TAILIEUCHUNG - Ebook Organic chemistry (2nd edition): Part 2 - Jonathan Clayden, Nick Greeves, Stuart Warren

(BQ) Part 2 book "Organic chemistry" has contents: Alkylation of enolates, the aldol and claisen reactions; sulfur, silicon and phosphorus in organic chemistry; saturated heterocycles and stereoelectronics; participation, rearrangement and fragmentation;.and other contents. | This page intentionally left blank Suggested solutions for Chapter 25 25 PROB LE M 1 Suggest how these compounds might be made by alkylation of an enol or enolate. EtO2C CO2Et O Purpose of the problem An exercise in choosing good routes to simple compounds. Suggested solution As you can see from the carbonyl groups in these compounds, it is pretty obvious which is the new bond to be made. In both cases, the electrophile will need to be an allylic halide. These are good electrophiles for SN2 reactions so they will work well here. We need to use the electrophile twice in the first case and the enolate is that of diethyl malonate. The second case will require an enol or enolate equivalent to prevent self-condensation: a silyl enol ether (p. 595 in the textbook) or an enamine (p. 591 in the textbook) is ideal. If you use a silyl enol ether, don’t forget the Lewis acid! EtO2C H EtO2C CO2Et 1. EtO H 2. CO2Et repeat EtO2C H Br Br Me3SiCl O Et3N + OSiMe3 SnCl4 or other Lewis acid O CO2Et The reason why allylic halides make good electrophiles is discussed in the textbook on p. 341. 250 Solutions Manual to accompany Organic Chemistry PROB LE M 2 How might these compounds be made using alkylation of an enol or enolate as one step in the synthesis? O O O O Purpose of the problem An exercise in using enolate chemistry to make carbonyl compounds disguised as acetals. Suggested solution See p. 227 of the textbook for a reminder of how to make cyclic acetals. The only functional group in either compound is an acetal. Cyclic acetals are made from diols and carbonyl compounds so we need to have a look at the deprotected molecules before taking any further decisions. H O O O OH OH H O HO O O HO If we are going to use enolate chemistry, we have to make the diols by reduction of carbonyl compounds. As both diols have a 1,3-relationship between the OH groups, the carbonyl precursors will be the very enolizable 1,3-dicarbonyl compounds, which can be

• Hoá học
• Organic chemistry
• Alkylation of enolates
• The aldol and claisen reactions
• Saturated heterocycles
• Organic chemistry
• 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