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Orgo Functional Groups .pdf



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Chem Factsheet
April 2003

Number 52

Reactions of Functional Groups - A Summary
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.

Reactions of alkenes

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

CO2 + H2O
Alkane
H2
electrophilic
heat,
addition
Ni catalyst

Di-halogenoalkane
halogen

hydrogen
halide

electrophilic
addition

Halogenoalkane
electrophilic
addition

oxidation
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 in
conjunction with Factsheets 27, 31, 32, 33, 34 and 39, which show the
reactions in a more detailed format.

NaBr(s) +
H2SO 4(conc.)
to make HBr

nucleophilic
substitution

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

iodo-alkane
nucleophilic
substitution

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

dry PCl5

halogenation

Propane and oxygen (combustion)
C3H8 + 5O2

heat

Alcohol

3CO2 + 4H2O
dehydration

Propane and chlorine (free radical substitution)
C3H8 + Cl2

uv light

C3H7Cl + HCl

conc. H2SO4

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

heat to
170 o C

oxidation
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

Alkenes

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
H 2O

Preparation

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 /
polymerisation

boil under reflux
conc. H2SO4
Na2CO3
or NaHCO 3

Diacid
+
H+(aq)
Diol

Carboxylic
Acid
aqueous

Sodium Salt +
CO2 + H2O
neutralisation

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

dry

HCN

PCl5

Acyl Chloride
nucleophilic
substitution

2

reduction
LiAlH4
in ether

silver
nitrate in
ammonia
warm
solution

Fehlings
solution

H2SO4

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)

H 2O

Amide

nucleophilic
substitution

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

Alkane

NH3

warm

Positive Fehlings
Test
redox

Chem Factsheet

Reactions of Functional Groups - A Summary
Reactions of Aldehydes

Reactions of Amino Acids
Secondary
Alcohol

Hydroxy-nitrile
compound

reduction

HCN

reduction

NaBH4 in
ethanol

alkali

Amino Acids

neutralisation

Secondary
Alcohol

nucleophilic addition
trace of
KOH

acid

Salt

Salt
neutralisation

Reactions of Phenol

LiAlH4
in ether

2,4,6tribromophenol

Phenate ion

Ketones

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

Salts

Substituted
Amides

nucleophilic addition /
neutralisation

nucleophilic
substitution

Reactions of Benzene
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
polymerisation

hydrolysis

alkali

acid

Nitriles

heat under
reflux

heat under
reflux

Br2

Nitrobenzene

Alkylbenzene
electrophilic substitution

Sn,
conc. HCL,
NaOH

Carboxylic
acid

Fe cat. dry
HNO3

electrophilic substitution

Reactions of Nitrites
Carboxylic
acid salt

Fe cat.
dry

KMnO 4

in alkali
heat under
reflux

hydrolysis

Phenylamine

LiAlH4
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 +
CO2

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

hydrolysis

3


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