functional groups are a characteristic feature of organic molecules that behave in a predictable,...
TRANSCRIPT
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
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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:consumedfrom lighters
Carbon tetrachloride:Used for solvent abuse
Hydrocarbons
Cl
Cl Cl
Cl
CH3
CH3
C4H10
CCl4
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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
CH3
CH3
N+
O-
O
N+
O-
O
N+
O-
O
NH N
O
O
O
OH
OH
cyclic moleculescyclic molecules
CC
C
H H
H
H
H
H
CH2
CH2
CH2
Cyclopropane
C
C C
C
H
H
H
H
H
H
H
H
CH2
CH2 CH2
CH2
Cyclobutane
C
C
C
C
C
H HH H
HH
HH
HH
CH2
CH2
CH2
CH2
CH2
Cyclopentane
C
CC
C
CC
H HH
H
H
H
HH
H
H
H
HCH2
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.
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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
CH3 O CH3 NCH3
O
OH
OH
OCH3
O
NH2
N+
H
H
O
Cl-
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.
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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:
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KetonesFire accelerants Drugs
Explosives Dyes
Acetone:(Dimethyl ketone)flash point -20 degrees C; ignition temperature 465.4 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
CH3 CH3
O CH3
NH
CH3
O
O
O
4. Ketones
In a ketone, the carbon of the carbonyl group is attached to two other carbon atoms.
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Acetone
Chapter 18 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 1.
=>
Ketones Practice R-C-R
• Draw the condensed structural formula for 3-pentanone
Chapter 18 15
Examples
CH3 C
O
CH
CH3
CH3
3-methyl-2-butanone
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Esters
Fire accelerants Drugs
Explosives
Biodiesel refers to a non-petroleum-based diesel fuel consisting of short chain alkyl (methyl or ethyl) esters
Dibutylphatalate:Plasticizer used in explosives. Plasticizersare additives that increase the plasticity orfluidity.
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 givesa numbing effect (like purer cocaine should have).
OCH3
O
CH3
OO
NH2
O CH3
O
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.
CH3C
CH2 O
O
CH3
ethyl ethanoate
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 formulaeAlthough the previous structural formula are the clearest way of showing esters, they can draw out in a shortened form.
ethyl ethanoate
CH3CCH2 O
O
CH3
Either…Or…
CH3C CH2O
O
CH3
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.
ester fragrance
ethyl methanoate raspberries
3-methylbutyl ethanoate pears
ethyl 2-methylbutanoate apples
phenylmethyl ethanoate jasmine
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Alcohols
Fire accelerants Drugs
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 oC; ignition temp. 365 oC; explosive limits 3.5%-19.0%
Glycerol or glycerine: Used as starting material for nitro-glycerine
BTTN :Military propellant for missiles: the mixturecan be made by co-nitration of butanetriol and glycerol
Sudan Red G: It is considered carcinogenic andgenotoxic
CH3 OH
OH
OH
OH
O
OH
OH
NN
OHO
CH3
Alcohols
An alcohol contains the hydroxyl (-OH) functional group.(instead of an H in that place)
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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
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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 Common Name
CH4 methane
CH3─OH methanol methyl alcohol
CH3─CH3 ethane
CH3─CH2─OH ethanol ethyl alcohol
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Aldehydes
Drugs Dyes
4-amino-3-nitrobenzaldehyde: Hair dye
O
O
O
NH2
O
N+
O-
OPiperonal: 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.
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27
acetaldehydeformaldehyde
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Carboxylic acids
Drugs
Benzoylecgonine (ecgonine benzoate) is the primary metabolite of cocaine. It is formed in the liver by the metabolism of cocaine
O
O
N
CH3
OOH
Carboxylic Acids
Carboxylic acids contain the carboxyl group, which is a carbonyl group attached to a hydroxyl group.
O ║
— C—OH
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Acetic acid
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Amides
Drugs
Dyes Yellow 13: pigment
Fraud between drug dealers Lidocaine is often added to cocaine asa diluent because it numbs the gums when applied,giving the impression of higher cocaine purity
NN
NH
CH3
CH3O
CH3O
CH3
CH3
NH
O
O CH3
NN
ClCl
CH3
CH3
NHN CH3
CH3
O
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Amines
DrugsExplosives
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
NH
N+
O-
O
N+
O-
O
N+
O-
ON
+O
-
O
N+
O-
O
N+
O-
O
NH
NH
O
O
NHCH3
CH3
OH
Organic compounds with Carbon-Nitrogen bonds
1. AminesIn amines, the functional group is a nitrogen atom.
H H
C —N – H or C —N —C
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32
Methyl amineDimethyl amine
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
NH3 NH2R NH
R
R
N
R
R
RAmmonia A primary amine A secondary amine A tertuary amine
Examples:
R
R
R
NH2
R
R
R
OH
A primary amine A tertuary alkcohol
NH2
pentan-2-amine
NH2
cyclohexanamine
NH
N-methylcyclohexanamine
Amines are much more polar, than hydrocarbons, especially in acidic conditions
More biologically active amines…
H2N C OCH2CH3
O
benzocaine(a topical anesthetic)
Cl
N
N
H
O
O
diazepam (Valium)
N
N
O
NN
CH3
CH2CH2CH3
H
SOO
N
NCH3
CH3CH2O
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 O ║ ║
4) CH3─C─OH 5) CH3─C─O─CH3
alcohol
ether
amine
carboxylic acid ester
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