1-Introduction Organic Chemistry.ppt

  

Introduction :

Organic Chemistry

_{Rachmawati Ningsih}

presented by

  Lewis Carrol

  

“ The horror of the moment”, the King

went on, “I shall never, never forget!”

“You will though”, the Queen said, “ if

you don’t make a memorandum

  Ali bin Abi Thalib

  

If you want to bond the

knowledge, write it out

  Welcome at the

launching point of a new adventure called… Organic How to make this adventure well worth the journey…??

  By committing yourself to hard work and self discipline

  After all, you’re already a highly

  

skilled Organic Chemist…

  As you read these words,

  

Your eyes are using an organic compound ( retinal ) to convert visible light into nerve

impulses Absorbs light when we see

  H _O 11-cis-retinal When you picked up the book,

  Your muscles were doing chemical reactions on sugars to give you the energy you needed

  As you understand,

  Gaps between your brain cells are being bridged by simple organic molecules ( neurotransmitter amines )

so that nerve impulses can be

passed around your brain

  Human Neurotransmitter

  HO _{NH 2} N

_H serotonin And you did all that without consciously

thinking about it…!!!!

  Chemists cooperate with physicists & mathematicians

to understand how molecules

behave & with biologists to understand how molecules determine life processes

  What is

Organic Chemistry

  (Orchem)..??

Orchem is.

  The study of the chemistry of the

element carbon What is it about carbon

that makes this one

element the focus of an

entire branch of

chemistry ..??

  Carbon…

• • Form stable bonds to each other

  as well as to a wide variety of other elements
• Consist of chains & rings
• Bonding in ways that form an endless variety of molecules

  At this time,

  

Chemists have identifed and or

synthesized more than 10 million carbon-based compounds

  

…..and they add thousands of new

organic molecules to the list every month

  The roots of chemistry

  

Empirical discoveries

Development of chemical techniques

such as : metal smelting, textile dyeing, glass making & butter / cheese preparation Philosophies …

  Discussion of the nature of

matter and its transformation One of particular interest is

atomist Democritus (460 -370 B.C.)

Thought that atoms were solid

particles & existed in a void but could move about and

interact with each other

   thus forming the various

  

Aristotle & Plato

rejected

the atoms philosophy

  Socrates

felt that studying the nature of

man and his relationships

was much more important than studying the science of nature

  But..

  

Don’t underestimate

people that have

opposite in thinking

  

It can be beneft to the

  

Socrates insisting

defnitions & classifcation

be clear ,

arguments be logical & ordered

and that

there be rational skepticism

  

Plato adopted the four

elements philosophy :

  Fire , Air , Water , Earth

  

Aristotle added to

those 4 elements 4

associated qualities :

  Hot , Cold , Wet , Dry Aristotle believed that each element possesed

  2 of the 4 qualities

  

One element might be changed

(transmuted) into another element by changing its qualities

  Example :

Earth was dry & cold , but it could be transmuted into fre by changing its qualities to hot & The theories remained important for

nearly

  Jabir Ibn Hayyan

rejected the 4 elements

  theory because it was not ft to his research results

  

Jabir Ibn Hayyan’s

researches-1

• Sulphate acid
• Nitrate acid – by reacting iron sulphate & potassium nitrate, used as storage battery water
• Mercury sulphate or Zinjafr (Persi) – added to iron to prevent oxidation process
• Gold purifcation using acid from silver alloy

  

Jabir Ibn Hayyan’s

researches-2

• • White steel – by heating ore of steel in

  vinegar & mixture of soda, used as wall paint material
• Mercury crystal, caustic soda, arsenic oxide, pure mercury oxide, potassium carbon, sodium carbon, potassium nitrate, alkali nitrate, aluminium

  Jabir Ibn Hayyan’s

researches-3

• Chemical techniques, such as : condensation, fltration, purifcation, crystallization, fermentation, melting process, distillation, calcifcation, freezing process, bleaching process, hardening process, sufocating process, precipitation, etc

  Jabir Ibn Hayyan’s

researches-4

• • Malaki water – by reacting aluminium

  chloride & nitrate acid, used to melt

  the gold ore
• Gold-like ink – from copper sulphate as a gold ink substituted, used to write calligraphy

  Jabir Ibn Hayyan’s

  

Jabir Ibn Hayyan’s

  researches-5

  

researches-5

• Compound which can make fabric become water resistant

• • Paper that can’t be burned with fre -

  his teacher, Imam Ja’far Ash Shadiq,

  requested it to write knowledge

• • Author of Kitab As-Sumuum Wa Daf’u

  Mudhaarrihaa, about properties of

  Jabir ofered a new theory

  “There are seven mine materials in

nature : gold, silver, copper, iron,

steel, mercury and metal. The ingredients of those mine materials

are sulphate and mercury, which in

diferent composition produced

diferent mine material.”

  Ibnu Sina

• Disagreed with the Jabir’s theory
• Wrote in his book titled Asy-Syifaa’

  “ We can only add or remove the

  physical properties of mine material, but not the core. For example, we can’t make a gold if we don’t know the composition of a gold. ”

  Abu Yusuf Ya’qub Al Kindi

  Rejected Ibnu Sina’s theory

“ All things in nature already separated

automatically without any human being interfering. So its impossible for human to make things that similar to nature. “

  

Abu Nashr Muhammad al-

Farabi

“ Transformation process depend on

the properties which want to add

or remove. The core is impossible

to change. But its impossible to change the temporary properties. “

  

Alchemy

• In the end of the frst century B.C .

  ( Alexandria , Egypt )

• • A mixture of philosophy , religious

  or spiritual , ideas , astrology &

  empirical technical skill

  Many alchemist truly believed…

  that somewhere in nature there existed a procedure that would form precious metals from base materials

such as :

Convert lead / iron into gold / silver

  Their logic was quite sound…

  

It was the result of looking as

many dramatic changes they could see in nature

  Example :

in fre, wood simply disappeared leaving a small amount of ashes They had no way of knowing

that

converting lead to gold

involved

a tottaly diferent type of

change than that of using

fre to turn into ashes

  

Historian often call this

time period the dark age of science

  Modern Chemistry

  the alchemist’s 4 elements

• Replace

  with the understanding of atoms of a substance stayed the

• Identity

  same even when that substance became a part of another substance

• Example : Copper is always even when mixed with zinc to form
• Robert Boyle (1627 – 1691)

  Begin the study of gases/air

• Antoine Lavoisier (1743 – 1794)

  Recognized that oxygen was not just very pure air, but it was

a completely separate element

  Early in 19 th century

• Chemists mostly ignored orchem
• Viewing it as either

  medically/biologically related because nearly all the known organic compounds were derived

from living organism , both plant

Do you know…??

  A part of the beginnings of orchem was the study of compounds derived from the ORGANS of living creatures

  But..

  Lavoisier was very

interested in orchem and

considered it to be a part of

chemistry

  He looked at some organic

compounds and found that

  

At the time-1…

• • Organic compounds were much

  more complex & unstable than the inorganic being synthesized

• • Chemists thought that organic

  compounds were impossible to

  prepare At the time-2…

• • Chemist believed that organic

  compounds came only from living organism

• • The formation of the known organic

  compounds, such as : urea, starches, oil & sugar, required some

  vital force possessed by living

Orchem

  

became the study

of compounds having

a vital force or vitalism

  Vitalism is the belief that the synthesis of orchem

requires the vital force from some living Of course…

Several chemists

not believe the vitalism idea of

Michel Chevreul

• Study the composition of fats from several sources of animal fat & alkali using the saponifcation process
• Separated soap into several pure

  organic compounds & found that the

compounds were diferent from the

fat that he had started with – he

  But…

• • Previously people had not

  understood that a chemistry reaction took place during the soap making process

• • They thought that soap was

  simply a combination of the fat & alkali

• • Took a long time to recognize the

  

Friedrich Wöhler

Synthesis of urea in 1828

and he said :

“ without the use of a kidney ”

  (brought vitalism to its end..!!)

  Wöhler’s urea synthesis reaction

  Actually…

Wöhler’s goal

was not to synthesize He was trying to make

ammonium cyanate

(NH

  

compound he needed

for his research

  In fact, he may have become frustated because he tried to make

ammonium cyanate by

several diferent

  Route-1

  Reacting silver cyanate with ammonium chloride

  

Reasoning that silver chloride

is insoluble and would precipitate from solution

  Route-2 Reacting lead cyanate with

  ammonium hydroxide

  Route-3 Reacting ammonium

  

hydroxide and cyanogen But..

  every attempt led to the same white

  crystalline

  substance that was

  not the desired

  product Wöhler decided to identify the unknown substance and found out it as UREA …

  He recognized the importance of his discovery

  

Luck is

preparation

meet

opportunity Wöhler’s speech

  

“ The research gave the unexpected

result ….that is the more noteworthy inasmuch as it furnishes an example of the artifcial production of an organic , indeed a so-called animal substance from inorganic materials

  

Chevreul & Wöhler

had proved that compounds of

carbon can be synthesize without a living organism

  

The Organic

Compounds Marketing William Henry Perkin

  In 1856, at age 18

working in his home laboratory

on vacation from London’s

  Royal Collage of Chemistry while naively attempting

  H ₃ ^{CO HO N} Quinine A task not accomplished until 1944…

  But..

  He accidentally synthesized the

  

dye called Perkin’s mauve The next year…

• Using money borrowed from his father, he built a factory and marketed the new dye

  coal tar

• He found out that was a rich source of starting

  materials for a variety of new dyes

  The Bayer Company of Germany

• In 1895 established the

  pharmaceutical industry

• In 1899 began marketing

  aspirin , as a result of the Learned how to prepare aspirin from natural salicylic acid The idea :

  Felix Hofmann

• • For hundreds of years, people had

  chewed the bark of the willow tree to relieve minor pain
• Willow tree bark contains the

  Aspirin

  

Superior to salicylic acid as an

analgesic because it produces less irritation to the stomach and efectively treats the pain

  

Scientists…

• investigated questions & discovered other questions
• have learned that the answer to some questions must wait for the

  development of better investigate methods & tools

  Questions for you…

  Are you ever heading in one direction with a particular project only to fnd it turning out

  

diferently than you had expected …?? Do you just junk the project , or do you fnd yourself

  

trying to fgure out what

  went wrong or how you can use the project some other

  way …? Do you know…??

  Many of the great

  

discoveries of chemistry

  were made because the chemist investigated the reasons for an

  Roy J. Plunkett

• was working for Du Pont attempting to fnd a non toxic

  refrigerant

• • he opened the valve on a cylinder

  of tetrafuoroethylene to begin an experiment, but nothing came out

  Plunkett…

• pushed a wire into the valve to

  determine if it blocked, the wire went

  in freely
• had no understanding of what was wrong…
• decided to investigate , instead of discarding the ‘empty’ tank and getting

  

Plunkett opened the tank and found

it flled with a waxy white powder

The molecules of

tetrafuoroethylene

had reacted together to form

a polymer…!!!

  What caused it..??

On further investigation,

  

Plunkett found some iron oxide

inside the tank & discovered that it had catalyzed the polymerization reaction

  

This new polymer had some

remarkable properties…!!!

• not react with either strong

  acids/bases

• heat stable
• no solvent could dissolve it
• extremely slippery
• resistant to uranium hexafuoride

  Du Pont manufactured Plunkett’s polymer for the Manhattan Project under the name --

  Tefon ^TM Tefon’s usefulness

• coated cookware

• • artifcial hips & knee joints or

  aortas & pacemakers
• space suits, ware & cable insulation
• spaceship nose cones

  Orchem touches every aspect of your life

  The clothes you wear The food you eat

  The vehicles you drive largely of complex carbon

  Chemists learned how to synthesize complex molecules of life Orchem came back to its

  

All living creatures consist

• – containing molecules

  roots

  Study the organs of living

  creatures

  

Positive &

Negative

attributes of

Orchem

  Plastic

• Polymer industry highly

  impacted modern society in daily

  life
• Do not readily degradable  environmental problem

  

Hazardous Materials

  of industry

• Waste

  the soil, air & water

• Contaminating

• • Chemical ingredients in product that

  will cause harm to a customer or environment (to gain more proft )

  So…

  

besides being a consumer,

how could you ft into

orchem ..??

  Are you good at thinking up new ideas

or looking at old ideas in new ways ..?? The market place always welcomes new products

  Do you have a

concern for the

environment ..??

  

There is a worldwide need

for solutions to the multitude of environmental problems &

to fnd new products to

replace those products

causing harm to the environment Or…

You could use orchem as

an important foundation of your profession in medicine, industry or academic

  Ask those

questions

to yourself …

  How to develop the success method in studying organic chemistry…??? Next…