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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
CH3CH2CH2CH3 CH3CH2CH2CH3
4. Carbon can form multiple bonds to itself, oxygen, and nitrogen. Example:
Hydrocarbons
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
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
4. Members have similar chemical properties because they have the same functional group. 5. Members can be prepared by similar methods
Eg. Double bond (C=C) , triple bond (C=C) hydroxyl (-OH) ,carboxyl (COOH) , ester (COOR)
FUNCTIONAL GROUP
-C=C-C=C-OH
CnH2n , n =2,3,..
CnH2n-2 , n =2,3,..
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
1
2
IUPAC name
methane
ethane
3 4
5
propane butane
pentane
butpenthex-
6
7
8 9
10
heptoctnondec-
No. of C atoms
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
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
1. C4H10 2. C5H12
3. C6H14
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.
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
Longest chain
H-C-C-C-C-C-C-C-C-C-H
Br CH3
methyl Bromo
Cl Chloro
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
Physical Properties
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
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
Alkanes + O2 C + H2O
Percentage of = 5(12) carbon in pentane 5(12) +12(1) x 100 (C5H12) = 83.33% Percentage of carbon in octane (C8H18)
Because of % of carbon in octane is higher than in pentane , therefore octane burns with a more sooty flame compared to pentane
RH + X2 RX + HX
X=Cl ,Br
ii) propagation CH4 + Cl. step CH3. + Cl2 iii) termination step Cl. + Cl. CH3. + Cl. CH3. + CH3.
CH3. + HCl
Chemical equation
CH4 + Cl2
CH4 + 2 Cl2 CH4 + 3 Cl2
CH3Cl
+ HCl
CH4 + 4 Cl2
CCl4
+ 4 HCl
-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
IUPAC name
3 4
5
butpenthex-
6
7 8
heptoctnondec-
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 .
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 ?? .
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
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
Alkenes + O2 C + H2O
Comparison the sootiness of the flame between alkenes and alkanes with the same number of carbon atoms
-C=C- + X-Y
-C-Csaturated
X Y
-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
When X2 = Br2
no reaction
C4H8 + HOH
C4H9OH
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
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
C C
H H n
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
IUPAC name
methanol ethanol propanol butanol
2
3 4
5
6
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)
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
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 ?? .
Physical Properties
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
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
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
Alcohol + O2 C + H2O
**apparatus
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
CH3COOH + H2O
CH3CH2COOH + H2O
Alcohols
carboxylic acid
**apparatus
-C=C- + H2O
alkene
Chemical test to identify this product??
-C-C-
Dehydrating agents
Alcohol
H OH
Condition:
CH3CH2OH CH3CH2CH2OH
Alcohols
alkenes
**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??
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
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
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
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
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
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 ???
Pure ethanoic acid does not contain water , called glacial ethanoic acid
Oxidation of alcohols
**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
--COOH (carboxyl) as a functional group. REACTION 1 : REACTIONS WITH BASES (Neutralization reaction) Dissociation of carboxylic acid :
RCOOH
RCOO- + H+
ammonium ethanoate
2CH3CH2COOH + Zn (CH3CH2COO)2Zn + H2
zinc propanoate
Carboxylic acid + METAL CARBONATE Salt + H2O + CO2 Eg. 2CH3COOH + CaCO3 (CH3COO)2Ca + H2O + CO2
Calcium ethanoate
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??
1. Ethanoic acid and ethanol 2. propanoic acid and ethanol 3. Ethanoic acid and propanol
-General formula :
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
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??
***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
Oils and fats are esters . What the differences between oils and fats ??? Property Source
Physical state at Room temperature
Oils
Fats
Melting point
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
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
Melting point
Source
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-
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
Natural polymers
Synthetic polymers
Starch
protein
Natural rubber
nylon
PVC
Polyethene
perspex
Please write chemical equation shows the formation of polyisoprene from isoprene
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
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
Rubber molecules clump together .the latex has coagulated Rubber molecules are set free
Vulcanisation of rubber
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