DOCSLIB.ORG

Unit One Part 2: Naming and Functional Groups

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Unit One Part 2: Naming and Functional Groups gjr-–- 1 Unit One Part 2: naming and functional groups • To write and interpret IUPAC names for small, simple molecules • Identify some common functional groups found in organic molecules O CH3 H3C N H N O N N O H3C S N O N H3C viagra™ (trade name) sildenafil (trivial name) 5-(2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)phenyl)-1-methyl-3-propyl-1H- pyrazolo[4,3-d] pyrimidin-7(6H)-one dr gareth rowlands; [email protected]; science tower a4.12 http://www.massey.ac.nz/~gjrowlan gjr-–- 2 Systematic (IUPAC) naming PREFIX PARENT SUFFIX substituents / minor number of C principal functional functional groups AND multiple bond group index • Comprises of three main parts • Note: multiple bond index is always incorporated in parent section No. Carbons Root No. Carbons Root Multiple-bond 1 meth 6 hex Bond index 2 eth 7 hept C–C an(e) 3 prop 8 oct C=C en(e) 4 but 9 non C≡C yn(e) 5 pent 10 dec gjr-–- 3 Systematic (IUPAC) naming: functional groups Functional group Structure Suffix Prefix General form O –oic acid acid –carboxylic acid carboxy R-COOH R OH O O –oic anhydride anhydride –carboxylic anhydride R-C(O)OC(O)-R R O R O –oyl chloride acyl chloride -carbonyl chloride chlorocarbonyl R-COCl R Cl O –oate ester –carboxylate alkoxycarbonyl R-COOR R OR O –amide amide –carboxamide carbamoyl R-CONH2 R NH2 nitrile R N –nitrile cyano R-C≡N O –al aldehyde –carbaldehyde oxo R-CHO R H O ketone –one oxo R-CO-R R R alcohol R OH –ol hydroxy R-OH amine R NH2 –amine amino R-NH2 O ether R R –ether alkoxy R-O-R alkyl bromide bromo R-Br (alkyl halide) R Br (halo) (R-X) gjr-–- 4 Nomenclature rules 1. Parent - root derived from number of carbon in longest unbranched chain .containing functional group CH CH3 3 OH 4 2 H C CH H3C 3 3 5 3 1 4-methylheptane 2-propyl-1-pentanol 2. Suffix - basic name derived by adding ending of major functional group (FG) O CH3 O H3C OH H3C NH2 butanoic acid 3-methylbutanamide 3. Position - position of FG denoted by Arabic numeral placed before whole ....name or just before ending. Numbering achieves lowest number for FG O H3C CH3 2-pentanone pentan-2-one NOT 4-pentanone gjr-–- 5 Nomenclature rules II 4. Prefix - substituents are designated by prefix & Arabic number indicating ....position (lowest possible numbering) CH3 Cl CH3 H3C CH3 H3C CH3 H3C CH3 CH3 2,2,5-trimethylheptane 8-chloro-2,3-dimethylnonane NOT 3,6,6-trimethylheptane NOT 2-chloro-7,8-dimethylnonane 5. FG - if more than one FG name & number based on principle FG. List of ....priorities given in course notes. Multiple bonds are added to parent (end), ....all others are prefixes O O CH3 H3C OH HO OH H3C CH3 O 5-hydroxy-2,2-dimethylpentanoic acid 2-methyl-4-oxohex-2-enoic acid 6. Minor FG - halo-, nitro- (-NO2), nitroso- (-NO) & azo- (-N2-) are considered ....substituents & not FG for nomenclature only 7. Order - substituents are written in alphabetical order gjr-–- 6 Examples: structure to name OH O OH O H3C N CH3 H3C N CH3 H H N-ethyl-3-hydroxy-5-methylhept-6-enamide Step 1: root Step 7: complete OH O OH O 5 3 1 H3C N CH3 H3C N CH3 H 4 2 H hept 3-hydroxy-5-methylhept-6-enamide Step 2: suffix Step 5: substituents (prefix) OH O OH O 3 1 H3C N CH3 H3C N CH3 H 2 H hept amide 3-hydroxyhept-6-enamide 6 OH O Step 3: multiple- Step 4: functional bond index H3C 5 3 1 N CH3 groups (prefix) 4 2 H hept-6-enamide gjr-–- 7 Examples: name to structure • Draw the structure for 4-ethyl-3-hydroxycyclohexanone (please) O draw the root add major functional group 4-ethyl-3-hydroxycyclohexanone 4-ethyl-3-hydroxycyclohexanone O O OH H3C H3C add substituent add minor functional group 4-ethyl-3-hydroxycyclohexanone 4-ethyl-3-hydroxycyclohexanone gjr-–- 8 Functional groups: alkanes • Saturated hydrocarbons - contain only C & H and no multiple bonds • Non-cyclic alkanes have the formula CnH2n+2 H C H H H methane propane pentane cyclopentane CH4 C3H8 C5H12 C5H10 CH4 • Alkanes are a little dull - used as solvents or burnt as fuel • Methane is a fuel, a chemical feedstock & a green house gas propane gjr-–- 9 Functional groups: alkanes II isooctane 2,2,4-trimethylpentane C8H18 • Isooctane is used in petrol - branched structure means it burns smoothly • Octane is a long change and burns explosively • Octane number of petrol is based on isooctane = 100 & heptane = 1 Unleaded 91 petrol = 91% isooctane & 9% heptane • Structural isomers have same formula but different atoms joined differently • Isomers can have very different properties pentane 2-methylbutane 2,2-dimethylpropane bp 36.2˚C bp 28˚C bp 9.6˚C gjr-–- 10 Functional groups: alkenes H H H H ethene • Ethene - simplest alkene. Very important industrially • Carbon is trigonal planar - flat and triangular! • New form of isomerism - configurational isomers • All atoms bonded in the same manner but different orientation in space CH3 H3C CH3 H3C 1-butene trans-2-buten2e-butenecis-2-butene 2-methylpropene cyclobutane C4H8 C4H8 C4H8 C4H8 CH3 H3C CH3 H3C CH3 H3C (1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene α-pinene gjr-–- 11 Functional groups: alkynes & cyclic structures O H H OH O H C OME O ethyne 3 pent-3-yn-1-ol O O C2H2 NOT pent-2-yn-5-ol H3C O OH O MeHN HO • Ethyne is an explosive gas O CH3 • Triple bond makes molecular linear (cylinder) OH • Examples found in nature (example cleaves DNA) neocarzinostatin chromophore A Cycloalkanes and cycloalkenes H3C CH3 cyclopropane 1,3-dimethylcyclohexane cyclohexene benzene • Cyclic hydrocarbons are common - note that most are not flat gjr-–- 12 Cyclic structures in nature H3C CH3 CH3 H CH3 H H H3C (8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-(6- methylheptan-2-yl)-hexadecahydro-1H- cyclopenta[a]phenanthrene cholestane - steroid • Ring systems are common in natural products & pharmaceuticals • Example below shows the importance of another form of isomerism - stereoisomers CH3 CH3 H3C H3C H H (R)-1-methyl-4-(prop-1-en-2- (S)-1-methyl-4-(prop-1-en-2- yl)cyclohex-1-ene yl)cyclohex-1-ene (R)-limonene (S)-limonene smells of oranges smells of lemons gjr-–- 13 Functional groups: alcohols H3C CH primary 3 tertiary (1°) CH3 (3°) CH3 CH3 CH3 H CH3 H3C OH H3C H H H3C OH HO CH3 (R)-3,7-dimethyloct-6-en-1-ol cholesterol (R)-1-isopropyl-4- citronellol all animals methylcyclohex-3-enol citronella oil secondary terpinen-4-ol (2°) tea tree oil • Alcohols contain OH (hydroxy) group • Found in many natural systems (especially on Friday night) • Three classes depending on how many C attached to C–OH • Compounds can have more than one OH (improves water solubility) HO HO OH HO O HO OH HO 1,2-ethandiol 6-(hydroxymethyl)-tetrahydro- ethylene glycol 2H-pyran-2,3,4,5-tetraol antifreeze glucose sugar I guess! gjr-–- 14 Functional groups: phenols and ethers Phenols Cl OH OH Cl Cl phenol 2,4,6-trichlorophenol carbolic acid TCP antiseptic • Phenols are distinct from alcohols as attached to phenyl ring - acidic O–H Ethers O O O O H3C O CH3 O O ethoxyethane O diethyl ether tetrahydrofuran ether THF 18-crown-6 • Most commonly used as solvents • 18-Crown-6 enables metal cations (M+) to dissolve in organic solvents gjr-–- 15 Functional groups: alkyl halides and thiols Cl Cl H F Cl Cl O Cl H Cl F Cl Cl Cl H Cl dichloromethane dichlorodifluoromethane dieldrin H DCM Freon (refrigerant) a CFC • Alkyl halides are incredibly useful compounds - used extensively • Down side is they appear to be bad for us and the environment Thiols CH3 SH HS HS SH CH3 O HS H3C H H2N H3C CH3 H3C CH3 CO2H CH3 (R)-2-amino-3- 2-(4-methylcyclohex-3- propane-2,2-dithiol 4-methyl-4- sulfanylpropanoic acid enyl)propane-2-thiol sulfanylpentan-2-one cysteine taste of grapefruit • Thiols are the sulfur analogue of alcohols - and they smell, bad... • Humans can detect 2x10–5 ppb of the second compound (1 drop in a lake) • One of the last two compounds is the smelliest known - but no one is ...prepared to make them again to find out which! gjr-–- 16 Functional groups: amines CH3 O NH2 H3C N H2N OH H2N H CH3 triethylamine butane-1,4-diamine (S)-2-amino-3-phenylpropanoic acid smells of fish putrescine phenylalanine smells of decay amino acid • Vital in biological systems • Many smell (bad but not as bad as thiols) • Found in many compounds that are physiologically active... CH N 3 O CH3 O N H O CH N 3 O (S)-3-(1- methyl 3-(benzoyloxy)-8-methyl- methylpyrrolidin-2-yl) 8-aza-bicyclo[3.2.1]octane-2- pyridine carboxylate nicotine cocaine gjr-–- 17 Functional groups: amines II N H N H H3C H H3C NH2 N CH3 H H3C CH3 H3C ammonia methylamine dimethylamine trimethylamine 1° amine 2° amine 3° amine • Just to confuse, amines are labeled by the number of C attached • This is different to alcohols (labeled by C attached to C–OH) secondary position H (2°) N H3C CH CH3 O 3 H3C trimethylammonium ion H3C OH 4° ammonium (salt) NH2 valine primary If add four groups amine everything changes! (1°) gjr-–- 18 Functional groups: the carbonyl group • Carbonyl group C=O – analogous to alkene • Two groups, aldehydes RCHO and ketones R2C=O Aldehyde O OH OH O O O H HO H H H3C H OH OH H methanal ethanal benzaldehyde (2R,3S,4R,5R)-2,3,4,5,6- formaldehyde acetaldehyde pentahydroxyhexanal glucose Ketones CH3 CH3 O O O H C CH 3 3 HO H3C O H3C H H CH3 propanone (R)-2-methyl-5-(prop-1-en- (S)-2-methyl-5-(prop-1-en- 4-(4-hydroxyphenyl) acetone 2-yl)cyclohex-2-enone 2-yl)cyclohex-2-enone butan-2-one (R)-carvone (S)-carvone raspberry ketone spearmint caraway gjr-–- 19 Functional groups: carboxylic acids & derivatives H oxidation H oxidation H oxidation OH R C H R C H R C R C reduction reduction reduction H OH O O hydrocarbon alcohol aldehyde carboxylic acid • Many of the functional groups are 'linked' • If we replace one C–H at a time by a C–O we see how these groups relate CH O H3C CH3 3 O HO2C CO2H H3C OH H3C OH CO H OH 2 O CH3 ethanoic acid maleic acid (S)-2-hydroxypropanoic acid (2Z,4E)-3-methyl-5-(2,6,6- acetic acid L-(+)-lactic acid trimethyl-4-oxocyclohex-2- vinegar enyl)penta-2,4-dienoic acid abscisic acid leaf fall gjr-–- 20 Functional groups: derivatives O O + NaOH Na + HOH H3C OH H3C O ethanoic sodium sodium ethanoate water acid hydroxide carboxylate ion • Reaction of a carboxylic acid with a base (eg.
Load more

Recommended publications
  • Cinnamoyl Esters of Lesquerella and Castor Oil: Novel Sunscreen Active Ingredients David L
    Cinnamoyl Esters of Lesquerella and Castor Oil: Novel Sunscreen Active Ingredients David L. Compton*, Joseph A. Laszlo, and Terry A. Isbell New Crops and Processing Technology Research Unit, USDA, ARS, NCAUR, Peoria, Illinois 61604 ABSTRACT: Lesquerella and castor oils were esterified with querolin (2). Therefore, LO in essence contains two moles of cinnamic acid (CA) and 4-methoxycinnamic acid (MCA). Esteri- hydroxy functionality per mole of triglyceride (TG). fication of the hydroxy oils reached 85% completion with CA The hydroxy functionality of the FA of the TG can be ex- and 50% conversion with MCA. The hydroxy oils were esteri- ploited by esterification to form estolides. The majority of re- fied at 200°C under a nitrogen atmosphere within a sealed sys- search has focused on the estolides of hydroxy FA and TG tem. Unreacted CA and MCA were removed from the reaction formed with oleic acid. The esterification of hydroxy TG and mixtures by sublimation at 100°C under vacuum. The resultant free lesquerolic acid with oleic acid using a cobalt catalyst (4) methoxycinnamic oils possessed a broader, more blue-shifted or a lipase catalyst (5) has been reported. Also, the acid-cat- UV absorbance, 250 to 345 nm with a λmax of 305 nm, com- pared with the cinnamic oils, which absorbed from 260 to 315 alyzed formation of estolides from CO and LO with oleic acid has been patented (6). Recently, a detailed study of the effect nm, λmax of 270 nm. The methoxycinnamic oils provide better UV-B absorption and thus are better candidates to be used as of oleic acid concentration and temperature on catalyst-free sunscreen active ingredients.
    [Show full text]
  • Polymeric Reagents with Propane-1,3-Dithiol Functions and Their Precursors for Supported Organic Syntheses
    J. Org. Chem. 2000, 65, 4839-4842 4839 Polymeric Reagents with Propane-1,3-dithiol Functions and Their Precursors for Supported Organic Syntheses Vincenzo Bertini,*,† Francesco Lucchesini,† Marco Pocci,† and Angela De Munno‡ Dipartimento di Chimica e Tecnologie Farmaceutiche ed Alimentari, Universita´ di Genova, Via Brigata Salerno, I-16147 Genova, Italy, and Dipartimento di Chimica e Chimica Industriale, Universita´ di Pisa, Via Risorgimento, 35, I-56126 Pisa, Italy [email protected] Received January 19, 2000 Reliable completely odorless syntheses of soluble copolymeric reagents of styrene type containing propane-1,3-dithiol functions able to convert carbonyl compounds into 1,3-dithiane derivatives and to support other useful transformations are reported together with their progenitor copolymers containing benzenesulfonate or thioacetate groups perfectly stable in open air and suitable for unlimited storage. The effectiveness of the prepared reagents as tools for polymer-supported syntheses to produce ketones by aldehyde umpolung and alkylation is tested in the conversion of benzaldehyde to phenyl n-hexyl ketone starting from copolymers with different contents of active units and molecular weights. To facilitate the adaptation of the prepared soluble copolymeric reagents to other possible applications, a table of solvents and nonsolvents is presented. Introduction Scheme 1 Recently we have reported in a preliminary com- munication1 how to harness the great synthetic potenti- alities of thioacetals and thioketals by preparing, with a completely odorless synthesis, polymeric reagents2,3 of styrene type containing propane-1,3-dithiol functions effective in producing ketones by aldehyde umpolung and alkylation after the formation of 1,3-dithiane derivatives. Such polymeric reagents were obtained through a pro- cedure based on the use of the difunctional monomer 1 prepared from commercial 4-vinylbenzyl chloride (Scheme 1), its copolymerization with styrene, and chemical modification of its copolymers.
    [Show full text]
  • Polymer Exemption Guidance Manual POLYMER EXEMPTION GUIDANCE MANUAL
    United States Office of Pollution EPA 744-B-97-001 Environmental Protection Prevention and Toxics June 1997 Agency (7406) Polymer Exemption Guidance Manual POLYMER EXEMPTION GUIDANCE MANUAL 5/22/97 A technical manual to accompany, but not supersede the "Premanufacture Notification Exemptions; Revisions of Exemptions for Polymers; Final Rule" found at 40 CFR Part 723, (60) FR 16316-16336, published Wednesday, March 29, 1995 Environmental Protection Agency Office of Pollution Prevention and Toxics 401 M St., SW., Washington, DC 20460-0001 Copies of this document are available through the TSCA Assistance Information Service at (202) 554-1404 or by faxing requests to (202) 554-5603. TABLE OF CONTENTS LIST OF EQUATIONS............................ ii LIST OF FIGURES............................. ii LIST OF TABLES ............................. ii 1. INTRODUCTION ............................ 1 2. HISTORY............................... 2 3. DEFINITIONS............................. 3 4. ELIGIBILITY REQUIREMENTS ...................... 4 4.1. MEETING THE DEFINITION OF A POLYMER AT 40 CFR §723.250(b)... 5 4.2. SUBSTANCES EXCLUDED FROM THE EXEMPTION AT 40 CFR §723.250(d) . 7 4.2.1. EXCLUSIONS FOR CATIONIC AND POTENTIALLY CATIONIC POLYMERS ....................... 8 4.2.1.1. CATIONIC POLYMERS NOT EXCLUDED FROM EXEMPTION 8 4.2.2. EXCLUSIONS FOR ELEMENTAL CRITERIA........... 9 4.2.3. EXCLUSIONS FOR DEGRADABLE OR UNSTABLE POLYMERS .... 9 4.2.4. EXCLUSIONS BY REACTANTS................ 9 4.2.5. EXCLUSIONS FOR WATER-ABSORBING POLYMERS........ 10 4.3. CATEGORIES WHICH ARE NO LONGER EXCLUDED FROM EXEMPTION .... 10 4.4. MEETING EXEMPTION CRITERIA AT 40 CFR §723.250(e) ....... 10 4.4.1. THE (e)(1) EXEMPTION CRITERIA............. 10 4.4.1.1. LOW-CONCERN FUNCTIONAL GROUPS AND THE (e)(1) EXEMPTION.................
    [Show full text]
  • WIIINIPEG, I{ANI1.Oba October 1971
    THE UNTVERSITY OF FJAI,TTTOBA STTIDIES ON TSOTHTÁ.ZOIIU}.I SÂLTS AND REIATED CO},IPOUI{DS by GART ED}¡ARD BACIIERS A T}MSIS SIMÌ,1TTTED TO TI{E FACULTY OF GR]I.DUÀTE STIIDIES ÏN PIIRÎI/iL FULIi'TIJ'&Til'r OF TI# REQUTREI.Tiü{TS TÇR TI.III DEGREE I'IÂSTER 0F SCIEÎIICE DEPARTI'ÎE]VT 0F CI{EI,IISTRY WIIINIPEG, I{ANI1.oBA October 1971 üF fi "*i¡l,''ÉËR$$iY LT BRARY ACIOTOIILEDGH,ÍTÍüTS : The research degcribed in thís thesis has been undertaken at tho suggestion of Dr. D. Id. McKínnon, for v¡hose guidance, advice, æd ass*stance ï exprees r¡\y sincere appreciation" My gratitud.e ie also due the National Research CounciÌ of Canada for the scholarships provid.ed. d.uring the course of this research, and the University of }ianitoba for the provisíon of laboratory facilities. Finally, I should like to thank rny colleaguee, I'fiss Sheena Loosmore, Ivlr. Joe Buchsbriber, Iilr. Pat Ma, a¡rd. Mr. Jack Wong. Their forbearance during several unusually od.or-ous experiments was admirable. 11 TA3I,E 0F.coNTlNTS ABSTRACT.......... o.. ó..... o. ...:. r. o õ i.. o.... o.......iii INTRODUCTION Ggngial.. - - . ô. :.' ..... o. ... .. .. .. .. r. .. o. .. .... 1 fsothiazoles. o r . c o. o . ... .. o. ¡. 2 ' I s o thi azo 1 um s s i al t . c . o . c . , . , . , o . ! 4-rsothiazoline-3-thiones... o... ô........ o.... r........ 13 . 3-Isothiazoline-l-thiones....o.....,r........er........18 Thiothiophthenes and an aza arialogue.. o...... c o. o... .,.19 DISCUSSION Purpose of resgarch...... c.. o...^... r.............. o., o..2J Reaction of isothiazolium salts ç¡ittr sutf:p¡ ¡ o o.
    [Show full text]
  • Studies on the Chemistry of Paclitaxel
    STUDIES ON THE CHEMISTRY OF PACLITAXEL Haiqing Yuan Dissertation submitted to the Faculty of the Virginia Polytechnic Institute and State University in the partial fulfillment of the requirement for the degree of Doctor of Philosophy in Chemistry Dr. David G. I. Kingston, Chair Dr. Michael Calter Dr. Neal Castagnoli, Jr. Dr. Richard Gandour Dr. Larry Taylor August 11, 1998 Blacksburg, Virginia Keywords: Paclitaxel, Taxol®, synthesis, analog, SAR Copyright 1998, Haiqing Yuan STUDIES ON THE CHEMISTRY OF PACLITAXEL HAIQING YUAN (ABSTRACT) Paclitaxel is a natural occurring diterpene alkaloid originally isolated from the bark of Taxus brevifolia. It is now one of the most important chemotherapeutic agents for clinical treatment of ovarian and breast cancers. Recent clinical trials have also shown paclitaxel’s potential for the treatment of non-small-cell lung cancer, head and neck cancer, and other types of cancers. While tremendous chemical research efforts have been made in the past years, which established the fundamental structure-activity relationships of the paclitaxel molecule, and provided analogs for biochemical studies to elucidate the precise mechanism of action and for the development of second-generation agents, many areas remain to be explored. In continuation of our efforts in the structure-activity relationships study of A- norpaclitaxel, five new analogs modified at the C-1 substituent and analogs with expanded B-ring or contracted C-ring have now been prepared. Preliminary biological studies indicated that the volume rather than functionality at the C-1 position plays a role in determining the anticancer activity by controlling the relative position of the tetracyclic ring system, which in turn controls the positions of the most critical functionalities such as the C-2 benzoyl, the C-4 acetate, and the C-13 side chain.
    [Show full text]
  • Organic Chemistry Tests for Hydroxyl Group
    Chemistry Organic Chemistry Tests for Hydroxyl Group General Aim Method Identication of aliphatic alcohols through the chemical Detection of the presence of hydroxyl groups in detection of hydroxyl groups. aliphatic alcohols using special chemical tests. Learning Objectives (ILOs) Dene and determine aliphatic alcohols theoretically through their chemical structure. Classify organic compounds containing hydroxyl groups into aliphatic and aromatic. Compare between alcohols and other functional groups in terms of chemical structures, properties and reactions. Identify aliphatic alcohols experimentally. Select the appropriate reagents to dierentiate between alcohols and other organic compounds. Theoretical Background/Context - Aliphatic alcohols are non-aromatic hydrocarbons possessing at least one hydroxyl group within their structure. They can be either cyclic or acyclic compounds. Alcohols are considered to be neutral compounds. Aliphatic Cyclic Alcohol Aliphatic Acyclic Alcohol - Alcohols are also classied to primary, secondary and tertiary alcohols according to the number of carbon atoms attached to the carbon atom linked to the hydroxyl group. First: Preparation of Aliphatic Alcohols - Alcohols can be prepared through some chemical routes such as reduction of the corresponding aldehydes and ketones using some reducing agents such as lithium aluminum hydride or sodium borohydride. They can be also obtained from hydration of the corresponding alkenes. Some primary alcohols can be synthesized through the nucleophilic substitution of corresponding alkyl halides using potassium or sodium hydroxides. - Alcohols can be also obtained through some biological routes such as ethanol and butanol through fermentation processes in presence of glucose. Glucose is obtained from starch hydrolysis in the presence of yeast. 1 www.praxilabs.com Theoretical Background/Context (Cont’) Second: General Properties of Aliphatic Alcohols - Aliphatic alcohols are polar compounds and can form hydrogen bonds easily.
    [Show full text]
  • Ganic Compounds
    6-1 SECTION 6 NOMENCLATURE AND STRUCTURE OF ORGANIC COMPOUNDS Many organic compounds have common names which have arisen historically, or have been given to them when the compound has been isolated from a natural product or first synthesised. As there are so many organic compounds chemists have developed rules for naming a compound systematically, so that it structure can be deduced from its name. This section introduces this systematic nomenclature, and the ways the structure of organic compounds can be depicted more simply than by full Lewis structures. The language is based on Latin, Greek and German in addition to English, so a classical education is beneficial for chemists! Greek and Latin prefixes play an important role in nomenclature: Greek Latin ½ hemi semi 1 mono uni 1½ sesqui 2 di bi 3 tri ter 4 tetra quadri 5 penta quinque 6 hexa sexi 7 hepta septi 8 octa octo 9 ennea nona 10 deca deci Organic compounds: Compounds containing the element carbon [e.g. methane, butanol]. (CO, CO2 and carbonates are classified as inorganic.) See page 1-4. Special characteristics of many organic compounds are chains or rings of carbon atoms bonded together, which provides the basis for naming, and the presence of many carbon- hydrogen bonds. The valency of carbon in organic compounds is 4. Hydrocarbons: Compounds containing only the elements C and H. Straight chain hydrocarbons are named according to the number of carbon atoms: CH4, methane; C2H6 or H3C-CH3, ethane; C3H8 or H3C-CH2-CH3, propane; C4H10 or H3C-CH2- CH2-CH3, butane; C5H12 or CH3CH2CH2CH2CH3, pentane; C6H14 or CH3(CH2)4CH3, hexane; C7H16, heptane; C8H18, octane; C9H20, nonane; C10H22, CH3(CH2)8CH3, decane.
    [Show full text]
  • Preparation of Hydroxy Aromatic Carboxylic Acids and Ester Derivatives Thereof
    Europiisches Patentamt European Patent Office © Publication number: 0 049 616 Office europeen des brevets A1 EUROPEAN PATENT APPLICATION © Application number: 81304567.1 © int. ci.3: C 07 C 69/88 C 07 C 67/36 © Date of filing: 02.10.81 © Priority: 06.10.80 US 194201 © Applicant: CELANESE CORPORATION 1211 Avenue Of The Americas New York New York 10036IUS) © Date of publication of application: 14.04.82 Bulletin 82/15 © Inventor: McGinnes, James L 236 Raritan Avenue © Designated Contracting States: Middlesex New Jersey(US) BE DE FR GB IT NL © Inventor: Conciatori, Anthony B. 27. Orchard Road Chatham New Jersey(US) @ Representative: De Minvielle-Devaux, Ian Benedict Peter et al, CARPMAELS & RANSFORD 43, Bloomsbury Square London WC1 A 2RA(GB) © Preparation of hydroxy aromatic carboxylic acids and ester derivatives thereof. A process for preparing hydroxy aromatic carboxylic acids, or the ester derivatives thereof, comprises carbonylat- ing a hydroxy aromatic halide in the presence of a reactive alcohol solvent and a catalytic amount of a Group VIII metal catalyst. The process has particular applicability to the preparation of 6-hydroxy-2-naphthoic acid from 6-bromo-2- naphthol, which can be easily prepared from β-naphthol, a readily available and inexpensive starting material. This invention relates to a novel process for pre- paring hydroxy aromatic carboxylic acids or the corresponding ester derivatives thereof. This invention relates particular- ly to a novel process for the preparation of esters of hydroxy aromatic carboxylic acids such as 6-hydroxy-2- naphthoic acid by the carbonylation of a hydroxy aromatic halide, followed if desired by conversion of the esters to the acids.
    [Show full text]
  • Lipophilicity As a Central Component of Drug-Like Properties of Chalchones and Flavonoid Derivatives
    molecules Article Lipophilicity as a Central Component of Drug-Like Properties of Chalchones and Flavonoid Derivatives Teodora Constantinescu 1, Claudiu Nicolae Lungu 2,* and Ildiko Lung 3 1 Department of Chemistry, Faculty of Pharmacy, Iuliu Hatieganu University, 400012 Cluj-Napoca, Romania; [email protected] 2 Department of Chemistry, Faculty of Chemistry and Chemical Engineering, Babes-Bolyai University, 400028 Cluj-Napoca, Romania 3 National Institute for Research & Development of Isotopic and Molecular Technologies 67-103 Donath street, 400293 Cluj-Napoca, Romania; [email protected] * Correspondence: [email protected]; Tel.: +40-(0)-742-255-099 Received: 11 March 2019; Accepted: 10 April 2019; Published: 17 April 2019 Abstract: Lipophilcity is an important physico-chemical parameter that influences membrane transport and binding ability to action. Migration distance following complete elution of compounds was used to calculate different lipophilicity-related parameters. The aim of this study is to show that lipophilicity is a central component of thiazole chalcones and flavonoid derivatives regarding their drug-like properties. Experimental and computational methods were used. This study considers 44 previously synthesized compounds (thiazole chalcones, flavanones, flavones, 3-hydroxyflavones, and their acetylated derivatives). The concerned compounds have shown antitumoral hallmarks and antibacterial activity in vitro. The experimental method used to determine compounds’ lipophilicity was the reverse-phase thin layer chromatography (RP-TLC). Lipophilicity related 0 parameters—isocratic retention factor (RM), relative lipophily (RM ), slope (b), chromatographic hydrophobic index ('0), scores of principal components (PC1/RM)—were determined based on reverse-phase chromatography results. Keywords: lipophilicity; retention factor; chalcones; QSAR; chromatography; drug design 1. Introduction Lipophilicity is an important feature of molecules in pharmaceutical, biochemical, and medical chemistry fields.
    [Show full text]
  • United States Patent (19) 11 4,267,375 Maasbol Et Al
    United States Patent (19) 11 4,267,375 Maasbol et al. 45 May 12, 1981 54 PREPARATION OF THIOETHERS OTHER PUBLICATIONS 75) Inventors: Alfred G. Maasbol, Hamburg, Fed. I. Ruderman et al., J. Amer. Chem. Soc., 71, pp. Rep. of Germany; Lothar G. Dulog, 2264-2265, (1949). St. Martens Latem, Belgium Morrisson and Boyd, Organic Chemistry, 2nd edition, (1967), pp. 29–30. 73) Assignee: s.a. Texaco Belgium in.v., Brussels, T. Todsen et al., J. Amer. Chem. Soc., 72, pp. Belgium 4000-4002, (1950). Berichte Deutsch. Chemie, vol. 1, pp. 587-591, (1935), (21) Appl. No.: 945,273 Berlin. 22 Filed: Sep. 25, 1978 D. Gregg et al., J. Org. Chem., pp. 246-252, (1950). M. Malinovskii, Epoxides and Their Derivatives, pp. Related U.S. Application Data 131-136, (1965), Jerusalem, Daniel Davey & Co. Primary Examiner-Glennon H. Hollrah 63 Continuation of Ser. No. 703,045, Jul. 6, 1976, aban Assistant Examiner-M. C. Eakin doned. Attorney, Agent, or Firm-Carl G. Ries; Robert A. 30 Foreign Application Priority Data Kulason; Carl G. Seutter Nov. 19, 1975 GB United Kingdom ............... 47582/75 57 ABSTRACT .. 51 Int. Cl. ............................................ CO7C 149/30 Thioethers may be prepared by reacting a thiol, such as thiophenol, with an alcohol (having electron donor 52 U.S. C. ......................................... 568/57; 568/58 groups in the alpha or beta position to its hydroxyl 58 Field of Search ........................ 260/609 E, 609 R group) such as phenyl-1-hydroxy-phenethylsulfide. Re 56) References Cited action is carried out in the presence of a Lewis Acid U.S. PATENT DOCUMENTS metal halide, typically zinc chloride.
    [Show full text]
  • Identification of a Common Chemical Signal Regulating the Induction Of
    Proc. Nati. Acad. Sci. USA Vol. 85, pp. 8261-8265, November 1988 Medical Sciences Identification of a common chemical signal regulating the induction of enzymes that protect against chemical carcinogenesis (Michael acceptors/quinone reductase/glutathione S-transferase/anticarcinogens) PAUL TALALAY, MARY J. DE LONG, AND HANS J. PROCHASKA Department of Pharmacology and Molecular Sciences, The Johns Hopkins University School of Medicine, Baltimore, MD 21205 Contributed by Paul Talalay, July 19, 1988 ABSTRACT Carcinogenesis is blocked by an extraordi- al inducers act are less clear (3). This paper extends our nary variety of agents belonging to many different classes- earlier efforts to identify structural features important for e.g., phenolic antioxidants, azo dyes, polycyclic aromatics, phase II enzyme induction by diphenols and phenylenedia- flavonoids, coumarins, cinnamates, indoles, isothiocyanates, mines (5). Since the specific activity of QR in the Hepa lclc7 1,2-dithiol-3-thiones, and thiocarbamates. The only known murine hepatoma cells is raised by virtually all compounds common property of these anticarcinogens is their ability to that produce coordinate elevations of phase II enzymes in elevate in animal cells the activities of enzymes that inactivate vivo (4, 5, 7), this system was used to determine the potency the reactive electrophilic forms of carcinogens. Structure- of various types of enzyme inducers. Some inducers identi- activity studies on the induction of quinone reductase fied in cell culture were also tested as inducers
    [Show full text]
  • 514636-Unified-Chemistry.Pdf
    Qualification Accredited A LEVEL Exemplar Candidate Work CHEMISTRY A H432 For first teaching in 2015 H432/03 Summer 2017 examination series Version 1 www.ocr.org.uk/chemistry A Level Chemistry A Exemplar Candidate Work Contents Introduction 3 Question 3(b) 20 Commentary 21 Question 1(a) 4 Commentary 4 Question 3(c)(i) 22 Commentary 22 Question 1(b) 5 Commentary 5 Question 3(c)(ii) 23 Commentary 24 Question 1(c) 6 Commentary 6 Question 4(a)(i) 25 Commentary 26 Question 1(d) 7 Commentary 7 Question 4(a)(ii) 27 Commentary 28 Question 1(e) 8 Commentary 8 Question 4(b)(i) 29 Commentary 29 Question 2(a) 9 Commentary 11 Question 4(b)(ii) 30 Commentary 30 Question 2(b) 12 Commentary 12 Question 4(c)(i) 31 Commentary 31 Question 2(c) 13 Commentary 13 Question 4(c)(ii) 32 Commentary 32 Question 2(d)(i) 14 Commenary 14 Question 5(a)(i) 33 Commentary 33 Question 2(d)(ii) 15 Commentary 15 Question 5(a)(ii) 34 Commentary 34 Question 2(d)(iii) 16 Commentary 16 Question 5(a)(iii) 35 Commentary 35 Question 3(a)(i) 17 Commentary 18 Question 5(a)(iv) 36 Commentary 36 Question 3(a)(ii) 19 Commentary 19 Question 5(b) 37 Commentary 38 2 © OCR 2017 A Level Chemistry A Exemplar Candidate Work Introduction These exemplar answers have been chosen from the summer 2017 examination series. OCR is open to a wide variety of approaches and all answers are considered on their merits. These exemplars, therefore, should not be seen as the only way to answer questions but do illustrate how the mark scheme has been applied.
    [Show full text]