Chem Factsheet

April 2003 Number 52

Reactions of Functional Groups - A Summary
To succeed in this topic you need to: Reactions of alkenes
• Be able to recall and write out the functional groups represented
in this Factsheet; CO2 + H2O
• Have a thorough knowledge of the organic reactions and their Alkane
conditions (described in the Organic Chemistry Factsheets to H2 O2
electrophilic heat Di-halogenoalkane
date 27, 31, 32, 33, 34 and 39); heat,
addition
• Recognise the summarised versions of the equations in this Ni catalyst halogen electrophilic
Alkenes addition
Factsheet and be able to write them out in full under exam
conditions.
alkaline hydrogen
KMnO4(aq) halide Halogenoalkane
After working through this Factsheet you will: Diol
• Have revised the organic chemistry reactions that candidates electrophilic
oxidation addition
are required to learn for AS and A2 Chemistry modules. electrophilic addition
• Have a reference paper as you start to work through questions
on organic pathways and synthesis.
Reactions of alcohols
This Factsheet is designed to be used as a revision aid as candidates set
about the sometimes daunting task of learning all of the organic reactions bromo-alkane
required by the A2 Chemistry course.
nucleophilic substitution
These spider diagrams represent the reactions in a summarised version, in chloro-alkane iodo-alkane
a visual fashion that suits many learners. They should be used in NaBr(s) +
nucleophilic H2SO 4(conc.) nucleophilic
conjunction with Factsheets 27, 31, 32, 33, 34 and 39, which show the substitution to make HBr
reactions in a more detailed format. substitution

A good way of using this Factsheet to revise effectively would be as

dry PCl5 P(s) + I2(s)
follows: to make PI 3
1. Pick a group to revise (e.g. alkanes).
2. Pick a member of that group at random (e.g. propane). halogenation
3. Use the spider diagram to help you write out balanced chemical
reactions, with conditions, for the organic chemical you have chosen.

(e.g.) Propane and oxygen (combustion)

heat
Alcohol
C3H8 + 5O2 3CO2 + 4H2O
dehydration
Propane and chlorine (free radical substitution) oxidation

uv light
C3H8 + Cl2 C3H7Cl + HCl
conc. H2SO4 heat to primary
170 o C alcohols
In an exam, candidates are required to apply their knowledge of organic secondary
reactions to a wide variety of compounds, so the more of these you do, the alcohols
better!
Cr2O72−(aq) H+(aq)
Reactions of alkanes alkene Cr2O72−(aq) H+(aq)

aldehyde ketone
Carbon Dioxide O2 halogen Halogeno
Alkanes further oxidation
+ Water heat UV Light alkane
free radical Cr2O72−(aq) H+(aq)
combustion
substitution

carboxylic
acid

1
Reactions of Functional Groups - A Summary Chem Factsheet

Fig. 3 Halogenoalkane reactions Ester Reactions

Nitrile Alcohol
Carboxylic acid H 2O H 2O Carboxylic acid
nucleophilic nucleophilic
KCN in + Ester +
substitution NaOH(aq) substitution
water/ethanol Alcohol Alcohol
heat under acid alkaline
heat under reflux conditions conditions
reflux
Halogenoalkane
KOH in
NH3 in
ethanol
ethanol heat under Acyl Chloride Reactions
heat
reflux
Amines Alkene
nucleophilic nucleophilic Carboxylic
substitution elimination acid Ester
nucleophilic nucleophilic
Grignard Reagents substitution substitution

Preparation H 2O alcohol
Mg turnings
Grignard Reagent
Halogenoalkane Acyl
Dry ether solvent
"R-MgHal"
Chloride
Boil under reflux addition
primary
Reactions amine NH3

Primary
Alcohol N-substituted Amide
nucleophilic Amide
addition / hydrolysis nucleophilic
nucleophilic
substitution
substitution

methanal,
CH2=O(g) then use Secondary
Alkane Reactions of Aldehydes
+ H2O(l) dilute acid Alcohol
nucleophilic for hydrolysis
substitution nucleophilic
addition / hydrolysis Primary
H 2O H+(aq) Alcohol
Hydroxy-nitrile
aldehyde (not methanal) compound reduction Primary
Grignard Reagent + H2O(l)
"R-MgHal" nucleophilic addition Alcohol
CO2 (g) reduction
NaBH4 in
+ H2O(l) ketone H+(aq) trace of ethanol
H+(aq) + H2O(l) HCN
KOH LiAlH4
in ether
Carboxylic Tertiary
Aldehydes
Acid Alcohol 2,4-DNP in Fehlings
ethanol solution
nucleophilic nucleophilic H2SO4 silver
addition / hydrolysis addition / hydrolysis nitrate in
warm
2,4-DNP ammonia
warm
Derivative solution
Carboxylic Acid Reactions Positive Fehlings
nucleophilic Test
Polyester addition then Positive Silver redox
elimination Mirror Test
nucleophilic substitution /
Ester polymerisation redox

nucleophilic
Alcohol
substitution Diacid LiAlH4 reduction
alcohol + H+(aq) then
Diol H+(aq)
boil under reflux
conc. H2SO4 LiAlH4 in
dry ether
Carboxylic
Na2CO3 Acid
or NaHCO 3 PCl5
dry
aqueous
Sodium Salt + Acyl Chloride
CO2 + H2O nucleophilic
neutralisation substitution

2
Reactions of Functional Groups - A Summary Chem Factsheet

Reactions of Aldehydes Reactions of Amino Acids

Secondary acid alkali

Alcohol Salt Amino Acids Salt
Hydroxy-nitrile
compound reduction Secondary neutralisation neutralisation

nucleophilic addition Alcohol

reduction Reactions of Phenol
NaBH4 in
trace of HCN ethanol
KOH LiAlH4 2,4,6-
in ether
Phenate ion tribromophenol
Ketones
neutralisation electrophilic substitution
-
2,4-DNP in OH (aq)
H2SO4 Br 2(aq)
Phenol
2,4-DNP
Derivative
acyl chloride,
nucleophilic addition then
in NaOH(aq)
elimination

Reactions of Amines Ester

nucleophilic substitution
Substituted
Salts Amides
Reactions of Benzene
nucleophilic addition / nucleophilic
neutralisation substitution
Bromobenzene
acid electrophilic substitution
acyl chloride
Amines Br2 Fe cat.
dry
primary amines + acyl chlorides
if monomers contain 2 amine
groups and 2 acyl chloride groups Benzene

50o C conc
H2SO4 Fe cat. dry
Polyamides HNO3 Br2
nucleophilic substitution
polymerisation
Nitrobenzene Alkylbenzene
electrophilic substitution electrophilic substitution
Reactions of Nitrites
Sn, in alkali
Carboxylic alkali acid Carboxylic conc. HCL, KMnO 4 heat under
Nitriles NaOH reflux
acid salt acid
heat under heat under
hydrolysis reflux reflux hydrolysis
LiAlH4 Phenylamine Benzocarboxylic
in ether reduction acid
oxidation
Amine HNO2
+
reduction HCl

Benzenediazonium
Reactions of Amides
ions

Br2(l) +
P4 O10 NaOH(aq) Amine +
Nitrile Amides Acknowledgements: This Factsheet was researched and written by Kieron Heath
warm warm CO2
Curriculum Press, Unit 305B, The Big Peg, 120 Vyse Street, Birmingham, B18 6NF
dehydration
hydrolysis ChemistryFactsheets may be copied free of charge by teaching staff or students, provided that
their school is a registered subscriber. No part of these Factsheets may be reproduced, stored
in a retrieval system, or transmitted, in any other form or by any other means, without the
prior permission of the publisher. ISSN 1351-5136