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SCH 206

(ORGANIC ACIDS, AMINES, ESTERS AND

PHENOLS)

Dr Albert Ndakala

andakala@uonbi.ac.ke

0720443386

Basement of Chemistry (B-6)

ODL Lecture Timetable

Monday 2-4 pm (ChemLab-132)

Wednesday 2 -5 pm (ChemLab-132)

1

Course Outline

Ketones.

(2)EnolsandtheChemistryofEnolates. 2

Course Evaluation

(a) Assignments covering Aldehydes, Ketones and Carboxylic

Acids, Esters, Amides and Amines.

(b) Continuous Assessment Test covering Aldehydes, Ketones and Carboxylic Acids, Esters, Amides and Amines (c) Practicals. (d) Final Exam. 3

Reference Books

OrganicChemistrybyFrancisA.Carey

OrganicChemistrybyJohnMcMurry

Fundamentals of Organic Chemistry by T. W. Solomons

Organic Chemistry by Paula Bruice

Organic Chemistry by Jonathan Clayden

4

To the Student

reactionmechanism. 5

General Introduction

6

ALDEHYDES & KETONES

7

Introduction

Aldehydesand Ketones

8

C=Ogroup.

attacheddirectlytothecarbonylcarbon.

Naturally Occurring Aldehydes

9

Naturally OccuringKetones

10

IUPAC Nomenclature of Aldehydes

11 namesofopen-chainaliphaticaldehydesisal. suffixtotheIUPACnameoftheparentalkane. generatetheappropriatenameofthecompound.

IUPAC Nomenclature of Aldehydes

12 carbonchainlengthasshownbelow:

Number of

Carbons

Name of

Parent Alkane

Structure of

Aldehyde

Systematic Name of

Aldehyde

1MethaneMethanal

2EthaneEthanal

3PropanePropanal

4ButaneButanal

5PentanePentanal

HCH

OCH3CH

O

CH3CH2CH

O

CH3CH2CH2CH

O

CH3CH2CH2CH2CH

O

Guidelines for IUPAC Nomenclature of

Substituted Aldehydes

13 isderivedby: chainofthealdehyde. ofthealdehyde.ItisbydefaultC-1.

IUPAC Nomenclature of Substituted

Aldehydes

14 providetheparent(root)nameofthealdehyde. chainareindicatedwithlocants1,2,3etc.

IUPAC Nomenclature of Substituted

Aldehydes

15

FunctionalGroupsinNomenclature.

Acid > Aldehyde > Ketone > Alcohol > Amine> Alkyne >Alkene > Alkane

IUPAC Nomenclature of Substituted

Aldehydes

16

IUPAC Nomenclature of Cyclic Aldehydes

17

IUPAC Nomenclature of Substituted Cyclic

Aldehydes

18 tricarbaldehydeetc. isomers.

IUPAC Nomenclature of Ketones

19 ketonesisone. totheIUPACnameoftheparentalkaneoralkene.

IUPAC Nomenclature of Ketones

20 carbonchainlengthasshownbelow:

Number of

Carbons

Name of

Parent Alkane

Structure of

Ketone

Systematic Name

of Ketone

3PropanePropanone

4ButaneButanone

5PentanePentan-2-one

5PentanePentan-3-one

Guidelines for IUPAC Nomenclature of

Substituted Ketones

21
parent(principal)chainoftheketone. thelowestpossibleaddressnumber.

Guidelines for IUPAC Nomenclature of

Substituted Ketones

22

IUPAC Nomenclature of Substituted Ketones

23

IUPAC Nomenclature of Cyclic Ketones

24

Cyclicketonesarenamedascycloalkanones.

lowestpossiblenumber.

IUPAC Nomenclature of Cyclic Ketones

25

Cyclicketoneswithtwoketogroupsarenamedas

cycloalkanediones.

Alternative IUPAC Nomenclature of

Aromatic Ketones

26
groupandthesuffixophenone. directlytoabenzene(aromatic)system).

Nomenclature of PolycarbonylCompounds

27
oxo-group

Priority of Functional Groups in Nomenclature.

Acid > Aldehyde > Ketone > Alcohol > Amine> Alkyne >Alkene > Alkane

Names of Carbonyl Groups as Substituents

28

Number of

Carbons

PrefixStructure of

CarbonylGroup

Name of Carbonyl

Substituent

IUPAC Name

1Form-FormylMethanoyl

2Acet-AcetylEthanoyl

3Propion-PropionylPropanoyl

4Butyr-ButyrylButanoyl

5Valer-ValerylPentanoyl

carbonylsubstituent.

IUPAC Nomenclature of Polycarbonyl

Compounds

29
lengthofthesubstituent.

Synthesis of Aldehydesand Ketones

Introduction

30
preservationofbiologicalspecimen. commerciallyviableforexploitation. toaccessthem.

Synthesis of Aldehydesand Ketones

Preparative Strategies

31
whichaldehydesandketonesareprepared. andketonesarealcohols,alkenesandalkynes.

Synthesis of Aldehydesand Ketones

Oxidation of Alcohols to Aldehydesand Ketones

32
oxidationofaketoneisnotpossible.

Strong Oxidizing Agents

33
waytocarboxylicacids. maybeusedtoprepareketones consideralternativestrategies.

Strong Oxidizing Agents

34

ExamplesofStrongOxidizingAgents

Examples of Oxidations with Strong

Oxidizing Agents in Aqueous Media

36

Modified Chromium (VI) Reagents

Oxidation of Primary Alcohols to Aldehydesin Organic

Solvents

37
reagentsiscommonlyundertakenin.

Synthesis of Aldehydesand Ketones

PCC and PDC Oxidations of Alcohols

40
alcoholstoketonesbyPCC.

Synthesis of Aldehydesand Ketones

Ozonolysisof Alkenes Under Reductive Cleavage

41
reaction

Synthesis of Aldehydesand Ketones

Ozonolysisof Alkenes Under Reductive Cleavage

42
reaction

Synthesis of Aldehydesand Ketones

Mechanism of OzonolysisUnder Reductive Cleavage

43

Synthesis of Ketones

Reaction of Nitrileswith Grignard Reagents

Summary

Example

44CRNR'MgBrCRR'

NMgBrH3O+

CRR' O

Iminium salt

KetoneNitrileGrignard reagent

provideketones.

Synthesis of Ketones

Mechanism of Conversion of Nitrilesto Ketones

A Grignard or organolithium reagent attacks a nitrile to give the magnesium or lithium salt of an imine. Acidic hydrolysis of the imine leads to the ketone. 45

Synthesis of Aromatic Ketones

Friedel-Crafts Acylationof Arenes

46
ketones).

Examples

Synthesis of Aromatic Ketones

Mechanism of the Friedel-Crafts Acylation

47
The reaction is based on electrophilic aromatic substitution.

Reactions of Aldehydesand Ketones

Duality of Reactivity

chemistryofaldehydesandketones.

Itdoesthistwoways:

carbonylcarbon 48

Illustration

aldehydesandketones.

Reactions of Aldehydesand Ketones

Duality of Reactivity

49
overallsubstitutionreaction.

Oxidation of Aldehydesand Ketones

50
lengthastheparentaldehyde.

Oxidation of Aldehydesand Ketones

51
suchashydroxylgroups.

TollensTest for Aldehydes

(The Silver Mirror Test) 52

Thetestinvolvesaddingasolutionofasilver-

ammonicalcomplex(thereagent)toanunknown compound.

Tollenstest.

theTollenstestarethephenols.

TollensTest for Aldehydes

(Summary) 53
aldehydesfromketones. ketones)tometallicsilver.

AcetophenoneBenzaldehyde

NucleophilicAddition to Aldehydesand

Ketones

(General Principles) 54
electrophiliccarbonatomfromsp2tosp3. protonation

NucleophilicAddition to Aldehydesand

Ketones

(General Principles) 55

Suchreactionsareusuallyreversible.

addition

Reduction of Aldehydesand Ketones

Definitionofreduction:Option1

Additionoftheelementsofhydrogen

56

DefinitionofReduction:Option2

Removaloftheelementsofoxygen

andketones.

Reduction of Aldehydesand Ketones

57
ontheadditionofhydrogen.

Reduction of Aldehydesand Ketones

58
RC O H NaBH4 RC H H OHor

LiAlH4

RC Oquotesdbs_dbs17.pdfusesText_23