CHAPTER 18 KETONES AND ALDEHYDES

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Presentation transcript:

CHAPTER 18 KETONES AND ALDEHYDES PROBLEMS 1,3,4,6,7-11,12C 15,17,19,20,24,27A,C,31,33,34A,B,D,35A,C,39A-E,45A,B,51A-D,61,65,66

CARBONYL COMPOUNDS CONTAIN A C=O GROUP IMPORTANT MEMBERS ALDEHYDE KETONE CARBOXYLIC ACID ESTER ACID CHLORIDE AMIDE CHAPTER 18 CHAPTER 20 CHAPTER 21

STRUCTURE OF THE CARBONYL GROUP NOTE: NUC ATTACK OCCURS AT PI ORBITAL NOT BACKSIDE OF C=O CHAPTER 22

KETONES: ALKANONE, MUST NUMBER TO GIVE CARBONYL LOWEST NUMBER NOMENCLATURE IUPAC SYSTEM KETONES: ALKANONE, MUST NUMBER TO GIVE CARBONYL LOWEST NUMBER 5,5-DIMETHYL-3-HEXANONE (5,5-DIMETHYLHEXAN-3-ONE) BUT 4-HYDROXY-2-BUTANONE 3-OXOBUTANOIC ACID

ALDEHYDES - IUPAC ALDEHYDE CARBON IS NUMBERED “ONE” 3-ISOPROPYLHEXANAL 6 4 2 1 5 3 6 2 4 3 5 1 3-ISOPROPYLHEXANAL FORMYLCYCLPENTANE 3-ISOPROPYL-5-OXOHEXANAL

ALDEHYDES COMMON NAMES STEM PLUS ALDEHYDE HCHO HCO2H FORMALDEHYDE FORMICA - ANTS FORMIC ACID CH3CHO CH3COOH ACETALDEHYDE ACETUM - SOUR ACETIC ACID CH3CH2CHO CH3CH2CO2H PROPIONALDEHYDE PROTOS PION - FIRST FAT PROPIONIC ACID CH3CH2CH2CO2H CH3CH2CH2CHO BUTYRALDEHYDE BUTRYM - BUTTER BUTYRIC ACID CH3CH2CH2CH2CH2CHO CH3CH2CH2CH2CH2CO2H CAPROALDEHYDE CAPER - GOAT CAPROIC ACID

Ketones common names NAME RADICALS IN ALPHA ORDER + KETONE RADICAL SYSTEM NAME RADICALS IN ALPHA ORDER + KETONE Methyl phenyl ketone STEM CONVENTION - ALKYL METHYL KETONES NAME STEM OF ALKYL GROUP ACCORDING tTO THE PREVIOUS SLIDE FOLLOWED BY PHENONE ACETOPHENONE Write the structure for butyrophenone

SPECTROSCOPY OF ALDEHYDES AND KETONES 2. NMR Read pp 780-782 1. IR READ PAGE 780 MASS SPECTRA ALPHA CLEAVAGE TWO ACYLIUM IONS ARE ABOUT THE SAME THEREFORE ETHYL RADICAL IS MORE STABLE THAN METHYL RADICAL STABILITY CONTROLS FRAGMENTATION

McLAFFERTY REARRANGEMENT CHARACTERISTICS A GAMMA HYDROGEN IN THE PARENT CATION-RADICAL IS TRANSFERRED TO CARBONYL OXYGEN ATOM INTRAMOLECULARLY CLEAVAGE OF ALPHA-BETA CARBON (WITH RESPECT TO C=O OCCURS A STABLE ALKENE IS LOST AND A NEW RESONANCE STABILIZED CATION RADICAL(ENOL) IS FORMED NOTE- THE PARENT CATION, STABLE ALKENE LOST, AND THE NEW STABILIZED CATION RADICAL HAVE EVEN MOLECULAR MASSES

EXAMPLE g a b Even mw Even mw

MECHANISM OF McLAFFERTY REARRANGEMENT THERE IS A NICE SUMMARY ON BOTTOM OF PAGE 784. LOOK IT OVER.

REVIEW OF SYNTHESIS OF KETONES AND ALDEHYDES OXIDATION OF ALCOHOLS - LAST SEMESTER OZONOLYSIS OF ALKENES - LAST SEMESTER FRIEDEL ACEYLATION AND GATTERMAN KOCH WILL BE COVERED ON NEXT TEST HYDRATION OF ALKYNES - LAST SEMESTER HYDROBORATION AND OXIDATION - LAST SEMESTER

1,3-DITHIANE METHOD Dream up a mechanism for this reaction. PREPARATION OF 1,3-DITHIANES Dream up a mechanism for this reaction.

WHY HIGH ACIDITY OF 1,3-DITHIANES? Old explanation Vacant d-orbitals Modern explanation s* Thus

Synthetic Methodology 1. Deprotonation of 1,3-dithiane with n-BuLi 2. Alkylation or dithane anion (SN2) R must be methyl or primary R can not be Ar, CH2=CH 3. Hydrolysis of alkylated dithiane.

Preparation of Ketones via 1,3-dithianes INSTEAD OF STOPPING AT MONO-ALKYLATION STEP, ONE CAN REPEAT PROCESS USING THE REMAINING ACIDIC HYDROGEN ATOM

UMPOLUNG OF C=O "acyl anion equivalent"

Retrosynthetic analysis Prepare 1-phenyl-2-pentanone HSCH2CH2CH2SH n-BuLi n-BuLi PhCH2B CH3CH2CH2Br hydrolysis

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