DOCSLIB.ORG

Organic Nomenclature-IV.Pmd

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text

Load more

Concepts in Chemistry CHAPTER-IV TRIVIAL OR COMMON SYSTEM OF NOMENCLATURE Naming an organic compound on the basis of the rules recommended by IUPAC is absolutely essential for big and complex molecules. However, small molecules are more popularly addressed by their common names or the trivial or the primitive names. We already know before that IUPAC has accepted a few common names as official names e.g acetic acid, formic acid etc. for some compounds and isopropyl, sec-butyl, tert-butyl etc. as some groups. A detailed logically genesis of the common system is discussed below. TYPES OF CARBON ATOMS: There are four types of carbon atoms. (i) Primary or 10 carbon atom: carbon atom attached with 3 or 4 H atoms. (ii) Secondary(sec-) or 20 carbon atom: carbon atom attached with 2 H atoms. (iii) Tertiary(tert-) or 30 carbon atom: carbon atom attached with 1 H atom (iv) Quaternary or 40 carbon atom: carbon atom attached with no H atom. 0 0 0 1 1 1 CH3 0 0 CH3 0 0 CH3 1 3 0 4 2 3 Example: H3CCH C CH2 CH 0 0 1 1 CH3 CH3 In the above example, all the carbon atoms have been assigned with their types. SAQ IV.1. (i)Name the molecule in which a primary carbon atoms is linked with 4 H atom. (ii)Draw the structure and give the IUPAC name of the compound which contains one 40 and four 10 carbon atoms. TYPES OF ALKYL GROUPS: In common system alkyl groups are prefixed with the symbols n-, iso, sec-, tert- and neo. While naming the alkyl group all the carbon atoms present in the alkyl group are counted. Numbering of carbon atoms is not done in this case like IUPAC system. (i) normal or n-alkyl group: If all the carbon atoms of the alkyl group are connected in straight chain and there is no branching, it is called n-alkyl group. H3CCH2 CH2 H3CCH2 CH2 CH2 H3CCH2 CH2 CH2 CH2 n-propyl n-butyl n-pentyl or n-amyl (N.B: Note that methyl and ethyl groups are named as such; not as n-methyl and n-ethyl, because they do not have any other types like iso, sec- , tert- or neo) Nomenclature of Organic Compounds H3C (ii) isoalkyl group: The group beginning with CH unit and other carbon atoms if H3C any are connected in straight chain with no further branching is called isoalkyl group. H3C H3C H3C CH CH2 CH2 CH (isopropyl), CH CH2 (isobutyl) H3C H3C H3C isopentyl or isoamyl (iii) secondary or sec-alkyl group: When one H atom is removed from a secondary carbon atom, a sec- alkyl group results. Butane gives sec-butyl and propane gives sec-propyl groups. 0 2 H3CCH2 CH2 CH3 H3CCH2 CH CH3 H3CCH2 CH butane sec-butyl CH3 In sec-alkyl group the unfulfilled valency of the alkyl group(shown by dash mark) is connected to that carbon atom which is linking with one H atom. 0 2 H3C CH H3CCH2 CH3 H3CCHCH3 H3C propane sec-propyl Note that sec-propyl group is same as isopropyl as it satisfies the requirements of both types. Between the two names isopropyl is more popular and widely used. Note also that sec-alkyl group is restricted to sec-butyl only because larger sec-alkyl groups do not have unique structure. For example, sec-pentyl group can have two different structures which can be obtained from pentane by removing one H atom from C-2 and C-3. But butane gives only one sec-butyl group as C-2 position is unique. (iv) tertiary or tert-alkyl group: When one H atom is removed from a tertiary carbon atom, a tertiarty or tert- alkyl group results. CH3 CH3 CH3 CH3 0 0 3 3 H3CCH H3CC H3C CH2 CH H3C CH2 C CH3 CH3 CH3 tert-pentyl CH3 tert-butyl In tert-butyl group the unfulfilled valency of the alkyl group(shown by dash mark) is connected to that carbon atom which does not link with any H atom. The use of tert-alkyl group is limited to tert-butyl and tert-pentyl groups only as for higher tert-alkyl groups unique structures are not possible. (v) neopentyl group: The alkyl group beginning with the following part structure(I) and other carbon atoms if any are connected in straight chain is called neoalkyl group. Concepts in Chemistry CH3 CH3 CH3 H C C CH (neopentyl) H C C CH CH (neohexyl) H3CCCH2 (I) 3 2 3 2 2 and CH3 CH3 CH3 so on Note that while iso and neo prefixes are integrated with the names of the alkyl groups, n-, sec- and tert- prefixes remain separated from alkyl groups by a hyphen. SAQ IV.2: Draw the structures of the following alkyl groups (i)n-hexyl (ii)isohexyl (iii)neoheptyl NAMING OF COMPOUNDS USING COMMON OR TRIVIAL SYSTEMS: 1. ALKANES: (i) normal or n-alkane: When the carbon atoms are connected in straight chain and there is no branching, it is called a n-alkane. In other words one one H atom is attached with a n- alkyl group it becomes a n-alkane. H3CCH2 CH2 CH3 (n-butane), H3CCH2 CH2 CH2 CH3 (n-pentane) (ii) isoalkane: When one H atom is attached with an isoalkyl group, an isoalkane results. H3C H3C CH CH3 (isobutane) CH CH2 CH3 (isopentane) H3C H3C (iii) neoalkane: When one H atom is attached with a neoalkyl group, a neoalkane results. CH3 CH 3 H CCCH H CCCH CH 3 3 (neopantane) 3 2 3 (neohexane) CH3 CH 3 IMPORTANT: The names isobutane, isopentane and neopantane have been accepted as sytstematic IUPAC names for those alkanes. OLEFINES (ALKENES): The first member of alkene is called ethylene and all other alkenes are expressed as substituted ethylenes. Monosubstituted ethylene: If there is one alkyl substituent attached to any carbon atom of the C=C in place of one H atom, then it is called alkylethylene. It is a monosubstitued alkene. : H2CCH2 ethylene(ethene); H2CCHCH3 propylene or methyl ethylene(propene) Disubstituted ethylene Disubstituted alkenes are classifed as (i)symmetrical or sym-alkene and (ii)unsymmetrical or unsym-alkene. Nomenclature of Organic Compounds Symmetrical alkene: If one H atom from each of the two doubly bonded carbon atoms is substituted by same alkyl groups, it is a symmetrical alkene. Unsymmetrical alkene: If two H atoms of any one doubly bonded carbon atom are substituted by two same alkyl groups, it is an unsymmetrical alkene. The IUPAC names have been given inside parentheses for comparison. CH3 CH CH CH3 CH3 CCH2 CH3 sym-dimethylethylene unsym-dimethylethylen (but-2-ene) (2-methylpropene) Unsym-dimethylethylene(2-methylpropene) is also called isobutene or isobutylene. ALKYNE: The first member of alkyne is called acetylene and all other alkenes are expressed as substituted acetylenes- (i)monosubstituted- if one H atom is replaced by an alkyl group or (ii)disubstituted- if both the H atoms are replaced by alkyl groups H3C CH CCH HC CH H3CC CH H3CCCCH3 acetylene methylacetylene dimethylacetylene H3C isopropylacetylene SAQ IV.3: Draw the structures of the following compounds. Also give their IUPAC names. (i)isohexane (ii)neoheptane (iii)sec-butylethylene (iv)sym-diisopropylethylene (v)tert-butylacetylene (vi)ethylisobutylacetylene (vii)n-heptane ALKYL HALIDE(HALOALKANE): The haloalkanes are called alkyl halides in the common system. First the name of alkyl group according to common system is written which is followed by the term halide(fluoride, chloride, bromide, iodide) with a space in between. CH3 H3C CH Cl H3C C Br H3CCH2 CH2 I H3C CH3 isopropyl chloride tert-butylbromide n-propyl iodide (2-chloroprapane) (2-bromo-2-methylpropane) (1-iodopropane) SAQ IV.4: Give the common names of the following alkyl halides, also write their IUPAC names. H3C CH CH2 Br (i)CH3Br (ii)CH3-CH2-Cl (iii) (CH3)3C-I (iv) H3C SAQ IV.5: Draw the structures of the following and also give their IUPAC names. (i)sec-butyl chloride (ii)neopentyl iodide (iii)isohexylbromide (iv)tert-pentyl chloride (v) n-propyl iodide ALCOHOL: In common system, an alcohol is named as alkyl alcohol. First the name of the alkyl group is written according to common system, followed by the term alcohol with a space in between. Concepts in Chemistry CH3 H3C CH OH H3CCH2 CH OH H3CC CH2 OH CH3 H3C CH3 isopropyl alcohol sec-butyl alcohol neopentyl alcohol (propan-2-ol) (butan-2-ol) (2,2-dimethylpropan-1-ol) THIOALCOHOL: In common system thioalcohol is named as alkyl mercaptan. First the name of the alkyl group is written according to common system, followed by the term mercaptan with a space in between. H3C 3 SH 2 SH H3C CH H3C 3 1 sec-butyl mercaptan(butane-2-thiol) isopropyl mercaptan (propane-2-thiol); SALT OF ALCOHOL: RONa or ROK are the salts of alcohol which are named as metal alkoxides. The trivial name of the alkyl group is used to name the alkoxide. H3C O Na sodium isopropoxide(sodium propan-2-olate); H3C CH3CH2OK potassium ethoxide (potassium ethanolate) SAQ IV.6: Give the names of the following according to common system.Also give their IUPAC names. (i) CH3-CH2-OH (ii)CH3-OH (iii) CH3-CH2-CH2-OH (iv)CH3-CH(OH)-CH2- CH3 (v)(CH3)3COH (vi)(CH3)2CHCH2CH2OH SAQ IV.7: Draw the structures of the following alcohols. Also give their IUPAC names, (i) tert-pentyl alcohol (ii) n-butyl alcohol (iii) isopropyl alcohol (iv)isobutyl mercaptan (v) sodium tert-butoxide (vi)potassium methoxide KETONES: Ketone is named as alkyl alkyl ketone or dialkyl ketone having a space between any two words.The two alkyl groups attached to the carbonyl group are written first in alphabetical order followed by the term ketone.
Recommended publications
  • Report of the Advisory Group to Recommend Priorities for the IARC Monographs During 2020–2024

    Report of the Advisory Group to Recommend Priorities for the IARC Monographs During 2020–2024

    IARC Monographs on the Identification of Carcinogenic Hazards to Humans Report of the Advisory Group to Recommend Priorities for the IARC Monographs during 2020–2024 Report of the Advisory Group to Recommend Priorities for the IARC Monographs during 2020–2024 CONTENTS Introduction ................................................................................................................................... 1 Acetaldehyde (CAS No. 75-07-0) ................................................................................................. 3 Acrolein (CAS No. 107-02-8) ....................................................................................................... 4 Acrylamide (CAS No. 79-06-1) .................................................................................................... 5 Acrylonitrile (CAS No. 107-13-1) ................................................................................................ 6 Aflatoxins (CAS No. 1402-68-2) .................................................................................................. 8 Air pollutants and underlying mechanisms for breast cancer ....................................................... 9 Airborne gram-negative bacterial endotoxins ............................................................................. 10 Alachlor (chloroacetanilide herbicide) (CAS No. 15972-60-8) .................................................. 10 Aluminium (CAS No. 7429-90-5) .............................................................................................. 11
  • Brief Guide to the Nomenclature of Organic Chemistry

    Brief Guide to the Nomenclature of Organic Chemistry

    1 Brief Guide to the Nomenclature of Table 1: Components of the substitutive name Organic Chemistry (4S,5E)-4,6-dichlorohept-5-en-2-one for K.-H. Hellwich (Germany), R. M. Hartshorn (New Zealand), CH3 Cl O A. Yerin (Russia), T. Damhus (Denmark), A. T. Hutton (South 4 2 Africa). E-mail: [email protected] Sponsoring body: Cl 6 CH 5 3 IUPAC Division of Chemical Nomenclature and Structure suffix for principal hept(a) parent (heptane) one Representation. characteristic group en(e) unsaturation ending chloro substituent prefix 1 INTRODUCTION di multiplicative prefix S E stereodescriptors CHEMISTRY The universal adoption of an agreed nomenclature is a key tool for 2 4 5 6 locants ( ) enclosing marks efficient communication in the chemical sciences, in industry and Multiplicative prefixes (Table 2) are used when more than one for regulations associated with import/export or health and safety. fragment of a particular kind is present in a structure. Which kind of REPRESENTATION The International Union of Pure and Applied Chemistry (IUPAC) multiplicative prefix is used depends on the complexity of the provides recommendations on many aspects of nomenclature.1 The APPLIED corresponding fragment – e.g. trichloro, but tris(chloromethyl). basics of organic nomenclature are summarized here, and there are companion documents on the nomenclature of inorganic2 and Table 2: Multiplicative prefixes for simple/complicated entities polymer3 chemistry, with hyperlinks to original documents. An No. Simple Complicated No. Simple Complicated AND overall
  • Minutes of the IUPAC Chemical Nomenclature and Structure Representation Division (VIII) Committee Meeting Boston, MA, USA, August 18, 2002

    Minutes of the IUPAC Chemical Nomenclature and Structure Representation Division (VIII) Committee Meeting Boston, MA, USA, August 18, 2002

    Minutes of the IUPAC Chemical Nomenclature and Structure Representation Division (VIII) Committee Meeting Boston, MA, USA, August 18, 2002 Members Present: Dr Stephen Heller, Prof Herbert Kaesz, Prof Dr Alexander Lawson, Prof G. Jeffrey Leigh, Dr Alan McNaught (President), Dr. Gerard Moss, Prof Bruce Novak, Dr Warren Powell (Secretary), Dr William Town, Dr Antony Williams Members Absent: Dr. Michael Dennis, Prof Michael Hess National representatives Present: Prof Roberto de Barros Faria (Brazil) The second meeting of the Division Committee of the IUPAC Division of Chemical Nomenclature and Structure Representation held in the Great Republic Room of the Westin Hotel in Boston, Massachusetts, USA was convened by President Alan McNaught at 9:00 a.m. on Sunday, August 18, 2002. 1.0 President McNaught welcomed the members to this meeting in Boston and offered a special welcome to the National Representative from Brazil, Prof Roberto de Barros Faria. He also noted that Dr Michael Dennis and Prof Michael Hess were unable to be with us. Each of the attendees introduced himself and provided a brief bit of background information. Housekeeping details regarding breaks and lunch were announced and an invitation to a reception from the U. S. National Committee for IUPAC on Tuesday, August 20 was noted. 2.0 The agenda as circulated was approved with the addition of a report from Dr Moss on the activity on his website. 3.0 The minutes of the Division Committee Meeting in Cambridge, UK, January 25, 2002 as posted on the Webboard (http://www.rsc.org/IUPAC8/attachments/MinutesDivCommJan2002.rtf and http://www.rsc.org/IUPAC8/attachments/MinutesDivCommJan2002.pdf) were approved with the following corrections: 3.1 The name Dr Gerard Moss should be added to the members present listing.
  • Methyl- 5/7- Substituted -2- (3,4-Dichloro) Benzoyl-4H-L,4- Benzothiazines As Bifunctional Anticancer Agents

    Methyl- 5/7- Substituted -2- (3,4-Dichloro) Benzoyl-4H-L,4- Benzothiazines As Bifunctional Anticancer Agents

    Synthesis and Spectral studies of Nitrosourea derivatives of 3- Methyl- 5/7- Substituted -2- (3,4-dichloro) benzoyl-4H-l,4- Benzothiazines as Bifunctional Anticancer Agents. Rajni Gupta* and Vandana Gupta Department of Chemistry, University ofRajasthcm, Jaipur-302004, India Email: [email protected] Abstract: The synthesis of of 3-methyl-5/7- substituted-4- (N-propyl-N-nitrosoamido)- 2- (3,4-dichloro benzoyl) -4H- 1,4-Benzothiazines by the isocyanation and successive nitrosation of 3-methyl -5/7- substituted- 2- (3,4- dichlorobenzoyl) -4H-l,4-Benzothiazines has been reported. The synthesized compounds have been characterized by their elemental analyses and spectral characteristics. Introduction: Analogous to phenothiazines, benzothiazines possesss a wide spectrum of biological activities'. Their several derivatives are in clinical use2'7. They exhibit significant anticancer activities, which are assigned due to their interaction with DMA by complexation. Nitrosourea derivatives constitute an important class of anticancer agents and its several derivatives like MNNG, CNU, MNU, GANU, and CDL-7 etc. are clinically significant. They interact with DNA via alkylation 8"9. However their clinical use is limited because of cumulative and delayed side effects exerted by these compounds. Bone marrow toxicity being dose limiting, therefore it is worthwhile to develop a new series of nitrosoureas with minimum toxicity and side effects. 4H-1, 4- Benzothiazines are much less toxic and therefore it is anticipated that their nitrosourea derivatives will be potent anticancer agents with minimum toxicity, side effects etc. In 3-methyl-5/7- substituted-4- (N-propyl-N-nitrosoamido)- 2- (3,4-dichloro benzoyl) -4H-1.4- Benzothiazines heterocyclic nitrogen with a side chain at 4-position constitutes N-nitrosourea linkage and possess both 1,4-benzothiazines nucleus and a nitrosourea moiety .
  • Ethylene Glycol

    Ethylene Glycol

    Ethylene glycol Ethylene glycol (IUPAC name: ethane-1,2-diol) is an organic Ethylene glycol compound with the formula (CH2OH)2. It is mainly used for two purposes, as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odorless, colorless, sweet-tasting, viscous liquid. Contents Production Industrial routes Biological routes Historical routes Uses Coolant and heat-transfer agent Antifreeze Precursor to polymers Other uses Dehydrating agent Hydrate inhibition Applications Chemical reactions Toxicity Environmental effects Names Notes Preferred IUPAC name References Ethane-1,2-diol External links Other names Ethylene glycol 1,2-Ethanediol Production Ethylene alcohol Hypodicarbonous acid Monoethylene glycol Industrial routes 1,2-Dihydroxyethane Ethylene glycol is produced from ethylene (ethene), via the Identifiers intermediate ethylene oxide. Ethylene oxide reacts with water to CAS Number 107-21-1 (http produce ethylene glycol according to the chemical equation: s://commonche mistry.cas.org/d C2H4O + H2O → HO−CH2CH2−OH etail?cas_rn=10 7-21-1) 3D model (JSmol) Interactive This reaction can be catalyzed by either acids or bases, or can occur image (https://ch at neutral pH under elevated temperatures. The highest yields of emapps.stolaf.e ethylene glycol occur at acidic or neutral pH with a large excess of du/jmol/jmol.ph water. Under these conditions, ethylene glycol yields of 90% can be p?model=OCC achieved. The major byproducts are the oligomers diethylene glycol, O) triethylene glycol, and tetraethylene glycol. The separation of these oligomers and water is energy-intensive. About 6.7 million tonnes 3DMet B00278 (http://w are produced annually.[4] ww.3dmet.dna.af frc.go.jp/cgi/sho A higher selectivity is achieved by use of Shell's OMEGA process.
  • Monoazo Dyes of the Benzothiazole Series, Their Preparation and Use In

    Monoazo Dyes of the Benzothiazole Series, Their Preparation and Use In

    Europâisches Patentamt 0 013 809 (ij) QJJJ EuropeanEurooean Patent Office Qj)l'ï> Publication number: V ^- Office européen des brevets (lD EUROPEAN PATENT SPECIFICATION © Date of publication of patent spécification: 10.08.83 © Int. Cl.3: C 09 B 23/00, C 09 B 29/08, D 06 P 1/18 @^ Application number: 79302860.6 @ Dateof filing: 12.12.79 54) Monoazo dyes of the benzothiazole séries, their préparation and use in dyeing or printing hydrophobic fibres. (30) Priority: 25.12.78 JP 163617/78 @ Proprietor: SUMITOMO CHEMICAL COMPANY, 03.10.79 JP 128308/79 LIMITED 1 5 Kitahama 5-chome Higashi-ku Osaka-shi Osaka-fu (JP) © Date of publication of application: 06.08.80 Bulletin 80/16 @ Inventor: Yoshinaga, Kenja 10-3-314, Sonehigashinocho-2-chome @ Publication of the grant of the patent: Tokonaka-shi (JP) 1 0.08.83 Bulletin 83/32 Inventor: Hashimoto, Kiyoyasu 2-40, Hirata-1-chome Ibaraki-shi (JP) (84) Designated Contracting States: Inventor: Okaniwa, Tetsuo CH DE FR GB IT NL 27, Kuisehonmachi-1 -chome Amagasaki-shi (JP) Inventor: Kenmochi, Hirohito @ References cited: 9-1 5, Matsugaoka-4-chome DE - A - 1 959 777 Takatsuki-shi (JP) FR - A - 1 444 036 GB - A - 944 250 GB - A - 1 448 782 @ Representative: Harrison, Michael Robert et al, Urquhart-Dykes & Lord 47 Marylebone Lane London W1 M 6DL(GB) The file contains technical information submitted after the application was filed and not included in this specification Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted.
  • Source-Based Nomenclature for Single-Strand Homopolymers and Copolymers (IUPAC Recommendations 2016)

    Source-Based Nomenclature for Single-Strand Homopolymers and Copolymers (IUPAC Recommendations 2016)

    Pure Appl. Chem. 2016; 88(10-11): 1073–1100 IUPAC Recommendations Richard G. Jones*, Tatsuki Kitayama*, Karl-Heinz Hellwich, Michael Hess, Aubrey D. Jenkins, Jaroslav Kahovec, Pavel Kratochvíl, Itaru Mita†, Werner Mormann, Christopher K. Ober, Stanisław Penczek, Robert F. T. Stepto†, Kevin Thurlow, Jiří Vohlídal and Edward S. Wilks Source-based nomenclature for single-strand homopolymers and copolymers (IUPAC Recommendations 2016) DOI 10.1515/pac-2015-0702 Received July 10, 2015; accepted June 27, 2016 Abstract: IUPAC recommendations on source-based nomenclature for single-strand polymers have so far addressed its application mainly to copolymers, non-linear polymers and polymer assemblies, and within generic source-based nomenclature of polymers. In this document, rules are formulated for devising a satis- factory source-based name for a polymer, whether homopolymer or copolymer, which are as clear and rigor- ous as possible. Thus, the source-based system for naming polymers is presented in a totality that serves as a user-friendly alternative to the structure-based system of polymer nomenclature. In addition, because of their widespread and established use, recommendations for the use of traditional names of polymers are also elaborated. Keywords: apparent monomer; copolymer; end-groups; homopolymer; IUPAC; IUPAC nomenclature; monomer; nomenclature; polymers; polymer nomenclature; source-based names; traditional names. Dedicated to: The memory of Robert (Bob) Stepto, former president of the Polymer Division of IUPAC, whose recent death denied him the satisfaction of witnessing the publication of this manuscript on which he expended much effort. Article note: Sponsoring bodies: IUPAC Division of Chemical Nomenclature and Structure Representation and IUPAC Polymer Division, Sub-Committee on Polymer Terminology: see more details on p.
  • Chapter 23: Substituted Hydrocarbons and Their Reactions

    Chapter 23: Substituted Hydrocarbons and Their Reactions

    736-773_Ch23-866418 5/9/06 3:37 PM Page 736 CHAPTER 23 Substituted Hydrocarbons and Their Reactions Chemistry 2.b, 2.d, 2.h, 3.a, 3.g, 8.c, 10.a, 10.b, 10.e I&E 1.b, 1.c, 1.j What You’ll Learn ▲ You will recognize the names and structures of several important organic functional groups. ▲ You will classify reactions of organic substances as sub- stitution, addition, elimina- tion, oxidation-reduction, or condensation and predict products of these reactions. ▲ You will relate the struc- tures of synthetic polymers to their properties. Why It’s Important Whether you are removing a sandwich from plastic wrap, taking an aspirin, or shooting baskets, you’re using organic materials made of substituted hydrocarbons. These com- pounds are in turn made of molecules whose atoms include carbon, hydrogen, and other elements. Visit the Chemistry Web site at chemistrymc.com to find links about substituted hydrocarbons and their reactions. The spooled threads shown in the photo are made from large organ- ic molecules called polymers. 736 Chapter 23 736-773_Ch23-866418 5/9/06 3:37 PM Page 737 DISCOVERY LAB Making Slime Chemistry 10.b n addition to carbon and hydrogen, most organic substances con- Itain other elements that give the substances unique properties. In this lab, you will work with an organic substance consisting of long carbon chains to which many ϪOH groups are bonded. How will the properties of this substance change when these groups react to form bonds called crosslinks between the chains? Safety Precautions Do not allow solutions or product to contact eyes or exposed skin.
  • 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

    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.
  • The Mechanism of Pyridine Hydrogenolysis on Molybdenum-Containing Catalysts III

    The Mechanism of Pyridine Hydrogenolysis on Molybdenum-Containing Catalysts III

    View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Universiteit Twente Repository JOURNAL OF CATALYSIS 34, 215-229 (1974) The Mechanism of Pyridine Hydrogenolysis on Molybdenum-Containing Catalysts III. Cracking, Hydrocracking, Dehydrogenation and Disproportionation of Pentylamine J. SONNEMANS” AND P. MARS l’wente University of Technology, Enschede, The Netherlands Received October 30, 1973 The conversion of pentylamine on a MoOrA1203 catalyst was studied between 250 and 350°C at various hydrogen pressures. The reactions observed were cracking to pentene and ammonia, hydrocracking to pentane and ammonia, dehydrogenation to pentanimine and butylcarbonitrile, and disproportionation to ammonia and dipentylamine. The equilibrium between pentylamine, dipentylamine and ammonia appeared to be established under most of the experimental conditions. The equilibrium constant is about 9 at 250°C and about 5 at 320°C. The disproportionation reaction is zero order in hydrogen and of -1 order in the initial pentylamine pressure. Dehydrogenation was observed at low hydrogen pressures, and especially at higher temperatures; the reaction is first order in pentylamine. Both cracking and hydrocracking take place, mainly above 300°C. Hydrocracking appears to be half order in hydrogen; the rate of cracking is almost independent of the hydrogen pressure. The hydrocarbon formation is of zero order in pentyl- amine or dipentylamine. The same type of reactions (except hydrocracking) take place on alumina, but with a far lower reaction rate. INTRODUCTION catalysts at hydrogen pressures of about One of the intermediates formed in the 60 atm (Z-4). They reported a high rate hydrogenolysis of pyridine is pentylamine of ammonia formation from the primary (1).
  • WO 2012/092415 Al 5 July 2012 (05.07.2012) P O P C T

    WO 2012/092415 Al 5 July 2012 (05.07.2012) P O P C T

    (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2012/092415 Al 5 July 2012 (05.07.2012) P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every C07C 2/36 (2006.01) C07F 9/46 (2006.01) kind of national protection available): AE, AG, AL, AM, C07C 9/15 (2006.01) C07F 11/00 (2006.01) AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, (21) International Application Number: DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, PCT/US201 1/067709 HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, (22) International Filing Date: KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, 29 December 201 1 (29. 12.201 1) MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SC, SD, (25) Filing Language: English SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, (26) Publication Language: English TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: (84) Designated States (unless otherwise indicated, for every 12/980,457 29 December 2010 (29. 12.2010) US kind of regional protection available): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, (71) Applicant (for all designated States except US): CHEV¬ UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, RON PHILLIPS CHEMICAL COMPANY LP TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, [US/US]; 10001 Six Pines Drive, The Woodlands, Texas DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, 77380 (US).
  • Method for Producing Pyridine Compound

    Method for Producing Pyridine Compound

    (19) TZZ¥_¥¥_T (11) EP 3 159 339 A1 (12) EUROPEAN PATENT APPLICATION published in accordance with Art. 153(4) EPC (43) Date of publication: (51) Int Cl.: 26.04.2017 Bulletin 2017/17 C07D 413/04 (2006.01) C07D 471/04 (2006.01) A01N 43/76 (2006.01) A01N 43/90 (2006.01) (21) Application number: 15806287.7 (86) International application number: (22) Date of filing: 29.05.2015 PCT/JP2015/065512 (87) International publication number: WO 2015/190316 (17.12.2015 Gazette 2015/50) (84) Designated Contracting States: (72) Inventors: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB • WAKAMATSU, Takayuki GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO Oita-shi PL PT RO RS SE SI SK SM TR Oita 870-0106 (JP) Designated Extension States: • KASAI, Rika BA ME Osaka-shi Designated Validation States: Osaka 554-8558 (JP) MA (74) Representative: Vossius & Partner (30) Priority: 09.06.2014 JP 2014118457 Patentanwälte Rechtsanwälte mbB Siebertstrasse 3 (71) Applicant: Sumitomo Chemical Company, Limited 81675 München (DE) Tokyo 104-8260 (JP) (54) METHOD FOR PRODUCING PYRIDINE COMPOUND (57) To make it possible to produce a pyridine compound represented by formula (1) that is useful as an insecticide by reacting a compound represented by formula. (2) and a compound represented by formula (3). (In the formula, 1L represents a halogen atom; R2, R3, R4, R5, and R6 represent chain hydrocarbon groups, etc., having 1-6 carbon atoms optionally substituted by fluorine atoms. A 1 represents-NR7-, an oxygen atom, or a sulfur atom; A 2 represents a nitrogen atom or =CR8-.