Rules for Abbreviation of Protecting Groups (IUPAC Technical Report)*
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Common Names for Selected Aromatic Groups
More Nomenclature: Common Names for Selected Aromatic Groups Phenyl group = or Ph = C6H5 = Aryl = Ar = aromatic group. It is a broad term, and includes any aromatic rings. Benzyl = Bn = It has a -CH2- (methylene) group attached to the benzene ring. This group can be used to name particular compounds, such as the one shown below. This compound has chlorine attached to a benzyl group, therefore it is called benzyl chloride. Benzoyl = Bz = . This is different from benzyl group (there is an extra “o” in the name). It has a carbonyl attached to the benzene ring instead of a methylene group. For example, is named benzoyl chloride. Therefore, it is sometimes helpful to recognize a common structure in order to name a compound. Example: Nomenclature: 3-phenylpentane Example: This is Amaize. It is used to enhance the yield of corn production. The systematic name for this compound is 2,4-dinitro-6-(1-methylpropyl)phenol. Polynuclear Aromatic Compounds Aromatic rings can fuse together to form polynuclear aromatic compounds. Example: It is two benzene rings fused together, and it is aromatic. The electrons are delocalized in both rings (think about all of its resonance form). Example: This compound is also aromatic, including the ring in the middle. All carbons are sp2 hybridized and the electron density is shared across all 5 rings. Example: DDT is an insecticide and helped to wipe out malaria in many parts of the world. Consequently, the person who discovered it (Muller) won the Nobel Prize in 1942. The systematic name for this compound is 1,1,1-trichloro-2,2-bis-(4-chlorophenyl)ethane. -
Aldehydes and Ketones
12 Aldehydes and Ketones Ethanol from alcoholic beverages is first metabolized to acetaldehyde before being broken down further in the body. The reactivity of the carbonyl group of acetaldehyde allows it to bind to proteins in the body, the products of which lead to tissue damage and organ disease. Inset: A model of acetaldehyde. (Novastock/ Stock Connection/Glow Images) KEY QUESTIONS 12.1 What Are Aldehydes and Ketones? 12.8 What Is Keto–Enol Tautomerism? 12.2 How Are Aldehydes and Ketones Named? 12.9 How Are Aldehydes and Ketones Oxidized? 12.3 What Are the Physical Properties of Aldehydes 12.10 How Are Aldehydes and Ketones Reduced? and Ketones? 12.4 What Is the Most Common Reaction Theme of HOW TO Aldehydes and Ketones? 12.1 How to Predict the Product of a Grignard Reaction 12.5 What Are Grignard Reagents, and How Do They 12.2 How to Determine the Reactants Used to React with Aldehydes and Ketones? Synthesize a Hemiacetal or Acetal 12.6 What Are Hemiacetals and Acetals? 12.7 How Do Aldehydes and Ketones React with CHEMICAL CONNECTIONS Ammonia and Amines? 12A A Green Synthesis of Adipic Acid IN THIS AND several of the following chapters, we study the physical and chemical properties of compounds containing the carbonyl group, C O. Because this group is the functional group of aldehydes, ketones, and carboxylic acids and their derivatives, it is one of the most important functional groups in organic chemistry and in the chemistry of biological systems. The chemical properties of the carbonyl group are straightforward, and an understanding of its characteristic reaction themes leads very quickly to an understanding of a wide variety of organic reactions. -
Ep 2611776 B1
(19) TZZ ___T (11) EP 2 611 776 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C07D 211/36 (2006.01) C07D 471/04 (2006.01) 21.09.2016 Bulletin 2016/38 A61K 31/45 (2006.01) A61P 3/10 (2006.01) C07D 211/76 (2006.01) (21) Application number: 11822081.3 (86) International application number: (22) Date of filing: 25.08.2011 PCT/KR2011/006260 (87) International publication number: WO 2012/030106 (08.03.2012 Gazette 2012/10) (54) PRODUCTION METHOD OF INTERMEDIATE COMPOUND FOR SYNTHESIZING MEDICAMENT HERSTELLUNGSVERFAHREN FÜR EINE INTERMEDIATVERBINDUNG ZUR SYNTHESE EINES MEDIKAMENTS PROCÉDÉ DE PRODUCTION D’UN COMPOSÉ INTERMÉDIAIRE POUR LA SYNTHÈSE D’UN MÉDICAMENT (84) Designated Contracting States: EP-A2- 0 279 435 WO-A1-2006/104356 AL AT BE BG CH CY CZ DE DK EE ES FI FR GB WO-A1-2006/104356 US-A- 5 556 982 GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO US-A1- 2008 039 517 PL PT RO RS SE SI SK SM TR • KIM S ET AL: "Free Radical-Mediated (30) Priority: 03.09.2010 KR 20100086619 Carboxylation by Radical Reaction of Alkyl Iodides with Methyl Oxalyl Chloride", (43) Date of publication of application: TETRAHEDRONLETTERS, PERGAMON, GB, vol. 10.07.2013 Bulletin 2013/28 39, no. 40, 1 October 1998 (1998-10-01), pages 7317-7320, XP004133669, ISSN: 0040-4039, DOI: (73) Proprietor: LG Life Sciences Ltd 10.1016/S0040-4039(98)01568-8 Jongno-gu, Seoul 110-062 (KR) • CHRISTOPHE MORIN ET AL: "Synthesis and Evaluation of Boronated Lysine and (72) Inventors: Bis(carboranylated)[gamma]-Amino Acids as • KIM, Bong Chan Monomers for Peptide Assembly", EUROPEAN Daejeon 305-380 (KR) JOURNAL OF ORGANIC CHEMISTRY, vol. -
Carboxylic Acid Functionalized Butyl Rubber: from Synthesis to Applications
Western University Scholarship@Western Electronic Thesis and Dissertation Repository 2-7-2013 12:00 AM Carboxylic Acid Functionalized Butyl Rubber: From Synthesis to Applications Matthew John McEachran The University of Western Ontario Supervisor Dr. Elizabeth R. Gillies The University of Western Ontario Graduate Program in Chemistry A thesis submitted in partial fulfillment of the equirr ements for the degree in Master of Science © Matthew John McEachran 2013 Follow this and additional works at: https://ir.lib.uwo.ca/etd Part of the Materials Chemistry Commons, Medicinal-Pharmaceutical Chemistry Commons, and the Polymer Chemistry Commons Recommended Citation McEachran, Matthew John, "Carboxylic Acid Functionalized Butyl Rubber: From Synthesis to Applications" (2013). Electronic Thesis and Dissertation Repository. 1117. https://ir.lib.uwo.ca/etd/1117 This Dissertation/Thesis is brought to you for free and open access by Scholarship@Western. It has been accepted for inclusion in Electronic Thesis and Dissertation Repository by an authorized administrator of Scholarship@Western. For more information, please contact [email protected]. Carboxylic Acid Functionalized Butyl Rubber: From Synthesis to Applications (Spine title: Carboxylic Acid Functionalized Butyl Rubber) (Thesis format: Integrated Article) by Matthew John McEachran Graduate Program in Chemistry A thesis submitted in partial fulfillment of the requirements for the degree of Master of Science The School of Graduate and Postdoctoral Studies The University of Western Ontario London, -
Alkenes and Alkynes
02/21/2019 CHAPTER FOUR Alkenes and Alkynes H N O I Cl C O C O Cl F3C C Cl C Cl Efavirenz Haloprogin (antiviral, AIDS therapeutic) (antifungal, antiseptic) Chapter 4 Table of Content * Unsaturated Hydrocarbons * Introduction and hybridization * Alkenes and Alkynes * Benzene and Phenyl groups * Structure of Alkenes, cis‐trans Isomerism * Nomenclature of Alkenes and Alkynes * Configuration cis/trans, and cis/trans Isomerism * Configuration E/Z * Physical Properties of Hydrocarbons * Acid‐Base Reactions of Hydrocarbons * pka and Hybridizations 1 02/21/2019 Unsaturated Hydrocarbons • Unsaturated Hydrocarbon: A hydrocarbon that contains one or more carbon‐carbon double or triple bonds or benzene‐like rings. – Alkene: contains a carbon‐carbon double bond and has the general formula CnH2n. – Alkyne: contains a carbon‐carbon triple bond and has the general formula CnH2n‐2. Introduction Alkenes ● Hydrocarbons containing C=C ● Old name: olefins • Steroids • Hormones • Biochemical regulators 2 02/21/2019 • Alkynes – Hydrocarbons containing C≡C – Common name: acetylenes Unsaturated Hydrocarbons • Arene: benzene and its derivatives (Ch 9) 3 02/21/2019 Benzene and Phenyl Groups • We do not study benzene and its derivatives until Chapter 9. – However, we show structural formulas of compounds containing a phenyl group before that time. – The phenyl group is not reactive under any of the conditions we describe in chapters 5‐8. Structure of Alkenes • The two carbon atoms of a double bond and the four atoms bonded to them lie in a plane, with bond angles of approximately 120°. 4 02/21/2019 Structure of Alkenes • Figure 4.1 According to the orbital overlap model, a double bond consists of one bond formed by overlap of sp2 hybrid orbitals and one bond formed by overlap of parallel 2p orbitals. -
Reactions of Aromatic Compounds Just Like an Alkene, Benzene Has Clouds of Electrons Above and Below Its Sigma Bond Framework
Reactions of Aromatic Compounds Just like an alkene, benzene has clouds of electrons above and below its sigma bond framework. Although the electrons are in a stable aromatic system, they are still available for reaction with strong electrophiles. This generates a carbocation which is resonance stabilized (but not aromatic). This cation is called a sigma complex because the electrophile is joined to the benzene ring through a new sigma bond. The sigma complex (also called an arenium ion) is not aromatic since it contains an sp3 carbon (which disrupts the required loop of p orbitals). Ch17 Reactions of Aromatic Compounds (landscape).docx Page1 The loss of aromaticity required to form the sigma complex explains the highly endothermic nature of the first step. (That is why we require strong electrophiles for reaction). The sigma complex wishes to regain its aromaticity, and it may do so by either a reversal of the first step (i.e. regenerate the starting material) or by loss of the proton on the sp3 carbon (leading to a substitution product). When a reaction proceeds this way, it is electrophilic aromatic substitution. There are a wide variety of electrophiles that can be introduced into a benzene ring in this way, and so electrophilic aromatic substitution is a very important method for the synthesis of substituted aromatic compounds. Ch17 Reactions of Aromatic Compounds (landscape).docx Page2 Bromination of Benzene Bromination follows the same general mechanism for the electrophilic aromatic substitution (EAS). Bromine itself is not electrophilic enough to react with benzene. But the addition of a strong Lewis acid (electron pair acceptor), such as FeBr3, catalyses the reaction, and leads to the substitution product. -
Chem 341 • Organic Chemistry I Lecture Summary 07 • September 07, 2007
Chem 341 • Organic Chemistry I Lecture Summary 07 • September 07, 2007 Chapter 2 - Polar Covalent Bonds; Acids and Bases Alkyl Substituents When an alkane is a smaller part of a larger molecule (a substituent), it is called an ‘alkyl’ group. The parent name for the number of carbons remains the same, but it is given a ‘yl’ ending indicating it is a sub-part of the molecule. See for example several common names for some organic molecules shown below. Note that for chlorobutane, there are four different constitutional isomers possible. Normal butane refers to the straight chain. If the chlorine is moved to a secondary carbin it is called a secondary chloride. If the carbon skeleton is changed, it becomes an iso-butyl group and if the chlorine is attached to the tertiary carbon it is a tert-butyl group. These common names are still in use, though there is a more exact systematic naming system that is easier to understand (but longer names). H3C Cl OH methyl chloride ethyl alcohol Cl Cl Cl Cl n-butyl chloride sec-butyl chloride iso-butyl chloride tert-butyl chloride 1-chlorobutane 2-chlorobutane 1-chloro-2-methylpropane 2-chloro-2-methylpropane Degree of Alkyl Substitution We designate a kind of carbon (or kind of functional group attached to that carbon) according to how many other alkyl groups are attached to it. For example, a carbon on the end of a chain (with one alkyl group) would be a primary carbon. The hydrogens attached to that carbon would be called primary hydrogens. An alcohol attached to a primary carbon would be called a primary alcohol. -
Chapter 16 the Chemistry of Benzene and Its Derivatives
Instructor Supplemental Solutions to Problems © 2010 Roberts and Company Publishers Chapter 16 The Chemistry of Benzene and Its Derivatives Solutions to In-Text Problems 16.1 (b) o-Diethylbenzene or 1,2-diethylbenzene (d) 2,4-Dichlorophenol (f) Benzylbenzene or (phenylmethyl)benzene (also commonly called diphenylmethane) 16.2 (b) (d) (f) (h) 16.3 Add about 25 °C per carbon relative to toluene (110.6 C; see text p. 743): (b) propylbenzene: 161 °C (actual: 159 °C) 16.4 The aromatic compound has NMR absorptions with greater chemical shift in each case because of the ring current (Fig. 16.2, text p. 745). (b) The chemical shift of the benzene protons is at considerably greater chemical shift because benzene is aromatic and 1,4-cyclohexadiene is not. 16.6 (b) Among other features, the NMR spectrum of 1-bromo-4-ethylbenzene has a typical ethyl quartet and a typical para-substitution pattern for the ring protons, as shown in Fig. 16.3, text p. 747, whereas the spectrum of (2- bromoethyl)benzene should show a pair of triplets for the methylene protons and a complex pattern for the ring protons. If this isn’t enough to distinguish the two compounds, the integral of the ring protons relative to the integral of the remaining protons is different in the two compounds. 16.7 (b) The IR spectrum indicates the presence of an OH group, and the chemical shift of the broad NMR resonance (d 6.0) suggests that this could be a phenol. The splitting patterns of the d 1.17 and d 2.58 resonances show that the compound also contains an ethyl group, and the splitting pattern of the ring protons shows that the compound is a para-disubstituted benzene derivative. -
Docw R S Acquired by ERIC Include Many Informal Unpublished * Material - T Available Fromother Sources
DOCUMENT RESUME ED 135 584 SE 021 575 AUTHOR Zdravkovich, V. TITLE Organic Chemistry Self Instructional Package 4: Alkanes-Nomenclature. INSTITUTION Prince George's Community Coll., Largo, Md. PUB DATE 76 NOTE 41p.; For related Packages 1-17, see SE 021 572-588; Not available in hard copy due to copyright restrictions AVAILABLE FROM Prince George's Community College Bookstore, Largo, Maryland 20870 ($17.00 a set, $1.00 each) EDRS PRICE MF-$0.83 Plus Postage. MC Not Available from EDRS. DESCRIPTORS *Autoinstructional Aids; *Chemistry; *College Science; Higher Education; *Independent Study; Individualized Instruction; Individualized Programs; *Organic Chemistry; Science Education; Self Help Programs IDENTIFIERS Alkanes; Prince Georges Community College ABSTRACT This booklet, one of a series of 17 developed at Prince George's Community College, largo, Maryland, provides an individualized, self-paced undergraduate organic chemistry instruction module designed to augment any course in organic chemistry but particularly those taught using the text "Organic Chemistry" by Morrison and Boyd. The entire series of modules covers the first 13 chapters of the Morrison-Boyd text in great detail. Each module has been provided with from one to three audiotapes, available from PrinOe George's Community College, to provide students additional explanations of particular concepts. Each module includes a self-evaluation exercise, a reference guide, worksheets to be completed with the audiotapes, answer sheets for the worksheets, a progress evaluation, an answer sheet for the progress evaluation, an answer sheet for the self-evaluation exercise, an introduction to the topic covered by the module, and student performance objectives for the module. The topic of this module is alkanes. -
Organic and Biological Chemistry
CHAPTER 23 Organic and Biological Chemistry CONTENTS HO H 23.1 ▶ Organic Molecules and Their C Structures: Alkanes H H C 23.2 ▶ Families of Organic Compounds: HO O O C C Functional Groups 23.3 ▶ Naming Organic Compounds H CC 23.4 ▶ Carbohydrates:HO A Biological Example HO OH of Isomers H 23.5 ▶ Valence Bond TCheory and Orbital OverlapH Pictures H C 23.6 ▶ Lipids:HO A Biological EOxample ofO Cis–Trans IsomerismC C 23.7 ▶ Formal Charge and Resonance in Organic CompoundsH CC 23.8 ▶ Conjugated SystemsHO OH 23.9 ▶ Proteins: A Biological Example of Conjugation 23.10 ▶ Aromatic Compounds and Molecular Ascorbic acid, also known as vitamin C, is an essential nutrient in the human diet Orbital Theory because it is not synthesized in our body. We can eat citrus fruits or take pills that contain vitamin C to maintain health. 23.11 ▶ Nucleic Acids: A Biological Example of Aromaticity ? Which Is Better, Natural or Synthetic? The answer to this question can be found in the INQUIRY ▶▶▶ on page 1021. STUDY GUIDE M23_MCMU3170_07_SE_C23.indd 978 27/11/14 2:11 AM f the ultimate goal of chemistry is to understand the world around us on a molecular level, then a knowledge of biochemistry—the chemistry of living organisms—is a central part Iof that goal. Biochemistry, in turn, is a branch of organic chemistry, a term originally used to mean the study of compounds from living organisms while inorganic chemistry was used for the study of compounds from nonliving sources. Today, however, we know that there are no fundamental differences between organic and inorganic compounds; the same principles apply to both. -
The 9-Phenyl-9-Fluorenyl Group for Nitrogen Protection in Enantiospecific Synthesis
Molecules 2010, 15, 6512-6547; doi:10.3390/molecules15096512 OPEN ACCESS molecules ISSN 1420-3049 www.mdpi.com/journal/molecules Review The 9-Phenyl-9-fluorenyl Group for Nitrogen Protection in Enantiospecific Synthesis Essi J. Karppanen and Ari M. P. Koskinen * Laboratory of Organic Chemistry, Department of Chemistry, Aalto University, School of Science and Technology, PO Box 16100, Kemistintie 1, FI-00076 Aalto, Finland; E-Mail: [email protected] * Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel.: +358-9-470 22526; Fax: +358-9-470 22538. Received: 12 August 2010; in revised form: 13 September 2010 / Accepted: 14 September 2010 / Published: 17 September 2010 Abstract: One of the biggest challenges in asymmetric synthesis is to prevent racemization of enantiopure starting materials. However, at least some of the enantiopurity is lost in most of the existing reactions used in synthetic organic chemistry. This translates into unnecessary material losses. Naturally enantiopure proteinogenic amino acids that can be transformed into many useful intermediates in drug syntheses, for example, are especially vulnerable to this. The phenylfluoren-9-yl (Pf) group, a relatively rarely used protecting group, has proven to be able to prevent racemization in α-amino compounds. This review article showcases the use of Pf-protected amino acid derivatives in enantiospecific synthesis. Keywords: phenylfluorenyl; amino acid; nitrogen protecting group; enantiospecific; enantiopure 1. Introduction Of the 20 natural proteinogenic amino acids, 19 are chiral, and being readily commercially available, they are potentially useful educts for enantiospecific synthesis. Typically the nitrogen atom needs to be protected to allow further manipulations of the carboxylic acid center. -
Destabilized Carbenium Ions. Secondary and Tertiary
CORE Metadata, citation and similar papers at core.ac.uk Provided by Publications at Bielefeld University ORGANIC MASS SPECTROMETRY, VOL. 22, 437-443 (1987) Destabilized Carbenium Ions Secondary and Tertiary a-Acetylbenzyl Cations and a -Benzoylbenzyl Cations Anne-Marie Dommrose and Hans-Friedrich Grutzmacher Fakultat fur Chemie, Universitat Bielefeld, UniversitatsstraBe 25, D-4800 Bielefeld, FRG The secondary a-acetylbenzyl and a-benzoylbenzyl cations, as well as their tertiary analogues, have been generated in a mass spectrometer by electron impact induced fragmentation of the corresponding a-bromoketones. These ions belong to the interesting family of destabilized a-acylcarbenium ions. While primary a-acylcarbenium ions appear to be unstable, the secondary and tertiary ions exhibit the usual behaviour of stable entities in a potential energy well. This can be attributed to a ‘push-pull’ substitution at the carbenium ion centre by an electron-releasing phenyl group and an electron-withdrawing acyl substituent. The characteristic unimolecular reaction of the metastable secondary and tertiary a-acylbenzyl cations is the elimination of CO by a rearrangement reaction involving a 1,Zshift of a methyl group and a phenyl group, respectively. The loss of CO is accompanied by a very large kinetic energy release, which gives rise to broad and dish-topped peaks for this process in the mass-analysed ion kinetic energy spectra of the corresponding ions. This behaviour is attributed to the rigid critical configuration of a corner-protonated cyclopropanone derivative and a bridged phenonium ion derivative, respectively, for this reaction. For the tertiary a-acetyl-a-methylbenzyl cations, it has been shown by deuterium labelling and by comparison of collisional activation spectra that these ions equilibrate prior to decomposition with their ‘protomer’ derivatives formed by proton migration from the a-methyl substituent to the carbonyl group and to the benzene ring.