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Aromatic. Compounds. Good Aromatics. cinnamon. O ║. CH ═ CH – C – H . cinnamaldehyde. coffee. O ║. CH3. 3HC. N. N. O ║. N. N. CH3 . caffeine. vanilla. OH. OCH3. H – C ═ O. vanillin. Filipino BBQ goodness: puto (rice muffins). a niseed/anise. OCH3. CH ═ CH – CH3.

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aromatic

Aromatic

Compounds

slide2

Good

Aromatics

slide3

cinnamon

O

CH ═ CH – C – H

cinnamaldehyde

coffee
coffee

O

CH3

3HC

N

N

O

N

N

CH3

caffeine

vanilla
vanilla

OH

OCH3

H – C ═ O

vanillin

slide6

Filipino BBQ goodness: puto (rice muffins)

aniseed/anise

OCH3

CH ═ CH – CH3

ANETHOlE

cloves
cloves

OH

OCH3

CH2 – CH ═ CH2

eugenol

wintergreen
wintergreen

O

C – O – CH3

OH

Methyl salicylate

chamomile
chamomile

O

O

COUMARIN

slide10

Bad

Aromatics

benzene
benzene

benzene

naphthalene
naphthalene

nApHthalENE

burnt meat
burnt meat

PHEnANTHRENE

smoke belchers
smoke belchers

BEnZOPYRENE

smoke belchers1
smoke belchers

PYRENE

CORONENE

cigarettes
cigarettes

BEnZanthRacENE

diBEnZanthRacENE

cigarettes1
cigarettes

NO

N

N

nITROSONORNICOTINE

let us learn to dream gentlemen and then perhaps we shall learn the truth 1890 kekul
“ Let us learn to dream, gentlemen, and then perhaps we shall learn the truth.” -1890 Kekulé -
slide21

Some of the early researchers in organic chemistry became intriguedby fragrant oils that could be extracted from certain plants. The compounds responsible for thearomas, had similar chemical properties. As a result, they weregroupedtogether and calledAROMATICS COMPOUNDS.

slide22

As more and more aromatic compounds wereisolated and studied, chemist gradually realized that aromatic contained six carbon atoms and had low hydrogen – to – carbon ratios (relative to other hydrocarbon). They also realized that the term aromatic was not always accurate. Because there are many fragrant compounds do not have aromatic properties.

slide23

1825 – Michael Faradaydiscovered BENZENE in whaleoil.When BENZENE was found to have the formula C6H6, scientist was puzzled.They tried unsuccessfully to draw a straight – line structure for BENZENE.

benzene s possible structures
BENZENE’s possible structures

CH3— C ≡ C ─ C ≡ C — CH3

2,4 – hexadiyne

CH2═ CH ─ C ≡ C ─ CH ═ CH2

1,5 – hexadien – 3 – yne

slide27

Kekule was to say later that he must have dozed off at this point. In his dreamthe black balls of carbon turned into black impswith forked tails that began racing around the room and would soon be upsetting the apparatus of the laboratory. He was ready to run the rascals out. Then, almost suddenly, the confusion died away as each imp grabbed the tail of the one ahead of him, the six forming a whirling circle. One hand of each imp held a tail, the other a white handkerchief--and they waved to him as the group whirled by. He said that he came awake with a start, realizing that the imps were acting out the formula for benzene. As his hand grabbed the sketching pencil, the imps were back to black balls again and the handkerchiefs had changed to hydrogen atoms. How simple the arrangement turned out to be. “The carbon atoms of benzene form a ring."

slide28

1858 – Friedrich August von StradonitzKekulé.Suggested that the six carbon atoms formed a cyclic structure having three sets of alternating double bonds.1865 – Kekulé proposed that BENZENE had two structural formulas and that is alternated between them.

slide33

1931 – Linus Pauling To help explain molecules like benzene, he proposed resonance theory. (Pauling also gave us hybrid orbitals, electronegativity, and valence bond theory).That gave birth to the modern structure of BENZENE.

rule 1
Rule # 1
  • When a single hydrogen of the benzene ring is replaced, the compound can be named as a derivative of benzene.
examples
Examples:

Cl

chlorobenzene

CH2CH3

Br

NO2

ethylbenzene

nitrobenzene

bromobenzene

rule 2
Rule # 2
  • A number of benzene derivatives are known by common names that are also IUPAC – accepted and are used preferentially over other possibilities.
examples1
Examples:

CH3

NH2

O

OH

C — OH

Aniline

Toluene

Benzoic Acid

Phenol

slide42

O

C – H

EXAMPLES

O

C – CH3

benzaldehyde

acetophenone

O

C

benzophenone

rule 3
Rule # 3
  • Compounds formed by replacing a hydrogen of benzene with more complex hydrocarbon group can be named by designating the benzene ring as substituent.
  • We called them phenyl group.
  • benzyl
examples2
Examples:

3HC

CH3CHCH ═ CH2

Br

ا

ا

ا

CH3— C — C — C — CH3

ا

ا

ا

Br

3HC

3 – phenyl – 1 – butene

2,2 – dibromo – 4,4 – dimethyl – 3,3 – diphenylpentane

slide45

OH

CH2

2 – benzyl – 4 – chlorophenol

Cl

rule 4
Rule # 4
  • When two groups are attached to a benzene ring, three isomeric structures are possible. They can be designated by the prefixes ortho (o), meta (m), and para (p):
examples3
Examples:

CH3

CO2H

Cl

Br

NO2

O - bromochlorobenzene

Cl

m – nitrobenzoic acid

p - chlorotoluene

examples4
Examples:

CH3

CH3

CH3

CH3

CH3

1,2 – dimethylbenzene

1,4 - dimethylbenzene

CH3

p - xylene

O – xylene

1,3 - dimethylbenzene

m – xylene

rule 5
Rule # 5
  • When two or more groups are attached to a benzene ring, their positions can be indicated by numbering the carbon atoms of the ring so as to obtain the lowest possible numbers for the attachment positions.
  • Group that comes first in alphabeticalorder is given the lower number.
examples5
Examples:

CH3

Br

Cl

OH

O2N

NO2

Br

NO2

I

3 – bromo – 5 - nitrotoluene

1 – bromo – 2 – chloro – 4 – iodobenzene

NO2

2,4,6 – trinitrophenol

examples6
Examples:

CH3

NO2

NO2

2ON

TNT

NO2

NO2

NO2

1,3,5 – trinitrobenzene

2,4,6 - trinitrotoluene

preparation
Preparation
  • Major sources of aromatic compounds are petroleum and coal tar – (a sticky, dark – colored material derived from coal.
  • Natural sources
  • Can be synthesize synthetically
physical

Physical

Properties

physical properties
Physical Properties
  • Similar to those of ALKANES & ALKENES
  • Non – Polar
  • Insoluble in water (hydrophobic)
  • Flammable
  • Low density in water
chemical

Chemical

Properties

benzene reactions
Benzene Reactions
  • Halogenation
  • Nitration
  • Sulfonation
  • Alkylation
slide57

Industrial

Applications

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