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Detailed Notes Topic 6 Organic Chemistry I Edexcel Chemistry A Level

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Edexcel Chemistry A-level

Topic 6: Organic Chemistry I


Detailed Notes

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Topic 6A: Introduction to Organic Chemistry

Hydrocarbons

Organic chemistry mainly concerns the properties and reactions of ​hydrocarbons​, compounds
that contain ​only carbon and hydrogen​ atoms. Hydrocarbons are a series of compounds with
similar structures and formulas that can be represented in many different ways.

Nomenclature
Nomenclature is the set of rules that outline how different organic compounds should be ​named
and how their ​formulas are represented​.

Formulas
There are many different ways of writing and representing organic compounds:

1. Empirical Formula
- The simplest whole number ratio of atoms of each element in a compound.

2. Molecular Formula
- The true number of atoms of each element in a compound.

3. General Formula
- All members of a homologous organic series follow the general formula. For example,
alkanes have the general formula C​n​H​2n+2​.

4. Structural Formula
- Shows the structural arrangement of atoms within a molecule. For example,
CH​3​CH​2​COCH​3​.

5. Displayed Formula
- Shows every atom and every bond in an organic
compound.

6. Skeletal Formula
- Shows only the bonds in a compound and any
non-carbon atoms. The vertices are carbon
atoms and hydrogen is assumed to be bonded to
them unless stated otherwise.

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Homologous Series
Organic compounds are often part of a ​homologous series​, in which all members follow a
general formula​ and react in a very similar way. Each consecutive member ​differs by CH​2​ and
there is an​ increase in boiling points ​as chain length increases.

Example:

Each series has a ​functional group​ that allows that molecule to be recognised as being able to
react chemically in a certain way as a result of that group.

Example: Table of functional groups (ignore ethers)

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Naming Compounds

Compounds are named according to rules laid out by the ​International Union of Pure and
Applied Chemistry (IUPAC)​. This ensures each compound is universally named the same -
which helps to avoid potentially dangerous confusion.
As well as being able to name compounds from their structures, you should be able to draw
structures from IUPAC names.

Stem
The prefix of the chemical tells you ​the length of the longest unbroken chain of carbon
atoms​ in the compound. The first 10 are given below, using alkanes as an example:

Functional Groups
The ​ending ​of the compound’s name tells you the ​functional group​ present. If there is more
than one functional group present, they are added as a ​suffix​.

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If a ​halogen ​is present, it is represented by a ​prefix​:

Functional group Prefix

Fluorine Fluoro-

Chlorine Chloro-

Bromine Bromo-

Iodine Iodo-

Side Chains
Carbon side chains that are ​branches ​from the longest carbon chain are represented by a
prefix ​at the start of the word. These ​alkyl groups​ are made using the ​stems ​given above
(meth-, eth-, prop-, etc) and the ​suffix -yl.

General Rules
1. Functional groups and side chains are given, if necessary, with the number
corresponding to the carbon they are attached to.
2. Numbers are separated by commas.
3. Numbers and words are separated by hyphens.
4. If more than one particular side chain or functional group is present then one of the
following prefixes is added: di- (2), tri- (3), tetra- (4), etc.
5. The carbon chain is numbered in ascending order from the end of the chain nearest a
functional group.
6. If multiple prefixes are present, they are included in alphabetical order.

Examples

Example 1: The displayed structure of butan-2,3-diol.

This compound only has single carbon-carbon bonds, so is an alkane. Its longest chain of carbon atoms
is 4, giving the stem butan-, and it has two alcohol functional groups on carbons 2 and 3.

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Example 2: The displayed structure of 3-ethyl,5-methylhexan-2-ol.

Example 3: The displayed structure of propanone.

Propan-2-one is also correct, but since the C=O can only be in the 2 position for the compound to be a
ketone, the number is not necessary.

Example 4: The skeletal structure of 1,2-dichloropropane

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Reaction Mechanisms

Types of Reactions
Reactions can be classified according to what happens to the reactants during the reaction and
what the end products are. The main types of reaction are:

● Addition​ - In an addition reaction the reactants combine to form a ​single product.

● Substitution​ - In a substitution reaction one functional group is ​replaced​ by a ​different


functional group​.

● Oxidation​ - A species ​loses​ at least one electron, and is oxidised.

● Reduction​ - A species ​gains​ at least one electron, and is reduced.

● Polymerisation​ - A reaction in which many small molecules, known as ​monomers,​ join


together to form a long, repeating molecule called a ​polymer​.

Mechanisms
Mechanisms show the ​movement of electrons​ within a reaction, shown with ​curly arrows​.

Example:

Mechanisms are used to show the reactions of organic compounds.

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Isomerism

Isomers are molecules with the ​same molecular formula​ but a ​different arrangement​ of
atoms within the molecule.

Structural Isomers
Structural isomers have the same molecular formula but a ​different structural arrangement​ of
atoms. They can be ​straight ​chains or ​branched​ chains but will have the same molecular
formula.

Example:

Position Isomers
Position isomers have the ​functional group​ of the molecule in a ​different position​ of the
carbon chain.

Example:

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Functional Group Isomers
These have the same molecular formula so but the molecules have a ​different functional
group​.

Example:

Stereoisomers
Stereoisomers have the same structural formula but have a ​different spatial arrangement​ of
atoms and bonds. ​E-Z isomerism​ is a type of stereoisomerism, which occurs due to the ​limited
rotation​ around a double carbon bond. The limited rotation means that groups attached to the
C=C can either be ‘together’ or ‘apart’. The ​E​ isomer (german for ‘entgegen’ meaning apart) has
these groups ​apart​. The ​Z​ isomer (german for ‘zusammen’ meaning together) has these groups
together​ on the same side.

Example:

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Cahn-Ingold-Prelog (CIP) Priority Rules
There is a ​priority of different groups​ in molecules that can display E-Z isomerism. The atom
or group on each side of the double bond with the ​higher Ar or Mr​ is given the ​higher priority​.
These groups are used to determine if it is the E or Z isomer.

Example:

Therefore this molecule is the Z isomer as the highest priority


atoms are on the same side (both on top).

Cis- and Trans- Isomers


Stereoisomers can be named in the same process as above, but instead using ​Cis-​ for when
the groups are on the ​same side ​and ​trans- ​for when they are ​different sides​. Cis- and trans-
differs from E/Z isomerism in that cis- and trans- can only be used when there are ​hydrogen
atoms​ to compare the two other groups to. When there are more groups present, you have to
assign E/Z isomerism by using the ​Cahn-Ingold-Prelog (CIP) priority rules ​described above.

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Topic 6B: Alkanes
Introduction to Alkanes

Alkanes are ​saturated hydrocarbons ​where all carbon-carbon bonds are ​single​ ​bonds​. They
are part of a homologous series with the general formula​ C​n​H​2n+2​. Cycloalkanes are an
exception to this general formula but are still saturated hydrocarbons.

Fractional Distillation

Crude oil is a mixture​ of different


hydrocarbons. It can be separated into
the separate molecules by ​fractional
distillation​ as the different chain lengths
of molecules result in them having
different boiling points​.

Crude oil is separated in the following


way:

1. The mixture is ​vapourised ​and


fed into the fractionating column.

2. Vapours ​rise, cool​ and


condense​.

3. Products are ​siphoned off​ for


different uses.

Products with ​short ​carbon chains have


lower​ boiling points, meaning they ​rise
higher​ up the column before reaching
their boiling point. Therefore they are
collected at the top​ of the column.

Products with ​long​ carbon chains have ​higher​ boiling points, meaning they don’t rise very far
up the column before reaching their boiling point. They condense and are ​collected at the
bottom​ of the fractionating column.

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The compounds collected from the fractionating column are then ​broken down further ​via the
method of ​cracking​.

Some long-chain alkanes are also converted into ​branched alkanes​ and ​cyclic hydrocarbons
in a process known as ​reforming​. These products undergo ​combustion ​more ​efficiently ​than
straight-chain alkanes.

Cracking

Longer carbon chains are not very useful, so they are broken down to form ​smaller, more
useful molecules​. The carbon-carbon bonds are broken in order to do this, which requires
quite ​harsh reaction conditions​. There are two main types of cracking which result in slightly
different organic compounds.

Examples:

Thermal Cracking
Thermal cracking produces a high proportion of ​alkanes and alkenes​. High temperatures
around ​1200 K​ and pressures around ​7000 kPa​ are used to crack the carbon chains. The
reaction always forms an alkane, and the remaining atoms form at least one alkene, which have
the general formula C​n​H​2n​.

Catalytic Cracking
Catalytic cracking produces ​aromatic compounds​ with carbon rings. Lower temperatures
around ​720 K ​are used along with normal pressure, but a ​zeolite catalyst​ is also used to
compensate for these less harsh conditions.

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Combustion of Alkanes

Alkanes make good fuels as they ​release a lot of energy​ when burned. With sufficient oxygen
present, they undergo ​complete combustion​ to produce carbon dioxide and water.

Example:

If the oxygen present is insufficient, combustion is ​incomplete​ and ​carbon monoxide or


carbon particulates​ are produced alongside water.

Example:

Carbon monoxide is a ​toxic​, gaseous product that is especially dangerous to humans as it is


odourless and colourless. Carbon monoxide is dangerous because it ​replaces oxygen​ in the
blood, starving the brain and other organs of oxygen and causing people to ​suffocate​.

Oxides ​of ​nitrogen ​and ​sulfur ​are also produced as a byproduct of alkane combustion along
with​ carbon particulates​ from unburnt fuel. In clouds, these oxides can react with water and
form dilute acids, which result in ​acid rain​.

Catalytic Converters
These gaseous products can be removed from systems using a ​catalytic converter.​ This uses
a ​rhodium catalyst​ to convert harmful products into more stable products such as CO​2​ or H​2​O.

Example:

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Alternative Fuels
Alternative fuels are now being developed such as ​biofuels ​that release fewer, less harmful
products when burned. Carbon dioxide is released during the combustion of fuels. It is a
greenhouse gas​ so causes ​global warming​ and contributes to ​climate change.

Ethanol is a common ​biofuel​. It is said to be ​carbon neutral​ as the carbon given out when it is
burned is equal to the carbon taken in by the crops during the growing process. It is produced
by fermentation, where enzymes break down starch from crops into ​sugars​ which can then be
fermented to form ethanol​. It is produced in ​batches​, meaning it is a relatively slow process
with a ​low percentage yield. ​However,​ ​the environmental benefits make it viable.

The other advantage of biofuels is that they are ​sustainable​. This means their supply can be
maintained at the rate they are being used, so they will not run-out - unlike ​fossil fuels​.

Chlorination of Alkanes

Alkanes react with halogens in the presence of ​UV light​ to produce halogenoalkanes. The UV
light breaks down the halogen bonds (homolytic fission) producing reactive intermediates called
free radicals​. Free radicals are indicated with a dot, as shown below.

Free radicals are species containing an unpaired electron which is shown using a single dot.
These attack the alkanes resulting in a series of reactions; ​initiation, propagation and
termination​.

1. Initiation​ - the halogen is broken down in the presence of UV light.

Cl​2​ → 2Cl•

2. Propagation​ - a hydrogen is replaced and the Cl• radical reformed as a catalyst

Cl• + CH​4​ → •CH​3​ + HCl


•CH​3​ + Cl​2​ → CH​3​Cl + Cl•

3. Termination​ - two radicals join to end the chain reaction and form a stable product.

•CH​3​ + •CH​3​ → C​2​H​6

The propagation step can continue many times to result in ​multiple substitutions​, this is a
chain reaction​. The condition of the reaction can be altered to favour the termination step and
limit the number of substitutions, however, the nature of this reaction to produce ​multiple
products​ limits its use in organic synthesis.

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Topic 6C: Alkenes
Introduction to Alkenes

Alkenes and cycloalkenes are ​unsaturated hydrocarbons ​with at least one carbon-carbon
double​ ​bond​. They are part of a homologous series with the general formula​ C​n​H​2n​.
Cycloalkanes are saturated and follow this same general formula.

Structure and Reactivity

The carbon double bond is an area of ​high electron density​ making it susceptible to attack
from electrophiles (species that are attracted to ∂-areas). It consists of a normal covalent ​σ
bond ​and a​ π bond​.

Example:

Bromine water​ is used to identify an alkene double bond and other unsaturated compounds.
Alkenes cause bromine water to change colour from ​orange-brown to colourless. ​This is
because the C=C bond can ‘open up’ to accept bromine atoms, and thus become saturated.

Reactions of alkenes

The ​carbon-carbon double bond​ in alkenes makes them reactive. During their reactions, the
double bond opens up to form single bonds to other atoms.

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Alkanes
Alkenes can undergo​ electrophilic addition​ with ​hydrogen ​to produce ​alkanes​. The C=C
bond opens up and forms single bonds to each of the hydrogen atoms. This reaction requires a
nickel catalyst.

Example:

This reaction is also known as a ​hydrogenation ​reaction. ​Catalytic hydrogenation​ is used in


the manufacture of ​margarine ​from ​unsaturated vegetable oils​.

Halogenaoalkanes
Halogenoalkanes ​are organic compounds with single carbon bonds only and halogen
functional groups. Alkenes undergo ​addition​ ​reactions with ​halogens ​to form ​di-substituted
halogenoalkanes, ​and with ​hydrogen halides​ to form ​mono-substituted halogenoalkanes.
The mechanism for this reaction is given on the following page of these notes.

Alcohols
Alcohols ​are organic compounds with a ​hydroxyl ​functional group. Alkenes undergo ​addition
reactions with ​steam ​to form alcohols. This reaction requires an ​acid catalyst​, such as
phosphoric acid.

Example:
CH​2​CH​2​ + H​2​O → CH​3​CH​2​OH

Diols​, alcohols with two hydroxyl functional groups, can also be formed from alkenes through
an ​oxidation ​reaction. The double bond is oxidised by​ acidified potassium manganate(VII)
(KMnO​4​)​. The manganate ions must be cold, dilute and acidified.

Example:
CH​2​CH​2​ + H​2​O + [O] → CH​2​(OH)CH​2​(OH)

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Electrophilic Addition

Alkenes undergo electrophilic addition about the double bond.

Electrophiles
These are ​electron acceptors​ and are attracted to areas of ​high electron density​. Some of
the most common electrophiles are:

● HBr
● Br​2
● H​2​SO​4

They can be used in the presence of steam to form ​alcohols ​or with hydrogen to produce
alkanes​ from alkenes.

Electrophilic Addition
Electrophilic addition is the reaction mechanism that shows how electrophiles attack the double
bond in alkenes. When the double bond is broken, a ​carbocation​ forms. This is a carbon atom
with only​ three bonds​, meaning it has a ​positive​ charge.

Carbocations can have ​varying stability​, with tertiary being the most stable and primary the
least. The ​more stable​ the carbocation, the ​more likely​ it is to form. Therefore in an addition
reaction, multiple products can form but the ​major product​ will always be the one that is formed
via the ​most stable carbocation intermediate ​possible.

Mechanisms

Mechanism: ​Alkene + Halogen → Dihalogenoalkane

The π bond causes the bromine molecule to gain a temporary


dipole so that electrons are transferred.

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Mechanism:​ Alkene + Hydrogen Halide → Halogenoalkane

Example: Electrophilic addition of hydrogen bromide to ethene

Example: Electrophilic addition of hydrogen bromide to propene

Hydrogen bromide​ is ​polar​ due to the difference in the electronegativities of hydrogen and
bromine. The ​electron pair​ in the double bond attracts ​Hδ+​
​ , forming a covalent bond between
carbon and hydrogen. This produces a positively charged ​carbocation intermediate​ which
attracts the negatively charged bromide ion.

The hydrogen joins to the carbon atom which is bonded to the most hydrogen atoms. The
bromide ion bonds to the carbon atom which is joined to the most carbon atoms. This is why
2-bromopropane ​forms more often than 1-bromopropane in the mechanism of propene with
hydrogen bromide.

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Addition Polymers

Addition polymers are produced from ​alkenes​ where the double bond is broken to form a
repeating unit​. Alkenes are short chain ​monomers​ which join together to form ​long chain
polymers.

Example:

The repeating unit must always be shown with ​extended bonds through the brackets​,
showing that it bonds to other repeating units on both sides.

The ​energy ​and ​resources ​used to make polymers are large. Polymers are made from alkenes
which are obtained from​ crude oil​, a non-renewable resource. The extraction and cracking of
crude oil are both high energy processes and additional energy is then needed to convert these
alkenes into polymers.

Uses of Polymers
Polymers are unreactive hydrocarbon chains with ​multiple strong, non-polar covalent bonds​.
This makes them useful for manufacturing many everyday plastic products such as poly(ethene)
shopping bags.

However, the unreactive nature of the bonds in addition polymers means they are ​not
biodegradable ​and cannot be broken down by species in nature.

Disposal of Polymers
Addition polymers are ​non-biodegradable​ which means disposal of them can be difficult.
Waste polymers can be processed in different ways. Some can be ​recycled​, some are used as
feedstock​ for cracking and some are ​incinerated​ to produce energy for other industrial
processes. Incineration can release ​toxic gases​ which must be removed to reduce the impact
on the environment.

As well as this, scientists are developing ​biodegradable polymers​ to overcome these waste
issues.

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Topic 6D: Halogenoalkanes

Introduction to Halogenoalkanes
Halogenoalkanes contain ​polar bonds​ since the halogens are more electronegative than a
carbon atom. This means electron density is drawn towards the halogen, forming ​∂+ and ∂-
regions​.

Example:

Halogenoalkanes can be classed as ​primary, secondary or tertiary ​halogenoalkanes


depending on the position of the halogen within the carbon chain.

Relative Reactivity
Reactivity varies depending on the halogen present in the molecule. ​Electronegativity​ of the
halogens ​decreases down the group,​ meaning that a carbon-fluorine bond is much more
polar​ than a carbon-iodine bond. Along with the fact that the carbon-fluorine bond is ​shorter​,
this means that the carbon-fluorine bond is much stronger than the carbon-iodine bond.

The ​greater the Mr​ of the halogen in the polar bond, the ​lower the bond enthalpy. ​A​ ​lower
bond enthalpy means the bond can be ​broken​ more easily. Therefore, the ​rate of reaction
increases​ for halogenoalkanes as you move ​down ​the group.

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Reactions of Halogenoalkanes

To Produce Alcohols
Halogenoalkanes can react with ​aqueous alkali​, such as aqueous sodium or potassium
hydroxide, to produce ​alcohols ​in a ​nucleophilic substitution ​reaction. The ​hydroxide ion
acts as a ​nucleophile​.

To Produce Alkenes
Halogenoalkanes can react with ​ethanolic potassium hydroxide​ (KOH) to produce ​alkenes ​in
an ​elimination ​reaction. The ​hydroxide ion​ acts as a ​base​.

Hydrolysis with Silver Nitrate


Halogenoalkanes can be​ broken down​ in their reaction with ​aqueous silver nitrate and
ethanol. ​The ​water ​in the solution acts as a ​nucleophile ​which leads to the break down of the
halogenoalkane, releasing the halide ions into the solution. The ​halide ions​ then react with the
silver ions​ from silver nitrate to form ​silver precipitates​.

The ​colour ​of the precipitate allows you to identify the halide ion present. The rate at which the
precipitates forms allows you to identify the ​relative stability​ of the halogenoalkanes, because
the faster the precipitate forms, the ​less stable​ the halogenoalkane, and therefore the more
quickly it is ​hydrolysed​.

Cl​- Br​- I​-

White precipitate Cream precipitate Yellow Precipitate


(AgCl) (AgBr) (AgI)

Reactivity ​depends on the ​strength ​of the ​C-X bond ​(where X is a halogen atom) and not the
bond polarity. Bond strength ​decreases ​with ​increasing Mr​. Therefore, iodoalkanes would
react faster than bromoalkanes and chloroalkanes, and bromoalkanes would react faster than
chloroalkanes.

To Produce Amines
Halogenoalkanes can react with ​alcoholic ammonia​ (for example, with ethanolic NH​3​) to form
amines ​in a​ nucleophilic substitution ​reaction. ​Ammonia ​acts as a ​nucleophile​.

To Produce Nitriles
Halogenoalkanes can react with ​alcoholic potassium cyanide ​(KCN) to form ​nitriles ​in a
nucleophilic substitution ​reaction. The ​cyanide ion, CN​-​, acts as a ​nucleophile​. This
reaction adds on a carbon atom, so it can be used in synthesis routes to increase the length of
carbon chains.

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Nucleophilic Substitution

Nucleophiles
These species are ​‘positive liking’​. They contain a lone electron pair that is attracted to​ ∂+
regions ​of molecules. Some of the most common nucleophiles are:

● CN​:-​
● :​NH​3
-​
● :​OH

They must be shown with the ​lone electron pair ​indicating they are nucleophiles.

Nucleophilic Substitution
This is the reaction mechanism that shows how nucleophiles attack halogenoalkanes. Starting
from halogenoalkanes, aqueous potassium hydroxide is the reactant used to produce ​alcohols,
potassium cyanide is the reactant used to produce ​nitriles​ and ammonia is the reactant used to
produce​ amines​.

The ​greater the Mr​ of the halogen in the polar bond, the ​lower the bond enthalpy​ meaning it
can be broken more easily. Therefore the rate of reaction for these halogenoalkanes is faster.
Nucleophilic substitution reactions can only occur for ​1o​​ (primary) and 2​o​ (secondary) ​alkanes.

Mechanism - Formation of alcohols

The nucleophile attacks the ∂+ carbon and the electrons are transferred to the chlorine.

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Mechanism - Formation of amines

The intermediate has a positively charged nitrogen (N+​ ​).


Electrons are transferred to the nitrogen by the loss of a hydrogen atom.

Topic 6E: Alcohols


Introduction to Alcohols

Alcohols contain an ​-OH functional group​ and follow the general formula ​C​n​H​2n+1​OH​. They can
be produced via two main methods of fermentation or hydration. Alcohols are named according
to ​IUPAC​ rules and have the suffix -ol. Alcohols can be ​primary (1​o​), secondary (2​o​) ​or ​tertiary
(3​o​)​ depending on the position of the hydroxyl group.

Example:

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Hydration
This method produces ​alcohols from alkenes​ in the presence of an ​acid catalyst, ​such as
phosphoric acid. The reaction is also carried out in ​aqueous conditions at 300​o​C​ and under
high pressures.

Example:

This process has a ​very high percentage yield​ as ethanol is the only product. Therefore the
hydration method is favoured as an industrial process.

Fermentation
In this process, enzymes break down the starch in crops into ​sugars​ which can then be
fermented to form alcohol​. This method is ​cheaper​ than hydration as it can be carried out at a
lower temperature. However, the reaction is carried out in ​batches​, meaning it is a much slower
process with a ​lower percentage yield​.

Ethanol is a common ​biofuel​ produced in this way. It is said to be ​carbon neutral​ as the
amount of carbon dioxide given out when it is burned is equal to the carbon dioxide taken in by
the crops during the growing process.

Example:

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Reactions of Alcohols

Combustion
When burned in air, alcohols react with ​oxygen ​to form​ carbon dioxide ​and ​water​. Alcohols
make good fuels by reacting in this way as lots of ​energy ​is also released.

Example:

Reactions with Halogenating Agents


Alcohols can react with ​halogenating agents​ via ​nucleophilic substitution. ​The ​-OH​ group is
replaced by a ​halogen​, producing a ​halogenoalkane​.

PCl​5​ is used to produce ​chloroalkanes​. This can be used as a ​test for alcohols ​because their
reaction with PCl​5​ produces ​white steamy fumes​ that turn damp blue litmus paper red.

A reaction mixture of 50% concentrated ​sulfuric acid​ and ​potassium bromide​ can be used to
produce ​bromoalkanes. ​The potassium bromide reacts with the sulfuric acid to form HBr. This
then reacts with the alcohol to produce the bromoalkane.

CH​3​CH​2​OH + HBr → CH​3​CH​2​Br + H​2​O

A reaction mixture of ​red phosphorus​ with iodine can be used to produce ​iodoalkanes​. First,
the phosphorus reacts with the iodine to produce ​phosphorus(III) iodide​. This then reacts with
the alcohol to form the iodoalkane.

2P + 3I​2​ → 2PI​3

3CH​3​CH​2​OH + PI​3​ → 3CH​3​CH​2​I + H​3​PO​3

Elimination Reactions
Alkenes can be formed from the ​dehydration of alcohols​, where a molecule of ​water is
removed​ from the molecule. In order to do this, ​concentrated phosphoric acid​ is added as a
reagent.

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Oxidation of Alcohols

Primary ​and​ secondary ​alcohols can be ​oxidised​ to produce various products but​ tertiary
alcohols are​ not easily oxidised​.

When primary alcohols are heated in the presence of ​acidified potassium dichromate(VI)​,
they are ​oxidised ​to​ ​aldehydes​.​ ​Distillation​ is required to separate the ​aldehyde​ product

Example:

When heated under ​reflux​ conditions, primary alcohols are ​oxidised further​ to ​carboxylic
acids​.

Example:

Secondary alcohols can be oxidised in the presence of ​acidified potassium dichromate​ to


produce ​ketones​.

Example:

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Potassium Dichromate (K​2​Cr​2​O​7​)
Potassium dichromate(VI) is used in the oxidation of alcohols as the ​oxidising agent​. It is
reduced as the alcohol is oxidised. A colour change from ​orange to green​ is observed when
the alcohol is oxidised with potassium dichromate(VI).

Example:

Test for Aldehydes


Aldehydes are tested for using​ Benedict’s/F​ehling’s solution.

A few drops of ​Fehling’s solution​ are added and the test tube is gently warmed. If an aldehyde
is present a ​red precipitate​ will form. If no aldehyde is present the solution will remain ​blue​.

Ketones​ will not give a positive result when added to Benedict’s/Fehling’s solution.

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Experimental Techniques

There are many different techniques that can be used to ​prepare ​and then ​purify ​an organic
compound.

Heating under Reflux


Reflux apparatus is used to ​continually heat​ the contents of the flask to allow reactions like the
oxidation​ of primary alcohols to proceed all the way to the formation of carboxylic acids. The
condenser​ helps ensure the vapours condense and ​return ​to the flask for further heating. This
ensures the product vapours can not escape.

Separating Funnel
A separating funnel is used to separate two liquids with​ different densities​. The mixture is
added to the flask and the liquids are allowed to ​separate ​into​ two layers​. The tap can then be
opened to collect the bottom, denser liquid in one flask and the second, less dense liquid in a
second flask.

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Distillation
Distillation apparatus is used to separate liquids with ​different boiling points​. The pear-shaped
flask is heated and the liquid with the lower boiling point will ​evaporate ​first. It rises out of the
flask and into the attached tubing which is surrounded by a condenser. The condenser causes
the vapour to ​cool and condense​ back into a liquid, which is then collected in a separate flask.

Drying
A compound can be dried by the addition of an ​anhydrous ​(contains no water) ​salt.​ The
anhydrous salt will ​absorb moisture and water​ present, thus drying and purifying the
compound. A common anhydrous salt used for drying is ​sodium sulphate.

Boiling Point Determination


Finding the boiling point of a compound and comparing it to a databook value is a way of testing
its ​purity​. The purer a substance, the ​closer ​to the databook boiling point value it will be. If a
sample has a low purity, the melting/boiling point will take place over a ​range​ of temperatures.

To determine the boiling point, the substance is packed into a ​Thiele tube​ which has an
inverted capillary tube​ in it. The substance is heated to above its boiling point and allowed to
cool. When it ​condenses ​into a liquid it will be drawn into the capillary tube and the temperature
at which this change occurs is taken to be the boiling point.

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