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Functional Groups Functional groups are

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Presentation on theme: "Functional Groups Functional groups are"— Presentation transcript:

1 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.

2 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. Butane Gas: consumed from lighters C4H10 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 Carbon tetrachloride: Used for solvent abuse CCl4 This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

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

4 cyclic molecules

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

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

7 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. Diethyl ether Copyright © by Pearson Education, Inc. Publishing as Benjamin Cummings

8 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.

9 Ether Example CH3-CH2-CH2-CH2-O-CH2-CH3 IUPAC Name: ethoxybutane

10 Ether Practice R-O_R Draw the condensed structural formula of methoxy propane:

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

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

13 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 => Chapter 18

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

15 Examples 3-methyl-2-butanone Chapter 18

16 Esters Fire accelerants Drugs Explosives
Biodiesel refers to a non-petroleum-based diesel fuel consisting of short chain alkyl (methyl or ethyl) esters Explosives 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). Dibutylphatalate: Plasticizer used in explosives. Plasticizers are additives that increase the plasticity or fluidity. This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

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

18 Names of esters end in –oate.
Naming Names of esters end in –oate. Named after alcohol & carboxylic acid from which they are derived. O let’s name some esters! C CH3 CH3 CH2 O ethyl ethanoate ‘let’s name some esters’ action button links to slide 10 – check notes on slide 10 this part comes from the alcohol & is named after it this part from the acid and is named after it

19 In this version the acid part has been written first
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 the acid part has been written first ethyl ethanoate Or… O Either… O CH3 C O CH2 CH3 CH3 CH2 O C CH3 Identify the group attached to the C=O – this is from the acid The group attached to the –O- is from the alcohol.

20 Esters Practice R-O-C-R
Draw the condensed structure for butyl hexanoate

21 Wait! What’s that smell? ester fragrance ethyl methanoate raspberries
3-methylbutyl ethanoate pears ethyl 2-methylbutanoate apples phenylmethyl ethanoate 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.

22 Alcohols Fire accelerants Drugs Explosives Dyes
Ethyl Alcohol – Ethanol: (C2H5OH), flash point 13 oC; ignition temp. 365 oC; explosive limits 3.5%-19.0% 4-hydroxybutanoic acid (GHB): Date rape drug. GHB has been used in cases of drug-related sexual assault Explosives Dyes 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 This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

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

24 Alcohols water alcohol phenol
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 © by Pearson Education, Inc. Publishing as Benjamin Cummings

25 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 Common Name CH4 methane CH3─OH methanol methyl alcohol CH3─CH3 ethane CH3─CH2─OH ethanol ethyl alcohol

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

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

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

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

30 Amides Dyes Drugs 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

31 Amines Explosives Drugs Dyes
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 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

32 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 Methyl amine Dimethyl amine Copyright © by Pearson Education, Inc. Publishing as Benjamin Cummings

33 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” diethylamine (CH3CH2)2NH; trimethylamine (CH3)3N

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

35 More biologically active amines…

36 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 O ║ ║ 4) CH3─C─OH 5) CH3─C─O─CH3 alcohol ether amine ester carboxylic acid


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