TAILIEUCHUNG - Chapter 11: ALDEHYDES-KETONES

Common names: carboxylic acid - “aldehyde” is substituted for “ic acid”. Lower priority than ester - “oxo” group. Derived names: alkyls + ketone. IUPAC names: hydrocarbon + one. | ORGANIC CHEMISTRY Dr Nam T. S. Phan Faculty of Chemical Engineering HCMC University of Technology Office: room 211, B2 Building Phone: 8647256 ext. 5681 Email: ptsnam@ Chapter 11: ALDEHYDES-KETONES C=O C=C SP2 carbon NOMENCLATURE OF ALDEHYDES IUPAC names: hydrocarbon + al Common names: carboxylic acid “aldehyde” is substituted for “ic acid” Lower priority than ester “oxo” group NOMENCLATURE OF KETONES Derived names: alkyls + ketone IUPAC names: hydrocarbon + one PREPARATION OF ALDEHYDES & KETONES Aldehydes & ketones from alkenes In the presence of an oxidizing agent, the products will be ketones / carboxylic acids Aldehydes & ketones from alkynes Markovnikov’s rule Anti-Markovnikov Aldehydes & ketones from alcohols Can NOT be isolated PCC: pyridinium chlorochromate Aldehydes from esters, acyl chlorides Note: LiAlH4 alcohols Preparation of aromatic ketones Gatterman-Koch synthesis of benzaldehyde Can NOT be prepared & isolated REACTIONS OF ALDEHYDES & KETONES I The partial positive carbon can be attacked by nucleophiles The addition of nucleophiles to the carbon atom of the carbonyl group in nucleophilic addition reactions Reactions with Grignard reagents Only for the reaction of HCHO Numbers 1 & 2 are used to indicate that the acid is not added until the reaction with the Grignard reagent is complete Reactions with acetylide ions Weak acid, will NOT react with the triple bond Reactions with hydrogen cyanide Converted back to carbonyl in basic solutions Nitriles carboxylic acids Nitriles amines Reactions with primary amines Reaction mechanism: Reactions with secondary amines Reaction mechanism: Reactions with water Reactions with alcohols Reaction mechanism: Reactions with sulfur nucleophiles Reduction reactions – with hydride ion NaBH4 can reduce aldehyde, ketones, acyl chlorides, but NOT alkenes & alkynes LiAlH4 is a stronger reducing agent than NaBH4, but NOT safe to use for aldehydes & ketones Reduction reactions to hydrocarbons NOTE: Oxidation reactions Aldehydes are generally easier to oxidize than primary alcohols Tollens reagent Too weak to oxidize an alcohol or any other functional groups Should be used when oxidizing aldehydes containing double bond REACTIONS OF ALDEHYDES & KETONES II – REATIONS AT a-C Aldol additions Reaction mechanism: Aldol additions occur more slowly with ketones Nucleophilic additions Aldol condensations = Additions + dehydrations Easier to dehyrate than other alcohols because the double bond is conjugated with the carbonyl group Aldol condensations sometimes occur under the aldol addition conditions without additional heating NOT isolated Mixed / crossed Aldol additions 4 addition products NOT useful Very strong base Halogenations at a-C Only 1 hydrogen is replaced in acidic solution The haloform reactions Only for methyl ketones

• Hoá học
• organic chemistry
• hóa hữu cơ
• công nghệ hóa học
• Chemical Engineering
• alhehydes
• ketones
• In this workbook
• experiments are elaborated using small scale glassware and equipments from a Small Lab Kit
• developed at the Department of Chemistry
• Faculty of Science
• Chulalongkorn University in Thailand
• This Small Lab Kit was created as a result of the research project entitled “Chemistry Laboratory Based on Chemical Safety and Pollution Minimization” sponsored by Thai Research Fund (RDG 3 07 2543)
• One of the outcomes of this project is the organic laboratory book entitled “Organic Chemistry Laboratory Based on Chemical Safety and Pollution Minimization” written in Thai by professors from 7 universities in this project
• They compiled
• adjusted and tested the experiments taken from several traditional organic chemistry laboratory books using the prototype of Small Lab Kit
• Currently
• some selected experiments from this Thai organic chemistry laboratory text have further been modified
• rewritten and edited in English as appeared in this workbook
• Some experiments ar
• Ebook Organic chemistry
• Nucleophilic substitution
• Determining organic structures
• nucleophilic addition
• Organic structures
• Electrophilic aromatic substitution
• Principles of organic chemistry
• Methods of organic chemistry
• The methane series
• The acetylene series
• Polybasic acids
• High school
• University entrance exam
• Teaching organic chemistry
• Organic chemistry exam question
• Interdisciplinary science
• Advanced practical organic chemistry
• Functional groups
• Organic synthesis reagents
• The structure
• Reactions of organic names
• Fundamentals of organic chemistry
• Carbonyl alpha substitution reactions
• Condensation reactions
• Structure determination
• The organic chemistry
• Organic chemistry principles in context
• Starch to the principles
• The structures of organic molecules
• Mass spectrometers
• Infrared spectrometers
• Nuclear magnetic resonance spectrometers
• Modern physical organic chemistry
• Strain and stability
• Covalent binding forces
• Electronic organic materials
• Thermal pericyclic reactions
• The study of organic chemistry
• Stereochemistry and resonance
• Identification of organic compounds
• Elimination reactions
• Electrophilic addition reactions
• Electron delocalization
• Organic compounds
• Cyclic hydrocarbons
• Aromatic alcohols
• Aromatic compounds containing
• Inorganic chemistry
• A guidebook to mechanism in organic chemistry
• Aromatic systems
• Linear free energy relationships
• Symmetry controlled reactions
• Fatty acid catabolism
• The chemistry of the carbonyl group
• The industrial road toward increasing efficiency
• Lecture Organic chemistry
• Hóa học hữu cơ
• Bài giảng Hóa học hữu cơ
• Chemistry of benzene
• Derivatives of benzene
• Summary of Organic Chemistry Dotoral Thesis
• Organic Chemistry Dotoral Thesis
• Natural Products Chemistry
• Biological evaluation
• Chemistry of natural compounds
• Ideas in chemistry
• Molecular sciences
• Synthetic chemistry
• Innovative processes in organic chemistry
• Predictive tools
• Organic chemical reactions
• Electronic Structure
• Electronic configurations of atoms
• Electronic configurations
• Wave properties of electrons
• Wave interactions
• Stereochemistry of alkanes
• Alkane conformations
• Chemical reactions
• Chlorination of Methane
• Chiral carbons
• Nonmobile conformers
• Alkyl Halides