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Friends Boys School

Unit 10
Organic Chemistry SL / 12 IB

Organic chemistry is the chemistry of carbon containing compounds.

• Carbon is in group IV of the Periodic Table. It has 4 electrons in the outer shell. Carbon atoms can combine
with each other and with other atoms of non metals (H, O, N, X = F, Cl, Br, I) to form millions of compounds.
These compounds are the basis of all kinds of life, hence the term is called organic.
• In these compounds, C atoms link with each other by covalent bonds to form long chains. The C atoms may
link with each other by single bonds or double bonds.
• In these compounds the octet of each C atom is 4 bonds, H one bond, O two bonds, N three bonds and X one
bond.
• The number of C atoms in the compound varies from one compound to another, starting from 1 to infinity. Also
rings of carbon atoms can be formed. Also the chains could be branched by smaller chains of C atoms.

• The molecular formula of an organic compound shows the number of every type of atom in a molecule.
• The structural formula shows the bonding between atoms in the molecule (shows unambiguously how the
atoms are arranged together.
1) A full structural formula (sometimes called a graphic formula or displayed formula) shows every atom
and bond, for example: hexane:

2) A condensed structural formula can omit bonds between atoms and can show identical groups bracketed
together, for example, for hexane:

CH3CH2CH2CH2CH2CH3 or CH3(CH2)4CH3

If one of the hydrogen atoms is removed what is left is known as an alkyl radical or an alkyl group (R•) (e.g
methyl CH3•; ethyl C2H5•).

The structural types of organic chemistry are divided into families of compounds characterized by the presence
of particular functional groups. Each family of compounds is called a homologous series.

◙ A functional group is defined as an atom or a group of atoms responsible for the characteristic reactions of
the molecule or the homologous series.

Families of organic compounds:


1- Hydrocarbons are defined as compounds containing carbon and hydrogen only.
a- Alkanes: CnH2n+2
b- Alkenes: CnH2n
c- Alkynes: CnH2n-2
2- Alcohols (Alkanoles): R-OH or (CnH2n+1OH)
3- Halogenoalkanes: R-X
4- Carboxylic acids (Alkanoic Acids): CnH2n+1COOH or (R-COOH)
5- Esters: R1COOR2
6- Aldehydes (Alkanals): RCHO
7- Ketones (Alkanones): R1COR2

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8- Amines: RNH2
9- Amides: RCONH2
10- Ethers (Alkoxy alkane): R1OR2
11- Nitriles: (RCN)
11- Aromatic compounds
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◙ A homologous series is defined as a group of organic compounds or as a series of organic chemicals with
same general formula where neighboring members differ by CH2.

The characteristics or the features of a homologous series:


1- The homologous series have the same general formula (CnH2n+2 in alkanes, CnH2n in alkenes, CnH2n+1OH in
alcohols).
2- The formulas of neighboring members differ by CH 2.
3- The individual members of a homologous series have similar chemical properties because the have the same
functional group.
4- The individual members of a homologous series show a gradual change in physical properties.
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Naming of organic compounds:

IUPAC system: International Union of Pure and Applied Chemistry

Hydrocarbons: A hydrocarbon is defined as a compound containing carbon and hydrogen only.

a- Alkanes: Alkanes are hydrocarbons in which all the bonds are single bonds.

General chemical formula: CnH2n+2


Naming:

1- The first part of the name refers to the number of carbon atoms in the LONGEST continuous carbon chain.
The following prefixes are used:

# of carbon atoms Prefix


1 meth
2- The second part of the 2 eth name specifies the homologous series
of the compound. In case of 3 prop alkanes add the suffix - ane.
4 but
Methane: CH4 5 pent
6 hex
Ethane: C2H6 CH3CH3 7 hept OR H3CCH3
8 oct
Propane: C3H8 9 non (CH3CH2CH3)
10 dec
Butane: C4H10 (CH3CH2CH2CH3 OR
CH3(CH2)2CH3)

Pentane: C5H12 (CH3CH2CH2CH2CH3 OR CH3(CH2)3CH3)

Hexane: C6H14 (CH3CH2CH2CH2CH2CH3 OR CH3(CH2)4CH3)

3- If the chain is branched then the name of the main chain is proceeded by the name of the branch and the
location of the branch in the chain. We start numbering from the end closer to the branch in case of
alkanes.

◙ Alkyl Groups (Alkyl Radicals) :CnH2n+1


To name a branch, add – yl to the name of the number of carbon atoms in the branch. If the branch is made
up of 1 C atom then its name is methyl. If the branch is made up of 2 C atoms then its name is ethyl.

Methyl: CH3•

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Ethyl: CH3CH2• OR C2H5•
Propyl: CH3CH2CH2• Or C3H7•
Butyl: CH3CH2CH2CH2• Or C4H9•

Example: 2 – methylpentane CH3CH(CH3)CH2CH2CH3

4- If more than one branch is present, then the name and the location of each branch must be specified. They
are listed in alphabetical order.

3-ethyl-2, 2, 4-trimethylheptane

CH3C(CH3)2CH(C2H5)CH(CH3)CH2CH2CH3

5- If more than one identical branch are present, the prefixes di, tri, and tetra are used before the name of the
branch. The location of each one must be specified.

2, 2, 3– trimethylhexane CH3C(CH3)2CH(CH3)CH2CH2CH3

Name these compounds using IUPAC system:

1- (CH3)3CH 2- (CH 3)4C

b- Alkenes:
Alkenes are hydrocarbons characterized by the presence of at least one carbon – carbon double bond.
Functional group: C = C

General chemical formula: CnH2n

Naming – 1st Method:

1- In case of alkenes add the suffix – ene to the name of the number of carbon atoms inside the chain.

2- If the location of the double bond is 1, then you could drop the location.

ethene CH2=CH2 OR H2C=CH2 OR CH2CH2


3- In alkenes, the location of the double bond in the chain must be specified. We start numbering from
the end closer to the functional group which is the double bond in case of alkenes. We write the location
before the name of the chain.

2-butene CH3CH=CHCH3 OR CH3CHCHCH3

Naming – 2nd Method:

1- Place the location of the double bond between the suffix – ene and the name of the number of carbon atoms
inside the chain.

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prop-1-ene (propene) CH2=CHCH3 OR CH2CHCH3

pent-2-ene CH3CH=CHCH2CH3 OR CH3CHCHCH2CH3

◙ Name the following compound using IUPAC system:

(CH3)2CCH(CH2)2CH3

c- Alkynes:
Alkynes are hydrocarbons characterized by the presence of at least one carbon to carbon triple bond.
Functional group: C ≡ C

General chemical formula: CnH2n-2

Naming – 1st Method:

1- In case of alkynes add the suffix – yne to the name of the number of carbon atoms inside the chain.

2- If the location of the triple bond is 1, then you could drop the location.

ethyne CH≡CH OR HC≡CH OR CHCH


3- In alkynes, the location of the triple bond in the chain must be specified. We start numbering from the
end closer to the functional group which is the triple bond in case of alkynes. We write the location
before the name of the chain.

2-butyne CH3C≡CCH3 OR CH3CCCH3

Naming – 2nd Method:

1- Place the location of the triple bond between the suffix – yne and the name of the number of carbon atoms
inside the chain.

prop-1-yne (propyne) CH≡CCH 3 OR CHCCH3

pent-2-yne CH3C≡CCH2CH3 OR CH3CCCH2CH3

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Alcohols (Alkanols)
R - OH

Functional group: – OH (hydroxyl group)

General chemical formula: CnH2n+1OH

Naming – 1st Method:


1- The compound is named as an alkane. Replace the -e with -ol.
2- The location of the -OH group is identified by a number. We start numbering from the end closer to the
functional group (-OH group)
2–pentanol

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CH3CH(OH)CH2CH2CH3

3- If the location of the -OH is 1, then you could drop the location.

1–ethanol (ethanol)

CH3CH2OH OR (C2H5OH)

4- In the presence of a branch we start numbering from the end closer to the functional group (-OH
group)

2–methyl–1–propanol (2–methylpropanol)

CH3CH(CH3)CH2OH

5- If two -OH groups are present, then the location of each one is identified and the prefix di is used
before the -ol.
1,3-pentandiol

CH2(OH)CH2CH(OH)CH2CH3

2nd Method:
1- The compound is named as an alkane. Drop the e.
2- Write the location of the -OH group after the parent name. Then add -ol.

propan–2-ol

CH3CH(OH)CH3

3- In the presence of a branch we start numbering from the end closer to the functional group (-OH group)

2–methylpropan–1-ol
CH3CH(CH3)CH2OH

4- If two -OH groups are present, then the prefix di is used before the -ol. In this case the –e at the end of the
name of the alkane is not dropped.

ethane-1,2-diol propane–1,3–diol propane–1,2,3–triol

CH2(OH)CH2(OH) CH2(OH)CH2CH2(OH) CH 2(OH)CH(OH)CH2(OH)

Name this compound: C(CH3)3OH

There are three types of alcohols:

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1- Primary alcohols: R-CH2-OH: the alcohol in which the carbon atom that is directly bonded to the functional
group OH is surrounded by one alkyl group and two H atoms.

Example: Ethanol

2- Secondary alcohols: R2-CH-OH: the alcohol in which the carbon atom that is directly bonded to the
functional group OH is surrounded by two alkyl groups and one H atom.

Example: propan-2-ol

3- Tertiary alcohols: R3-C-OH: The C atom that is directly bonded to the functional group OH is surrounded by
three alkyl groups and no H atoms.

Example: 2- methylpropan-2-ol

Question: Write the primary, secondary and tertiary alcohol for the formula C 4H9OH. Name each one

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Halogenoalkanes (Alkyl Halides)
R–X

Functional group: -X (F, Cl, Br, I)

Naming:

1- Name the compound as an alkane.


2- The halogen is a branch. Its name comes before the name of the parent compound. The halogen is named
as fluoro, chloro, bromo or iodo.

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3- The location of the halogen atom must be identified. We start numbering from the end closer to the
functional group (-X atom).
2–chlorobutane

CH3CHClCH2CH3

4- If the location of the halogen is 1, then you could drop the location.

1–bromoethane (bromoethane)

CH3CH2Br OR CH2BrCH3

5- If more than one halogen atom is present, then the name and the location of each one must be specified.
They are listed in alphabetical order.
1–chloro–2–fluoropentane

CH2ClCHFCH2CH2CH3
6- If more than one identical halogen are present, the prefixes di, tri, and tetra are used before the name of the
halogen. The location of each one must be specified.

2,2 – dibromopropane difluoromethane

CH3CBr2CH3 CH2F2

triiodomethane tetrachloromethane

CHI3 CCl 4

7- In the presence of a branch we start numbering from the end closer to the functional group (-X atom).
The names of the branch and the halogen atom are listed in alphabetical order.

2 – chloro-3-methylbutane CH3CHClCH(CH3)CH3

2-chloropropene CH2=CClCH3

There are three types of halogenoalkanes:

1- Primary halogenoalkanes: R-CH2-X: The halogenoalkane in which the carbon atom that is directly bonded to
the functional group X is surrounded by one alkyl group and two H atoms.

Example: 1- chlroethane

2- Secondary halogenoalkanes: R2-CH-X: The halogenoalkane in which the carbon atom that is directly
bonded to the functional group X is surrounded by two alkyl groups and one H atom.

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Example: 2 – chloropropane

3- Tertiary halogenoalkanes: R3-C-X: The halogenoalkane in which the carbon atom that is directly bonded to
the functional group X is surrounded by three alkyl groups and no H atoms.

Example: 2 – chloro – 2 - methylpropane

Question: write the primary, secondary and tertiary halogenoalkane from the formula C 5H11Br. Name
each one.

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Carboxylic acids (Alkanoic Acids)
R-COOH

Functional group: -COOH (the carboxyl group)


Naming:
1- Name the compound as an alkane. The C atom of the functional group is counted.
2- Drop the -e and add -oic acid.

methanoic acid ethanoic acid (acetic acid) propanoic acid

HCOOH CH 3COOH CH 3CH2COOH

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OR (C2H5COOH)

3- In the presence of a branch we start numbering from the end closer to the functional group (-COOH).
The C atom of the functional group is counted.

2-methylbutanoic acid CH3CH2CH(CH3)COOH

3- If two -COOH are present, then name the compound as an alkane. Do not drop the –e at the end of the
name. Add -oic acid to the name of the alkane. The location of each functional group is identified and the
prefix di is used before the –oic.

1,4 – butanedioic acid or butane-1,4-dioic acid HOOCCH 2CH2COOH

2,6-dichlorohexanoic acid CH2ClCH2CH2CH2CHClCOOH

Name this compound: (CH3)3CCH(CH3)CHBrCOOH

4- To name the salt of a carboxylic acid, name the compound as an alkane. The C atom of the functional
group is counted. Drop the -e and add -oate. Write the name of the metal before the name of the
compound.

Sodium ethanoate CH3COONa

Potassium propanoate CH3CH2COOK

Magnesium methanoate (HCOO)2Mg

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Esters (Alkyl alkanoates)
R1 - C OO – R2

Functional group: - COO-


Naming:

1- The group of carbon atoms attached to oxygen is named first.


2- Add -yl to the name of the number of carbon atoms attached to oxygen.

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3- The second part (which contains the functional group) is named as an alkanoic acid. Drop the -ic and
replace by -ate. The C atom of the functional group is counted.

methylmethanoate ethylmethanoate
HCOOCH3 HCOOCH 2CH3

butylethanoate ethylethanoate
CH3COOCH2CH2CH2CH3 CH 3COOCH2CH3

Name this compound: CH3CH2OOCCH2CH2CH3

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Ethers: R1 - O – R2
(Alkoxy Alkanes)
Functional group: - O -
Naming:
1- The two chains attached to the oxygen atom are named separately.
2- Add –yl to name of the number of carbon atoms in each chain
3- List the two names in alphabetical order
4- Add the word ether

ethyl methyl ether (methoxyethane)

CH3OCH2CH3

5- If the two chains are identical then use the prefix di before the name of the branch.

diethyl ether (ethoxyethane) dimethyl ether (methoxymethane)


CH3CH2OCH2CH3 CH3OCH3

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Aldehydes (Alkanals)

R - CO – H OR RCHO

Functional group: - CO - H
Naming:

1- Name the compound as an alkane


2- Drop the -e and add -al.

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Methanal ethanal propanal

HCHO CH 3CHO CH 3CH2CHO

◙ Name this compound: CH3CH(CH3)CH2CH(CH3)CHO

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Ketones (Alkanones)
R1 - CO – R2

Functional group: - CO -

1- Name the compound as an alkane.


2- Drop the -e from the end of the name of the parent and add -one.
3- The location of the carbonyl group is identified by a number where the chain is numbered starting from the
end closer to the functional group.

2–propanone (acetone) 2 – butanone


(propan-2-one) (butan-2-one)
CH3COCH3 CH 3COCH2CH3

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Amines: R - NH2

● Functional group: - N or - NH2

● Name of functional group: amino

a- Naming of primary amines: R – NH2

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1st Method: This method is used when the number of carbon atoms is small (one, two or three):

1- R is named as a branch. Add -yl to the name of the number of C atoms.

2- Add the suffix amine.

3- The location of the – NH2 functional group must be indicated. We start numbering from the end closer to the
functional group.

Examples:
Methylamine ethylamine

1-propylamine or propylamine 1-butylamine or butylamine

2nd Method: Used for any number of carbon atoms:

1- Name R as an alkane. Add the prefix amino.

2- The location of the – NH2 functional group must be indicated. We start numbering from the end closer to the
functional group.

3- When there are two functional groups then the prefix diamino is used and the location of each functional
group must be indicated.

Examples:
Aminoethane 2-aminopentane

1-aminohexane or aminohexane 1,6-diaminohexane

b- Secondary amines: R1 – NH – R2

1- The longest alkyl group is considered the parent compound. Name it as an alkane. Drop the –e- and add the
suffix amine.

2- The other alkyl group is named as a branch. Add –yl to the number of carbon atoms.

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3- The location of the branch is indicated by the prefix N.

Examples:
N-methylethanamine N-ethylpropaneamine.

R3
c- Tertiary amines: R1 – N – R2

1- The longest alkyl group is considered the parent compound. Name it as an alkane. Drop the –e- and add the
suffix amine.

2- The other two alkyl groups are named as branches. Add –yl to the number of carbon atoms.

3- The location of each branch is indicated by the prefix N.

4- If the two branches are identical then the prefix di is used.

5- If the two branches are not identical, then their names are listed in alphabetical order.

Examples:
N,N-dimethylethanamine N-ethyl-N-methylpropanamine.

Amides: R - C - NH2

Functional group: - C – N or - CONH2

a- Primary amides: R – C – NH2

1- Name the compound as an alkane. The carbon atom of the functional group is counted.

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2- Drop the –e- and add the suffix amide.

Example:
ethanamide 2-methylpropanamide

Nitriles: R – CN

● Functional group: - C ≡ N or – CN (Nitrile)

Name the compound as an alkane. The C atom of the nitrile group is counted. Add the suffix nitrile.

Examples:
ethanenitrile propanenitrile butanenitrile

Cycloalkanes and cycloalkenes

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Aromatic or aryl compounds:

Instead of R representing an alkyl group, it can also represent an aryl group. Aryl groups contain a benzene
ring. Benzene itself is C6H6, and in aryl compounds one of the hydrogen atoms has been substituted by a
functional group.
The simplest aryl group is the phenyl group, -C6H5. The name of the functional group in aromatic or aryl
compounds is the benzene ring or arene.

Benzene is the simplest member of aromatic compounds (an aromatic unsaturated hydrocarbon). Aromatic
compounds are all derivatives of benzene. The structure of benzene can be described as follows:

It has the chemical formula C6H6. It has a cyclic structure. The benzene ring is a planar hexagon. Each C of
benzene is attached to other three atoms. Two C atoms and one H atom. Benzene is often represented by a
hexagonal ring with a circle in the middle of it:

Examples of aromatic compounds:

1- Phenol, C6H5OH:

2- Phenylamine: C6H5NH2

3- Chlorobenzene: C6H5Cl:

4- Methyl 2-hydroxy benzoate

Isomers

Isomers (Isomerism): are molecules with the same molecular formula but they have different structural
formulas. They differ in the sequence in which the atoms are joined together.

There are three types of isomers:

1- Structural isomers:

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a) They have the same functional group b) They belong to the same homologous series.
c) They have different physical properties d) They have similar chemical properties.

• By changing the location of the functional group and by creating branches and changing their locations new
isomers are obtained.

• Methane is the only alkane with the molecular formula CH 4. Ethane is the only one with C 2H6. Propane is
the only one with C3H8.

Starting from C4H10, more than one compound have this molecular formula. The number of structural
isomers of an alkane increases with chain length.

◙ C4H10: two alkanes

CH3CH2CH2CH3 CH 3CH(CH3)CH3
n-butane 2-methylpropane

◙ C5H12: three alkanes

CH3CH2CH2CH2CH3 CH 3CH(CH3)CH2CH3 CH3C(CH3)2CH3

n-pentane 2-methylbutane 2,2-dimethylpropane

◙ C6H14: five alkanes

CH3CH2CH2CH2CH2CH3 CH3CH(CH3)CH2CH2CH3 CH3CH2CH(CH3)CH2CH3


n-hexane 2-methylpentane 3-methylpentane

CH3CH(CH3)CH(CH3)CH3 CH 3C(CH3)2CH2CH3

2.3-dimethylbutane 2,2-dimethylbutane

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Question: Draw the possible structural isomers for each of the following:

1) C4H9Br

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2) C4H8
3) C5H10

4) C3H5Cl3

2- Functional group isomers:


a) They have different functional group b) They belong to different homologous series.
c) They have different physical properties d) They have different chemical properties.

The following compounds are always isomers to each other:

a- CnH2nO: aldehyde and ketone


b- CnH2nO2: carboxylic acid and ester (an alkene with two hydroxyl groups could also be drawn)
c- CnH2n+2O: alcohol and ether

Examples:

a- C3H6O: one aldehyde and one ketone

CH3CH2CHO CH3COCH3
propanal propan-2-one (Acetone)

b- C2H4O2: one carboxylic acid and one ester

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CH3COOH HCOOCH 3
ethanoic acid methylmethanoate

c- C3H8O: two alcohols and one ether.

CH3CH2CH2OH CH3CH(OH)CH3 CH3OCH2CH3

propanol propan-2-ol ethylmethylether


(methoxy ethane)

◙ Write the possible isomers for each of the following:

1) C4H8O

2) C3H6O2

3) C4H10O

Homologous Functional Group General formula Example


series

1.Hydrocarbons

a. Alkanes Hydrogen or its alkyl CnH2n+2 2-methylpropane


substituents

b. Alkenes Alkenyl group CnH2n ethene

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c. Alkynes Alkynyl group CnH2n-2 propyne

2. Alkanols Hydroxyl group CnH2n+1OH


(alcohols)
(R-OH)

3. Halide R-X 2-chloro-2-methylpropane


Halogenoalkanes
(X: F, Cl, I, Br)

4. Aldehydes Carbonyl group/Formyl RCHO 2-methylbutanal


group
(alkanals)
(CHO)

5. Ketones Carbonyl group RCOR’ 3-methylpentan-2-one


(alkanones)

6. Ethers Ether group ROR’ ethyl methyl ether

(alkyl ether)
(alkoxyalkane)

7. Carboxylic acid Carboxyl group RCOOH propanoic acid

(alkanoic acids)

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8. Esters Ester group ethyl methanoate
RCOOR’
(alkylalkanoate)

9. Nitriles Nitrile group RCN 2-methylbutannitrile

(alkannitrile) CH3 – CH – CH2 – CH3

CN

10. Primary Amine group RNH2 2-aminopropane


amines

(aminoalkane) 2

11. Primary carboxamide group RCONH2 propanamide


amides

(alkanamide)

12. Aromatic Phenyl Group Benzene ring chlorobenzene


derivative

Physical properties of organic compounds:

1- Hydrocarbons (cyclic and noncylic):

a) They are nonpolar. The forces of attraction between the molecules are London dispersion forces of
attraction. As number of carbon atoms increases, Mr, size and the surface area will increase. As a result there
will greater and stronger London dispersion forces of attraction between the molecules. More energy will be
needed to break these forces and as a result the boiling point will increase.

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b) Unbranched isomers have a larger surface area than branched isomers. So, there will be greater and stronger
London dispersion forces of attraction between the molecules. More energy will be needed to break these forces
and as a result the boiling point will increase.
c) Hydrocarbons are insoluble in water because they are nonpolar and can’t hydrogen bond to water
molecules.

2- Halogenoalkanes, Esters, ethers, Aldehydes and Ketones:

a) Esters, ethers, aldehydes and ketones are polar due to the electronegativity difference between C and O in
the functional groups. Halogenoalkanes are polar due to the electronegativity difference between C and the
halogen atom.
b) They bond to each other by dipole - dipole interactions and London dispersion forces of attraction.
Dipole – dipole interactions between their molecules are stronger than van der Waals’ interactions. As the
number of carbon atoms increases, Mr, size and the surface area will increase. As a result there will be greater
and stronger London dispersion forces of attraction between the molecules. More energy will be needed to break
these forces and as a result the boiling point will increase.
c) Unbranched isomers have a larger surface area than branched isomers. So, there will be greater and stronger
London dispersion forces of attraction between the molecules. More energy will be needed to break these forces
and as a result the boiling point will increase.
d) Short chained molecules can bond to water molecules through their partial positive and partial negative ends
and hence they have small solubility in water. They make hydrogen bond with water molecules. As the
number of carbon atoms increases, the molecule will become mostly a non polar chain which can’t hydrogen
bond to water molecules and as a result the solubility in water will decrease more and more till it becomes
insoluble in water.

3- Carboxylic Acids, Alcohols, Amines and Amides:


a) Carboxylic acids and alcohols are polar due to the electronegativity difference between H and O in their
functional groups. Amines and amides are polar due to the electronegativity difference between N and H in their
functional groups.
b) They bond to each other by hydrogen bonds and London dispersion forces of attraction.
c) Carboxylic acids and alcohols experience hydrogen bonding because they contain hydrogen bonded to
oxygen while amines and amides experience hydrogen bonding because they contain hydrogen bonded to
nitrogen. Hydrogen bonding between their molecules is stronger than van der Waals’ interactions. As the
number of carbon atoms increases, Mr, size and the surface area will increase. As a result there will greater and
stronger London dispersion forces of attraction between the molecules. More energy will be needed to break
these forces and as a result the boiling point will increase.
d) Unbranched isomers have a larger surface area than branched isomers. So, there will be greater and stronger
London dispersion forces of attraction between the molecules. More energy will be needed to break these forces
and as a result the boiling point will decrease.
e) Short chained molecules can hydrogen bond to water molecules and hence they are soluble in water. As
the number of carbon atoms increases, the molecule will become mostly a non polar chain which can’t hydrogen
bond to water molecules and as a result the solubility in water decreases more and more till it becomes insoluble
in water.

Important Note:
Each two molecules of a carboxylic acid can bond to each other by two hydrogen bonds. For example, ethanoic
acid exists as a dimmer in non polar solvents like benzene because of the strong intermolecular hydrogen
bonding. For that, its Mr will be equal to 120 g/mol. It exists as a monomer in aqueous solutions because it
hydrogen bonds with water. For that, its M r will be equal to 60 g/mol.

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◙ The order of boiling points for compounds with different functional groups but with similar Mr values:

Hydrocarbons < halogenoalkanes, aldehydes, ketones, esters < amines < alcohols < carboxylic acids <
amides

Amides make more and stronger hydrogen bonds between each other than carboxylic acids. Carboxylic acids
make more and stronger hydrogen bonds between each other than alcohols. Alcohols make stronger hydrogen
bonds between each other than amines

Amide > Carboxylic acids > Alcohols > Amines

Hydrogen bond strength decreases


for compounds of the similar Mr

The O atom in alcohols is more electronegative than the N atom in amines. This will cause a larger
electronegativity difference between O and H than between N and H. The O – H bond in alcohols is more polar
than the N – H bond in amines and hence there is stronger hydrogen bonding in alcohols than amines. Hydrogen
bonds in amides, carboxylic acids, alcohols and amines are stronger than dipole - dipole attractions which are
found in esters, aldehydes, halogenoalkanes and ketones. The dipole - dipole attractions in esters, aldehydes,
halogenoalkanes and ketones are stronger than London dispersion forces of attractions which are found in
hydrocarbons.

◙ The order of solubility in water for compounds with different functional groups but with similar Mr values:

Hydrocarbons < halogenoalkanes, aldehydes, ketones, esters < amines, alcohols, carboxylic acids,
amides

Amides, carboxylic acids, alcohols and amines make hydrogen bonds with water molecules while
halogenoalkanes, esters, aldehydes and ketones make dipole – dipole attractions with water molecules. For that,
amides, carboxylic acids, alcohols and amines are more soluble in water. Hydrocarbons with London dispersion
forces of attractions cannot hydrogen bond to water molecules and hence they are insoluble in water.

Important note: Amides, Carboxylic acids, alcohols, amines, aldehydes, ketones, ethers and esters,
make hydrogen bonds with water molecules while halogenoalkanes make dipole – dipole attractions
with water molecules. For that these functional groups are more soluble in water than halogenoalkanes.
Hydrocarbons with London dispersion forces of attractions cannot hydrogen bond to water molecules
and hence they are insoluble in water.

◙ Acidic and basic nature of some organic compounds:

Some functional groups can react with water molecules and hence affect the pH of the resulting solution.

1- Carboxylic acids are acids because they are proton donors. They are weak acids because they ionize
partially in water. The pH is < 7.

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Like acids, they react with metals like Mg and Na to produce a salt and bubbles of H 2 gas and with metal
carbonates like Na2CO3 (aq) to produce a salt, water and bubbles of CO 2 gas. Carboxylic acids can be
recognized from their pungent smell.

CH3COOH(aq) + H2O(l) ↔ CH3COO-(aq) + H3O+(aq)

Mg(s) + CH3COOH(aq) → (CH3COO)2Mg(aq) + H2(g)

Na2CO3(s) + CH3COOH → CH3COONa(aq) + CO2(g) + H2O(l)

2- Amines are bases because they are proton acceptors. They are weak bases because they ionize partially
in water. The pH is > 7.

CH3CH2NH2(aq) + H2O(l) ↔ CH3CH2NH3+(aq) + OH-(aq)

3- Alcohols act as acids because they are proton donors. They are weak acids because they ionize partially
in water. The pH is < 7. They are much weaker than carboxylic acids. They do not react with metal
carbonates and most metals.
Like carboxylic acids, they react with Na to produce bubbles of H 2 gas. Unlike carboxylic acids, they do not
react with Na2CO3 (aq) or Mg. No bubbles of CO2 gas or H2 gas are produced.

CH3CH2OH + H2O ↔ CH3CH2O- + H3O+

Na + CH3CH2OH → CH3CH2ONa + H2

4- Esters: Their solutions in water are neutral. Their pH = 7. Esters can be recognized from their sweet smell.

Order of increasing acidity: amines < esters < alcohols < carboxylic acids.
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Combustion of hydrocarbons:

Their combustion with oxygen (also called oxidation) is highly exothermic (∆H is negative) and one of the most
common sources of energy in life. During their combustion, products have less enthalpy than reactants and
hence energy is released.

Hydrocarbons are used as fuels. When they burn completely in oxygen (oxidized with oxygen) H 2O and CO2 are
produced in addition to heat energy. The number of moles of H2O and CO2 produced depends upon the
chain length. Also the amount of heat energy depends upon the chain length. Although the C-C and C-H bonds
are strong, the C=O and O-H bonds in the products are even stronger so the reaction is very exothermic. If
insufficient oxygen is present then carbon (soot) and CO gas are also produced as products.

Carbon monoxide (CO) is a highly toxic gas. It is poisonous. It interferes with oxygen transport in the body
because it combines with hemoglobin to form carboxyhemoglobin and as a result it reduces oxygen carrying
capacity of hemoglobin.

Carbon (soot) is harmful to the respiratory system and increases atmospheric turbidity.

• Complete Combustion (Excess of Oxygen):

Hydrocarbon + Oxygen gas → Water + Carbon dioxide -∆H

CH4 (alkane) + 2O2  2H2O + CO2


C2H6 (alkane) + 7/2O2  3H2O + 2CO2
C2H4 (alkene) + 3O2  2H2O + 2CO2

• Incomplete Combustion: (Shortage of Oxygen)

Hydrocarbon + Oxygen gas → Water + Carbon monoxide -∆H

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CH4 (alkane) + 3/2O2  2H2O + CO
C2H6 (alkane) + 5/2 O2  3H2O + 2CO
C2H4 (alkene) + 2O2  2H2O + 2CO

A possible equation for a reaction involving the incomplete combustion of octane is:

C8H18 (l) + 9O2 (g)  C (s) + 5CO (g) + 9H2O (l) + 2CO2 (g)

IB Question:
In many cities around the world, public transport vehicles use diesel, a liquid hydrocarbon fuel, which
often contains sulfur impurities and undergoes incomplete combustion. All public transport vehicles in
New Delhi, India, have been converted to use compressed natural gas (CNG) as fuel. Suggest two ways
in which this improves air quality, giving a reason for your answer.

Diesel which is a liquid hydrocarbon fuel contains sulfur impurities. During combustion, SO 2 is produced which
causes acid rain. Also, its incomplete combustion produces CO, which is a toxic or a poisonous gas. CNG,
Compressed Natural Gas, CH4 (l), is a better fuel because it undergoes complete combustion or more
combustion and so less CO is produced and also does not contain sulfur impurities and so no SO 2 is produced.

Reactivity of alkanes:

Alkanes are a homologous series of saturated hydrocarbons. Saturated is defined as containing only single
carbon to carbon bonds.
Alkanes are unreactive or have low chemical reactivity because:

1- They contain C – H of low polarity.

2- They contain strong C – C and C – H bonds with high bond energies.

Apart from combustion, the only other type of reaction that alkanes undergo is substitution reactions with
halogens in ultraviolet light. Alkanes can react with chlorine or (bromine) in the presence of ultraviolet light to
form hydrogen chloride and a substituted alkane (a halogenoalkane), e.g. methane can react with chlorine to
form chloromethane and ethane can react with bromine to form bromoethane. (In the dark there is no reaction).
In these reactions:
●The reagent needed is chlorine or bromine
●The condition is ultraviolet light
●The type of reaction is substitution.

●Substitution: is defined as replacement of one atom or group in a molecule by another. In this reaction one
hydrogen atom is replaced by one halogen atom.

Alkane + Halogen uv light halogenoalkane + hydrogen halide

R-H + X2 uv light R-X + HX

uv light
C2H6 + Cl2 C 2H5Cl + HCl

● When chemical bonds break they may break by photochemical homolytic fission or by heterolytic
fission.

Photochemical Homolytic fission is defined as breaking of a covalent bond to give two fragments with an
electron each or bond breaking in which each product takes one electron from the bond. The products from

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homolytic fission are called free radicals. Examples of free radicals in the equations above are (Cl.) and
(Br.).

uv light
Cl-Cl Cl• + Cl•
uv light
Br-Br Br• + Br•

● A free radical is defined as a species with an unpaired (single) electron. They are highly reactive.
Examples: Cl•, Br• and C2H5•.

Photochemical Heterolytic fission is defined as breaking of a covalent bond in a way so that the more
electronegative atom of the two atoms joined by the bond takes both of the electrons to form an anion and the
less electronegative atom forms a cation.

H-Cl H+ + Cl-

The free radical substitution (free radical mechanism):

Example: The reaction between methane and chlorine molecule in the presence of ultraviolet light.

1) The initiation step: The bond between two halogen atoms is weaker than the C-H or C-C bond and can
break homolytically in the presence of ultraviolet light to form chlorine free radicals.

2) The following two steps are known as the propagation step, because in each step radicals react to generate
(propagate) new radicals. This enables a chain reaction to occur as the process can repeat itself.

a) When the chlorine free radicals come into contact with a methane molecule they combine with a
hydrogen atom to produce hydrogen chloride and a methyl radical.

b) The methyl free radical is also extremely reactive and reacts with a chlorine molecule to form the
product, chloromethane, and regenerate another chlorine radical.

3) The termination step: It occurs when two radicals react together to produce a non radical product.

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In theory a single chlorine radical may cause up to 10,000 molecules of chloromethane to be formed.

● Starting from propane and on, isomers are produced when an alkane reacts with a halogen.

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Question: Write the free radical substitution mechanism for the reaction between:
1) Ethane and chlorine 2) propane and bromine
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The method used above to produce a halogenolakane can be used to produce a dihalogenoalkane, a
trihalogenoalkne or a tetrahalogenoalkane. This is shown below:

Reactivity of alkenes:

Alkenes are a homologous series of unsaturated hydrocarbons. Unsaturated hydrocarbon is defined as a


hydrocarbon that contains at least one carbon to carbon double bond.

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Alkenes are more reactive than alkanes because they contain double bonds. Double bonds are relatively
reactive because:

1- Double bonds are stronger than single bonds, but they are not twice as strong (the bond enthalpy of the C=C
double bond is 612 KJ mol-1, the bond enthalpy of the C-C single bond is 348 KJ mol -1). This means it is
energetically favorable for a double bond to be converted into single bonds.

2- The activation energy for these reactions is also relatively low, owing to the high electron density in the double
bond.

Addition reaction: the reaction in which the double bond of an alkene is broken down. Addition across a double
bond occurs at both C atoms.

Alkenes are said to be unsaturated, because they can undergo addition reactions across the double
bond. When this happens the product is said to be saturated, because both carbon atoms will then have
four single bonds to other atoms, and no further addition can occur.

Chemical reactions of alkenes:


1- Halogenation of alkenes:
The reaction between an alkene and a halogen molecule (X2) will produce a halogenoalkane. Reagent
needed is a halogen molecule. The type of the reaction is addition.

Bromine Test (Bromination):


The usual test for the presence of a double bond is to add bromine water to the compound. If a double bond
is present, the bromine water changes color from orange to colorless. Bromination can be used to distinguish
between alkanes and alkenes. Alkenes react with bromine water in dark(in the absence of UV light) and
decolorize it (changes color from orange to colorless) while alkanes have no effect on the color of
bromine water in the dark.

Alkene + Halogen → Halogenoalkane


CH2=CH2 + Br2 → CH2BrCH2Br
Orange colorless

◙ Notice that CH2=CH2 can be converted into CH 2BrCH2Br in a single step reaction. According to the above
mechanism CH2=CH2 can’t be converted into CH2=CHBr in a single step reaction. Also CH3CHBr2 can’t be
formed directly from CH2=CH2 because addition across a double bond occurs at both C atoms.

2- Alkenes and hydrogen halides:

The reaction between an alkene and a hydrogen halide (HX) will produce a halogenoalkane. Reagent
needed is a hydrogen halide molecule. The type of the reaction is addition. Condition: nonpolar solvent.

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Sometimes isomers are produced. The major isomer is the one in which the H atom will link to the C atom
that is surrounded by the greater number of hydrogen atoms.

Alkene + Hydrogen halide → Halogenoalkane


-C=C- HX

CH2=CH2 + HCl → CH 3CH2Cl


(CH2CH2)

CH3CH=CH2 + HBr → CH3CHBrCH3 + CH3CH2CH2Br


(CH3CHCH2) Major Minor
isomer isomer

3- Hydrogenation of alkenes:

Alkenes react with H2 gas to produce alkanes. Reagent needed is H2 gas. Condition is a transition metal
catalyst, Pt or Ni and heat (150°C-200 °C). The type of the reaction is addition. Unsaturated oils (have one
or more double bonds) can be hydrogenated to solid, saturated fats by the reaction with hydrogen gas in the
presence of nickel or platinum as a catalyst. Saturation raises the melting point of the product. For example, the
partial hydrogenation of liquid oil produces soft margarine.

Alkene + H2 gas Pt or Ni catalyst Alkane

CH2=CH2 + H2 Pt or Ni catalyst CH3CH3

4- Hydration of alkenes:

Alkenes react with water to produce alcohols. Reagent needed is water. Conditions are Heat and
concentrated H2SO4 as a catalyst. The type of the reaction is addition. Hydration of ethene is used in the
manufacture of ethanol. Sometimes isomers are produced. The major isomer is the one in which the H atom
will link to the C atom that is surrounded by the greater number of hydrogen atoms and the OH will link
to the C atom that is surrounded by the greater number of alkyl groups.

concentrated H2SO4
Alkene + water alcohol
+ Heat

concentrated H2SO4
CH2=CH2 + H2O + Heat CH 3CH2OH

concentrated H2SO4
CH3CH=CH2 + H2O + Heat CH 3CH(OH)CH3 + CH3CH2CH2OH
Major isomer Minor isomer

5- Polymerization of alkenes:

◙ Polymers: are defined as long chain molecules that are formed by the joining together of a large number of
small molecules called monomers. Polymers are usually referred to as plastics.

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◙ Addition polymerization: is defined as a process in which unsaturated monomers combine to form a
polymer without the elimination of any atoms or molecules. In this type of polymerization the monomers contain
double bonds and in the addition reaction the double bonds are replaced with single bonds between the
monomers. This means that the structural feature needed in the monomer is the presence of a carbon –
carbon double bond.

The conditions of addition polymerization are:


1) high pressure 2) high temperature 3) a catalyst.

● The type of this polymerization reaction is addition polymerization.


● The type of polymer is addition polymer.

Notice that the monomers have smaller molecules than the polymers and hence the monomers have smaller
surface area than the polymers. As a result weak London dispersion forces are present in the monomers while
strong London dispersion forces are present in the polymers. For that the monomers are often gases or
volatile liquids, whereas the polymers are solids.

- Addition polymers consist of a wide range of monomers and form the basis of the plastics industry.

Examples of addition polymers:

a) Polyethene: It is produced by the polymerization of ethene monomers.

b- Polyvinyl chloride (PVC) or polychloroethene: It produced by the polymerization of vinyl chloride


(chloroethene) monomers.

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c- Polypropene: It is produced by the polymerization of propene monomers.

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The economic importance of alkenes:

30
1- Manufacture of margarine: The addition of hydrogen to polyunsaturated vegetable oils (triesters) is used
industrially to make solid margarine. Hydrogenation reduces the number of double bonds in the polyunsaturated
vegetable oils present in the margarine which cause it to become a solid at room temperature. To enable a
mixture of vegetable oils to solidify for use as margarine, some of the carbon – to – carbon double bonds are
hydrogenated by using a nickel catalyst under pressure. This enables the long – chain molecules to pack more
closely, which increases the van der Waals’ attractive forces between them and so increases the melting point.

2- Manufacture of ethanol: Ethanol has many industrial uses, principally as a solvent, as a fuel, and as an
intermediate in the production of other organic chemicals. Ethene is an important product formed during the
cracking of oil. Although ethanol can be made from the fermentation of starch and sugars, much industrial
ethanol is formed from the addition of steam to ethene (hydration of ethene).

3- Manufacture of plastics: A whole variety of addition polymers or plastics can be formed from different
alkenes. The range of addition polymers is vast, and much of modern society relies heavily on polymers. Even
with just one chemical monomer the product can be altered to produce polymers with very different properties.

Question: Outline the reasons why polymers of alkenes are of economic importance.

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Combustion of alcohols:
All alcohols burn readily in a plentiful supply of oxygen to form carbon dioxide and water. The general equation
for an alcohol combusting in oxygen is:

CnH(2n+1)OH + (2n-1)O2 → nCO2 + (n+1)H2O

C2H5OH + 3O2 → 2CO2 + 3H2O

Alcohols are already partially oxidized, as they contain an oxygen atom so they release less energy than burning
an alkane of comparable mass. However, it can be obtained by the fermentation of biomass so in some
countries it is mixed with gasoline to produce gasohol which decreases the dependence on crude oil.

IB Q: Both C5H12 and C5H11OH can be used as fuels. Predict which compound would release a greater
amount of heat per gram when it undergoes complete combustion. Suggest two reasons to support your
prediction.
C5H12 releases more energy. This is because alcohols are already partially oxidized, as they contain an oxygen
atom which contributes nothing to the energy released so they release less energy. Also, the total energy
produced in bond formation is the same for both but the total bond strength in the alcohol is higher.

C5H12 + 8O2 → 5CO2 + 6H2O

C5H11OH + 15/2O2 → 5CO2 + 6H2O

Oxidation of alcohols: The combustion of alcohols is clearly an oxidation process, but normally when we refer
to the oxidation of organic compounds we tend to restrict this to the oxidation of the functional group and assume
that the carbon chain remains intact.

Primary alcohols can undergo oxidation to an aldehyde or a carboxylic acid.

31
• The oxidizing agent needed is acidified potassium dichromate (VI), K 2Cr2O7 or acidified
potassium manganate (VII)
• Reagents needed are potassium dichromate (VI) and sulfuric acid.
• Conditions are: heat and sulfuric acid.

● Heating ethanol with an acidified solution of potassium dichromate will oxidize ethanol to ethanal or ethanoic
acid.
The color of the oxidizing agent (acidified potassium dichromate (VI)) changes from orange to green during
the oxidation process. During the process the orange dichromate (VI) ion, Cr2O7-2, is reduced from an
oxidation state of + 6 to the green Cr+3 ion.

The color of the oxidizing agent (acidified potassium manganate (VII)), will change from purple to colorless
and the purple manganate (VII), MnO4-1, is reduced from an oxidation state of + 7 to the colorless Mn +2 ion.

A- Oxidation of primary alcohols:

K2Cr2O7 + H2SO4 K2Cr2O7 + H2SO4


Alcohol Aldehyde Carboxylic Acid
(Alkanol ) + Heat +distill off Alkanal) + Heat + reflux (Alkanoic acid)

Step (1) Step (2)

K2Cr2O7 + H2SO4 K2Cr2O7 + H2SO4


CH3CH2OH CH 3CHO CH 3COOH
+ Heat +distill off + Heat + reflux
Ethanol Ethanal Ethanoic acid
Step (1) Step (2)

C2H6O → C 2H4O → C 2H4O2

CnH2n+2O → C nH2nO → C nH2nO2


Alcohol alkanal alkanoic acid

◙ To obtain ethanal: (Partial or mild oxidation of primary alcohol, ethanol)


1- As soon as ethanal is formed, it is distilled off.
2- Use a limited amount of the oxidizing agent.

Conditions to obtain the aldehyde in the oxidation process: Heat and as soon as the aldehyde is formed, it is
distilled off. This technique works because the aldehyde has a low boiling point and this prevents further
oxidation. Usually it is harder to obtain the aldehyde because it is more easily oxidized into a carboxylic acid
unless it is removed. When the aldehyde is formed, the alcohol is said to be partially oxidized.

32
◙ To obtain ethanoic acid: (complete oxidation of primary alcohol, ethanol)
1- The mixture is heated under reflux so that ethanal cannot escape further oxidation to ethanoic acid.
2- Use an excess amount of the oxidizing agent.

Conditions to obtain the carboxylic acid in the oxidation process: The mixture is heated under reflux so that the
aldehyde cannot escape further oxidation to a carboxylic acid. This technique works because all the alcohol is
oxidized to a carboxylic acid. When the carboxylic acid is formed, the alcohol is said to be completely oxidized.
Usually the K2Cr2O7 is in excess when a carboxylic acid if to be produced.

B- Oxidation of secondary and tertiary alcohols:

1- Secondary alcohols are always oxidized to ketones, which cannot undergo further oxidation, by
heating them in the presence of an acidified solution of potassium dichromate (VI), K 2Cr2O7. The oxidizing
agent needed is acidified potassium dichromate (VI). Reagents needed are potassium dichromate (VI) and

33
sulfuric acid. Condition is heat under reflux. The color of the oxidizing agent changes from orange to green
during the oxidation process. The type of the reaction is oxidation.

2- Tertiary alcohols do not undergo oxidation by an acidified solution of potassium dichromate (VI) as they have
no hydrogen atoms attached directly to the carbon atom containing the –OH group. When heated in the
presence of an acidified solution of potassium dichromate, the color of the oxidizing agent will not change
from orange to green. It is not true to say that tertiary alcohols can never be oxidized, as they burn
readily, but when this happens the carbon chain is destroyed.

Chemical test to differentiate between primary, secondary and tertiary alcohols:

The test is oxidation using an acidified solution of potassium dichromate (VI):

1- A primary alcohol produces an aldehyde when partially oxidized and a carboxylic acid when completely
oxidized. The oxidizing agent changes color from orange to green in both cases. When completely oxidized, the
product is acidic.

2- A secondary alcohol produces a ketone which is not acidic and the oxidizing agent changes color from
orange to green. The ketone cannot undergo further oxidation.

3- A tertiary alcohol cannot be oxidized and the color of the oxidizing agent will not change from orange to
green. It will stay orange.

Oxidation of aldehydes, ketones and ethers:

a- Ketones and ethers cannot be oxidized using an acidified solution of potassium dichromate (VI) and the
color of the oxidizing agent will not change from orange to green. It will stay orange.

34
b- An aldehyde will be oxidized into a carboxylic acid using an acidified solution of potassium dichromate
(VI) and the color of the oxidizing agent will change from orange to green.

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Summary:
The oxidation reactions of alcohols can be used to distinguish between primary, secondary, and tertiary alcohols:
● Primary alcohols are first oxidized by acidified potassium dichromate (VI), first to aldehydes then to
carboxylic acids.
● Secondary alcohols are oxidized to ketones, which cannot undergo further oxidation.
● Tertiary alcohols cannot be oxidized by acidified potassium dichromate (VI) as they have no hydrogen atoms
attached directly to the carbon atom containing the OH group.
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Nucleophilic substitution reactions:

In halogenoalkanes, the greater electronegativity of the halogen atom compared with the carbon atom, makes
the bond polar. This means that the carbon atom carries a slight positive charge. Because of this, it is suitable to
attack by nucleophiles and a substitution reaction occurs.

Halogenoalkanes are more reactive than alkanes. They can undergo (nucleophilic) substitution
reactions.

A nucleophile is an electron-rich species containing a lone pair that it donates to an


electron-deficient carbon.

Typical nucleophiles are OH-1, CN-1 and NH3.

These reactions of halogenoalkanes with nucleophiles are called nucleophilic substitution reactions. In these
reactions, a nucleophile (OH-1) reacts with a halogenoalkane to give an alcohol and a leaving group (the halide
ion which was displaced).

R-X + NaOH → R-OH + NaX


-The reagent is NaOH or KOH.
-The nucleophile is OH-1.
-The condition is a warm dilute aqueous solution of NaOH or KOH.
-The type of reaction is substitution.
Examples:

1) CH3CH2Br + NaOH → CH3CH2OH + NaBr

Reagent: warm dilute aqueous solution of NaOH or KOH

OR CH3CH2Br + OH- → CH3CH2OH + Br-


1-bromoethane nucleophile

2) (CH3)2CHBr + NH3 → (CH3)2CH-NH2 + HBr


2-bromo-2-propane nucleophile

3) (CH3)3CBr + NaCN → (CH3)3C-CN + NaBr

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OR (CH3)3CBr + CN- → (CH3)3C-CN + Br-
2-bromo-2-methylpropane nucleophile

A nucleophilic substitution reaction is defined as replacement of an atom or group in a molecule by a species


with a lone pair of electrons. In these reactions nucleophiles act as Lewis bases, because they donate a pair of
electrons.

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Preparation of esters:

● A carboxylic acid reacts with an alcohol in the presence of concentrated sulfuric acid, H 2SO4, and heat
to produce an ester. The other product is water. Conditions are heat and concentrated sulfuric acid,
H2SO4, as a catalyst.
The reaction does not proceed to completion because of the equilibrium established. The type of the
reaction is condensation or esterification. A condensation reaction is one in which two small molecules
combine to form a larger molecule with the elimination of a smaller molecule such as water.

● The H2SO4 has two functions:

1- It acts as a catalyst that lowers the activation energy, E a, of the reaction by providing an alternative
pathway. As a result, the rate of the reaction increases.

2- It acts as a dehydrating agent. It reacts with the water formed to shift the position of the equilibrium to
the right side (Le Chatelier’s principle) to produce more from the ester.

● In the above reactions note that the carbon to oxygen bond on the acid that breaks, not the carbon to
oxygen bond on the alcohol.

● Esters are sweet smelling compounds and their production is distinguished by this smell. Because of
their sweet smell, they have the following uses:

1- Flavoring agents in the food industry.


2- In plasticizers.
3- In solvents.
4- In perfumes.
5- Making aspirin.

● When an ester is heated with water and sulfuric acid, hydrolysis occurs. In hydrolysis, the reverse
reaction takes place and the same equilibrium is established. The products are a carboxylic acid and an
alcohol.

36
Describe the preparation of ethyl propanoate.

● When an ester is heated with NaOH (aq), the reaction goes to completion because the acid formed
reacts with the base to produce the salt of the acid. The products are salt and an alcohol.

● Notice that esters do not react with bromine water since they do not contain C=C double bond.

Crude oil:
Although organic compounds do occur naturally (for example, ethane is produced when bananas ripen), they do
not occur in any great quantities.
Crude oil is mainly a mixture of many different alkanes. After the fractional distillation of crude oil the alkanes
are grouped into different boiling ranges, known as fractions. About 10 % of crude oil is converted by certain
processes into alkenes, which are then used as a chemical feedstock to make other organic chemicals. The
products obtained from crude oil are economically important because they are used to make motor fuel
and other important products such as plastics, pesticides, food additives, pharmaceuticals, detergents
cosmetics, dyes and solvents.

Tests used to distinguish between organic compounds:

a- Physical tests to differentiate between an ester and a carboxylic acid:

1- The pH value: Esters are neutral and have a pH = 7. Carboxylic acids are acids and
their pH is < 7.
2- The smell: Carboxylic acids have a pungent smell while esters have a sweet smell.

37
3- The boiling point: The boiling points of carboxylic acids are higher.

b- Chemical tests to differentiate between an alcohol and a carboxylic acid:

1- The reaction with Na: H2 gas bubbles will form slowly with alcohols and rapidly with
carboxylic acids.
2- The reaction with Mg: No gas bubbles will form with alcohols and H 2 gas bubbles will
form with carboxylic acids.
3- The reaction with Na2CO3 solution: No gas bubbles will form with alcohols and CO 2
gas bubbles will form with carboxylic acids.

c- Physical tests to differentiate between an alcohol and a carboxylic acid:

1- The pH value: Both have a pH < 7. Carboxylic acids have a lower pH.
2- The boiling point: The boiling points of carboxylic acids are higher.

d- Chemical test to differentiate between an alkane and an alkene:

Alkenes react with bromine water and decolorize it (changes color from orange to colorless) while alkanes
have no effect on the color of bromine water.

Reaction pathways:

Using the scheme below which summarizes the organic reactions in this unit, it is possible to devise reaction
pathways. These should involve no more than two steps and should include the reagents, conditions and
relevant equations. (Two steps for SL and four steps for HL)

38
Example: To convert but-2-ene to butan-2-one

Step 1: Heat but-2-ene with water in the presence of concentrated H 2SO4 as a catalyst to form butan-2-ol

39
Step 2: Oxidize butan-2-ol to butan-2-one by heating with acidified potassium dichromate (VI)

Question 1: Write a two stages synthesis for the conversion of propane into 2-propanol.

Question 2: Write two stages synthesis for the conversion of but-1-ene into butanal.

Question 3: Write two stages synthesis for the conversion of 1-bromopropane into propanal.

40
Question 4: Write two stages synthesis for the conversion of 2-chlorobutane into 2-butanone.

Aromatic compounds (Arenes)

41
42
43
44
45
IB Question:

Answer:

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IB Question:

(a)
46
(b)

(c)

(d) Explain, with reference to the types of reaction and your answer to part (b), why reaction I
is more likely to occur than reaction II.

Answer:
(a)

(b)

(c)

(d)

47