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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


Good

Aromatics


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


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


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



HISTORY leads to that occurrence…


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 -


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.


As more and more aromatic compounds were intriguedisolated 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.


1825 – Michael Faraday intrigueddiscovered 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 intrigued

CH3— C ≡ C ─ C ≡ C — CH3

2,4 – hexadiyne

CH2═ CH ─ C ≡ C ─ CH ═ CH2

1,5 – hexadien – 3 – yne


Kekule intrigued 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."


1858 – intriguedFriedrich 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.


1931 – intriguedLinus 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.



Nomenclature
Nomenclature intrigued


Rule 1
Rule # 1 intrigued

  • When a single hydrogen of the benzene ring is replaced, the compound can be named as a derivative of benzene.


Examples
Examples: intrigued

Cl

chlorobenzene

CH2CH3

Br

NO2

ethylbenzene

nitrobenzene

bromobenzene


Rule 2
Rule # 2 intrigued

  • A number of benzene derivatives are known by common names that are also IUPAC – accepted and are used preferentially over other possibilities.


Examples1
Examples: intrigued

CH3

NH2

O

OH

C — OH

Aniline

Toluene

Benzoic Acid

Phenol


O intrigued

C – H

EXAMPLES

O

C – CH3

benzaldehyde

acetophenone

O

C

benzophenone


Rule 3
Rule # 3 intrigued

  • 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: intrigued

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


OH intrigued

CH2

2 – benzyl – 4 – chlorophenol

Cl


Rule 4
Rule # 4 intrigued

  • 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: intrigued

CH3

CO2H

Cl

Br

NO2

O - bromochlorobenzene

Cl

m – nitrobenzoic acid

p - chlorotoluene


Examples4
Examples: intrigued

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 intrigued

  • 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: intrigued

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: intrigued

CH3

NO2

NO2

2ON

TNT

NO2

NO2

NO2

1,3,5 – trinitrobenzene

2,4,6 - trinitrotoluene


Preparation
Preparation intrigued

  • 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 intrigued

Properties


Physical properties
Physical Properties intrigued

  • Similar to those of ALKANES & ALKENES

  • Non – Polar

  • Insoluble in water (hydrophobic)

  • Flammable

  • Low density in water


Chemical

Chemical intrigued

Properties


Benzene reactions
Benzene Reactions intrigued

  • Halogenation

  • Nitration

  • Sulfonation

  • Alkylation


Industrial intrigued

Applications


Medicine
Medicine intrigued


Medicine1
Medicine intrigued


Antiseptic
Antiseptic intrigued



Disinfectant
Disinfectant intrigued


Synthetic fiber
Synthetic Fiber intrigued


Plastic
Plastic intrigued


Preservatives
Preservatives intrigued


Dyes intrigued


Fuel additives
Fuel Additives intrigued


intriguedfin –


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