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. Functional Groups 1

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Fire accelerants Drugs 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 Carbon tetrachloride: Used for solvent abuse Hydrocarbons C 4 H 10 CCl 4

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Aromatic compounds Fire accelerants Toluene Benzene Drugs Explosives Tri-Nitro Toluene (TNT) Dyes Alizarin Benzodiazepines: Psychoactive drugs with varying hypnotic, sedative, anxiolytic, anticonvulsant, muscle relaxant and amnesic properties

cyclic molecules

Nomenclature for Cyclic Alkanes For compounds with a single ring, add the prefix “cyclo-” to the root name for the alkane comprising the ring.

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Ethers Fire accelerants Drugs Dyes Ethyl Ether - diethyl ether: flash point -45 degrees C; ignition temperature 180 degrees C; explosive limits 1.9% - 36% Codeine: Opiate alkaloid Rhodamine 123

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 7 Diethyl ether

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:

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Ketones Fire accelerants Drugs Explosives Dyes Acetone:(Dimethyl ketone) flash point -20 degrees C; ignition temperature degrees C; explosive limits 2.6%- 13.0% ACETONE: precursor of TATP. TATP: The synthesis of the explosive is made through oxidation of acetone using hydrogen peroxide Methcathinone: 2-(methylamino)- propiophenone. Psychoactive stimulant. Addictive. Can be smoked, injected, or taken orally. 9,10-dioxoanthracene

4. Ketones In a ketone, the carbon of the carbonyl group is attached to two other carbon atoms. Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings 12 Acetone

Chapter 1813 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. =>

Ketones Practice R-C-R Draw the condensed structural formula for 3-pentanone

Chapter 1815 Examples 3-methyl-2-butanone

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Esters Fire accelerantsDrugs Explosives Biodiesel refers to a non- petroleum-based diesel fuel consisting of short chain alkyl (methyl or ethyl) esters 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).

14 | 17 Esters Ester – a compound that has the following general formula: Section 14.4

Naming Named after alcohol & carboxylic acid from which they are derived. Names of esters end in –oate. CH 3 C CH 2 O O CH 3 ethylethanoate this part from the acid and is named after it this part comes from the alcohol & is named after it let’s name some esters!

Structural formulae Although the previous structural formula are the clearest way of showing esters, they can draw out in a shortened form. ethylethanoate CH 3 C CH 2 O O CH 3 Either… Or… CH 3 C CH 2 O O CH 3 In this version the acid part has been written first 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? 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. esterfragrance ethyl methanoateraspberries 3-methylbutyl ethanoatepears ethyl 2-methylbutanoateapples phenylmethyl ethanoatejasmine

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Alcohols Fire accelerantsDrugs Explosives Dyes 4-hydroxybutanoic acid (GHB): Date rape drug. GHB has been used in cases of drug-related sexual assault Ethyl Alcohol – Ethanol: (C2H5OH), flash point 13 o C; ignition temp. 365 o C; explosive limits 3.5%-19.0% Glycerol or glycerine: Used as starting material for nitro-glycerine 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

Alcohols An alcohol contains the hydroxyl (-OH) functional group. (instead of an H in that place) Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings Ethanol

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. water alcohol phenol Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings 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. FormulaIUPACCommon Name CH 4 methane CH 3 ─OH methanol methyl alcohol CH 3 ─CH 3 ethane CH 3 ─CH 2 ─OH ethanol ethyl alcohol 25

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Aldehydes Drugs Dyes 4-amino-3-nitrobenzaldehyde: Hair dye Piperonal: Precursor of MDMA (Ecstasy: 3,4- methylenedioxy-N- methylamphetamine)

Aldehydes An aldehyde contains a carbonyl group (C=O), which is a carbon atom with a double bond to an oxygen atom. Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings 27 acetaldehyde formaldehyde

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Carboxylic acids Drugs Benzoylecgonine (ecgonine benzoate) is the primary metabolite of cocaine. It is formed in the liver by the metabolism of cocaine

Carboxylic Acids Carboxylic acids contain the carboxyl group, which is a carbonyl group attached to a hydroxyl group. O ║ — C—OH Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings 29 Acetic acid

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Amides Drugs Dyes Yellow 13: pigment 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 Dyes Indigo: found in foodstuff and textiles (jeans) Hexanitrodiphenylamine: 40% part of an explosive called hexanite; rest 60% TNT. Obsolete explosive from WWII Ephedrine: found in cold remedies, but used to Enhance performance. Overdose can lead to death. Similar chemical structure than methamphetamine

Organic compounds with Carbon- Nitrogen bonds 1. Amines In amines, the functional group is a nitrogen atom. H H C —N – H or C —N —C Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings 32 Methyl amine Dimethyl amine

Naming simple amines Simple 1º amines are named as “alkylamine” –Examples: methylamine CH 3 NH 2 ethylamine CH 3 CH 2 NH 2 butylamine CH 3 CH 2 CH 2 CH 2 NH 2 Symmetrical 2º or 3º amines are named as “dialkylamine” or “trialkyamine ” –Examples : diethylamine (CH 3 CH 2 ) 2 NH; trimethylamine (CH 3 ) 3 N

Examples: Amines are much more polar, than hydrocarbons, especially in acidic conditions

More biologically active amines…

Learning Check Classify each of the following as: alcohol, ether, aldehyde, ketone, carboxylic acid, ester, amine or amide. 1)CH 3 ─CH 2 ─CH 2 ─OH 2) CH 3 ─O─CH 2 ─CH 3 3) CH 3 ─CH 2 ─NH 2 O O ║ ║ 4) CH 3 ─C─OH 5) CH 3 ─C─O─CH 3 alcohol ether amine carboxylic acid ester 36