CIE AS Chemistry: 21.1 Organic Synthesis

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CIE AS Chemistry Your notes
21.1 Organic Synthesis

Contents
Organic Synthesis
Multi-Step Synthesis
Synthetic Routes
Page 1 of 17
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Organic Synthesis
Your notes
Elucidating Organic Molecules
You are expected to be able to identify organic functional groups, their properties, how to test
for their presence and how they are made
Functional groups
The table below summarises the tests to identify the presence of certain functional groups and
the reactions to make them
Functional groups, their reactions & identifying tests table
Functional Group Test Production
Hydrogenation of alkenes using

H2 , Pt/Ni catalyst and heat
Alkane
Cracking of crude oil using heat
and Al2 O 3 catalyst
Elimination of halogenoalkanes
by heating it with NaOH(ethanol)
Dehydration of alcohols using
Alkene Decolourises bromine water hot Al2 O 3 catalyst
Cracking of crude oil using heat
and Al2 O 3 catalyst
Fee-radical substitution of
alkanes using UV and a halogen
Electrophilic addition of
Form silver halide precipitate hydrogen halides to alkenes
Halogenoalkane with dilute nitric acid, silver
nitrate and dilute ammonia Nucleophilic substitution of an
(primary, secondary and tertiary) alcohol, e.g. by reaction with HX
solution (AgCI = white, AgBr =
cream and AgI = yellow) (g) or with KCl and concentrated
H2 SO 4 or concentrated H3PO 4
or with PCl3 and heat or with
PCl5 or with SOCl2
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Alcohol React with carboxylic acid and Electrophilic addition of alkenes

sulfuric acid to make esters using hot steam, concentrated
(primary, secondary and tertiary) which have fruity smells phosphoric(VI) acid as a catalyst Your notes
Primary alcohols get oxidised to Oxidation of alkenes using cold,
aldehydes (give positive test dilute KMnO 4 to form a diol
with Fehling's and Tollens'
solution and carboxylic acids Nucleophilic substitution of
halogenoalkanes using heat and
Secondary alcohols are NaOH (aq)
oxidised to ketones (positive
test with 2,4-DNPH but not Reduction of aldehydes and
Fehling's and Tollens' solution) ketones using NaBH4 and LiAlH4
(aldehydes are reduced to
Tertiary alcohols can not be primary alcohols and ketones are
oxidised reduced to secondary alcohols)
Reduction of carboxylic acid
using LiAlH4
Hydrolysis of esters using dilute
acid or dilute alkali
Silver mirror in Tollens' reagent

and red precipitate in Fehling's Oxidation of primary alcohols by
solution reagent and red slowly adding
Aldehyde warm alcohol to acidified
Orange precipitate with 2,4- K2 Cr2 O 7 or KMnO 4 and
DNPH distillation
Oxidation of secondary
alcohols by reagent and red
Orange precipitate with 2,4-
Ketone slowly adding warm alcohol to
DNPH
acidified K2 Cr2 O 7 or KMnO 4 and
distillation
Carboxylic Acid React with carbonates to form Oxidation of aldehydes and
CO 2 gas which will turn limewater ketone acidified K2 Cr2 O 7 or
cloudy KMnO 4 and refluxing
Hydrolysis of nitriles with dilute
acid or dilute alkali followed by
acidification
Page 3 of 17
Hydrolysis of ester with dilute

acid or dilute alkali followed by
acidification Your notes
Condensation reaction of
alcohols and carboxylic acids
Ester Have sweet, fruity smells
with hot, concentrated H2 SO 4 as
catalyst
Nucleophilic substitution of
Turns universal indicator blue / halogenoalkanes when heated
Amine
purple under pressure with NH3
(ethanol)
Nucleophilic substitution of
halogenoalkanes when heated
Nitrile
under pressure with KCN
(ethanol) and heat
Types of reactions
You should also be aware of the different type of reactions that functional groups can undergo
Reactions of functional groups table
Type of reaction Definition Reagents Products
The addition of alkenes

Hydrogenation H2 , Pt / Ni catalyst Alkanes
with hydrogen
The process in which
large, less useful
hydrocarbon molecules
Cracking are broken down into Al2 O 3 catalyst and heat Alkanes and alkenes
smaller, more useful
molecules in an oil
refinery
Free-radical The reaction in which Halogen and UV light Halogenoalkane
substitution halogen atoms
substitute for hydrogen
atoms in alkanes, The
mechanism involves
steps in which reactive
Page 4 of 17
free radicals are

produced (initiation),
regenerated Your notes
(propagation) and
consumed (termination)
The mechanism of the
reaction in which an
Electrophile (eg. Br2 ,
electrophile attacks the
Electrophilic Addition NaOH, KCN, NH3 and Halogenoalkane
C=C bond and addition
HBr)
across the double bond
occurs
reaction in which a
nucleophile attacks the
Halogenoalkane,
Nucleophilic Addition carbon atom in a Nucleophile (e.g. HCN)
alcohol, nitrile or amine
carbonyl group and
addition across the
C=O bond occurs
The replacement of an
atom by another atom or
Electrophilic group of atoms after Electrophile (eg. Br2 ,
Substitution initial attack by an NaOH, KCN, NH3 and HBr
electron—deficient
species
organic reaction in
which a nucleophile
attacks a carbon atom
carrying a potential
Nucleophilic
positive charge. This Nucleophile (eg. HCN)
Substitution
results in the
replacement of an atom
carrying a partial
negative charge by the
nucleophile
The loss of electrons or Oxidising agent such as Alcohol, aldehyde,
Oxidation gain of oxygen of an acidified K2 Cr2 O 7 or ketone or carboxylic
atom, ion or molecule KMnO 4 acid
The gain of electrons or Alkene, aldehyde,
Reducing agent such as
Reduction loss of oxygen of an primary and secondary
NaBH4 or LiAlH4
atom, ion or molecules alcohol, carboxylic acid
Page 5 of 17
Hydrolysis The breakdown of a Water or dilute acid or

compound by water or alkali
by dilute acids or alkali Your notes
A reaction in which two
organic molecules join
together an din the
Two molecules that can Small molecule and a
Condensation process eliminate a
react with each other larger molecule
small molecule such as
water or hydrogen
chloride
.
Oxidising & reducing agents

Certain functional groups only react with specific oxidising and reducing agents which you
should be aware of
Oxidising & reducing agents table
Oxidising Agent
Oxidises Oxidation Product Colour Change
Aldehydes then
Primary alcohols Orange to green
carboxylic acids
Secondary alcohols Ketones Orange to green

Acidified potassium
dichromate (K2 Cr2 O 7 / Tertiary alcohols X
H2 SO 4)
Aldehydes Carboxylic acids Orange to green
Ketones X
Acidified potassium Aldehydes then

permanganate Primary alcohols Purple to colourless
carboxylic acids
(K2 Mn2 O 4 / H2 SO 4)
Secondary alcohols Ketones Purple to colourless
Tertiary alcohols X
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Aldehydes Carboxylic acids Purple to colourless Your notes
Ketones X
Alkenes Diol Purple to colourless
Reducing Agent
Reduces Reduction Product
Carboxylic acids X
Aldehyde Primary alcohol

Sodium borohydride (NaBH4)
Ketone Secondary alcohol
Alkene X
Carboxylic acids Aldehyde then primary alcohol
Aldehyde Primary alcohol

Lithium aluminium hydride (LiAlH4)
Ketone Secondary alcohol
Alkene X
Hydrogen and Pt / Ni Catalyst

(H2 , Pt / Ni catalyst) Carboxylic acids X
Aldehyde X
Ketone X
Page 7 of 17
Alkene Alkane
Your notes
Tests
The test also requires you to distinguish between the different tests that identify functional
groups in a compound
Tests identifying functional groups in a compound table
Functional Group Tested Colour Change
Clear blue solution turns opaque

Fehling's Solution Aldehydes red/orange as a precipitate is
formed
Tollens' Reagent Aldehydes Silver mirror
Bromine water changes from

Bromine water Alkenes
orange/yellow
2,4—dinitrophenylhydraz ine (2,4 Carbonyl compounds
Orange precipitate
—DNPH) (aldehydes and ketones)
Yellow precipitate of
lodoform Methyl ketone (CH3CO—) group
triiodomethane
AgCl = white AgBr = cream & Agl =
Silver nitrate and ammonia Halogens
yellow
Page 8 of 17
Worked example
Your notes
Identify which tests give positive results with the following compounds and which oxidising and
reducing agents the compounds react with.
Answers:
Page 9 of 17
Your notes
Page 10 of 17
Your notes
Page 11 of 17
Multi-Step Synthesis
Your notes
Multi-step Synthetic Routes
Many organic molecules are made in multi-step synthetic routes
You should be able to recall the different reactions each functional group undergoes and apply
this knowledge when devising multi-step synthetic routes for preparing organic molecules
Page 12 of 17
Worked example
Your notes
Devise multi-step synthetic routes for preparing the following organic molecules from propan-1-
ol
1. 2-hydroxybutanoic acid
2. Ethyl propanoate
3. Sodium propanoate salt
Answers:
1. 2-hydroxybutanoic acid
2. Ethyl propanoate
Page 13 of 17
Your notes
3. Sodium propanoate salt
Page 14 of 17
Your notes
Page 15 of 17
Synthetic Routes
Your notes
Analysis of Synthetic Routes
Worked example
The synthesis of compound X takes place in 2 steps:
OHCCH2 CHO step 1 step 2

⎯⎯⎯⎯⎯⎯ intermediate ⎯⎯⎯⎯⎯⎯ HO2 CCH(OH)CH2 CH(OH)CO2 H
compound X
Which reagents could be used for this synthesis?
Answer:
The first step involves a nucleophilic addition of CN- using NaCN as catalyst and heat to form
a hydroxynitrile
In the second step, the nitrile is refluxed with dilute aqueous sulfuric acid causing hydrolysis
of the nitrile forming a carboxylic acid and ammonium salt
Page 16 of 17
Worked example
Your notes
The synthesis of hexanoic acid takes place in 2 steps
1-chloropentane reagent X compound Z reagent Y hexanoic acid

⎯⎯⎯⎯⎯⎯⎯⎯⎯ ⎯⎯⎯⎯⎯⎯⎯⎯⎯
Which reagents could be used for this synthesis?
Answer:
Halogenoalkanes can undergo nucleophilic substitution with ethanolic KCN in which the
CN- ion acts as a nucleophile and replaces the chlorine atom in 1-chloropentane to form a
nitrile.
The treatment of nitriles with concentrated hydrochloric acid will produce a carboxylic acid
and an ammonium salt.
In this case, hexanoic acid and ammonium chloride will be formed.
Page 17 of 17

CIE AS Chemistry: 21.1 Organic Synthesis

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CIE AS Chemistry Your notes

21.1 Organic Synthesis

Functional Group Test Production

Hydrogenation of alkenes using

Alcohol React with carboxylic acid and Electrophilic addition of alkenes

Silver mirror in Tollens' reagent

Hydrolysis of ester with dilute

Type of reaction Definition Reagents Products

The addition of alkenes

free radicals are

Hydrolysis The breakdown of a Water or dilute acid or

Oxidising & reducing agents

Oxidises Oxidation Product Colour Change

Secondary alcohols Ketones Orange to green

Acidified potassium Aldehydes then

Aldehydes Carboxylic acids Purple to colourless Your notes

Alkenes Diol Purple to colourless

Reduces Reduction Product

Aldehyde Primary alcohol

Carboxylic acids Aldehyde then primary alcohol

Aldehyde Primary alcohol

Hydrogen and Pt / Ni Catalyst

Functional Group Tested Colour Change

Clear blue solution turns opaque

Tollens' Reagent Aldehydes Silver mirror

Bromine water changes from

3. Sodium propanoate salt

OHCCH2 CHO step 1 step 2

1-chloropentane reagent X compound Z reagent Y hexanoic acid

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