKENES

i) Sufficient or excess O2 (complete combustion) Alkenes + O2 CO2 + H2O + heat ii) Not enough O2 (incomplete combustion) Alkenes + O2 CO + H2O
OR

Alkenes + O2 C + H2O

Comparison the sootiness of the flame between alkenes and alkanes with the same number of carbon atoms

Percentage of = 5(12) x 100 carbon in pentane 5(12) +12(1) (C5H12) = 83.33%

= 5(12) Percentage of x 100 carbon in pentene 5(12) +10(1) (C5H10) = 85.71%

Because of % of carbon in pentene is higher than in pentane , therefore pentene burns with a more sooty flame compared to pentane

REACTION 2 : ADDITION REACTIONS

-functional group : -C=C-these make alkenes more reactive than alkanes. -Addition reaction is a reaction in which a molecule adds to the two carbon,C atoms of a double bond .

Addition reaction in general :

Chemical unsaturated compounds

-C=C- + X-Y

-C-Csaturated

X Y

i) Addition of hydrogen gas , H2(hydrogenation)

-C=C- + H-H

-C-CHH

Condition: -Alkene vapour and hydrogen gas -passed over a catalyst (Pt/Ni)
-heated to 1800C Eg: C2H4 + H2 C3H6 + H2 Alkenes

C2H6
C3H8 alkanes

ii) Addition of halogen , X2(halogenation)

-C=C- + X-X -C-CX X

X= Cl , Br Condition: -alkene reacts with Cl2/CCl4 and Br2/CCl4 -room temperature

-the product is haloalkane Eg: C2H4 + Cl2 C3H6 + Br2 Alkenes C2H4Cl2 C3H6Br2 haloalkanes

When X2 = Br2

-Useful as a test for unsaturation (the presence of double or triple bonds)

-useful to distinguish alkenes and alkanes CH3CH=CH2 + Br2 CH3CHBrCH2Br

Observation : The colour changes from reddish-brown to colourless CH3CH2CH3 + Br2

dark

no reaction

Observation : reddish-brown colour of bromine remains unchanged

iii) Addition of hydrogen halide , HX

-C=C- + H-X -C-CHX

X= Cl , Br Condition: -alkene reacts with HCl and HBr -room temperature

-the product is haloalkane Eg: C2H4 + HCl C3H6 + HBr Alkenes C2H5Cl C3H7Br haloalkanes

iv) Addition of water, H-OH / hydration

-C=C- + H-OH -C-CH OH

Condition: -mixture of alkene with steam -passed over a catalyst (H3PO4)

-T = 3000C , P = 60 atm The product is alcohol Eg: C3H6 + HOH C3H7OH

C4H8 + HOH

C4H9OH

v) Addition of acidified KMnO4 solution

-C=C- + [O] + H2O -C COH OH

Condition: -alkene reacts with KMnO4 solution acidified with sulphuric acid -room temperature
The product is alcohol (alkanediol) Eg: C3H6 + [O] + H2O C2H4 + [O] + H2O C3H6(OH)2 C2H4(OH)2

-Useful as a test for unsaturation (Baeyer test) the presence of double or triple bonds) -useful to distinguish alkenes and alkanes
CH3CH=CH2+ [O] + H2 CH3CH(OH)CH2OH

Observation : The colour changes from purple to colourless CH3CH2CH3 + KMnO4 Observation : no reaction

purple colour of KMnO4 remains unchanged

REACTION 3 : POLYMERIZATION Polymerization

-the process of chemically joining small molecules (monomer) to form a polymer

Addition Polymerization
-involves combining monomers that have multiple bonds

Condensation Polymerization
-involves combining monomers that have at least two functional groups

Polymer is a long chain molecule made up of smaller molecules called monomers that are join end to end
Alkenes forms polymers by undergoes addition polymerization

H H T = 3000C n H-C=C-H P = 100atm

H H

C C
H H n

Comparison Between Alkanes And Alkenes SIMILARITIES -physical properties ALKANES

DIFFERENCES Functional group Type of reaction General formula Reaction with Br2/CCl4 Reaction with KMnO4/H+
Combustion(no. of C is the same)

ALKENES

Type of compound

-General formula :

CnH2n+1OH ,n =1,2,3,..

-functional group : -OH , hydroxyl -each member of alcohols contains at least one OH group . -Naming use IUPAC nomenclature - alcohols are named by substituting the ending e in the name of the corresponding alkane with ol -ending ol : indicates the compound is a member of alcohols family

NAME OF STRAIGHT CHAIN ALCOHOLS

Number of C atoms
1 alkanes methane ethane propane butane

IUPAC name
methanol ethanol propanol butanol

2
3 4

5
6

pentane hexane heptane

octane nonane

pentanol
hexanol heptanol octanol nonanol decanol

7
8 9

10

decane

Steps :

IUPAC NOMENCLATURE

1.Find the longest continuous carbon chain containing the hydroxyl group (main chain). use the name of this chain as the base name of the compound. 2.Identify the substituent group 3.The location of the hydroxyl group is shown by a number. The numbering starts from the end of the main chain that gives a lower number to the C-OH. (also state the location of substituent and -OH group)

4.When two or more substituents are present ,list them in alphabetical order . Use prefix di-(two), tri-(three), tetra-(four).
5.Number and number (,) number and alphabet(-) 6.Alcohols containing two and three hyrroxyl group are known as alkanediol and alkanetriol respectively .(add diol and triol)

EXAMPLE ON NAMING THE ALCOHOLS

H HCH H H H H OH

H-C-C-C-C- C-C-H
H HH H H H C H

H
Step 1 longest continuous chain contains -OH , 7 C atoms . - base name : heptanol

HCH H H H H OH H HH H H H C H H

methyl

H-C-C-C-C- C-C-H

Step 2 identify substituent group -substituent group : methyl

HCH H H H H OH H HH H H H C H H

methyl

H-C-C-C-C- C-C-H

Step 3 number the carbon atom in the main chain . How??? From right C-OH on C 1, methyl on the C 4 .

HCH H H H H OH H HH H H H C H H

methyl

H-C-C-C-C- C-C-H

From left- C-OH on C 7 , methyl on the C 4 Which one is the correct way ?? .

Name of the alcohol : 4-methylheptan-1-ol

Did alcohols shows isomerism ???

Let us draw the isomers for C3H7OH , C4H9OH and C5H11OH

Please name all the isomers according to the IUPAC nomenclature .

Physical Properties

a) Melting and Boiling Point

* Low boiling points and melting points because Van der Waals forces between molecules are weak

Boiling points and melting points increase as number of carbon atoms per molecule increases. Then, size of molecules increases (molecular mass increases)
Forces between molecules (van der Waals forces) are stronger More heat energy is needed to overcome the forces

b) Physical State at Room Temperature

C1 C12 >C13 : liquid : solid

c) Solubility
* Simple alcohols (first 3 members) soluble in water. Why??? Alcohols molecules form hydrogen bond with water molecules (because it has hydroxyl group) .

d) Density
* The density of the alcohols increases with increasing number of carbon atoms per molecule , BUT is less than water.

e) Electrical Conductivity

Do not conduct electricity because : alcohols are covalent compounds, do not have free moving ions but are made up of molecules

PHYSICAL PROPERTIES OF ETHANOL

Colourless liquid at room temperature

Completely miscible with water Has low boiling point (780C)

Highly volatile Density < H2O (0.79 gml-1)

MAKING ALCOHOLS (especially Ethanol)

Industry

laboratory

Fermentation Hydration of reaction of ethene glucose How??? How??? -ethene vapour mix -fermenting starchy together with steam . or sugary substances -T=3000C -catalyst : zymase -P = 60 atm -catalyst : phosphoric acid enzyme(in yeast) C6H12O6 2 C2H5OH C2H4 + HOH C2H5OH + 2 CO2

CHEMICAL PROPERTIES OF ALCOHOLS --OH (hydroxyl) as a functional group. REACTION 1 : COMBUSTION OF ALKENES

i) Sufficient or excess O2 (complete combustion)

Alcohol + O2 CO2 + H2O + heat ii) Not enough O2 (incomplete combustion) Alcohol + O2 CO + H2O
OR

Alcohol + O2 C + H2O

ii) Oxidation of alcohols

**apparatus

General reaction : RCH2OH

Alcohol

RCOOH
Carboxylic acid

Condition: -add acidified potassium dichromate(VI) solution into alcohols and heat the mixture
Oxidising agent Observation K2Cr2O7/H+ Orange solution turns to green solution KMnO4/H+ Purple colour of the solution is decolourised

Eg: CH3CH2OH + 2[O]

CH3CH2CH2OH + 2[O]

CH3COOH + H2O
CH3CH2COOH + H2O

Alcohols

carboxylic acid

iii) Dehydration of alcohols

**apparatus
-C=C- + H2O
alkene
Chemical test to identify this product??

-C-C-

Dehydrating agents

Alcohol

H OH

Condition:

1. Concentrated sulphuric acid ,H2SO4 at 1800C @

2. alumina/porcelain chips at 3500C (heated catalyst) @

3. Concentrated phosphoric acid ,H3PO4 at 3500C

CH3CH2OH CH3CH2CH2OH

CH2=CH2 + H2O CH3CH=CH2 + H2O

Alcohols

alkenes

iv) Esterification reaction

**apparatus

Concentrated O O sulphuric acid R-C-OH + ROH R-C-OR + H2O Ester Carboxylic Alcohol acid How can we identify

Condition:

this product??

Catalyst : concentrated sulphuric acid

Write down the chemical equation for reaction :

1. Ethanoic acid and ethanol 2. propanoic acid and ethanol 3. Ethanoic acid and propanol

-General formula :

CnH2n+1COOH ,n =0 1,2,3,..

-functional group : -COOH , carboxyl -each member of carboxylic acids contains at least one COOH group . -Naming use IUPAC nomenclature - carboxylic acids are named by substituting the ending e in the name of the corresponding alkane with oic , continue with acid -ending oic acid : indicates the compound is a member of carboxylic acid family

NAME OF STRAIGHT CHAIN CARBOXYLIC ACIDS

Number of C atoms 1 2 3 4 5 6 7 alkanes methane ethane propane butane pentane hexane heptane IUPAC name methanoic acid ethanoic acid propanoic acid butanoic acid

pentanoic acid
hexanoic acid heptanoic acid

8
9 10

octane
nonane decane

octanoic acid
nonanoic acid decanoic acid

Steps :

IUPAC NOMENCLATURE

1.Find the longest continuous carbon chain containing the carboxyl group (main chain). use the name of this chain as the base name of the compound. 2.Identify the substituent group 3.The location of the carboxyl group is always number 1. The numbering starts from carboxyl group . (also state the location of substituent group)

4.When two or more substituents are present ,list them in alphabetical order . If theyre same -use prefix di-(two), tri(three), tetra-(four).
5.Number and number (,) number and alphabet(-) 6.Carboxylic acid containing two and three carboxyl group are known as dicarboxylic acid and tricarboxylic acid respectively

EXAMPLE ON NAMING THE CARBOXYLIC ACIDS

H
HCH H H H H O

H-C-C-C-C- C-C-OH
H HH H H C H
H

Step 1 longest continuous chain contains -COOH , 7 C atoms . - base name : heptanoic acid

H
HCH H H H H O

methyl

H-C-C-C-C- C-C-OH
H HH H H C H
H Step 2 identify substituent group -substituent group : methyl

H
HCH H H H H O H HH H H C H H

methyl

H-C-C-C-C- C-C-OH

Step 3 number the carbon atom in the main chain . How??? From right COOH start no. 1, methyl on the C 4 .

H
HCH H H H H O H HH H H C H H

methyl

H-C-C-C-C- C-C-OH

carboxyl

Name of the alcohol : 4-methylheptanoic acid

Did carboxylic acids show isomerism ??? Concept : functional group isomerism ???

Let us draw the isomers for C4H8O2 , C5H10O2 Please name all the isomers according to the IUPAC nomenclature .

Physical Properties

a) Melting and Boiling Point

* Boiling points and melting points are higher than that of alkanes with the same number of carbon atoms.(-COOH)

Boiling points and melting points increase as number of carbon atoms per molecule increases. Then, size of molecules increases (molecular mass increases)
Forces between molecules (van der Waals forces) are stronger More heat energy is needed to overcome the forces

b) Physical State at Room Temperature

C1 C9 >C10 : liquid : solid

c) Solubility
* Simple carboxylic acids (C1-C4) soluble in water. Why??? carboxylic acids molecules form hydrogen bond with water molecules (because it has carboxyl group) . * As number of C atom permolecule increases , solubility decreases . Why ???

PHYSICAL PROPERTIES OF ETHANOIC ACID

Clear and colourless liquid at room temperature Very soluble in water Boiling point (1180C)

It has a characteristic smell

It tastes sour

Pure ethanoic acid does not contain water , called glacial ethanoic acid

MAKING CARBOXYLIC ACIDS (especially Ethanoic acid / acetic acid)

Oxidation of alcohols

General reaction : RCH2OH

Alcohol

**apparatus RCOOH
Carboxylic acid

Condition: -add acidified potassium dichromate(VI) solution into alcohols and heat the mixture
Oxidising agent Observation

K2Cr2O7/H+ KMnO4/H+

Orange solution turns to green solution Purple colour of the solution is decolourised

CH3CH2OH + 2[O]
CH3CH2CH2OH + 2[O]

CH3COOH + H2O
CH3CH2COOH + H2O

CHEMICAL PROPERTIES OF CARBOXYLIC ACIDS

--COOH (carboxyl) as a functional group. REACTION 1 : REACTIONS WITH BASES (Neutralization reaction) Dissociation of carboxylic acid :

RCOOH

RCOO- + H+

Carboxylic acid + BASE Salt + H2O

Eg. CH3COOH + NaOH CH3COONa + H2O

Sodium ethanoate

CH3COOH + NH3 CH3COONH4

ammonium ethanoate

REACTION 2: REACTIONS WITH METALS

Carboxylic acid + METAL Salt + H2 Eg. 2CH3COOH + Mg (CH3COO)2Mg + H2
magnesium ethanoate

2CH3CH2COOH + Zn (CH3CH2COO)2Zn + H2
zinc propanoate

REACTION 3: REACTIONS WITH METAL CARBONATE

Carboxylic acid + METAL CARBONATE Salt + H2O + CO2 Eg. 2CH3COOH + CaCO3 (CH3COO)2Ca + H2O + CO2
Calcium ethanoate

2CH3CH2COOH + Zn (CH3CH2COO)2Zn + H2O + CO2

zinc propanoate

4) Esterification reaction

**apparatus

Concentrated O O sulphuric acid R-C-OH + ROH R-C-OR + H2O Ester Carboxylic Alcohol acid How can we identify

Condition:

this product??

Catalyst : concentrated sulphuric acid

Write down the chemical equation for reaction :

1. Ethanoic acid and ethanol 2. propanoic acid and ethanol 3. Ethanoic acid and propanol

-General formula :

CnH2n+1COOCmH2m+1 , n =0 1,2,3,.. ,m=1,2,3,..

-functional group : -COOR , carboxylate

-each member of esters contains at COOR group.

-Naming use IUPAC nomenclature - the name of esters is derived from the name of alcohol and carboxylic acid that reacted together to produce it.

1.Alkyl from alcohol continue with carboxylic acid . 2.Replace oic with oate

ESTERS SIMPLE ESTERS - found in fruits and flowers - Responsible for the fruity smells and pleasant fragrances - More volatile compare to complex esters COMPLEX ESTERS

- found in animal fats and vegetable oil

- Do not produce the familiar pleasant smells of the simple esters - less volatile compare to simple esters

Esterification reaction
Concentrated O O sulphuric acid R-C-OH + ROH R-C-OR + H2O Ester Carboxylic Alcohol acid How can we identify

Condition:
CH3COOH + CH3CH2OH Ethanoic acid Ethanol

this product??

Catalyst : concentrated sulphuric acid

CH3COOCH2CH3 + H2O Ethyl ethanoate

***Gives examples

HYDROLYSIS OF ESTERS(need to reflux) Esters can be hydrolysed to carboxylic acid with the use of acid or base as catalyst Alkaline hydrolysis also known as saponification

Write down the chemical equation for reaction :

O R-C-OR + H-OH H+ O R-C-OH + ROH

O O OHR-C-OR + H-OH R-C-O+ ROH Also known as saponification reaction

Oils and fats are esters . What the differences between oils and fats ??? Property Source
Physical state at Room temperature

Oils

Fats

Found in plants Found in animals Liquid

Solid or semi-solid
More than 200C

Melting point

Less than 200C

1. Oils and fats are esters formed from carboxylic acids called fatty acids and alcohol called 1,2,3-propanetriol/ propane-1,2,3-triol
2. A fatty acid is a carboxylic acid that has a long chain of about 10 to 20 carbon atoms with one carboxyl group . 3. Eg of fatty acids: palmitic acid(C15H31COOH), stearic acid(C17H35COOH), linoleic acid(C17H31COOH), oleic acid(C17H33COOH) 3. 1,2,3-propanetriol or glycerol is an alcohol that has three hydroxyl groups .

The esterification reaction between fatty acids and glycerols produces oils and fats . Fatty acid + glycerol
Oleic acid + glycerol

Oil or fat
Triolein/ glyceryl trioleate Trilinolein/ glyceryl trilinoleate

+ H2O
+ H2O

linoleic acid

+ glycerol

+ H2O

Show the reaction !!!!!

Fats
Saturated fats
- fat that has more saturated fat molecules compared to unsaturated fat molecules - A molecules of fat is saturated if its fatty acid chains do not have any double bonds between carbon atoms .

Unsaturated fats
- fat that has more unsaturated fat molecules compared to saturated fat molecules - A molecules of fat is unsaturated if its fatty acid chains have double bonds between carbon atoms . (monounsaturated and polyunsaturated)

What the differences between saturated and unsaturated fats ??? Property
Proportion of molecules
Physical state at Room temperature Unsaturated fats Saturated Fats Higher proportion Higher proportion of unsaturated fat of saturated fat molecules molecules

Liquid Less than 200C

Solid or semi-solid More than 200C

Melting point

Source

Found in plants Found in animals

Converting unsaturated fats to saturated fats -by using hydrogenation reaction -carried out by passing hydrogen gas, through the unsaturated fat at 1500C to 2000C . A catalyst such as nickel is required. Concept :

-C=C- + H2 -C-C-

Check (revision book )- process to convert an oil to a fat ( such as margarine )

Please do some studies on the effects of fats on health ,industrial production of palm oil , palm oil in food production , research on oil palm in Malaysia and the palm oil industry in Malaysia

POLYMERS Large molecules formed from smaller molecules called monomers

Natural polymers

Synthetic polymers

Starch

protein

How can we convert to glucose ??

Natural rubber

nylon

PVC

Polyethene
perspex

- Natural rubber contains polyisoprene molecules

- Monomer is isoprene (2-methylbut-1,3-diene) -Isoprene undergoes addition polymerisation to form polyisoprene molecules

Please write chemical equation shows the formation of polyisoprene from isoprene

Properties of natural rubber Property Elasticity Resistance to oxidation Description

Natural rubber is elastic.It will return to its original after you stretch it Natural rubber is easily oxidised by oxygen. O2 adds to the -C=CNatural rubber cannot withstand heat. High T - soft and sticky , Low T-becomes hard and brittle

Effect of heat
Effect of solvent

Acidic and alkaline solvents can attack and destroy natural rubber.

COAGULATION OF LATEX
made up of a protein membrane that surrounds many rubber molecules Negative charges are found on the surface of the membrane Negatively-charge rubber particles repel each other, preventing themselves from combining and coagulating

LATEX -is a

colloid (mixture of rubber particles and water)

The effect of adding acid into the latex LATEX

Adding acid
H+ ions from an acid neutralise the negative charges found on the surface of the membrane These neutral rubber particles collide with each other Outer membrane of the rubber particles break up

Rubber molecules clump together .the latex has coagulated

Rubber molecules are set free

The effect of adding alkali (NH3 solution) into the latex LATEX
Adding NH3 solution
OH- ions from an alkali neutralise the H+ ions produced by lactic acid as a result of bacterial attack on protein

The rubber particles repel each other, preventing themselves from combining and coagulating

The rubber particles remain negatively charged

The effect of exposing the latex to the surrounding air LATEX

Left overnight
H+ ions produced by lactic acid as a result of bacterial attack on protein neutralise the negative charge of the membrane of the rubber particles

Rubber molecules clump together .the latex has coagulated Rubber molecules are set free

These neutral rubber particles collide with each other

Outer membrane of the rubber particles break up

Vulcanisation of rubber

Definition : the process of chemically treating natural rubber with sulphur,S

-This process convert raw rubber into a tough useful product (vulcanised rubber-rubber with sulphur cross-links between rubber molecules ). -in industry heating the mixture of natural rubber and sulphur , ZnO as catalyst. -in lab dipped the natural rubber in the solution of disulphur dichloride (S2Cl2) in methylbenzene

Vulcanisation of rubber
During the vulcanisation process
Adding S to the rubber molecules S react with C=C in rubber molecules S atoms form crosslinks between adjacent chains of rubber polymer at the C=C These crosslinks prevent rubber molecules from sliding too much when stretched.

Mr rubber
Melting point
More tougher and can withstand heat

Vulcanised rubber cannot easily oxidised by O2

The formation of cross-links decreases the C=C in the rubber molecules