1

B15

Medicines by Design..
Revision of reagents, conditions and
reaction types.

Click to go to a particular section……

 Aliphatic chemistry reagents and conditions

 Aliphatic chemistry reaction types
 Aromatic chemistry reagents and conditions
 Aromatic chemistry reaction types
 Key words and definitions.
 A10. Aliphatic Reactions. Add the 2
reagents and conditions.

O
9 O
R H 2 9 7 O
R C R C
C R CH2 OH
C H R C O R'
9 OH
H H
X10 8

Heat + reflux
SCl2O
4
5

O
6 O
R CH2 Br R CH2 CN R C
R C
1 NaCN in ethanol/H2O Cl
NH2
Heat + reflux

 Print a hard copy of this

Heat + reflux
Dil H2SO4

6 page
3 4  Add reagents and
conditions to the arrows
 Using the hyperlinks will
O direct you to the relevant
R C Notes
R CH3 R CH2 NH2 R CH2 COOH NH R'  Click here to check your
answers once you have
finished.
 3

A12. Aliphatic reagents and conditions

X12
O
R O
H O
R C R C
C C Click
R here
CH2
toOHgo back to the menu H R C O R'
OH
H H

O
O
R CH2 Br R CH2 CN R C
R C
Cl
NH2

 Print some hard copies

of this page to practice
reagents and conditions

R C
R CH3 R CH2 NH2 R CH2 COOH NH R'

Click here to go back to the menu

 4

A11. Aliphatic reagents and conditions

X11
K2Cr2O7(aq)/dil H2SO4
K2Cr2O7(aq)/dil H2SO4 heat + reflux
heat + reflux O R’OH/conc H2SO4 cat
Al2O3 O Heat + reflux
R H 300oC
O
R C R C
C R CH2 OH Dil HCl or H2SO4 or
C H
NaOH R C O R'
OH
H H NaBH4 Heat + reflux
Room temp
Heat + reflux
NaOH(aq)

Heat + reflux
SCl2O
reflux
heat +

p
m
tem
H2SO4

O te
Ro p

R’ oom
Co om + conc

R
nc NaBr(s)
HB
r
150oC + 5 atm
H2/Ni cat

O Conc NH3
Room temp O
R CH2 Br R CH2 CN R C
R C
NaCN in ethanol/H2O Cl
NH2
Heat + reflux

Br2(l)  Print a hard copy of

sunlight
this page
Heat + reflux
Dil H2SO4

Room temp
 Learn the reagents and
Heat + reflux

R’NH2
Conc NH3

conditions
 Click here to go to a blank
copy of this page to
practice with
O

R C
R CH3 R CH2 NH2 R CH2 COOH NH R'

Click here to go back to the menu

 5

X13 A13. Aliphatic Reactions. Add the reaction types.

O
R O
H O
R C R C
C R CH2 OH
C H R C O R'
OH
H H
150oC + 5 atm
H2/Ni cat

O
O
R CH2 Br R CH2 CN R C
R C
Cl
NH2

 Print a hard copy of

this page
 Add the reaction types
to the arrows
 Click here to go to the
Key words and
O
definitions for help
R C
R CH3 R CH2 NH2 R CH2 COOH NH R'
your answers once you
have finished.
 6

A14. Aliphatic Reaction types

X14 Esterification or
O condensation
Elimination or Oxidation Oxidation O
R H dehydration O
R C R C
C R CH2 OH
C H R C O
H H substitution Click here Reduction
to go back to the menu OH Hydrolysis
R'

Nucleophilic

Nucleophilic
substitution or
ution
acylation
substit
Electrophilic c
addition ophili
Nucle

Nucleophilic
hydrogenation
Addition or

O substitution or
acylation O
R CH2 Br R CH2 CN R C
R C
Nucleophilic Cl
NH2
substitution

Substitution or
Nucleophilic
Hydrolysis

Radical  Print a hard copy of this

Nucleophilic
substitution

acylation
substitution page
 Learn the reagents and
conditions
 Click here to go back to
O a blank page that you
R C can print off a few
R CH3 R CH2 NH2 R
times to help you
CH2 COOH NH R'

practice
 7

Click here to go back to the menu

 8

A1. The addition reactions of alkenes with the following:

bromine, hydrogen in the presence of a catalyst, hydrogen
bromide, and water in the presence of a catalyst.

CI 12.2

Ethene is unsaturated it has a double C to C bond. It undergoes electrophilic addition reactions in

which another molecule is added on. A saturated compound is produced.

a. Ethene with bromine (g) or (l) or dissolved in an organic solvent.

Ethene will decolourise orange bromine; it reacts rapidly to form a colourless compound. This
occurs at room temperature.
H H
H2C CH2(g) + Br Br(g) H C C H(l)
Br Br
1,2-dibromoethane (colourless)

R
(reagent) is Br2(g) or Br2(l) or Br2 in an organic solvent. (NB Salters includes catalysts in this
category if required)

C
(conditions) are room temperature. (NB Salters includes pressures here if required).

b. Ethene with Bromine water Br2(aq)

H H
H2C CH2 (g) + Br2 (aq) + H2O(l) H C C H (l) + HBr(aq)

(orange) Br OH
a bromoalcohol (colourless)
Bromine water (bromine dissolved in water) is more convenient and safer to use as a test of
unsaturation, than bromine(g) or bromine(l) or bromine dissolved in an organic solvent such as
cyclohexane.

R
(reagent) is Br2(aq)

C
(conditions) are room temperature.

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 9

C. Ethene with concentrated hydrobromic acid, HBr(aq)

CH2 CH2 + HBr CH3 CH2Br

Bromoethane (now saturated)

R
conc. HBr(aq)

C
room temperature.

d. Ethene with hydrogen(g) Hydrogenation

CH2 CH2 + H2 CH3 CH3

ethane

R
H2(g) and Ni (or Pt) catalyst, finely powdered

C
1500C and 5 atm with the Ni. (or room temp. and pressure with the Pt).
NB Pt is white gold:- very expensive

e. Ethene with water H2O(g) (it is steam at 3000C)

The catalyst is phosphoric acid absorbed onto silica ( I imagine silica as being like pure white
sand and that it is soaked in the acid which is a liquid).

CH2 CH2 + H2O CH3 CH2OH

ethanol

R
H2O(g) cat. Phosphoric acid absorbed onto silica.

C
3000C and 60 atmospheres pressure.

Note:
 Reactions a,b,c,d, and e are all examples of addition reactions.
 Reactions a, b, c and e are examples of electrophilic addition reactions.
 Reaction d involves a catalyst and has a different mechanism.

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 10

The mechanism of the electrophilic addition reaction between

bromine and alkenes.

CI 12.2

Mechanism for reaction in a above

H H
curly arrows
C C
show movement of a H
pair of electrons. H H + H

Br 
H C C + Br
H
Br
Br 
a carbocation and a bromide ion
 The bromine molecule is polarised i.e. it has a + and a -
atom, like when the bond is polar. This happens because the The carbocation has a C with a
electrons in the Br2 molecule are repelled by the electrons positive charge.
in the C=C. That C had a half share of the two
 The Br + end now acts as an electrophile. Electrophiles electrons in the bond, which was
are attracted to a negatively charged region (the C=C is broken.
made up of 4 electrons) and go on to accept a pair of It now has no share
electrons (2 points in the definition). of that pair.
-
It is now a C atom with one less e so
it has a single + charge.

NB philic means like

phobic means hate

 The bromide ion is written Br

 One of the lone pairs has come from the bond in the Br2 molecule.
 It had a share of the bonding pair, but now has both electrons.
 It has now overall gained an electron, so the Br atom now has a - charge.

Then we have the next step:

H H H
H
+
H C C H C C H
Br H Br Br
1,2-dibromoethane
Br

This is electrophilic addition. It is very important that you understand this mechanism and are
able to explain it. The other reactions of ethene proceed by a similar mechanism.
 11

A2. The dehydration of alcohols to form alkenes.

CI 13.4

In a dehydration reaction, a molecule of water is lost. Sometimes, this is called an elimination reaction.
Saturated  Unsaturated
This is the reverse of an addition reaction.
What are the alternative reagents and conditions for this reaction?
E.g. CH3CH2OH  CH2=CH2 + H2O
Reagents: Ethanol passed over
alumina (Al2O3) catalyst.
Conditions: 300oC

NB Phenols and carboxylic acids do not undergo dehydration reactions.

The meaning of the term elimination reaction.

CI 13.4

In an elimination reaction, a small molecule (e.g. water) is lost. Dehydration of alcohols are elimination
reactions.

Write 2 equations for the elimination of water from propan-1-ol. In the first, use full structural
formulae. In the second, use skeletal formulae.

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 12

A3. The reaction of alkanes with halogens.

CI 6.3

Examples: CH4 + Cl2  CH3Cl + HCl :equation (1)

C6H14 + Br2  C6H13Br + HBr

These are both radical substitution reactions where the halogen replaces hydrogen. This type of
reaction leads to a mixture of halogen substituted products because we cannot control the radicals that
are produced.

Mixture of products
The reaction of methane (CH4) with chlorine in the presence of sunlight proceeds via a radical chain
reaction. The overall equation for the reaction is equation (1) above.

Complete the reaction mechanism below:

Initiation:
Cl2 h 2Cl.

Propagation:
CH4 + Cl.  CH3. + HCl
CH3. + Cl2  CH3Cl + Cl. (chloromethane made)
CH3Cl + Cl.  CH2Cl. + HCl
CH2Cl. + Cl2  CH2Cl2 + Cl. (dichloromethane made)

Termination:
 Back to map 13

A4. Nucleophilic substitution reactions of the

halogenoalkanes with hydroxide ions and ammonia.
CI 13.1, Act A4.1b
The feature of a halogenoalkane molecule that allows it to undergo substitution reaction is the presence
of a polar bond between the halogen atom and the carbon atom to which it is bonded. The halogen
atom is slightly negatively charged and the carbon atom is slightly positively charged. This carbon
atom is attacked by nucleophiles.

+ -
C Br

Why is the carbon – halogen bond polar?

Complete this table for 2 common nucleophiles:

Formula Structure Reaction Organic product
(inc. lone pairs)
OH - _ ..
:O:H R-X + OH-  R-OH + X- Alcohol
..
NH3 Amine

The mechanism of nucleophilic substitution in halogenoalkanes.

CI 13.1

In general:

where X – is any nucleophile and the curly arrow shows the movement of a pair of electrons.
The C – Hal bond will break heterolytically !

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 14

A5. An outline of the preparation of a halogenoalkane from

an alcohol.
Act A4.2
One way to make a halogenoalkane is to start with an alcohol and replace the – OH group by a
halogen atom.

Reaction in Activity A4.2:

CH 3
CH 3

CH 3 C OH + H Cl CH 3 C Cl + H2O

CH 3 CH 3

2 – methylpropan – 2 – ol 2 – chloro – 2 methylpropane

This is an example of nucleophilic substitution – the alcohol group is first protonated in the strongly
acid solution before it can be displaced by the Cl – nucleophile ( water is lost).

Give the mechanism for this reaction: (CI 13.1, page 303 may help)

R NaBr(s) and concentrated H2SO4

C Heat and reflux

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 15

A6. Amines can act as nucleophiles with acyl chlorides

CI 13.8

ammonia / amines react with acyl chlorides:

ammonia + acyl chloride primary amide + HX

primary amine + acyl chloride secondary amide + HX

These are nucleophilic substitution reactions.

Complete the following equations;

O
H N H + +
Cl C CH3
H
primary amide
ammonia an acylchloride

O
CH3 N H + Cl C CH3 +
H

methylamine an acylchloride secondary amide

(a primary amine)

These reactions are very vigorous even at room temperature.

-
+
O The C has two more electronegative
groups attached so
they are very attractive to nucleophiles
CH3 C e.g. NH3, amines.
-
Cl

The reactions of amines and acyl chlorides are sometimes called acylation
reactions.
 16

Back to map

A7. Ester formation from alcohols or phenols

CI 13.5

Esters are named after the alcohol and the acid from which they are made:

Complete the following table:

Acid Alcohol Resulting Ester

O H
H C
O C H
H
methyl methanoate

H H O H
H C C C H C OH
H H OH H
propanoic acid methanol

O H H H
H C
OH H C C C OH
methanoic acid H H H
propan-1-ol
 17
Back to map

Examples:

Acid + alcohol ester + water

water

H O
O H
a.
H C
3
C + H C OH
H C
3
C + H O
O CH
OH 3
H
ethanoic acid + methanol methyl ethanoate + water

b. H H O
O H H
H C
3
C + H C C OH
H C
3
C + O
OH O CH CH
2 3
H H
ethanoic acid
+ ethanol ethyl ethanoate
+ water
c. H H H
O O
H3C C + H C C C OH H3C C
+ H O H
OH H H H O CH2 CH2 CH3

ethanoic acid + propanol propyl ethanoate + water

N.B. All of these reactions in which esters are made are reversible reactions.
 The forward reaction is called esterification
 The backward reaction is called hydrolysis. In Act WM2, an ester was hydrolysed. The catalyst
was sodium hydroxide solution.

When making an ester using a phenol rather than an alcohol, a more vigorous reagent than a carboxylic
acid is needed. The OH group in a phenol is less reactive than the OH group in an alcohol.

Method 1
O
HO
OH + C CH3 O C CH3 + H2O
O
Phenol + carboxylic acid ester +water

(conc. H2SO4 catalyst and heat under reflux is needed even with an alcohol).

Back to map
 18

Method 2
O
C CH3 O HO
OH + O O C CH3 + C CH3
C CH3 O
O

Phenol + acid anhydride ester + carboxylic acid

(This does not need heat and reflux. It is reactive but not too dangerous. This method was used to make
aspirin in WM.)

Method 3
O
Cl
OH + C CH3 O C CH3 + HCl
O

Phenol + acyl chloride ester + hydrochloric acid

(Faster but ethanoyl chloride is toxic and hazardous as it is so very reactive.)

Why do you think both methods 2 and 3 must be carried out in the absence of
water?

Both acid anhydrides and acyl chlorides are called acylating agents:

O
-OH on alcohol or on phenol is replaced by R C in the ester. This is an acyl group.
O

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 19

A8. The hydrolysis of esters

CI 13.5

The reverse of esterification is hydrolysis. Hydrolysis is bond breaking involving water.

H H O
O
H C C + H O
H H C C OH + H C
3
C
3 OH
O CH CH H H
2 3
Ethyl ethanoate + water ethanol + ethanoic acid

On hydrolysis, the sweet smell of the ester disappears. To speed up this reaction NaOH(aq) is often
used, when heating under reflux. This reaction was used in the hydrolysis of Oil of Wintergreen in
WM.

What ion is produced instead of ethanoic acid if NaOH(aq) is used as a catalyst?

Give name and full structural formula.

What needs to be added now to produce ethanoic acid from the ethanoate ion?

A9. The following reactions involving aldehydes and ketones:

formation by oxidation of alcohols, oxidation to carboxylic
acids and reduction to alcohols.

CI 13.7

Recognising aldehydes and ketones.

Aldehydes and ketones are both carbonyl compounds which have the carbonyl group:

O
Back to map
C
 20

Aldehydes are made when a primary alcohol is oxidised.

examples: H O
(2 C’s => eth suffix al)
H C C H
23 24

H
ethanal
H H O (3 C’s => prop, suffix al)
H C C C H
H H
propanal
In aldehydes the carbonyl group is always on the end of the C chain so no number is required in the
name.

Ketones are made when a secondary alcohol is oxidised.

O
examples:
H3C C CH3
41

propanone
(The carbonyl group is midway along the carbon
H H H O H chain. A number may be required to show which
C C C C H C atom has the carbonyl group)
H C 45 46 47 48
44

H H H H
pentan-2-one

Formation of aldehydes and ketones from alcohols.

Remember a triangle!

1ry alcohol oxidation aldehyde oxidation carboxylic acid

2ry alcohol oxidation ketone
3ry alcohol
A good oxidising agent is acidified potassium dichromate (VI) solution.
Back to map
Here is the half equation showing what happens to the dichromate ions:
Cr2O72- + 14H+ + 6e-  2Cr3+ + 7H2O
6+ (acid) 3+
orange green
This is the half equation for the oxidation of ethanol:
CH3-CH2-OH + H2O  CH3CHO + 2H+ + 2e-

Combine the 2 half equations above and write an overall

equation for the redox reaction:
 21

Definitions of oxidation are:

 Gain of oxygen
 Loss of hydrogen
 Loss of electrons
 Increase in oxidation number.

Give four definitions of reduction:

Is the chromium in the half equation above oxidised or reduced?

A closer look at the reaction of the 1ry alcohol:

H H H
H
O O
H C C OH H C C H C C
H OH
H H Back to map H H

1ry alcohol a aldehyde b carboxylic acid

Why are both of these steps described as oxidation?

a.

b.
 22

A closer look at the reaction of a 2ry alcohol:

H H H
H H H

C C H H C C OH
H C C C H H C

H H O H H O
H OH

2ry alcohol ketone carboxylic acid

Why doesn’t oxidation of the ketone occur?

A closer look at the reaction of a 3ry alcohol:

H

H C H
H H
H H

H C C C H
H C C C H

H O H
H OH H
3ry alcohol ketone

Why doesn’t oxidation of a 3ry alcohol occur?

NB. Phenols and carboxylic acids are not oxidised either!

Back to map
It is important that you can quote the reagents and conditions for these oxidations:
Reagents – K2Cr2O7(aq), dilute HCl(aq) or dilute H2SO4(aq)
Conditions – Heat and reflux.
If oxidation occurs, there will be a colour change from orange to green.

Reduction of carbonyls to alcohols.

 23

Aldehyde  1ry alcohol R = NaBH4(aq) Name the reagent:

Ketone  2ry alcohol C = room temperature

Give the formulae of the carbonyl componds which would be reduced to these alcohols:

This would be reduced to the alcohol on the

right…..
OH CH3

CH3 CH2 CH CH CH3

This would be reduced to the alcohol on the

right…..
CH3

CH3 C CH2 OH

CH3

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 25
Aromatic. Add the reagents and conditions.  Print a hard copy of this
page
Br Cl
 Add reagents and
conditions to the arrows
 Using the hyperlinks will
R7 direct you to the
1 relevant Notes
H2(g), Ni cat 1
 Click here to check your
300oC, 30 atm.
answers once you have
finished

SO2OH 3. 2 NO2 Sn + conc HCl NH2

Heat + reflux

6
5
4

+
N N Cl-

R
C
R 6

Click Nhere to
N
go back to theOH
menu
 26
Aromatic reagents and conditions

Br Cl
 Print a hard copy of this page
 Learn the reagents and
conditions
R8  Click here to go to a blank page
Br2(l), FeBr3 cat to print off and practice with
H2(g), Ni cat room temp. Cl2(g), AlCl3 cat
300oC, 30 atm. room temp/ anhydrous

conc. H2SO4. Sn + conc HCl

SO2OH heat + reflux. conc. HNO3, conc. H2SO4 cat NO2 Heat + reflux NH2
<55oC.

NaNO2(aq)/dil HCl
RCOCl(l), AlCl3 cat. <5oC
RCl(l), AlCl3 cat heat + reflux/ anhydrous
heat + reflux/ anhydrous.
+
N N Cl-

R
C
R alkaline phenol
<5oC

Click Nhere to
N
go back to theOH
menu
 27

Aromatic reagents and conditions

Br Cl
 Run off a few hard copies
of this page
 Use it to practice reagents
R9
and conditions.

SO2OH NO2 NH2

+
N N Cl-

R
C
R

Click Nhere to
N
go back to theOH
menu
 28
Aromatic Reaction types
 Run off a hard copy of this
Br Cl page
 Add the reaction types
 Click here to go to the key
words for help
C10
 Click here to check your
answers once you have
finished

SO2OH NO2 NH2

+
N N Cl-

R
C
R

Click Nhere to
N
go back to theOH
menu
 29

Aromatic reaction types

Br Cl
 Run off a hard copy of this page
 Learn the reaction types
 Click here to go to a blank page
C11 you can print to practice with
Electrophilic
Hydrogenation substitution Electrophilic
substitution

Electrophilic
SO2OH substitution Electrophilic NO2 Reduction NH2
substitution

Electrophilic Diazotisation
Substitution or Electrophilic
Friedel Crafts alkylation Substitution or
Friedel Crafts acylation
+
N N Cl-

R
C
R Coupling
reaction

Click here to go back to the menu

 30

R1. Halogenation of the ring in arenes.

CI 12.4.
Electrophilic Substitution……
Step 1:
The bromine molecule is polarised as it
approaches the benzene ring.

+
+ The FeBr3 helps to polarise the bromine
Br
Br Br + by accepting a lone pair of electrons from
one of the bromine atoms.
-
Br-
Br FeBr4-

FeBr3 The bromine molecule is so polarised that

it splits.

Step 2:
Br
Br+ FeBr4- H Br FeBr3

Br+ becomes bonded to a ring C and The H+ reacts with the FeBr4-. FeBr3 is regenerated as it is a catalyst
H+ is lost. Br+ is an electrophile: in the reaction.
 Has a + charge
 Attracted to electron rich centre
 Accepts pair of electrons to form Why does the benzene attract electrophiles?
a dative covalent bond.

R Br2(l) and either FeBr3 or Fe(s)

C
Room temperature.

E C6H6 + Br2  C6H5Br + HBr

What would the formula of the product have been if addition had occurred rather than
substitution?

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 31

Chlorine reacts in a similar way to bromine. Complete the

mechanism:

Electrophilic Substitution……
Step 1:
The chlorine molecule is polarised as
it approaches the benzene ring.

+
+ The AlCl3 helps to polarise the chlorine by
Cl
Br Br + accepting a lone pair of electrons from one
of the chlorine atoms.
-
Cl-
Br FeBr4-

FeBr
AlCl33 The chlorine molecule is so polarised that
it splits.

Step 2:
Br
Br+ FeBr4- H Br FeBr3

Cl+ becomes bonded to a ring C and

H+ is lost. Cl+ is an electrophile:
 Has a + charge
The H+ reacts with the AlCl4-. AlCl3 is regenerated as it is a catalyst
 Attracted to electron rich centre
in the reaction.
 Accepts pair of electrons to form
a dative covalent bond.

R Cl2(l) and AlCl3(s)

C Room temperature, anhydrous.

E C6H6 + Cl2  C6H5Cl + HCl

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 32

R2. The nitration of benzene.

CI 12.4.
Electrophilic substitution.

R Conc. Nitric acid and conc. sulphuric acid as a catalyst.

< 55oC. Explain why…..

E C6H6 + HNO3  C6H5NO2 + H2O

Step 1:
HNO3 + 2H2SO4 NO2+ + 2HSO4- + H2O
The nitrating mixture

NO2+ is an electrophile.

Step 2:
NO2
NO2+ + HSO4 - + H2SO4

Why do we say that the sulphuric acid is a catalyst?

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 33

R3. The sulphonation of benzene.

CI 12.4.
Electrophilic substitution.

O
OH
S
E
+ H2SO4 O + H2O

R Conc. sulphuric acid

C Heat and reflux

Draw the structural formula of Name the organic product of

the electrophile and name it: this reaction:

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 34

R4. The Friedel-Crafts alkylation of benzene.

CI 12.4
Electrophilic substitution

CH3
E + CH3Cl + HCl

Why Friedel-Crafts?

Why alkylation?

Give the reagents and conditions:

How would you do this experiment differently if you wanted to make ethylbenzene rather than
methylbenzene?

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 35

R5. The Friedel-Crafts acylation of benzene.

CI 12.4.

In these reactions, an acyl group is introduced into the

benzene ring.
O

C
CH3

Acyl chlorides also have acyl groups in. Draw the full
structural formula of propanoyl chloride and also circle the
acyl group:

O
O
C
E + CH3 C CH3
+ HCl
Cl

R Give the reagents:

C
Give the conditions:

Friedel-Craft reactions are so useful to Chemists because they provide a way of adding carbon atoms to
the benzene ring.

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 36

R6. The formation of azo dyes by coupling reactions

involving diazonium compounds.

CI 13.10.

Coupling reactions:

Diazonium salt + Coupling agent  Azo compound

Diazonium salts:
A typical diazonium salt is benzenediazonium chloride;

+
N N Cl-

This is made from phenylamine. The reaction is called diazotization.

+
NH2 + HNO2 + HCl N N Cl- + 2H2O

R = NaNO2(aq) and dilute HCl

Name the reagents:

Why does the temperature have to be less than 5oC?

Azo compounds:

This is an azo compound. Circle the azo group:

R N N R'

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 37

If R and R’ are aromatic then the azo compound is more stable than if they were
aliphatic. This is because the azo compound then has an extended delocalised system
of electrons. Aromatic azo compounds are coloured and used as dyes.

The coupling agent reacts with the diazonium salt to make the azo compound.

The coupling agent is another compound containing a benzene ring e.g. phenol or
phenylamine.

+
N N Cl- + OH N N OH + HCl

Name the 2 organic reagents above…..

R = The phenol is in an alkaline solution for this reaction.

C = At temperature less than 5oC, the coloured azo compound is
formed immediately.

Is the diazonium salt an electrophile or a nucleophile here?

What colour is the azo compound above?

Write the equation for the formation of another azo

compound:

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Key Words

Acylation The introduction of an acyl group, RCO-, using an acyl chloride.

Typical of alcohols, amines, ammonia and arenes.

Addition The addition of atoms or groups of atoms across a double bond.

Typical of alkenes, aldehydes and ketones.

Alkylation The introduction of an alkyl group, R, using a chloroalkane.

Typical of arenes.

Carbocation An organic molecule containing a carbon atom with a + charge.

Intermediates in the electrophilic addition reactions of alkenes.

Condensation A reaction in which two molecules join together and a small

molecule such as H2O or HCl is eliminated.
An example is the formation of an ester.

Coupling reaction The reaction between a diazonium ion and another aromatic
compound to form an azo compound, R-N=N-R’
Used to make azo dyes.

Dehydration A term sometimes used to describe the elimination of a water

molecule from an alcohol to form an alkene.

Diazotisation The formation of a diazonium salt from an aromatic amine.

Electrophile  Positive ion or molecule with +

 Attracted to an electron rich centre
 Accepts a pair of electrons to make a dative covalent bond.

Electrophilic addition Typical of alkenes.

Electrophilic Typical of arenes since delocalisation is retained.

substitution
Elimination The loss of atoms or groups of atoms to produce an unsaturated
compound.
Typical of 1ry and 2ry alcohols.

Esterification A rection in which an ester is formed from an alcohol and a

carboxylic acid.

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Friedel Crafts The introduction of an acyl group, RCO-, into a benzene ring.
acylation Named after it’s discoverers.

Friedel Crafts The introduction of an alkyl group into a benzene ring.

alkylation Named after it’s discoverers.

Hydrogenation The addition of hydrogen atoms across a C=C.

Hydrolysis A bond breaking reaction involving water, often catalysed by dilute

acid or alkali.
Typical of esters, amides and nitriles (R-CN).

Nucleophile  A negative ion or a molecule with a lone pair of electrons

 Attracted to a positive/electron deficient centre
 Donates a pair of electrons to form a dative covalent bond.

Nucleophilic addition Typical of aldehydes and ketones.

Nucleophilic Typical of halogenoalkanes.

substitution
Oxidation  Gain of oxygen
 Loss of electrons
 Loss of hydrogen
 Increase in oxidation number
Typical of 1ry alcohols, 2ry alcohols and aldehydes.

Radical Atom or molecule with an unpaired electron. These are very

reactive.

Radical substitution Typical of alkanes.

Reduction  Loss of oxygen

 Gain of electrons
 Gain of hydrogen
 Decrease in oxidation number
Typical of alkenes, aldehydes and ketones.

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