Chemistry Organic Flowcharts

C hem F actsheet April 2003

Number 52

Reactions of Functional Groups - A Summary Reactions of alkenes

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 to date 27, 31, 32, 33, 34 and 39); Recognise the summarised versions of the equations in this • Factsheet and be able to write them out in full under exam conditions. •

CO2 + H2O Alkane H2 electrophilic heat, addition Ni catalyst

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.

Diol

Alkenes

Di-halogenoalkane halogen

hydrogen halide

electrophilic addition

Halogenoalkane electrophilic addition

oxidation electrophilic electrophilic addition

Reactions of alcohols bromo-alkane nucleophilic substitution

chloro-alkane

These spider diagrams represent the reactions in a summarised version, in a visual fashion that suits many learners. They should be used used in conjunction with Factsheets 27, 31, 32, 33, 34 and 39, which show the reactions in a more detailed format.

NaBr(s) + H 2SO 4(conc.) to make HBr

nucleophilic substitution

A good way of using this Factsheet to revise effectively would be as follows: 1. Pick Pick a gro group up to to revi revise se (e.g (e.g.. alkan alkanes es). ). 2. Pick Pick a membe memberr of that that group group at at random random (e.g. (e.g. propan propane). e). 3. Use the the spider spider diagram diagram to help you write write out balanc balanced ed chemica chemicall reactions, with conditions, for the organic chemical you have chosen.

iodo-alkane nucleophilic substitution

P(s) + I2(s) to make PI 3

dry PCl5

halogenation

Prop Propan anee and and oxyg oxygen en (co (comb mbus usti tion on)) C3H8 + 5O2

heat

Alcohol

3CO2 + 4H2O dehydration

Propane and chlorine (free radical substitution) C3H8 + Cl2

uv light

C3H7Cl + HCl

conc. H2SO 4

In an exam, candidates are required to apply their knowledge of organic reactions to a wide variety of compounds, so the more of these you do, the better!

Carbon Dioxide + Water

oxidation

heat to 17 0 o C

primary alcohols

Cr2O72 (aq) −

O2 heat

halogen

Alkanes

+

UV Light

Cr2O72 (aq) −

aldehyde Halogeno alkane

further oxidation Cr2O72 (aq) −

free radical substitution

H (aq) +

carboxylic acid

1

secondary alcohols

H (aq)

alkene

Reactions of alkanes

combustion

heat

alkaline KMnO4(aq)

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 required by the A2 Chemistry course.

(e.g.)

O2

H (aq) +

ketone

Chem Factsheet

Reactions of Functional Groups - A Summary Ester Reactions

Fig. 3 Halogenoalkane reactions Alcohol

Nitrile nucleophilic substitution

KCN in water/ethanol

Carboxylic acid + Alcohol

nucleophilic substitution

NaOH(aq)

heat under reflux

heat under reflux

Carboxylic acid + Alcohol

H 2O

Ester acid conditions

alkaline conditions

Halogenoalkane KOH in ethanol

NH3 in ethanol

H 2O

heat under reflux

heat

Amines

Acyl Chloride Reactions

Alkene nucleophilic elimination

nucleophilic substitution

Grignard Reagents

Carboxylic acid

Ester

nucleophilic substitution

nucleophilic substitution

Preparation

H2O

alcohol

Mg turnings

Grignard Reagent "R-MgHal"

Halogenoalkane Dry ether solvent Boil under reflux

Acyl Chloride

addition

primary amine

Reactions Primary Alcohol

N-substituted Amide

nucleophilic addition / hydrolysis

nucleophilic substitution

ketone + H2O(l)

H +(aq)

nucleophilic addition / hydrolysis

nucleophilic addition / hydrolysis

nucleophilic addition / hydrolysis

2,4-DNP Derivative nucleophilic addition then elimination

Polyester nucleophilic substitution /   poly mer isa tio n

boil under reflux conc. H2SO4 Na 2CO 3 or NaHCO3

Diacid + H+(aq) Diol

Carboxylic Acid aqueous

Sodium Salt + CO2 + H2O neutralisation

reduction LiAlH 4 then H+(aq) LiAlH4 in dry ether

dry

HCN

PCl 5

Acyl Chloride nucleophilic substitution

2

reduction LiAlH 4 in ether

H2SO4 warm

silver nitrate in ammonia solution

Positive Silver Mirror Test redox

Alcohol alcohol

Primary Alcohol

NaBH4 in ethanol

Aldehydes 2,4-DNP in ethanol

Carboxylic Acid Reactions

nucleophilic substitution

reduction

nucleophilic addition trace of  KOH

Tertiary Alcohol

Primary Alcohol

Hydroxy-nitrile compound

H+(aq)

Carboxylic Acid

Ester

nucleophilic substitution

Reactions of Aldehydes

aldehyde (not methanal) + H2O(l)

Grignard Reagent "R-MgHal" CO2 (g) + H2O(l)

Secondary Alcohol

H+(aq)

H2O

Amide

nucleophilic substitution

methanal, CH2=O(g) then use + H2O(l) dilute acid for hydrolysis

Alkane

NH3

Fehlings solution warm

Positive Fehlings Test redox

Reactions of Functional Groups - A Summary

Chem Factsheet

Reactions of Aldehydes

Reactions of Amino Acids Secondary Alcohol

Hydroxy-nitrile compound

reduction

HCN

Salt neutralisation

Reactions of Phenol

reduction

NaBH4 in ethanol

alkali

Amino Acids

neutralisation

Secondary Alcohol

nucleophilic addition trace of  KOH

acid

Salt

LiAlH 4 in ether

Ketones

Phenate ion

2,4,6tribromophenol

neutralisation

electrophilic substitution OH -(aq)

2,4-DNP in H2SO4

Br 2(aq)

Phenol

2,4-DNP Derivative

acyl chloride, in NaOH(aq)

nucleophilic addition then elimination

Ester

Reactions of Amines

nucleophilic substitution

Substituted Amides

Salts nucleophilic addition /  neutralisation

Reactions of Benzene

nucleophilic substitution

Bromobenzene acid

electrophilic substitution

acyl chloride

Amines

Br2

primary amines + acyl chlorides if monomers contain 2 amine groups and 2 acyl chloride groups

Benzene 50o C conc H2SO4

Polyamides nucleophilic substitution  poly mer isa tio n

hydrolysis

alkali

acid

Nitriles

heat under reflux

heat under reflux

Br2

Alkylbenzene

electrophilic substitution

electrophilic substitution

Sn, conc. HCL, NaOH

Carboxylic acid

Fe cat. dry HNO3

Nitrobenzene

Reactions of Nitrites Carboxylic acid salt

Fe cat. dry

KMnO 4

in alkali heat under reflux

hydrolysis

Phenylamine

LiAlH 4 in ether

reduction

Benzocarboxylic acid oxidation

HNO2 + HCl

Amine reduction

Benzenediazonium ions

Reactions of Amides

Nitrile dehydration

P4 O10 warm

Amides

Br2(l) + NaOH(aq) warm

Amine + CO 2

 Acknowledgements: This Factsheet was researched and written by Kieron Heath Curriculum Press, Unit 305B, The Big Peg, 120 Vyse Street, Birmingham, B18 6NF ChemistryFactsheetsmay 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 

hydrolysis

3