Clayden organic chemistry pdf - uploadsstrikinglycdncom
Clayden organic chemistry pdf Organic Chemistry, second edition Jonathan Clayden, Nick Greeves, Stuart Warren published by OUP (March 2012); ISBN 978-0-19-927029-3 Solutions Manual for Problems accompanying Organic Chemistry, 2nd edition Jonathan Clayden and Stuart Warren published by OUP (May 2013); ISBN 978-0-19-966334-7
SuggestedsolutionsforChapter28( - Chemistry
2(SolutionsManualtoaccompanyOrganicChemistry2eH N O 2NNO2 C–N nucleophilic aromatic sub tion H2 O Cl + Cl O2N NO2 Cl HNO3 H2SO4 i-PrNH2 H N O2N NO2 analysis synthesis FortheetherweagainhaveachoicefromtwoC–Odisconnections
Clayden Organic Chemistry 2nd Edition
Download Free Clayden Organic Chemistry 2nd Edition Clayden Organic Chemistry 2nd Edition Getting the books clayden organic chemistry 2nd edition now is not type of challenging means You could not single-handedly going subsequently book accrual or library or borrowing from your links to entre them
SuggestedsolutionsforChapter14 - Chemistry
SolutionsforChapter14–Stereochemistry 5 O H H O H H O H H O H H enantiomers of the cis compound enantiomers of the trans compound PROBLEM(5(In each case state, with explanations, whether the products of these
Organic Chemistry Clayden Solution Manual Free
Manual FreeSolution Manual To Organic Chemistry Clayden pdf - Free Organic Chemistry Clayden Solutions Manual free download Organic Chemistry Jonathan Clayden, Nick Geeves, Stuart Warren Paperback, 1508 Pages First Edition, 20 Juli 2000 ISBN: 0-198-50346-6 Oxford University Press Page 18/29
Clayden Organic Chemistry Answers - downloadtruyenyycom
Clayden Organic Chemistry Answers organic chemistry answers, but end up in infectious downloads Rather than reading a good book with a cup of tea in the afternoon, instead they are facing with some harmful virus inside their computer clayden organic chemistry answers is available in our digital library an online access to it is set as public so
Organic Chemistry-III CH-423
CH423&Course&on&Organic&Synthesis;&Course&Instructor:&KrishnaP &Kaliappan& CH-423 (2013)/Chem/IIT-B Dr Kaliappan, Krishna P Organic Chemistry III Classification of reactions: A brief introduction to substitution, elimination, addition, oxidation, reduction, rearrangement and pericyclic reactions
Organic chemistry by clayden pdf download - WordPresscom
organic chemistry by clayden greeves warren and wothers pdf download PDF icon, Sample Material pdf An organic synthesis self-study guide, for advanced undergraduates and beginning graduates, is available from this web site www byinquisition
Organic chemistry clayden download pdf
organic chemistry clayden pdf solutions manual A first and second year undergraduate organic chemistry textbook, specifically geared to British and European courses and courses offered in better To introduce the chemistry of the carbonyl functional groups
Chemistry 432 – Lecture Notes
Chemistry 432 – Lecture Notes Updated: Spring 2016 Course Organization: Things You Need to Know 1 Named Reactions and Reagents 2 Vocabulary 3 Concepts 4 HOW TO DO SYNTHESIS Nucleophiles and Electrophiles: The Basis of Organic Chemistry notes_01
[PDF] nomenclature chimie organique 1ere s
[PDF] nomenclature chimie organique priorité
[PDF] nomenclature chimie exercices
[PDF] exercice nomenclature chimie organique pdf
[PDF] qcm chimie organique pdf
[PDF] qcm paces ue1
[PDF] atomistique cours et exercices corrigés pdf
[PDF] qcm chimie organique medecine
[PDF] cours de chimie organique terminale s
[PDF] les alcools exercices corrigés pdf
[PDF] cours de chimie organique generale pdf
[PDF] chimie organique terminale s exercice
[PDF] chimie terminale d pdf
[PDF] fiche chimie terminale s
Krishna P. Kaliappan Department of Chemistry Indian Institute of Technology-Bombay Mumbai 400 076 INDIA http://www.chem.iitb.ac.in/~kpk kpk@iitb.ac.in
9/3/14
Organic Chemistry-III CH-423
Syllabus
CH-423 (2013)/Chem/IIT-B Dr. Kaliappan, Krishna P. Organic Chemistry III Classification of reactions: A br ief introductio n to substitution, elimination, addition, oxidation, reduction, rearrangement and pericyclic reactions. Functional group transformations: alcohols to alkylat ing agents, Mitsunobu and related reactions, introduction of functional groups by nucleophilic substitution at saturated carbon, nucleophilic cleavage of C-O bonds in ethers and esters an d inter-conv ersion of carbox ylic acid derivatives. Oxidation: Metal based oxidizing reagents: A review and detailed discussion of chromium, manganese, ruthenium, silver and other metal-based reagents. Non-metal based oxidizing reagents: D MSO, peroxide, peracid and oxygen based oxidation. Miscellaneous oxidizing reagents like IBX, DMP, CAN, DDQ, periodate etc.
Syllabus
CH-423 (2013)/Chem/IIT-B Dr. Kaliappan, Krishna P. Organic Chemistry III Reduction: Homogeneous and heterogeneous hydr ogenations; Discussion on borane b ased racemic and c hiral reagents, aluminum, tin, silic on based reducing agents. Dissolving metal reductions. Selectivity and protec ting groups: Illustration of chemoselectivity, regioselectivity and stereoselectivity wi th examples; p rotecting groups for alcohols, amines, acids, ketones and aldehydes. Cycloaddition reactions: Diels-Alder reaction; general features, dienes, dienophiles, selec tivity, intramolecular and intermolec ular reactions, hetero-Diels Alder reaction. 1,3-dipolar cycloaddition reactions; general features, dipoles, dipolarophiles. [2+2] cycloaddition reactions; general features, selected examples. Molecular rearran gements: Illustration of electron deficient and electron rich skeleta l rearrangements with examples; Sigmatropic rearrangements-Claisen and related rearrangements, Cope and oxy-Cope rearrangements; 2,3-sigmatropic rearrangements and ene reaction.
Syllabus
Suggested Books/Reviews: Jerry March, "Advanced Organic Chemistry", Fifth Ed., Wiley, 2007. F. A. Carey and R. J. Sundburg, "Advanced Organic Chemistry, Part B", Fifth Ed., Springer, 2007. J. Clayden, N. Greeves, S. Warren and P. Wothers, "Organic Chemistry", First Ed., Oxford University Press, 2001. W. Carruthers, I. Coldham , "Modern Methods of Organic Synthesis", Cambridge University Press K. Peter C. Vollhardt and Neil E. Schore "Organic Chemistry" W. H. Freeman and Company, 1999. Evaluation Pattern Mid-Semester 30% End Semester + Assignment 50% Quiz (2) 20% -There will be a total of 36 (1h) lectures, and 7 tutorials
Functional Groups
Only With Carbon and Hydrogen
CCCCWith Heteroatoms
With One Oxygen Atom: 1. Alcohol: 2. Ether:
ROHPrimaryalcoholOHRRsecondary alcoholROHRRtertiary alcoholODiethyl etherOanisoleOdiphenyl etherFunctional Groups
5. Epoxide, Cyclic Ethers: 4. Aldehyde: 3. Ketone:
With One Oxygen Atom:
Functional Groups
With Two Oxygen Atoms: With Heteroatoms 1. Acid:
OHOAcetic acidOHOBenzoic acid
2. Ketal:
RROR'OR'
3. Acetal:
RHOR'OR'
4. Ester:
OEtOEthyl acetateOOEthyl benzoate
Functional Groups
With Two Oxygen Atoms: 6. Peroxides: With Three Oxygen Atoms: 1. Anhydrides: With heteroatoms 5. Lactones (Cyclic Esters):
OOγ-lactoneOOδ-lactoneROOROOOAcetic anhydrideFunctional Groups
With Three Oxygen Atoms: 3. Peracids: With Heteroatoms 2. Hydroxy acids: OOHOHOOHOHOOHOHγ-hydroxy acidβ-hydroxy acidα-hydroxy acidOOOHClmeta-chloro perbenzoic acidFunctional Groups
With Heteroatoms 1) Amines: With One Nitrogen AtomH3CNH2H3CHNCH3NMethyl amine(primary amine)Dimethyl amine(secondary amine)Triethyl amine (tertiary amine)
2) Aromatic Amines:
NH2Aniline
3) Nitriles:
H3CCNAcetonitrile
Functional Groups
4) Aziridines: With Heteroatoms With One Nitrogen Atom
HNaziridine
5) Aromatic Amines:
NNHPyridinePyrrole
6) Imines:
RHNHPrimary aldimineRHNRSecondary aldimineRRNHPrimary KetimineRRNRSecondary KetimineFunctional Groups
With Heteroatoms With Two Nitrogen Atoms
H2CN2Diazomethane
1) Diazo:
NNRR2) Azo:
NNBenzenediazonium cation
3) Diazonium: With Three Nitrogen Atoms 1) Azides:
RNNNNNHNNNHN1,2,3-triazole1,2,4-triazole
2) Triazole:
NNNHN1-triatrazole
1) Tetrazole: With Four Nitrogen atoms
Functional Group
With Heteroatoms With One Nitrogen Atom and One Oxygen Atom 1) Amides: 2) Lactams:3) Oximes: 4) Nitroso: 5) Nitrile Oxides:
Functional Group
With Heteroatoms With One Nitrogen Atom and Two Oxygen Atoms 1) Nitro: 2) Nitrones:RNO2NORR
With Two Nitrogen Atom and One Oxygen Atom 1) Urea:H2NNH2O
Functional Group
With Heteroatoms (Sulfur) 1) Thiols:
SHSHThiophenolEthanethiol
2) Thio Ethers:
RSR3) Thio carbonyl:
RRSS4) Thiirane: 5) Heterocycles:
SThiophene
Functional Group
With Heteroatoms (Halogens) 1) Halides: 2) Halohydrin: 3) Dihalides: 4) Acid Chloride: 5) Halolactones:
H3CIBrMethyl iodideEthyl bromideHOClROHRIClCl1,2-dichloroethaneClOAcetyl chlorideOOIFunctional Group Transformations
OrganicSynthesis and Music: What is Common Between Them? Reactions Can be Classified into Seven Types Elimina'onOxida'onPericyclic
Functional Group Transformations
1. Addition Reaction: a. Nucleophilic Addition
RR'ONuRR'ONuERR'OENu
Reaction is categorized by first step and not by second step b. Electrophilic AdditionBr2BrBrBrBrX.X.Y.YX
c. Radical AdditionFunctional Group Transformations
2. Elimination Reactions E
1 , E 2 , E 1CB , syn, anti, pyrolyticOAcOOHAcOHOAcHAcOHSyn eliminationOHNaHCS2, MeIOHH
Side reactions like Wagner-Meerwein rearrangement can take place Syn Elimination:OSMeSHXanthate ester
HSSMeOCOS + MeSH
Functional Group Transformations
3. Substitution Reactions a. Aromatic Substitution b. Aliphatic Substitution 1. Nucleophilic Substitution S
N 1, S N 2, S N i 1. Nucleophilic SubstitutionFNO2ORNO2OR
2. Addition- Elimination
CNBrNaNH2CN
via Benzyne 2. Electrophilic E1, E2, E1CB, syn, anti, pyrolyticBase must be non nucleophilic
NHOHOOMorphine (Acute pain killer)Ac2OH+NAcOAcOOHeroinFunctional Group Transformations
Esters Ways to make esters
ROOHCH2N2ROOMeROOHH2CN2ROOH3CN2
If compound containing nitrogen having more nitrogen content (more than 50%), then compound may be explosive (CH
2 N 2 is explosive) OHCH2N2OMeROHCH2N2ROMeProton must be acidic enough to pick by CH2N2OHOHCH2N2OHOMeWays to Make Esters
Functional Group Transformations
R'-IRCO2H+RCO2R'baseR'OHRCO2H+RCO2R'DCCNCNN,N'-Dicyclohexylcarbodiimide (DCC)NCNROOHR'OHHNCNOORRCO2R'NHONHDicyclohexyl urea
+ Sometimes its difficult to separate product from DCU, in that case, use EDCI instead of DCCFunctional Group Transformations
Ways to Make Esters
Baeyer-Villiger Oxidation
OOOmCPBA
Favorskii Rearrangement
OBrCO2EtNaOEt/EtOH
MitsunobuReaction
R'OH+RCO2HDEAD, PPh3RCO2R'NNCO2EtEtO2CPh3PNNCO2EtEtO2CPh3POROHNNHCO2EtEtO2CPh3PROHRCO2+ROORCO2R'OPPh3+HNNHCO2EtEtO2C+ROPPh3
Functional Group Transformations
Ways to Make Esters
Mitsunobu Reaction
RR1OHPPh3, DIADR2CO2HRR1OR2ONNCO2RRO2CR = iPr, DIAD Diisopropyl azodicarboxylateR = Et, DEADDiethyl azodicarboxylateOOOBnO?OOOBnOH+, H2OHOOBnOOHOPPh3, DEAD
Functional Group Transformations
RR1OHPPh3DEADOHRR1OPh
26Functional Group Transformations
Mitsunobu Reaction
Nitrogen Nucleophile:
OBnOHPPh3, DEADTsNHCH3OBnNTsH3CNHNOPPh3DEADOHNNO
Intramolecular Mitsunobu Reaction:
HNHOCO2EtCO2EtPhPPh3DEADNCO2EtCO2EtPh
Weak Nitrogen Nucleophile:
OBnOOBnOHBnONHRPPh3, DEADOBnOOBnBnONR
27Functional Group Transformations
Mitsunobu Reaction
Azides:
ROH + PPh3 + DEADHN3PPh3 +ROHNHNCO2EtEtO2CRN3RN3 + Ph3PONNCO2EtEtO2CPPhOOPhOHO(PhO)2PN3
Can be used instead of HN
3NNCO2EtEtO2C(PhO)2PN3OPPh3NNCO2EtEtO2CPPhOOPhOPPh3OHRNNCO2EtEtO2CPPhOOPhOHROPPh3+NNNRN3 + PhPOO(PhO)2PN3ROH ++ PPh3 + DEAD
Alcohols
Reduction: Primary alcohols
RNaOH, H2O2BH3ROHHCHORMgXRCH2OHRCHONaBH4RCO2RLiAlH4RCO2HLiAlH4Functional Group Transformations
Secondary Alcohols
RR'OreductionRCHORMgXROxymercurationRMgXHCO2Rsymmetrical 2o alcohol formate esterTertiary Alcohols
RR'ORMgXROxymercurationRMgXRCO2R
Functional Group Transformations
Alcohols
ROHPyridine, MsclROMsMesylateROHPyridine, TsclROTsTosylateROHPyridine, BrclROBsBrosylateROHPyridine, NsclRONsNosylateROHPyridine, Tf2OROTfTriflateROTsNaBrAcetoneRBr
Finkelstein reaction
Alcohols are important class of compounds but they are not good leaving group xOH is not a reactive alkylating agent. Reactivity can be enhanced by converting into a better leaving group like sulfonate esters or halides Most reactive
Functional Group Transformations
Activation of Hydroxyl Group
Preparation of Sulfonate Esters:
ROHClSOClOSOClRCl
Functional Group Transformations
Preparation of Alkyl Halides:
RCl++SO2Cl
Alkyl halides are involved in the formation of C-C bond by nucleophilic substitutionInversion of configuration
But, if reaction is taking place in solvent like 1,4-dioxaneOSOClROOOORClRCl
Retention of configuration
Reaction with SOCl
2Activation of Hydroxyl Group
PClClRO2ROHPORORRO
Functional Group Transformations
PClClClROH
Reaction with Phosphorous Halides
- HCl The reaction will stop at this stage if it is carried out in presence of an aminePORORROH+
When amine is not present
POROROHClR2RCl+POHOHOH
Inversion of configuration
Drawbacks: Not suitable for acid sensitive compounds Amines can not be usedOHOOBrOO?RClPHOROR+O
Activation of Hydroxyl Group
Ph3PBrBrBrPh3PBr+ROHROPPh3Br- HBr
Reaction with Alkoxyphosphonium Salts
RBrOPPh3
Formation of strong phosphoryl double bond is the driving forceHOPh3PBr2BrROHPPh3+RBrOBrBrBrBr
+Bromide sourceFunctional Group Transformations
Activation of Hydroxyl Group
PPh 3 / CCl 4CCl3ROHPh3PClRCl
Hexachloroacetone can be used as chloride source
PPh 3 / I 2 / ImidazoleNNHI2ROHPPh3RI
Functional Group Transformations
Ph3PIIPh3PIRHO-HIImidazoleROPPh3IRI
Activation of Hydroxyl Group
Functional Group Transformations
Reaction with 2-Halo-3-alkylbenzoxazolium Cation
ONClRHOAdditionEliminationONORClONORCl
Mitsunobu Reaction
Activation of Hydroxyl Group
HBrBrBrOBrBrHBrHBrOHBrHOBrHBrH2OBrBrBrBr
Functional Group Transformations
Mild Method
OHMsClPyOMsLiClClMsOLi
Some Other Methods
OOActivation of Hydroxyl Group
Functional Group Transformations
Nitriles
DehydrationRCONH2AbnormalBeckmannRearrangementNROHRCNLAHH2/ Pd-CRCH2NH2H3O+RCO2HR'MgBrRCOR'DIBAL-HRCHO
RX + NaCN
AlkylationR'R'CN
Functional Group Transformations
Preparation of Nitriles
RXNaCNRCNRONH2P2O5RCN
aldoxime Beckmann rearrangenment can also occur Reaction proceed faster in polar aprotic solventsNHONH2OH+NHNOH2ONOHNOH2NNCH+
tertiary carbocation -H+RNHOHp-TsCl, PyAcCl, PyRCNFunctional Group Transformations
Preparation of Nitriles
RCH2Br + KCN18-Crown-6CH3CN83oC
RCH 2 CNRCHOROHCN
stable under mild acidic condition unstable under basic conditionOH-RCHO+CN-RCHOROTMSCNKCNH+TMSCNZnBr2
RCNR'MgBrH+/H2OROR'RCNLDAR'IRCNR'RCNRCNRCNRCNLAHorH/Pd-CRCH2NH2partial hydrolysisRONH2H3O+RefluxRCO2HSnCl2/HClDIBAL-HROH
Stephen reaction
Utility of Nitriles
Functional Group Transformations
Functional Group Transformations
Azides
RN3NFN3ROHPPh3, HN3DEADROHP(OPh)2ON3DBUROHH2/ Pd-CRNH2PPh3, H2ORNH21,3-DipolarcycloadditionNNNRNaN3, DMSOR'CH2BrR'CH2BrNaN3, PTC