(1) Nomenclature, Synthesis and Reactions of Aldehydes Ketones (2) Enols Both aldehydes and ketones are characterised by the presence of the C=O
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SCH 206
(ORGANIC ACIDS, AMINES, ESTERS ANDPHENOLS)
Dr Albert Ndakala
andakala@uonbi.ac.ke0720443386
Basement of Chemistry (B-6)
ODL Lecture Timetable
Monday 2-4 pm (ChemLab-132)
Wednesday 2 -5 pm (ChemLab-132)
1Course Outline
Ketones.
(2)EnolsandtheChemistryofEnolates. 2Course Evaluation
(a) Assignments covering Aldehydes, Ketones and CarboxylicAcids, Esters, Amides and Amines.
(b) Continuous Assessment Test covering Aldehydes, Ketones and Carboxylic Acids, Esters, Amides and Amines (c) Practicals. (d) Final Exam. 3Reference Books
OrganicChemistrybyFrancisA.Carey
OrganicChemistrybyJohnMcMurry
Fundamentals of Organic Chemistry by T. W. SolomonsOrganic Chemistry by Paula Bruice
Organic Chemistry by Jonathan Clayden
4To the Student
reactionmechanism. 5General Introduction
6ALDEHYDES & KETONES
7Introduction
Aldehydesand Ketones
8C=Ogroup.
attacheddirectlytothecarbonylcarbon.Naturally Occurring Aldehydes
9Naturally OccuringKetones
10IUPAC 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
HCHOCH3CH
OCH3CH2CH
OCH3CH2CH2CH
OCH3CH2CH2CH2CH
OGuidelines 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
15FunctionalGroupsinNomenclature.
Acid > Aldehyde > Ketone > Alcohol > Amine> Alkyne >Alkene > AlkaneIUPAC Nomenclature of Substituted
Aldehydes
16IUPAC Nomenclature of Cyclic Aldehydes
17IUPAC 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 Ketone3PropanePropanone
4ButaneButanone
5PentanePentan-2-one
5PentanePentan-3-one
Guidelines for IUPAC Nomenclature of
Substituted Ketones
21parent(principal)chainoftheketone. thelowestpossibleaddressnumber.
Guidelines for IUPAC Nomenclature of
Substituted Ketones
22IUPAC Nomenclature of Substituted Ketones
23IUPAC Nomenclature of Cyclic Ketones
24Cyclicketonesarenamedascycloalkanones.
lowestpossiblenumber.IUPAC Nomenclature of Cyclic Ketones
25Cyclicketoneswithtwoketogroupsarenamedas
cycloalkanediones.Alternative IUPAC Nomenclature of
Aromatic Ketones
26groupandthesuffixophenone. directlytoabenzene(aromatic)system).
Nomenclature of PolycarbonylCompounds
27oxo-group
Priority of Functional Groups in Nomenclature.
Acid > Aldehyde > Ketone > Alcohol > Amine> Alkyne >Alkene > AlkaneNames of Carbonyl Groups as Substituents
28Number of
Carbons
PrefixStructure of
CarbonylGroup
Name of Carbonyl
Substituent
IUPAC Name1Form-FormylMethanoyl
2Acet-AcetylEthanoyl
3Propion-PropionylPropanoyl
4Butyr-ButyrylButanoyl
5Valer-ValerylPentanoyl
carbonylsubstituent.IUPAC Nomenclature of Polycarbonyl
Compounds
29lengthofthesubstituent.
Synthesis of Aldehydesand Ketones
Introduction
30preservationofbiologicalspecimen. commerciallyviableforexploitation. toaccessthem.
Synthesis of Aldehydesand Ketones
Preparative Strategies
31whichaldehydesandketonesareprepared. andketonesarealcohols,alkenesandalkynes.
Synthesis of Aldehydesand Ketones
Oxidation of Alcohols to Aldehydesand Ketones
32oxidationofaketoneisnotpossible.
Strong Oxidizing Agents
33waytocarboxylicacids. maybeusedtoprepareketones consideralternativestrategies.
Strong Oxidizing Agents
34ExamplesofStrongOxidizingAgents
Examples of Oxidations with Strong
Oxidizing Agents in Aqueous Media
36Modified Chromium (VI) Reagents
Oxidation of Primary Alcohols to Aldehydesin OrganicSolvents
37reagentsiscommonlyundertakenin.
Synthesis of Aldehydesand Ketones
PCC and PDC Oxidations of Alcohols
40alcoholstoketonesbyPCC.
Synthesis of Aldehydesand Ketones
Ozonolysisof Alkenes Under Reductive Cleavage
41reaction
Synthesis of Aldehydesand Ketones
Ozonolysisof Alkenes Under Reductive Cleavage
42reaction
Synthesis of Aldehydesand Ketones
Mechanism of OzonolysisUnder Reductive Cleavage
43Synthesis of Ketones
Reaction of Nitrileswith Grignard Reagents
Summary
Example
44CRNR'MgBrCRR'
NMgBrH3O+
CRR' OIminium 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. 45Synthesis of Aromatic Ketones
Friedel-Crafts Acylationof Arenes
46ketones).
Examples
Synthesis of Aromatic Ketones
Mechanism of the Friedel-Crafts Acylation
47The reaction is based on electrophilic aromatic substitution.
Reactions of Aldehydesand Ketones
Duality of Reactivity
chemistryofaldehydesandketones.Itdoesthistwoways:
carbonylcarbon 48Illustration
aldehydesandketones.Reactions of Aldehydesand Ketones
Duality of Reactivity
49overallsubstitutionreaction.
Oxidation of Aldehydesand Ketones
50lengthastheparentaldehyde.
Oxidation of Aldehydesand Ketones
51suchashydroxylgroups.
TollensTest for Aldehydes
(The Silver Mirror Test) 52Thetestinvolvesaddingasolutionofasilver-
ammonicalcomplex(thereagent)toanunknown compound.Tollenstest.
theTollenstestarethephenols.TollensTest for Aldehydes
(Summary) 53aldehydesfromketones. ketones)tometallicsilver.
AcetophenoneBenzaldehyde
NucleophilicAddition to Aldehydesand
Ketones
(General Principles) 54electrophiliccarbonatomfromsp2tosp3. protonation
NucleophilicAddition to Aldehydesand
Ketones
(General Principles) 55Suchreactionsareusuallyreversible.
additionReduction of Aldehydesand Ketones
Definitionofreduction:Option1
Additionoftheelementsofhydrogen
56DefinitionofReduction:Option2
Removaloftheelementsofoxygen
andketones.Reduction of Aldehydesand Ketones
57ontheadditionofhydrogen.
Reduction of Aldehydesand Ketones
58RC O H NaBH4 RC H H OHor
LiAlH4
RC O R' NaBH4 RC H R' OHorLiAlH4
Aldehyde
KetoneSecondary alcohol
Primary alcohol
Examples
Reduction of Aldehydesand Ketones
Mechanism of Reduction
59Reduction with Lithium aluminium hydride
Reduction with Sodium borohydride
Reductive Deoxygenationof Aldehydesand
Ketones
(Wolff-KishnerReduction) thecarbonylgrouptoprovideahydrocarbon.Example
effectthereduction. 60Mechanism of the Wolff-KishnerReduction
61andprotonations.
Reactions of Aldehydeswith Weak
Nucleophiles
(Hydration) 62RCHO+H2ORCH
OHOHAldehydeAldehyde hydrate
(Geminal diol) aldehydehydrates.Reactions of Aldehydeswith Weak
Nucleophiles
(Hydration) 63stableandisolable.
Reaction of Ketoneswith Weak
Nucleophiles
Hydration
64stablehydrate. lessreadilythanaldehydes.
Example
Mechanism of Hydration of Aldehydesand
Ketones
65Reaction of Aldehydesand Ketoneswith
Weak Nucleophiles
Acyclic Hemiacetaland AcetalFormation
66catalyst,thesereactionsarereversible.
Example
Mechanism of Hemiacetaland Acetal
Formation
67lossofaproton.
Mechanism of Hemiacetaland AcetalFormation
68intoagoodleavinggroup.
Mechanism of Hemiacetaland Acetal
Formation
69(deprotonation).
Reaction of Aldehydesand Ketoneswith
Weak Nucleophiles
Cyclic Hemiacetaland AcetalFormation
70cyclichemiacetal.
Reaction of Aldehydesand Ketoneswith
Weak Nucleophiles
Mechanism of Cyclic HemiacetalFormation
71Reaction of Aldehydesand Ketoneswith
Weak Nucleophiles
Cyclic AcetalFormation
72catalysedconditionstoformcyclicacetals.
Reaction of Aldehydesand Ketoneswith
Weak Nucleophiles
Mechanism of Cyclic Hemiacetaland AcetalFormation
73Reaction of Aldehydesand Ketoneswith
Weak Nucleophiles
Cyclic AcetalFormation
74conditionstoformcyclicacetals. formationsarepossible.
Intramolecular version
Intermolecular version
Reaction of Aldehydesand Ketoneswith HCN
CyanohydrinFormation
75groupattachedtothesamecarbonatom. cyanohydrins. 76
astrongnucleophile. acidicliquidthatboilsat26oC.
Cyanohydrin
Formation
Reaction of Aldehydeswith HCN
Mechanism of CyanohydrinFormation
NaOH catalysed reaction
77Reaction of Ketoneswith HCN
Mechanism of CyanohydrinFormation
78NaCN catalysed reaction
Cyanohydrins in Biological Systems
79variedrolesinthesesystems. beforesprayingthepoisonatanenemy.
Reaction of Primary Amines with Aldehydes
and KetonesImineFormation
80formimines.
Mechanism of ImineFormation
81Other ImineDerivatives of Aldehydesand
Ketones
82ketonestoformvariousderivatives.
Qualitative Tests for Aldehydesand Ketones
83Test precipitate.
Qualitative Tests for Aldehydesand Ketones
84ketonesbytheireaseofoxidation. silvermirroronthesidesofatesttube).
Qualitative Tests for Aldehydesand Ketones
85(c) The Benedicts Test for Reducing Sugars browndepositofCu2O.
Reaction of Aldehydesand Ketoneswith
Strong Nucleophiles
OrganometallicReagents
86acetylidereagents)toprovidealcohols.
Reactionwithsodiumacetylide
Reactions with OrganometallicReagents
Mechanism of Addition to the Carbonyl Group
87theadditionreaction.