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52 REACTIONS OF FUNCTIONAL GROUPS- A Summary.pdf

52 REACTIONS OF FUNCTIONAL GROUPS- A Summary.pdf

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Reactions of Functional Groups - A Summary
C
 hem
 F
 actsheet
April 2003Number 52
1
To succeed in this topic you need to:
Be able to recall and write out the functional groups representedin this Factsheet;
Have a thorough knowledge of the organic reactions and theirconditions (described in the Organic Chemistry Factsheets todate 27, 31, 32, 33, 34 and 39);
Recognise the summarised versions of the equations in thisFactsheet and be able to write them out in full under examconditions.After working through this Factsheet you will:
Have revised the organic chemistry reactions that candidatesare required to learn for AS and A2 Chemistry modules.
Have a reference paper as you start to work through questionson organic pathways and synthesis.
This Factsheet is designed to be used as a revision aid as candidates setabout the sometimes daunting task of learning all of the organic reactionsrequired by the A2 Chemistry course.These spider diagrams represent the reactions in a summarised version, ina visual fashion that suits many learners. They should be used inconjunction with Factsheets 27, 31, 32, 33, 34 and 39, which show thereactions in a more detailed format.A good way of using this Factsheet to revise effectively would be asfollows:1.Pick a group to revise (e.g. alkanes).2.Pick a member of that group at random (e.g. propane).3.Use the spider diagram to help you write out balanced chemicalreactions, with conditions, for the organic chemical you have chosen.(e.g.)Propane and oxygen (combustion)C
3
H
8
+ 5O
2
 
heat
3CO
2
+ 4H
2
OPropane and chlorine (free radical substitution)C
3
H
8
+ Cl
2
 
uv light
C
3
H
7
Cl + HClIn an exam, candidates are required to apply their knowledge of organicreactions to a wide variety of compounds, so the more of these you do, thebetter!
Reactions of alkanes
O
2
heathalogenUV Light
combustionfree radicalsubstitution
HalogenoalkaneCarbon Dioxide+ WaterAlkanes
Reactions of alkenes
AlkenesCO
2
+ H
2
ODi-halogenoalkaneHalogenoalkaneDiolAlkane
heatO
2
halogenhydrogenhalidealkalineKMnO
4
(aq)heat,Ni catalyst
electrophilicadditionelectrophilicadditionelectrophilicadditionelectrophilic addition
oxidationH
2
Reactions of alcohols
Alcoholhalogenationbromo-alkaneiodo-alkanechloro-alkane
nucleophilicsubstitutionnucleophilicsubstitutionnucleophilic substitution
NaBr(s) +H
2
SO
4
(conc.)to make HBrP(s) + I
2
(s)to make PI
3
dry PCl
5
dehydrationoxidationalkene
heat to170
o
Cconc. H
2
SO
4
primaryalcoholssecondaryalcoholsaldehydecarboxylicacid
Cr
2
O
72
(aq)H
+
(aq)further oxidationCr
2
O
72
(aq)H
+
(aq)
ketone
Cr
2
O
72
(aq)H
+
(aq)
 
Chem Factsheet
2
Reactions of Functional Groups - A Summary
Grignard Reagent"R-MgHal"HalogenoalkaneAlkane
Grignard Reagents
Preparation
addition
Mg turningsDry ether solventBoil under reflux
ReactionsGrignard Reagent"R-MgHal"PrimaryAlcoholSecondaryAlcoholTertiaryAlcoholCarboxylicAcid
nucleophilicaddition / hydrolysisnucleophilicaddition / hydrolysisnucleophilicsubstitutionnucleophilicaddition / hydrolysisnucleophilicaddition / hydrolysis
H
2
OCO
2
(g)+ H
2
O(l)H
+
(aq)H
+
(aq)ketone+ H
2
O(l)CH
2
=O(g)+ H
2
O(l)H
+
(aq)aldehyde (not methanal)+ H
2
O(l)methanal,then usedilute acidfor hydrolysis
EsterCarboxylicAcidPolyesterAlcoholAcyl ChlorideSodium Salt +CO
2
+ H
2
O
reductionnucleophilic substitution /  polymerisationnucleophilicsubstitutionnucleophilicsubstitutionneutralisation
alcoholNa
2
CO
3
or NaHCO
3
aqueousLiAlH
4
thenH
+
(aq)dryDiacid+DiolPCl
5
LiAlH
4
indry etherH
+
(aq)boil under refluxconc. H
2
SO
4
Carboxylic Acid ReactionsEster Reactions
Carboxylic acid+Alcohol
alkalineconditionsacidconditions
Carboxylic acid+AlcoholEster
H
2
O H
2
O
CarboxylicacidAcylChlorideEsterAmideN-substitutedAmide
nucleophilicsubstitutionnucleophilicsubstitution
alcoholprimaryamineNH
3
H
2
O
nucleophilicsubstitutionnucleophilicsubstitution
Acyl Chloride Reactions
Hydroxy-nitrilecompoundAldehydesPrimaryAlcoholPrimaryAlcoholPositive FehlingsTestPositive SilverMirror Test
reductionreductionnucleophilic additionredoxredox
HCNsilvernitrate inammoniasolutionwarmwarmFehlingssolutionNaBH
4
inethanoltrace of KOHLiAlH
4
in ether
2,4-DNPDerivative
nucleophilicaddition thenelimination
2,4-DNP inethanolH
2
SO
4
Reactions of Aldehydes
Fig. 3 Halogenoalkane reactions
Halogenoalkane
nucleophilicsubstitution
NitrileAlcohol
nucleophilicsubstitution
AminesAlkene
nucleophiliceliminationnucleophilicsubstitution
KCN inwater/ethanolheat underrefluxheatNH
3
inethanolNaOH(aq)heat underrefluxKOH inethanolheat underreflux

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