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Functional Groups Functional groups are • a characteristic feature of organic molecules that behave in a predictable, similar way. • composed of an atom or group of atoms. • groups that replace a hydrogen atom in the corresponding alkane. • a way to classify families of organic compounds. 1 Hydrocarbons Drugs Fire accelerants Petrol: It is petroleum-derived, and consists mostly of aliphatic hydrocarbons enhanced with iso-octane or the aromatic hydrocarbons toluene and benzene to increase its octane rating. Diesel: Diesel is produced from oil and is a hydrocarbon mixture, obtained in the fractional distillation of crude oil between 200 °C and 350 °C at atmospheric pressure Butane Gas: consumed from lighters CH3 H3C C4H10 Carbon tetrachloride: Used for solvent abuse CCl4 Cl Cl Cl Cl This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Aromatic compounds Fire accelerants HN N Benzene Toluene Explosives N O Benzodiazepines: Psychoactive drugs with varying hypnotic, sedative, anxiolytic, anticonvulsant, muscle relaxant and amnesic properties CH3 O Drugs - CH3 + Dyes O N O O + O O - N OH - + OH O O Tri-Nitro Toluene (TNT) Alizarin This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License cyclic molecules H H H H C H H CH2 CH2 H H C C H CH2 CH2 H C C H CH2 CH2 H Cyclobutane H H C C H H HH C H H H H C C C C C H CH2 Cyclopentane C H CH2 CH2 CH2 H H H H CH2 C C Cyclopropane H H H CH2 C C H H H CH2 H H CH2 CH2 CH2 CH2 CH2 Cyclohexane Nomenclature for Cyclic Alkanes • For compounds with a single ring, add the prefix “cyclo-” to the root name for the alkane comprising the ring. Ethers Fire accelerants Drugs Codeine: Opiate alkaloid H3C O HO CH3 N CH3 O Ethyl Ether - diethyl ether: flash point -45 degrees C; ignition temperature 180 degrees C; explosive limits 1.9% 36% HO Dyes H H + N Cl - Rhodamine 123 O NH2 O O CH3 This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Ethers In an ether, an oxygen atom is bonded to two carbon atoms. –C–O–C– . has a common name that gives the alkyl names of the attached groups followed by ether. Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings Diethyl ether 7 Ethers are named in two ways: the common naming system, and the IUPAC naming system •IUPAC Names: The carbon(s) attached to the oxygen atom are named as branches by adding the –oxy suffix to the stem name. Ether Example CH3-CH2-CH2-CH2-O-CH2-CH3 • IUPAC Name: ethoxybutane Ether Practice R-O_R • Draw the condensed structural formula of methoxy propane: Ketones Fire accelerants O H 3C CH3 Acetone:(Dimethyl ketone) flash point -20 degrees C; ignition temperature 465.4 degrees C; explosive limits 2.6%13.0% Explosives Drugs H3C O Methcathinone: 2-(methylamino)propiophenone. Psychoactive stimulant. Addictive. Can be smoked, injected, or taken orally . Dyes O ACETONE: precursor of TATP. TATP: The synthesis of the explosive is made through oxidation of acetone using hydrogen peroxide CH3 NH 9,10-dioxoanthracene O This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License 4. Ketones In a ketone, the carbon of the carbonyl group is attached to two other carbon atoms. Acetone Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings 12 IUPAC Names for Ketones • Replace -e with -one. Indicate the position of the carbonyl with a number. • Number the chain so that carbonyl carbon has the lowest number. • For cyclic ketones the carbonyl carbon is assigned the number 1. Chapter 18 13 Ketones Practice R-C-R • Draw the condensed structural formula for 3-pentanone O CH3 Examples C CH CH3 CH3 3-methyl-2-butanone Chapter 18 15 Esters Fire accelerants Biodiesel refers to a nonpetroleum-based diesel fuel consisting of short chain alkyl (methyl or ethyl) esters Drugs O O CH3 H2N Explosives CH3 O H3C O O O Dibutylphatalate: Plasticizer used in explosives. Plasticizers are additives that increase the plasticity or fluidity. Benzocaine (local anaesthetic) : Benzocaine is often favoured by drug dealers to bulk out their cocaine supplies. while many dealers use the cheaper paracetamol or corn flour, Benzocaine gives a numbing effect (like purer cocaine should have). This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Esters • Ester – a compound that has the following general formula: 14 | 17 Section 14.4 Names of esters end in –oate. Naming Named after alcohol & carboxylic acid from which they are derived. O C CH3 CH2 CH3 let’s name some esters! O ethyl this part comes from the alcohol & is named after it ethanoate this part from the acid and is named after it Structural formulae Although the previous structural formula are the clearest way of showing esters, they can draw out in a shortened form. In this version ethyl ethanoate O Either… CH3 CH2 O C CH3 Or… O CH3 C the acid part has been written first O CH2 CH3 Identify the group attached to the C=O – this is from the acid The group attached to the –O- is from the alcohol. Esters Practice R-O-C-R • Draw the condensed structure for butyl hexanoate Wait! What’s that smell? ester ethyl methanoate 3-methylbutyl ethanoate ethyl 2-methylbutanoate phenylmethyl ethanoate fragrance raspberries pears apples jasmine • Esters have strong, sweet smells. • Their bouquet is often floral or fruity. • This means they are used in food flavourings & perfumes. • Also, very good at dissolving organic compounds so often used as solvents. Alcohols Fire accelerants Drugs OH H3C OH HO O Ethyl Alcohol – Ethanol: (C2H5OH), flash point 13 oC; ignition temp. 365 oC; explosive limits 3.5%-19.0% Explosives OH OH Glycerol or glycerine: Used as starting material for nitro-glycerine 4-hydroxybutanoic acid (GHB): Date rape drug. GHB has been used in cases of drug-related sexual assault Dyes OH O CH3 N N OH BTTN :Military propellant for missiles: the mixture can be made by co-nitration of butanetriol and glycerol Sudan Red G: It is considered carcinogenic and genotoxic This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Alcohols An alcohol contains the hydroxyl (-OH) functional group. (instead of an H in that place) Ethanol Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings Alcohols An alcohol contains a hydroxyl group (—OH) attached to a carbon chain. A phenol contains a hydroxyl group (—OH) attached to a benzene ring. Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings water alcohol phenol 24 Naming Alcohols The names of alcohols • in IUPAC replace the -e with -ol. • with common names use the name of the alkyl group followed by alcohol. Formula IUPAC CH4 methane CH3─OH methanol CH3─CH3 ethane CH3─CH2─OH ethanol Common Name methyl alcohol ethyl alcohol 25 Aldehydes Drugs O Dyes O O O Piperonal: Precursor of MDMA (Ecstasy: 3,4methylenedioxy-Nmethylamphetamine) N NH2 + O O - 4-amino-3-nitrobenzaldehyde: Hair dye This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Aldehydes An aldehyde contains a carbonyl group (C=O), which is a carbon atom with a double bond to an oxygen atom. formaldehyde Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings acetaldehyde 27 Carboxylic acids Drugs CH3 N O Benzoylecgonine (ecgonine benzoate) is the primary metabolite of cocaine. It is formed in the liver by the metabolism of cocaine O HO O This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Carboxylic Acids Carboxylic acids contain the carboxyl group, which is a carbonyl group attached to a hydroxyl group. O ║ — C—OH Acetic acid Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings 29 Amides Dyes Yellow 13: pigment O CH3 CH3 NH N O H3C N Cl Cl N N O Drugs CH3 NH N O CH3 CH3 CH3 CH3 O NH CH3 CH3 Fraud between drug dealers Lidocaine is often added to cocaine as a diluent because it numbs the gums when applied, giving the impression of higher cocaine purity This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Amines Drugs Explosives O O O - - O N O - O N + N + + OH + O N O NH - CH3 NH CH3 + O - + N O O - N O Ephedrine: found in cold remedies, but used to Enhance performance. Overdose can lead to death. Similar chemical structure than methamphetamine Hexanitrodiphenylamine: 40% part of an explosive called hexanite; rest 60% TNT. Obsolete explosive from WWII Dyes O N H H N O Indigo: found in foodstuff and textiles (jeans) This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Organic compounds with CarbonNitrogen bonds 1. Amines In amines, the functional group is a nitrogen atom. H H C —N – H or C —N —C Methyl amine Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings Dimethyl amine 32 Naming simple amines • Simple 1º amines are named as “alkylamine” – Examples: • methylamine CH3NH2 • ethylamine CH3CH2NH2 • butylamine CH3CH2CH2CH2NH2 • Symmetrical 2º or 3º amines are named as “dialkylamine” or “trialkyamine” – Examples: • diethylamine (CH3CH2)2NH; • trimethylamine (CH3)3N R R NH3 R NH NH2 N R R Ammonia A primary amine R A tertuary amine A secondary amine Examples: R R R NH2 R A primary amine NH2 OH R R A tertuary alkcohol pentan-2-amine NH2 NH N-methylcyclohexanamine cyclohexanamine Amines are much more polar, than hydrocarbons, especially in acidic conditions More biologically active amines… H O O H N CH3CH2O Cl CH3 N N N N N CH2CH2CH3 O O S N O diazepam (Valium) O H2N C OCH2CH3 benzocaine (a topical anesthetic) N CH3 Sildenafil (Viagra) Learning Check Classify each of the following as: alcohol, ether, aldehyde, ketone, carboxylic acid, ester, amine or amide. 1) CH3─CH2─CH2─OH 2) CH3─O─CH2─CH3 3) CH3─CH2─NH2 O ║ 4) CH3─C─OH carboxylic acid alcohol ether amine O ║ 5) CH3─C─O─CH3 ester 36