chemistry organic flowcharts

Reactions of Functional Groups - A Summary

ChemFactsheetApril 2003 Number 52

1

To succeed in this topic you need to:• Be able to recall and write out the functional groups represented

in this Factsheet;• Have a thorough knowledge of the organic reactions and their

conditions (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 candidates

are required to learn for AS and A2 Chemistry modules.• Have a reference paper as you start to work through questions

on 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 chemical

reactions, with conditions, for the organic chemical you have chosen.

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

C3H

8 + 5O

2 heat 3CO

2 + 4H

2O

Propane and chlorine (free radical substitution)

C3H

8 + Cl

2 uv light C

3H

7Cl + HCl

In 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

O2

heat

halogen

UV Light

combustionfree radicalsubstitution

Halogenoalkane

Carbon Dioxide+ Water Alkanes

Reactions of alkenes

Alkenes

CO2 + H

2O

Di-halogenoalkane

HalogenoalkaneDiol

Alkane

heatO2

halogen

hydrogenhalide

alkalineKMnO

4(aq)

heat,Ni catalyst electrophilic

addition

electrophilicaddition

electrophilicaddition

electrophilic additionoxidation

H2

Reactions of alcohols

Alcohol

halogenation

bromo-alkane

iodo-alkanechloro-alkane

nucleophilicsubstitution


nucleophilic substitution

NaBr(s) +H

2SO

4(conc.)

to make HBr

P(s) + I2(s)

to make PI3

dry PCl5

dehydrationoxidation

alkene

heat to170oC

conc. H2SO

4primaryalcohols

secondaryalcohols

aldehyde

carboxylicacid

Cr2O

72−(aq) H+(aq)

further oxidation

Cr2O

72−(aq) H+(aq)

ketone

Cr2O

72−(aq) H+(aq)

Chem Factsheet

2


Grignard Reagent"R-MgHal"

Halogenoalkane

Alkane

Grignard Reagents

Preparation

addition

Mg turnings

Dry ether solventBoil under reflux

Reactions

Grignard Reagent"R-MgHal"

PrimaryAlcohol

SecondaryAlcohol

TertiaryAlcohol

CarboxylicAcid

nucleophilicaddition / hydrolysis





H2O

CO2(g)

+ H2O(l)

H+(aq)

H+(aq)

ketone+ H

2O(l)

CH2=O(g)

+ H2O(l)

H+(aq)

aldehyde (not methanal)+ H

2O(l)

methanal,then usedilute acidfor hydrolysis

Ester

CarboxylicAcid

Polyester

Alcohol

Acyl ChlorideSodium Salt +CO2 + H2O

reduction

nucleophilic substitution /polymerisation


nucleophilicsubstitutionneutralisation

alcohol

Na2CO

3

or NaHCO3

aqueous

LiAlH4

thenH+(aq)

dry

Diacid+

Diol

PCl5

LiAlH4 in

dry ether

H+(aq)

boil under refluxconc. H

2SO

4

Carboxylic Acid Reactions

Ester Reactions

Carboxylic acid+

Alcoholalkaline

conditionsacid

conditions

Carboxylic acid+

AlcoholEster

H2O H

2O

Carboxylicacid

AcylChloride

Ester

AmideN-substitutedAmide



alcohol

primaryamine NH

3

H2O



Acyl Chloride Reactions

Hydroxy-nitrilecompound

Aldehydes

PrimaryAlcohol

PrimaryAlcohol

Positive FehlingsTest

Positive SilverMirror Test

reduction

reduction

nucleophilic addition

redox

redox

HCN

silvernitrate inammoniasolution

warmwarm

Fehlingssolution

NaBH4 in

ethanoltrace ofKOH LiAlH

4

in ether

2,4-DNPDerivative

nucleophilicaddition thenelimination

2,4-DNP inethanol

H2SO

4

Reactions of Aldehydes

Fig. 3 Halogenoalkane reactions

Halogenoalkane


Nitrile Alcoholnucleophilicsubstitution

Amines Alkenenucleophilicelimination


KCN inwater/ethanol

heat underreflux

heat

NH3 in

ethanol

NaOH(aq)

heat underreflux

KOH inethanol

heat underreflux

Chem Factsheet

3


Hydroxy-nitrilecompound

Ketones

SecondaryAlcohol

SecondaryAlcohol

reduction

reduction

nucleophilic addition

HCN

NaBH4 in

ethanoltrace ofKOH LiAlH

4

in ether

2,4-DNPDerivative

nucleophilic addition thenelimination

2,4-DNP inH

2SO

4

Reactions of Aldehydes

Reactions of Amines

Salts

Amines

SubstitutedAmides


nucleophilic addition /neutralisation

acidacyl chloride

Polyamides

nucleophilic substitutionpolymerisation

primary amines + acyl chloridesif monomers contain 2 amine

groups and 2 acyl chloride groups

Reactions of Nitrites

Carboxylicacid salt

NitrilesCarboxylic

acid

hydrolysishydrolysis

acidalkali

Amine

reduction

heat underreflux

heat underreflux

LiAlH4

in ether

Reactions of Amides

Nitrile AmidesAmine +

CO2

hydrolysisdehydration

Br2(l) +

NaOH(aq)P4O

10

warm warm

Salt Amino Acids

neutralisation

alkaliacid

Reactions of Amino Acids

Salt

neutralisation

Reactions of Phenol

Phenate ion

Phenol

2,4,6-tribromophenol

electrophilic substitutionneutralisation

OH-(aq)

Br2(aq)

Ester

nucleophilic substitution

acyl chloride,in NaOH(aq)

Benzene

Bromobenzene

electrophilic substitution

Fe cat.dry

Br2

Nitrobenzene

Fe cat. dryBr

2HNO

3

50oC concH

2SO

4

Alkylbenzene

electrophilic substitution electrophilic substitution

Phenylamine

reduction

Benzocarboxylicacid

oxidation

in alkaliheat underreflux

KMnO4

Sn,conc. HCL,NaOH

HNO2

+HCl

Benzenediazoniumions

Acknowledgements: This Factsheet was researched and written by Kieron HeathCurriculum Press, Unit 305B, The Big Peg, 120 Vyse Street, Birmingham, B18 6NFChemistryFactsheets may be copied free of charge by teaching staff or students, provided thattheir school is a registered subscriber. No part of these Factsheets may be reproduced, storedin a retrieval system, or transmitted, in any other form or by any other means, without theprior permission of the publisher. ISSN 1351-5136

Reactions of Benzene

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