DOCSLIB.ORG

Cyclyoalkanes , Cycloalkenes and Alkadienes Cycloalkanes

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Cyclyoalkanes , Cycloalkenes and Alkadienes Cycloalkanes B.Sc. - I, Sem. –II Chem-III Notes by Prof. Dr.M.M.Mane 1 Cyclyoalkanes , Cycloalkenes and Alkadienes Cycloalkanes Cycloalkanes (also called naphthenes - not to be confused with naphthalene) are types of alkanes that have one or more rings ofcarbon atoms in the chemical structure of their molecules.Cycloalkanes are cyclic saturated hydrocarbons having general formula CnH2n Cycloalkanes with a single ring are named analogously to their normal alkane counterpart of the same carbon count: cyclopropane, cyclobutane, cyclopentane, cyclohexane, etc. The larger cycloalkanes, with greater than 20 carbon atoms are typically called cycloparaffins. Cycloalkanes are classified into small, common, medium, and large cycloalkanes, where cyclopropane and cyclobutane are the small ones, cyclopentane, cyclohexane, cycloheptane are the common ones, cyclooctane through cyclotridecane are the medium ones, and the rest are the larger ones. Methods of preparations 1) From Carbene Carbenes are highly reactive carbon species and they add to alkene to form cyclopropane derivaties. Carbene being highly reactive intermediate it cannot be isolated, hence reaction is carried out by reacting alkene wih compounds generating carbene. H3C H3C h + CH2N2 -N2 H3C H3C 2-Butene 1,2-dimethyl cyclopropane 2) From dihalo alkane( Freunda method) Dihalo alkane on treatment with sodium , gives cycloalkane. Br H2C CH2 + 2 Na H2C CH2 -2NaBr Br 1,4-dibromo butane cyclo butane. 3) From Diel’s Alder reaction Cycloaddition of conjugated diene and dienophile to give cyclic compound is called Diel’s Alder reaction CH CH 2 2 473 K Reduction + CH2 CH 2 1,3-Butadiene cyclohexene cyclohexane R.B.M. College Chandgad. Dept. of Chemistry B.Sc. - I, Sem. –II Chem-III Notes by Prof. Dr.M.M.Mane 2 4) From Aromatic compounds. Aromatic compound on catalytic hydrogenation gives corresponding cyclic compound. H2 / Ni Reduction Chemical Properties: 1) Photohalogenation Cycloalkanes on halogenations in presenceof sunlight forms substitution product. Cl h + Cl Cl + HCl 2) Catalytic halogenations: Cycloalkanes on reaction with halogen in presence of catalyst forms addition product by ring opening CH FeBr3 Br 2 Br Br Br CH + 2 CH addition 2 Cyclo propane 1,3-dibromo propane 3) Catalytic hydrogenation: Cycloalkanes reacts with hydrogen in presence of catalyst to form corresponding alkane by ring opening. Ni / CH2 H H C + 2 3 CH addition 3 Cyclo propane propane 4) Effect of Heat: Cycloalkanes on heating in presence of catalysts like Pt, decomposes and form corresponding alkene by ring opening. Pt / CH2 H C 2 CH 3 Propene 5) Reaction with hydrogen halide. Cycloalkanes reacts with ydrogen halide and forms corresponding alkyl halide by ring opening. CH2 Br + HBr H C CH2 3 Propyl bromide Cycloalkene: Cyclic unsaturated hydrocarbon having general molecular formula CnH2n is called cycloalkene. They are named by attaching prefix cyclo to the name of corresponding alkene 1,5-cyclooctadiene R.B.M. College Chandgad. Dept. of Chemistry B.Sc. - I, Sem. –II Chem-III Notes by Prof. Dr.M.M.Mane 3 Preparation: 1) Hoffmann elimination : Cyclopropane can be prepared by elimination of cyclopropyl trimethyl ammonium hydroxide H O + CH3 + N(CH3)3 + 2 N - OH CH3 CH H 3 Cyclopropene 2) By dehydrohalogenation When bromo cyclopentane is treated with alcoholic KOH it forms cyclopeneten by dehydrohalogenation. Br alco. KOH -HBr Cyclopentene 3) Dehydration: Cycloalkanol on heating with Conc. H2SO4 undergo dehydration to form cycloalkaene. OH Conc.H2SO4 + H2O Cyclohexanol cyclohexene Chemical Properties 1) Hydrogenation: Cycloalkenes reacts with hydrogen in presence of catalyst and forms cycloalkanes. catalyst + H2 addition Cyclohexene cyclohexane 2) Addition of halogen: Cycloalkenes undergo addition reaction with halogen to give dihalo compound. Br Br + Br Br addition Cyclopentene 1,2-dibromo cyclopentane 3) Addition of hydrogen acid: Cycloalkenes undergo addition reaction with hydrogen halide to give halo compound. Br + HBr addition Cyclohexene bromo cyclohexane 4) Allylic halogenations Cycloalkenes on reaction with halogen in presence of sunlight and NBS( N-Bromo Succinamide) , undergo halogenations at allylic position. Br NBS + Br Br h Bromo cyclohexene Alkadiene Aliphatic unsaturated hydrocarbons containing two Carbon carbon double bonds and having general formula CnH2n-2 are called alkadiene. Nomenclature: They are named by replacing ‘ane’ of parent alkane by ‘diene’ with position of two double bonds. 2 1 CH2 4 H2C 3 1,3-Butadiene R.B.M. College Chandgad. Dept. of Chemistry B.Sc. - I, Sem. –II Chem-III Notes by Prof. Dr.M.M.Mane 4 Classification: They are calssified depending on position of two double bonds as, 1) Isolated diene: Here two double bonds are separated by more than one C-C Single bond 2 4 1 5 H C 2 CH2 3 1,4-Pentadiene 2) Conjugated diene: Here two C-C double bond are separated by one C-C single bond. e.g. 1,3-Butadiene 3) Cumulated diene: Here two double bonds are present on three succession Carbon atoms. They are also called as alllenes. e.g. 2 1 C H2C CH2 3 1,2-Propadiene 1,3-Butadiene It is conjugated diene and exist in following resonance structure. + + CH CH CH2 CH CH2 CH 2 - CH - etc H2C CH H C CH 2 H2C Thus double bond in butadiene is delocalized and actual structure is hybride of all these resonating structures H CH3 H3C H Molecular Orbital picture. In 1,3-Butadiene each Carbon is SP2 hybridise and forms three covalent bond with carbon and hydrogen atoms to form paler molecule. The angle between any two bond is 1200. Now each C contains one unhybridised P orbital, having dumbel shape and perpendicular to the hybride orbital and contains single electron. Delocalized pi H H 2 4 electon cloud H CH3 3 H 1 H3C Unhybridised p orbital H H The four P orbitals on C1,C2,C3 and C4 undergo lateral overlapping to form delocalized π electon cloud.Half of cloud is above the plane and half is below the plane of the molecule. Method of preparation : 1) From Cyclohexene: When vapors of cyclohexene are passed over heated nichrome alloy, retro Diel’s Alder takes place to form Butadiene. CH2 2 CH2 1 CH2 4 + H2C nichrome CH 3 2 CH2 Butadiene R.B.M. College Chandgad. Dept. of Chemistry B.Sc. - I, Sem. –II Chem-III Notes by Prof. Dr.M.M.Mane 5 2) From Butane: Butane or Butene on heating with chromium oxide undergo dehydrogenation to form butadiene. CH Cr2O3 2 CH3 H2C H3C CH Cr2O3 2 CH3 H C H2C 3 Butane 3) From acetylene: Acetylene and acetaldehyde undergo following series of reactions to give butadiene. OH OH NaNH2 Partial reduction HC CH H C CH HC CH +H3C CHO 3 2 3 H H CH2 Al2O3 H2C -H O 2 4) From Butan -1,3-diol Butan-1,3-diol on heating with acid catalyst undrgo dehydration to form butadiene + CH CH3 H 2 H2C -H2O OH OH 5) From Ethanol and acetaldehyde: When mix. Of ethanol and acetaldehyde is passed over heated catalyst butadiene is formed CH2 H C H C CHO 3 + 3 H2C OH Chemical properties: 1) Reaction with hydrogen halide: When 1,3-butadiene is treated with HCl, a mix. Of two products namely 3-chloro-1-butene and 1-chloro-2-butene is formed. Here addition takes place across C1 and C2 (1:2 addition ) and at C1 and C4 ( 1:4 addition) to give mix of products. Cl CH 1: 2 2 H3C CH CH2 HCl 3 chloro 1 butene H2C CH addition 1: 4 H3C Cl 1 chloro 2 butene 2) Reaction with halogens: a) With one molar equivalent of bromine butadiene forms two products due to 1:2 and 1:4 addition CH 1: 2 2 Br CH CH 2 Br Br2 H2C CH 3,4 dibromo 1 butene addition 1: 4 Br Br 1,4 dibromo 2 butene b) With two molar equivalents of bromine butadiene forms single product tetrabromo butane R.B.M. College Chandgad. Dept. of Chemistry B.Sc. - I, Sem. –II Chem-III Notes by Prof. Dr.M.M.Mane 6 CH CH2 H C CH Br Br 2 + Br Br Br Br 1,2,3,4- tera bromo butane 3) Diel’s Alder reaction Cycloaddition of conjugated diene and dienophile to form cyclic product is called Diel’s Alder reaction. CH2 CH2 + CH2 CH2 Cyclohexene 4) Reduction : Butadiene on catalytic reduction gives mixture of 1-butene and 2-butene. CH 1: 2 2 H3C CH CH2 H2 H2C CH 1 butene addition 1: 4 CH3 H3C 2 butene 5) Oxidation( ozonolysis) : Butadiene on ozonolysis forms formaldehyde and glyoxal. O O CH CH2 Zn OHC CHO 2 O H C CH HC 2 H CHO H2C CH + 3 2 CH2 + O O O O Formaldehyde glyoxal 6)Polymerization: In presence of catalyst ( Sodium) butadiene polymerise to give polybutadiene, called as BuNa rubber. Here monomers are linked by 1:4 linkage. CH CH CH CH2 2 Na CH2 CH2 H2C CH n H C CH H2C CH 2 n 2 + 1: 4 addition CH CH BUNA rubber R.B.M. College Chandgad. Dept. of Chemistry .
Load more

Recommended publications
  • C9-14 Aliphatic [2-25% Aromatic] Hydrocarbon Solvents Category SIAP
    CoCAM 2, 17-19 April 2012 BIAC/ICCA SIDS INITIAL ASSESSMENT PROFILE Chemical C -C Aliphatic [2-25% aromatic] Hydrocarbon Solvents Category Category 9 14 Substance Name CAS Number Stoddard solvent 8052-41-3 Chemical Names Kerosine, petroleum, hydrodesulfurized 64742-81-0 and CAS Naphtha, petroleum, hydrodesulfurized heavy 64742-82-1 Registry Solvent naphtha, petroleum, medium aliphatic 64742-88-7 Numbers Note: Substances in this category are also commonly known as mineral spirits, white spirits, or Stoddard solvent. CAS Number Chemical Description † 8052-41-3 Includes C8 to C14 branched, linear, and cyclic paraffins and aromatics (6 to 18%), <50ppmV benzene † 64742-81-0 Includes C9 to C14 branched, linear, and cyclic paraffins and aromatics (10 to Structural 25%), <100 ppmV benzene Formula † and CAS 64742-82-1 Includes C8 to C13 branched, linear, and cyclic paraffins and aromatics (15 to 25%), <100 ppmV benzene Registry † Numbers 64742-88-7 Includes C8 to C13 branched, linear, and cyclic paraffins and aromatics (14 to 20%), <50 ppmV benzene Individual category member substances are comprised of aliphatic hydrocarbon molecules whose carbon numbers range between C9 and C14; approximately 80% of the aliphatic constituents for a given substance fall within the C9-C14 carbon range and <100 ppmV benzene. In some instances, the carbon range of a test substance is more precisely defined in the test protocol. In these instances, the specific carbon range (e.g. C8-C10, C9-C10, etc.) will be specified in the SIAP. * It should be noted that other substances defined by the same CAS RNs may have boiling ranges outside the range of 143-254° C and that these substances are not covered by the category.
    [Show full text]
  • Transport of Dangerous Goods
    ST/SG/AC.10/1/Rev.16 (Vol.I) Recommendations on the TRANSPORT OF DANGEROUS GOODS Model Regulations Volume I Sixteenth revised edition UNITED NATIONS New York and Geneva, 2009 NOTE The designations employed and the presentation of the material in this publication do not imply the expression of any opinion whatsoever on the part of the Secretariat of the United Nations concerning the legal status of any country, territory, city or area, or of its authorities, or concerning the delimitation of its frontiers or boundaries. ST/SG/AC.10/1/Rev.16 (Vol.I) Copyright © United Nations, 2009 All rights reserved. No part of this publication may, for sales purposes, be reproduced, stored in a retrieval system or transmitted in any form or by any means, electronic, electrostatic, magnetic tape, mechanical, photocopying or otherwise, without prior permission in writing from the United Nations. UNITED NATIONS Sales No. E.09.VIII.2 ISBN 978-92-1-139136-7 (complete set of two volumes) ISSN 1014-5753 Volumes I and II not to be sold separately FOREWORD The Recommendations on the Transport of Dangerous Goods are addressed to governments and to the international organizations concerned with safety in the transport of dangerous goods. The first version, prepared by the United Nations Economic and Social Council's Committee of Experts on the Transport of Dangerous Goods, was published in 1956 (ST/ECA/43-E/CN.2/170). In response to developments in technology and the changing needs of users, they have been regularly amended and updated at succeeding sessions of the Committee of Experts pursuant to Resolution 645 G (XXIII) of 26 April 1957 of the Economic and Social Council and subsequent resolutions.
    [Show full text]
  • Brittain-DR-1965-Phd-Thesis.Pdf
    POLYMETHYLENE PYRIDINES , A thesis submitted by David Robert Brittain in partial fulfilment of the requirements for the degree of DOCTOR OP PHILOSOPHY in the University of London Organic Chemistry Department, dune, 1965. Imperial College, LONDON, S.W.7. ABSTRACT This thesis describes a series of attempts to syn- thesise 2,5- and 1,4-polymethylene bridged pyridines. Nuclear magnetic resonance theory predicts that protons, which are held directly over an aromatic ring, will be abnormally shielded compared with protons in aliphatic straight-chain hydrocarbons. This prediction has been verified for the central methylene protons of paracyclo- phanes. The degree of shielding, expressed in terms of the distance from the aromatic ring, is a measure of the induced ring current and hence the aromaticity of the benzene ring. Similar measurements upon 2,5- or 1,4— polymethylene bridged pyridines would make it possible to determine the degree of aromaticity of the pyridine ring relative to benzene. A review of the subject of aromaticity is presented in which special reference has been made to its inter- pretation by nuclear magnetic resonance. The synthetic work has not been brougL.t to a truly satisfactory conclusion. However, the synthetic routes to 2,5-dialkylpyridines have been thoroughly investigated and a wide variety of such compounds prepared. The functional groups at the ends of the alkyl chains have been varied in an effort to produce a derivative which would cyclise to give a 2,5-bridged pyridine. The attempted intramolecular oxidative coupling of 2,5-dihex- 51 -ynylpyridine received much attention. In the attempts to obtain a 1,4-bridged pyridine, two tricyclic compounds, each containing two quaternised pyridine rings linked by polymethylene chains, were obtained.
    [Show full text]
  • Heterocyclic Chemistry Updated
    1 | Page Heterocyclic Chemistry By Dr Vipul Kataria Definition: A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements (N, O, S, P) as members of its ring. Introduction: Heterocyclic compounds may be defined as cyclic compounds having as ring members atoms of at least two different elements. It means the cyclic compound has one another atom different than carbon. Heterocyclic compounds have much importance in organic chemistry because of abundant presence of heterocyclic compounds in present pharmaceutical drugs. Like other organic compounds, there are several defined rules for naming heterocyclic compounds. IUPAC rules for nomenclature of heterocyclic systems (SPU 2012, 2 Marks) The system for nomenclature for heterocyclic systems was given by Hantzsch and Widman. The Hantzsch-Widman nomenclature is based on the type (Z) of the heteroatom; the ring size (n) and nature of the ring, whether it is saturated or unsaturated. This system of nomenclature applies to monocyclic 3-to-10-membered ring heterocycles. Type of the heteroatom: The type of heteroatom is indicated by a prefix as shown below for common hetreroatoms. Dr Vipul Kataria, Chemistry Department, V. P. & R. P. T. P. Science College, VV Nagar 2 | Pag e When two or more of the same heteroatoms are present, the prrefix di, tri, tetra… are used. e.g. dioxa, triaza, dithia. If the heteroatoms are different their atomic number in that grroup is considered. Thus order of numbering will be O, S, N, P, Si. Ring size: The ring size is indicated by a suffix according to Table I below.
    [Show full text]
  • First Principles Prediction of Thermodynamic Properties
    2 First Principles Prediction of Thermodynamic Properties Hélio F. Dos Santos and Wagner B. De Almeida NEQC: Núcleo de Estudos em Química Computacional, Departamento de Química, ICE Universidade Federal de Juiz de Fora (UFJF), Campus Universitário Martelos, Juiz de Fora LQC-MM: Laboratório de Química Computacional e Modelagem Molecular Departamento de Química, ICEx, Universidade Federal de Minas Gerais (UFMG) Campus Universitário, Pampulha, Belo Horizonte Brazil 1. Introduction The determination of the molecular structure is undoubtedly an important issue in chemistry. The knowledge of the tridimensional structure allows the understanding and prediction of the chemical-physics properties and the potential applications of the resulting material. Nevertheless, even for a pure substance, the structure and measured properties reflect the behavior of many distinct geometries (conformers) averaged by the Boltzmann distribution. In general, for flexible molecules, several conformers can be found and the analysis of the physical and chemical properties of these isomers is known as conformational analysis (Eliel, 1965). In most of the cases, the conformational processes are associated with small rotational barriers around single bonds, and this fact often leads to mixtures, in which many conformations may exist in equilibrium (Franklin & Feltkamp, 1965). Therefore, the determination of temperature-dependent conformational population is very much welcomed in conformational analysis studies carried out by both experimentalists and theoreticians.
    [Show full text]
  • Condensed Cyclic Compound, Composition Including The
    (19) TZZ¥_ _T (11) EP 3 184 522 A1 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) Int Cl.: 28.06.2017 Bulletin 2017/26 C07D 403/14 (2006.01) H01L 51/00 (2006.01) (21) Application number: 16205894.5 (22) Date of filing: 21.12.2016 (84) Designated Contracting States: • INAYAMA, Satoshi AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Yokohama-city, Kanagawa 230-0027 (JP) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO • ISHII, Norihito PL PT RO RS SE SI SK SM TR Yokohama-city, Kanagawa 230-0027 (JP) Designated Extension States: • SHIBATA, Katsunori BA ME Yokohama-city, Kanagawa 230-0027 (JP) Designated Validation States: • ITO, Mitsunori MA MD Yokohama-city, Kanagawa 230-0027 (JP) (30) Priority: 22.12.2015 JP 2015250531 (74) Representative: Scheuermann, Erik Elkington and Fife LLP (71) Applicant: Samsung Electronics Co., Ltd. Prospect House Gyeonggi-do 16677 (KR) 8 Pembroke Road Sevenoaks, Kent TN13 1XR (GB) (72) Inventors: • KATO, Fumiaki Yokohama-city, Kanagawa 230-0027 (JP) (54) CONDENSED CYCLIC COMPOUND, COMPOSITION INCLUDING THE CONDENSED CYCLIC COMPOUND, ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE CONDENSED CYCLIC COMPOUND, AND METHOD OF MANUFACTURING THE ORGANIC LIGHT-EMITTING DEVICE (57) A condensed cyclic compound, a composition including the condensed cyclic compound, an organic light-emit- ting device including the condensed cyclic compound, and a method of manufacturing the organic light-emitting device are provided. EP 3 184 522 A1 Printed by Jouve, 75001 PARIS (FR) EP 3 184 522 A1 Description FIELD OF THE INVENTION 5 [0001] One or more embodiments relate to a condensed cyclic compound, a composition including the condensed cyclic compound, an organic light-emitting device including the condensed cyclic compound, and a method of manufac- turing the organic light-emitting device.
    [Show full text]
  • Syntheses and Eliminations of Cyclopentyl Derivatives David John Rausch Iowa State University
    Iowa State University Capstones, Theses and Retrospective Theses and Dissertations Dissertations 1966 Syntheses and eliminations of cyclopentyl derivatives David John Rausch Iowa State University Follow this and additional works at: https://lib.dr.iastate.edu/rtd Part of the Organic Chemistry Commons Recommended Citation Rausch, David John, "Syntheses and eliminations of cyclopentyl derivatives " (1966). Retrospective Theses and Dissertations. 2875. https://lib.dr.iastate.edu/rtd/2875 This Dissertation is brought to you for free and open access by the Iowa State University Capstones, Theses and Dissertations at Iowa State University Digital Repository. It has been accepted for inclusion in Retrospective Theses and Dissertations by an authorized administrator of Iowa State University Digital Repository. For more information, please contact [email protected]. This dissertation has been microfilmed exactly as received 66—6996 RAUSCH, David John, 1940- SYNTHESES AND ELIMINATIONS OF CYCLOPENTYL DERIVATIVES. Iowa State University of Science and Technology Ph.D., 1966 Chemistry, organic University Microfilms, Inc., Ann Arbor, Michigan SYNTHESES AND ELIMINATIONS OF CYCLOPENTYL DERIVATIVES by David John Rausch A Dissertation Submitted to the Graduate Faculty in Partial Fulfillment of The Requirements for the Degree of DOCTOR OF PHILOSOPHY Major Subject: Organic Chemistry Approved : Signature was redacted for privacy. Signature was redacted for privacy. Head of Major Department Signature was redacted for privacy. Iowa State University Of Science and Technology Ames, Iowa 1966 ii TABLE OF CONTENTS VITA INTRODUCTION HISTORICAL Conformation of Cyclopentanes Elimination Reactions RESULTS AND DISCUSSION Synthetic Elimination Reactions EXPERIMENTAL Preparation and Purification of Materials Procedures and Data for Beta Elimination Reactions SUMMARY LITERATURE CITED ACKNOWLEDGEMENTS iii VITA The author was born in Aurora, Illinois, on October 24, 1940, to Mr.
    [Show full text]
  • An Indicator of Triplet State Baird-Aromaticity
    inorganics Article The Silacyclobutene Ring: An Indicator of Triplet State Baird-Aromaticity Rabia Ayub 1,2, Kjell Jorner 1,2 ID and Henrik Ottosson 1,2,* 1 Department of Chemistry—BMC, Uppsala University, Box 576, SE-751 23 Uppsala, Sweden; [email protected] (R.A.); [email protected] (K.J.) 2 Department of Chemistry-Ångström Laboratory Uppsala University, Box 523, SE-751 20 Uppsala, Sweden * Correspondence: [email protected]; Tel.: +46-18-4717476 Received: 23 October 2017; Accepted: 11 December 2017; Published: 15 December 2017 Abstract: Baird’s rule tells that the electron counts for aromaticity and antiaromaticity in the first ππ* triplet and singlet excited states (T1 and S1) are opposite to those in the ground state (S0). Our hypothesis is that a silacyclobutene (SCB) ring fused with a [4n]annulene will remain closed in the T1 state so as to retain T1 aromaticity of the annulene while it will ring-open when fused to a [4n + 2]annulene in order to alleviate T1 antiaromaticity. This feature should allow the SCB ring to function as an indicator for triplet state aromaticity. Quantum chemical calculations of energy and (anti)aromaticity changes along the reaction paths in the T1 state support our hypothesis. The SCB ring should indicate T1 aromaticity of [4n]annulenes by being photoinert except when fused to cyclobutadiene, where it ring-opens due to ring-strain relief. Keywords: Baird’s rule; computational chemistry; excited state aromaticity; Photostability 1. Introduction Baird showed in 1972 that the rules for aromaticity and antiaromaticity of annulenes are reversed in the lowest ππ* triplet state (T1) when compared to Hückel’s rule for the electronic ground state (S0)[1–3].
    [Show full text]
  • Chapter 2: Alkanes Alkanes from Carbon and Hydrogen
    Chapter 2: Alkanes Alkanes from Carbon and Hydrogen •Alkanes are carbon compounds that contain only single bonds. •The simplest alkanes are hydrocarbons – compounds that contain only carbon and hydrogen. •Hydrocarbons are used mainly as fuels, solvents and lubricants: H H H H H H H H H H H H C H C C H C C C C H H C C C C C H H H C C H H H H H H CH2 H CH3 H H H H CH3 # of carbons boiling point range Use 1-4 <20 °C fuel (gasses such as methane, propane, butane) 5-6 30-60 solvents (petroleum ether) 6-7 60-90 solvents (ligroin) 6-12 85-200 fuel (gasoline) 12-15 200-300 fuel (kerosene) 15-18 300-400 fuel (heating oil) 16-24 >400 lubricating oil, asphalt Hydrocarbons Formula Prefix Suffix Name Structure H CH4 meth- -ane methane H C H H C H eth- -ane ethane 2 6 H3C CH3 C3H8 prop- -ane propane C4H10 but- -ane butane C5H12 pent- -ane pentane C6H14 hex- -ane hexane C7H16 hept- -ane heptane C8H18 oct- -ane octane C9H20 non- -ane nonane C10H22 dec- -ane decane Hydrocarbons Formula Prefix Suffix Name Structure H CH4 meth- -ane methane H C H H H H C2H6 eth- -ane ethane H C C H H H H C H prop- -ane propane 3 8 H3C C CH3 or H H H C H 4 10 but- -ane butane H3C C C CH3 or H H H C H 4 10 but- -ane butane? H3C C CH3 or CH3 HydHrydorcocaarrbobnos ns Formula Prefix Suffix Name Structure H CH4 meth- -ane methane H C H H H H C2H6 eth- -ane ethane H C C H H H H C3H8 prop- -ane propane H3C C CH3 or H H H C H 4 10 but- -ane butane H3C C C CH3 or H H H C H 4 10 but- -ane iso-butane H3C C CH3 or CH3 HydHrydoroccarbrobnsons Formula Prefix Suffix Name Structure H H
    [Show full text]
  • Classification of Chemicals
    Classification of Chemicals Flame & Detonation Arrester Specifications PROTECTOSEAL ® The Protectoseal Company recommends that the National Butadiene would qualify as a Group D material. In each of Electric Code (NEC) Article 500, rankings of various chemi - these cases, the chemicals were primarly listed in a higher cals be used, whenever possible, to determine the suitability category (Group B), because of relatively high pressure read - of a detonation arrester for use with a particular chemical. ings noted in one phase of the standard test procedure con - When no NEC rating of the particular chemical is available, ducted by Underwriters Laboratories. These pressures were the International Electrotechnical Commission (IEC) classifica - of concern when categorizing the chemicals because these tion (Groups IIA, IIB and IIC) is recommended as a secondary NEC groupings are also used as standard indicators for the source of information for determining the suitability of an ar - design strength requirements of electrical boxes, apparatus, rester for its intended service. In general, the IEC Group IIA is etc. that must withstand the pressures generated by an igni - equivalent to the NEC Group D; the IEC Group IIB is equiva - tion within the container. It should be noted that, in each of lent to the NEC Group C; and the IEC Group IIC includes these cases, the test pressures recorded were significantly chemicals in the NEC Groups A and B. In the event of a dis - lower than those commonly encountered when testing a deto - crepancy between the NEC and the IEC ratings, Protectoseal nation arrester for its ability to withstand stable and over - recommends that the NEC groups be referenced.
    [Show full text]
  • Organic Chemistry PEIMS Code: N1120027 Abbreviation: ORGCHEM Number of Credits That May Be Earned: 1/2-1
    Course: Organic Chemistry PEIMS Code: N1120027 Abbreviation: ORGCHEM Number of credits that may be earned: 1/2-1 Brief description of the course (150 words or less): Organic chemistry is an introductory course that is designed for the student who intends to continue future study in the sciences. The student will learn the concepts and applications of organic chemistry. Topics covered include aliphatic and aromatic compounds, alcohols, aldehydes, ketones, acids, ethers, amines, spectra, and stereochemistry. A brief introduction into biochemistry is also provided. The laboratory experiments will familiarize the student with the important laboratory techniques, specifically spectroscopy. Traditional high school chemistry courses focus on the inorganic aspects of chemistry whereas organic chemistry introduces the student to organic compounds and their properties, mechanisms of formations, and introduces the student to laboratory techniques beyond the traditional high school chemistry curriculum. Essential Knowledge and Skills of the course: (a) General requirements. This course is recommended for students in Grades 11-12. The recommended prerequisite for this course is AP Chemistry. (b) Introduction. Organic chemistry is designed to introduce students to the fundamental concepts of organic chemistry and key experimental evidence and data, which support these concepts. Students will learn to apply these data and concepts to chemical problem solving. Additionally, students will learn that organic chemistry is still evolving by reading about current breakthroughs in the field. Finally, students will gain appreciation for role that organic chemistry plays in modern technological developments in diverse fields, ranging from biology to materials science. (c) Knowledge and skills. (1) The student will be able to write both common an IUPAC names for the hydrocarbon.
    [Show full text]
  • AROMATIC COMPOUNDS Aromaticity
    AROMATICITY AROMATIC COMPOUNDS Aromaticity Benzene - C6H6 H H H H H H H H H H H H Kekulé and the Structure of Benzene Kekule benzene: two forms are in rapid equilibrium 154 pm 134 pm • All bonds are 140 pm (intermediate between C-C and C=C) • C–C–C bond angles are 120° • Structure is planar, hexagonal A Resonance Picture of Bonding in Benzene resonance hybrid 6 -electron delocalized over 6 carbon atoms The Stability of Benzene Aromaticity: cyclic conjugated organic compounds such as benzene, exhibit special stability due to resonance delocalization of -electrons. Heats of hydrogenation + H2 + 120 KJ/mol + 2 H2 + 230 KJ/mol calc'd value= 240 KJ/mol 10 KJ/mol added stability + 3 H 2 + 208 KJ/mol calc'd value= 360 KJ/mol 152 KJ/mol added stability + 3 H2 + 337 KJ/mol 1,3,5-Hexatriene - conjugated but not cyclic Resonance energy of benzene is 129 - 152 KJ/mol An Orbital Hybridization View of Bonding in Benzene • Benzene is a planar, hexagonal cyclic hydrocarbon • The C–C–C bond angles are 120° = sp2 hybridized • Each carbon possesses an unhybridized p-orbital, which makes up the conjugated -system. • The six -electrons are delocalized through the -system The Molecular Orbitals of Benzene - the aromatic system of benzene consists of six p-orbitals (atomic orbitals). Benzene must have six molecular orbitals. Y6 Y4 Y5 six p-orbitals Y2 Y3 Y1 Degenerate orbitals: Y : zero nodes orbitals that have the 1 Bonding same energy Y2 and Y3: one node Y and Y : two nodes 4 5 Anti-bonding Y6: three node Substituted Derivatives of Benzene and Their Nomenclature
    [Show full text]