TYPES OF CARBONYL COMPOUNDS General Name Name ...
TYPES OF CARBONYL COMPOUNDS General Name Name ...
TYPES OF CARBONYL COMPOUNDS General Name Name ...
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<strong>TYPES</strong> <strong>OF</strong> <strong>CARBONYL</strong> <strong>COMPOUNDS</strong><strong>General</strong> <strong>Name</strong><strong>Name</strong> formula suffixAldehydeROCOH-alKetone C -oneR' RCarboxylicOacid CR O H-oicacidAcid OX=halogen -oylhalideCR XhalideOAcidO -oicanhydrideanhydrideC CR OR<strong>Name</strong>Ester<strong>General</strong>formulaRLactone(cyclic ester)AmideRLactam(cyclic amide)OCOOOCCNOCR'OR'R"NR'<strong>Name</strong>suffix-oate-amide
Detergents and "fatty acids" - amphiphilic moleculeshydrophobicCO 2hydrophilicCO 2 Homega-3-fattyacidH 2 OH 2 OH 2 OPhospholipids - Fatty acid estersof glycerolH 2 OgreaseH 2 OOHOHOHglycerola triolH 2 OMICELLEOOOOOOP OLIPID BILAYERONH 3Phosphatidylcholine
Amides in Peptides and ProteinsaOHH 2 NOOHH 2 NH 2 NOOO OHONH 2OHOHOHH 2 NH 2 NOOglycine alanine phenylalanine asparagine glutamic acidFive of the 20 amino acid building blocks that go into all proteinsAll a-aminoacidsProteins are polyamidesNHOHNONHOHNOEach protein is defined by aspecific primary sequence ofamino acidsCO 2 H
-LactamAntibioticsOther Penicillinsvaried at thispositionH 2 NHHSHNHHSNOHO2C6-Aminopenicillamic acidHOONHO2CHPenicillin Gb-lactam g-lactam d-lactamNHOONHNHOab O g aH 2 NOH H H 2 NOH2 NOHbd bO g aOb-amino acid g-amino acid d-amino acid
SUMMARY - SYNTHESIS <strong>OF</strong> ALDEHYDES AND KETONESR 11. Oxidation of alcohols Cl -N H CrO3OHR 1OHNa 2 Cr 2 O 7 will over-oxidize tocarboxylic acidNa 2 Cr 2 O 7OO1. R 2 MgBr R 2R 1R 2OHH 2 SO 4H 2. pH7R 1 R 2R 1R 1OH2. From alkynesOR 1 H Hg 2 + , H 2 O1. RBHR 1 H2R 1OH
SUMMARY - SYNTHESIS <strong>OF</strong> ALDEHYDES AND KETONES3. Friedel-Crafts AcylationOOClAlCl3RR4. Ozonolysis1. O 32. Zn/H 3 O + O OH
Overview of Reactions 4/27-5/9 - Reactions with carbonyls1. Nucleophilic Addition:Reactions with Aldehydes and Ketones (Chapter 19)A. O -O Nu H 3 O + HO NuRR'NuExample: Grignard Reaction Section 19.8CH MgBr +3OHOExample: Cyanohydrin FormationSection 19.7O HO CNHHCNH
Overview of Reactions 4/27-5/9 - Reactions with carbonyls1. Nucleophilic AdditionA. Hydration and Acetal FormationO H 2 O HO OH OHOOHOOSection 19.6H 3 O +Section 19.11OR HH +Electrophilic at C OH OH RO OHNo longer electrophilic at CROHHOH OHHOHOROH OHHHOH 2 OROHROHOROHProtected ( masked)aldehyde
Acetals as Protecting Groups for AldehydesBrOHXoM gBrMgOHOH OHH +BrOHOMgoBrMgOHOelectrophile1.OH2. pH7OHOHH 2 O/H +OHOHO
Overview of Reactions 4/27-5/9 - Reactions with carbonyls1. Nucleophilic AdditionA.PCH 3 -BrPCH 3BuLiP CH 2Otriphenyl phosphinePh 3 P CH 2Wittig ReactionPh 3 POOPh = PhenylSection 19.12
Overview of Reactions 4/27-5/9 - Reactions with carbonyls1. Nucleophilic AdditionB. OH 2 O-O Nu H 3 O + R R'NuNuRR'Nu
Overview of Reactions 4/27-5/9 - Reactions with carbonyls1. Nucleophilic AdditionB. continuedExample: Imine FormationOOHNH 2H 3 O +H 2 OHNHHH 2 NHHH 2 OHNNHNHSometimes called a Schiff base in biochemistrySection 19.9
SUMMARY - Synthesis of Carboxylic Acids1. Oxidative cleavage of alkeneR'KMnO 4HO HORROR'O2. Oxidation of 1 alcohols and aldehydesORHJones OxidationOOHHROHRH3. Carboxylation of Grignard ReagentsORMgBrCO 2ROH
Overview of Reactions 4/27-5/9 - Reactions with carbonyls2. Nucleophilic Acyl Substitution:Reactions with Carboxylic Acid derivatives (Chapter 21)O-O NuORYYY -RNuNuY = Leaving GroupOLiAlH 4OLiAlH 4OHEster hydride reductionOR H H Chapter 17.5RO - Li +nucleophilic substitutionnucleophilic additionMeMgBr O MeMgBr OHOMeMeMeOR RO - Li +nucleophilic substitution nucleophilic additionEster grignard reactionSection 21.6
Overview of Reactions 4/27-5/9 - Reactions with carbonyls2. Nucleophilic Acyl SubstitutionCarboxylic Acid DerivativesExample:Acyl Halide Section 21.4 Example:Ester Section 21.6OOHOClOOHOOEtSOCl2CH CH OH3 2HClOClO NR 2NHR2Example:AmideSection 21.7
Overview of Reactions 4/27-5/9 - Reactions with carbonyls3. Alpha Substitution: Enolate/Enol ChemistryOOOHamust have " " H( pKa 10-20)enolateOHOHE + =electrophileOEenolOHBr 2OBrAlpha Halogenation Section 22.3HAlpha AlkylationO OLi O Section 22.8LDA (base)CH 3 ILiNLDA =
Overview of Reactions 4/27-5/9 - Reactions with carbonyls4. Condensation Reactions: Enolate/Enol ChemistryO O ObaseR'OH OHRR R' R''R''RAldol Reaction Section 23.2-23.7ObaseOOHOHCHHCH3 2OH 3 CCH 2HH 3 CHClaisen CondensationSection 23.8-23.9EtOOCH3baseEtOOCH2OH 3 COCH 2OOEt-+ OEtH 3 COEtKey in fatty acid biosynthesis
Overview of Reactions 4/27-5/9 - Reactions with carbonyls4. Condensation Reactions: Enolate/Enol ChemistrycontinuedMichael Reaction Section 23.11O O O ONaOEtOOEtOMe EtO MeH H HOEtOHMeHOEtMeHOMeOOEtOHMeHOHMe
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