CHEMISTRY DEPARTMENT
c
SCH 402: CONCEPTS OF ORGANIC SYNTHESIS
c c c c c
MWITA JAMES MWING’A
c c
LECTURE NOTES c
pg.c1
,PurposecTocprovidecknowledgecforcunderstandingcofcapplicationcofcsomeccommoncchemic
alcreactionscandcthecstrategiescinvolvedcincthec preparationscorcsynthesescofcsomeco
rganicccompoundscusefulcinclife
Objectives
Learnercshouldcbecablecto:
Tocstatecthecimportancecofcorganiccsynthesiscincmodernclifec
designcsyntheticcroutescforcvariouscorganicccompounds
describecchemistrycinvolvedcincvariouscreactioncthatcleadctocbondcformationc.
outlinecacsurveycofcvariouscreagentscavailablecforccarryingcoutcfunctionalc
groupcintercconversions.
statecandcillustratecmeanscofcprotectingcvariouscfunctionalcgroupscincanycor
ganiccsynthesis.
performcexperimentctocillustratecspecificcmethodscinvolvedcincsynthesiscofcv
ariouscorganicccompounds
Courseccontent
Retrosyntheticcanalysiscandcdesigncofcsyntheticcroutescincorganiccsynthesis.cMethodsco
fcformingccycliccandcalicyclicccarboncbonds:caldol,cGrignard,cWittigcandcacyloinccon
densation,cthecDieckmannccyclisation,cthecDiels-
Aldercreaction:ccarboncoxygencbondcformation:ccarbon-
nitrogencbondcformation.cDissolvingcmetal,cmetalchydride,cdiimidecandcClaisen,cCop
ecDemyanov,cRayostic,cBeckmancandcFriescrearrangements.cOxidationcreactions,ci
mprovedcmethodscforccatalyticcreductions.cAdditioncreactionsctocalkenescandcalkyne
s,csynthesiscofc alkenescbyc Wittigcreactioncandceliminations.cSynthesiscofcalkynes.cR
earrangementcreactions.cCarbocation,ccarbanion,coxidationcsuchcascthecusecofccrownc
ethers.cHydroborationcandcstereochemistry.c Bayer-
Villagercreactions,cepoxidations.cUsecofcprotectingcgroupscincorganiccsynthesis.
Practicalscwillcbecchosenctocillustratecspecificcreactions,cpracticalcTechniquescandcid
entificationcofcproducts.
Methodology:
Lectures,cdiscussionscorctutorials,cdemonstrations,claboratorycexperiments
Materials:
Chalkcandcboard,chandcouts,cmodels,ccharts,cinternet,cjournals
Assessment
Thecassessmentcwillcbecascfollows:
30%cfromccontinuouscassessmentctestsc(CATS).cThesecCATScmayc i
ncludecassignments,cwrittenctestcandclaboratorycreports
70%cfromcthecmaincexaminationcthatcwillcbecofc2chourcduration
pg.c2
, CONTENTS
Chapter 1: Retrosynthetic analysis and basics of designing an Organ
c c c c c c c c c
ic synthesis
c
1.0 Introduction
1.1 Organiccsynthesiscandcitscapplicationcincscience
1.2 Designingcacanycsynthesis
1.3 Theoreticalcconsiderationscbeforecdesigningcacsynthesis
1.4 Disconnectingcactargetcmoleculec(TM):cRetrosyntheticcanalysis
1.5 Synthonscandcsyntheticcequivalents
1.6 ConsiderationscwhencdisconnectingcacTM
1.7 Functionalcgroupscorganiccsynthesis
1.8 Summary
1.9 Questionscandcsolutions
Chapter 2: Methods of forming Carbon-Carbon Bonds I
c c c c c c c
2.0 Introduction
2.1 Reviewcofcthecchemistrycofctheccarbonylcgroup
2.2 Basecandcacidccatalysiscofccarbonylcgroup
2.3 Aldolccondensation
2.4. Claisenc–cSchimdtcreaction
2.5 Claisenccondensation
2.6 Intramolecularccondensationcreactions
2.6.1 IntramolecularcAldolccondensation
2.6.2 IntramolecularcClaisenccondensation
2.7 Summary
2.8 Questionscandcsolutions
Chapter 3: Methods of forming Carbon-Carbon Bonds II
c c c c c c c
3.0 Introduction
3.1 Darzensccondensation
3.2 Acyloinccondensation
3.3 MichaelcAdditioncreaction
3.4 SpecialccasecofcMichaelcreaction
3.5 CycliccCarbonc–
ccarboncbondcformation:cRobinsoncAnnulationcreactionc3.6
3.7 Summary
3.8 Questionscandcsolutions
pg.c3
, Chapter 4: Methods of forming carbon-Carbon Bonds III
c c c c c c c
4.0 Introduction
4.1 Wittigcreaction
4.2 Dielsc–Alderscreaction
4.4 Reactionscinvolvingcenamines
4.5 Summary
4.6 Questionscandcsolutions
Chapter 5: reactions of alkenes and alkynes
c c c c c c
5.0 Introduction
5.1 Additioncreactionscofcalkenes
5.2 Additioncofchydrogenchalidesctoccarbon-ccarboncdoublecbonds
5.3 Additioncofchalogensctoccarbon-ccarboncdoublecbonds
5.4 Reactionscofcalkenescwithccarboxylations
5.5 Alkynes:cSynthesiscandcreactions
5.6 Summary
5.7 Questionscandcsolutions
Chapter 6: Reduction
c c
6.0 Introduction
6.1 Catalyticchydrogenation
6.2 Reductioncbychydridectransfercreagents
6.3 Reductioncofctheccarbonylcfunctionalcgroup
6.4 Summary
6.5 Questionscandcsolutions
6.6 Furthercreading
Chapter 7: Oxidation
c c
7.0 Introduction
7.1 Oxidationcofcalcohols,caldehydescandcketones
7.2 Baeyer-Villagerscoxidation
7.3 Oxidationcofccarbon-ccarboncdoublecandctriplecbonds
7.4 Ozonolysiscofccarbon-carboncdoublecandctriplecbonds
7.5 UsecofcCrowncetherscincoxidation
7.6 Summary
7.7 Questionscandcsolutions
7.8 Furthercreading
pg.c4
c
SCH 402: CONCEPTS OF ORGANIC SYNTHESIS
c c c c c
MWITA JAMES MWING’A
c c
LECTURE NOTES c
pg.c1
,PurposecTocprovidecknowledgecforcunderstandingcofcapplicationcofcsomeccommoncchemic
alcreactionscandcthecstrategiescinvolvedcincthec preparationscorcsynthesescofcsomeco
rganicccompoundscusefulcinclife
Objectives
Learnercshouldcbecablecto:
Tocstatecthecimportancecofcorganiccsynthesiscincmodernclifec
designcsyntheticcroutescforcvariouscorganicccompounds
describecchemistrycinvolvedcincvariouscreactioncthatcleadctocbondcformationc.
outlinecacsurveycofcvariouscreagentscavailablecforccarryingcoutcfunctionalc
groupcintercconversions.
statecandcillustratecmeanscofcprotectingcvariouscfunctionalcgroupscincanycor
ganiccsynthesis.
performcexperimentctocillustratecspecificcmethodscinvolvedcincsynthesiscofcv
ariouscorganicccompounds
Courseccontent
Retrosyntheticcanalysiscandcdesigncofcsyntheticcroutescincorganiccsynthesis.cMethodsco
fcformingccycliccandcalicyclicccarboncbonds:caldol,cGrignard,cWittigcandcacyloinccon
densation,cthecDieckmannccyclisation,cthecDiels-
Aldercreaction:ccarboncoxygencbondcformation:ccarbon-
nitrogencbondcformation.cDissolvingcmetal,cmetalchydride,cdiimidecandcClaisen,cCop
ecDemyanov,cRayostic,cBeckmancandcFriescrearrangements.cOxidationcreactions,ci
mprovedcmethodscforccatalyticcreductions.cAdditioncreactionsctocalkenescandcalkyne
s,csynthesiscofc alkenescbyc Wittigcreactioncandceliminations.cSynthesiscofcalkynes.cR
earrangementcreactions.cCarbocation,ccarbanion,coxidationcsuchcascthecusecofccrownc
ethers.cHydroborationcandcstereochemistry.c Bayer-
Villagercreactions,cepoxidations.cUsecofcprotectingcgroupscincorganiccsynthesis.
Practicalscwillcbecchosenctocillustratecspecificcreactions,cpracticalcTechniquescandcid
entificationcofcproducts.
Methodology:
Lectures,cdiscussionscorctutorials,cdemonstrations,claboratorycexperiments
Materials:
Chalkcandcboard,chandcouts,cmodels,ccharts,cinternet,cjournals
Assessment
Thecassessmentcwillcbecascfollows:
30%cfromccontinuouscassessmentctestsc(CATS).cThesecCATScmayc i
ncludecassignments,cwrittenctestcandclaboratorycreports
70%cfromcthecmaincexaminationcthatcwillcbecofc2chourcduration
pg.c2
, CONTENTS
Chapter 1: Retrosynthetic analysis and basics of designing an Organ
c c c c c c c c c
ic synthesis
c
1.0 Introduction
1.1 Organiccsynthesiscandcitscapplicationcincscience
1.2 Designingcacanycsynthesis
1.3 Theoreticalcconsiderationscbeforecdesigningcacsynthesis
1.4 Disconnectingcactargetcmoleculec(TM):cRetrosyntheticcanalysis
1.5 Synthonscandcsyntheticcequivalents
1.6 ConsiderationscwhencdisconnectingcacTM
1.7 Functionalcgroupscorganiccsynthesis
1.8 Summary
1.9 Questionscandcsolutions
Chapter 2: Methods of forming Carbon-Carbon Bonds I
c c c c c c c
2.0 Introduction
2.1 Reviewcofcthecchemistrycofctheccarbonylcgroup
2.2 Basecandcacidccatalysiscofccarbonylcgroup
2.3 Aldolccondensation
2.4. Claisenc–cSchimdtcreaction
2.5 Claisenccondensation
2.6 Intramolecularccondensationcreactions
2.6.1 IntramolecularcAldolccondensation
2.6.2 IntramolecularcClaisenccondensation
2.7 Summary
2.8 Questionscandcsolutions
Chapter 3: Methods of forming Carbon-Carbon Bonds II
c c c c c c c
3.0 Introduction
3.1 Darzensccondensation
3.2 Acyloinccondensation
3.3 MichaelcAdditioncreaction
3.4 SpecialccasecofcMichaelcreaction
3.5 CycliccCarbonc–
ccarboncbondcformation:cRobinsoncAnnulationcreactionc3.6
3.7 Summary
3.8 Questionscandcsolutions
pg.c3
, Chapter 4: Methods of forming carbon-Carbon Bonds III
c c c c c c c
4.0 Introduction
4.1 Wittigcreaction
4.2 Dielsc–Alderscreaction
4.4 Reactionscinvolvingcenamines
4.5 Summary
4.6 Questionscandcsolutions
Chapter 5: reactions of alkenes and alkynes
c c c c c c
5.0 Introduction
5.1 Additioncreactionscofcalkenes
5.2 Additioncofchydrogenchalidesctoccarbon-ccarboncdoublecbonds
5.3 Additioncofchalogensctoccarbon-ccarboncdoublecbonds
5.4 Reactionscofcalkenescwithccarboxylations
5.5 Alkynes:cSynthesiscandcreactions
5.6 Summary
5.7 Questionscandcsolutions
Chapter 6: Reduction
c c
6.0 Introduction
6.1 Catalyticchydrogenation
6.2 Reductioncbychydridectransfercreagents
6.3 Reductioncofctheccarbonylcfunctionalcgroup
6.4 Summary
6.5 Questionscandcsolutions
6.6 Furthercreading
Chapter 7: Oxidation
c c
7.0 Introduction
7.1 Oxidationcofcalcohols,caldehydescandcketones
7.2 Baeyer-Villagerscoxidation
7.3 Oxidationcofccarbon-ccarboncdoublecandctriplecbonds
7.4 Ozonolysiscofccarbon-carboncdoublecandctriplecbonds
7.5 UsecofcCrowncetherscincoxidation
7.6 Summary
7.7 Questionscandcsolutions
7.8 Furthercreading
pg.c4
