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Honors Chemistry
THICK
BOOK
Ch. 29 & 30
Organic
Chemistry
CD ROM 12 Intro.
Links to the IUPAC PEOPLE
WHY THE NAME “ORGANIC”?
There are over six million
organic compounds, both
natural: foods,
(carbohydrates, lipids,
proteins, and vitamins) , furs,
feathers, hides, skins,
petroleum products and the
organisms they came from...
and synthetic: plastics, fibers,
dyes, drugs, insecticides,
herbicides, perfumes and
flavoring agents.
SO WHY “ORGANIC”?
The name ORGANIC chemistry came from the word
organism. Scientists thought some "vital force" that living
organisms had was necessary to make an organic compound.
In attempting to prepare ammonium cyanate from silver
cyanide and ammonium chloride, a German chemist, Wöhler,
accidentally synthesized urea in 1828. This synthesis of an
ORGANIC substance from INORGANIC substances led to
the disappearance of this vital force theory.
“CARBON BASED LIFE FORMS”
WHY CARBON?
4 VALENCE ELECTRONS
4 COVALENT BONDS
CATENATION!
CD ROM
12.1 a
The EASY Ones
NAME THESE...
butane
propane
Try... then View some more!
One Change…
...Changes Everything!!!
Br
4
3
2
1
Br
butane becomes bromobutane
ACTUALLY... 2-bromobutane
NOW… 2,2-dibromobutane
VIEW organic reactions in progress !!!
VARIATIONS...
Branching
...like a crossword puzzle
Multiple Bonds
Substituents:
(hetero-atoms and functional groups)
Rings
View Site with condensed notes.
A BRANCH ON THE CHAIN...
Two Branches…
DRAW 2,2,4-trimethylpentane
TRY: 3,5 - dimethyl - 4 - isopropyl octane
C
C
C
C-C-C-C-C-C-C-C
C
C
ISOMERS
CD ROM
12.1 b
“isomers”
Isomers : compounds with identical molecular
composition but their structures are arranged
differently.
Isomerism : another reason why there are so many
organic compounds.
ISOMERS
Formula
C8H18
C10H22
C20H42
C40H82
Number of Isomers
18
75
366,319
6.25 x 1013 (approx.)
ENANTIOMERS
ARE THESE ISOMERS?
ENANTIOMERS
non-superimposable mirror images. Because of its tetrahedral bonding
geometry, a C atom bonded to 4 different atoms or different structural
groups can exist in 2 forms which are mirror images of one another and
which cannot be superimposed upon one another.
This is an important concept in
biology because organisms
usually contain (use or produce)
only one of two possible
enantiomers of a compound.
Such molecules (and the C atom)
are sometimes called chiral after
the Greek word for hand; your
left and right hands are the most
common examples of nonsuperimposable mirror images.
VIEW 5 MINUTE CLIP
“CHEMISTRY ORGANIC Chirality”
Chirality
Multiple Bonds...
CD ROM
12.2 a
Name
…endings
ethane
ethene
ethyne
…and Tell Where It Is
MORE ISOMERS
“cis” and “trans”!
cis-fluoroethene
trans-fluoroethene
Skeletal Formulae
CnH2n + 2
CnH2n
CnH2n-2... and so on
Play it safe...
Employ 2n + 2... then (-2) for each additional bond line!
Substituents...
hetero-atoms
4
3
2
1
side chains
Substituents...
CD 12.3
“FUNCTIONAL
GROUPS”
and
historic
references
Functional Groups
alcohol
Propanol or Propyl Alcohol
Really should use an address… what is isopropyl alcohol?
Functional Groups
CARBOXYLIC
ACID
-oic
ALDEHYDE
KETONE
-one
ESTER
-oate
-al
ETHER
AMIDE
-ide
dimethyl ether
ASSIGNMENT:
RESEARCH AN ORGANIC
COMPOUND
CREATE A 3 SLIDE
PRESENTATION
http://en.wikipedia.org/wiki/List_of_organic_compounds
SOME REALLY INTERESTING COMPOUNDS:
For example… Sodium thiopental, better known as Sodium Pentothal
Thiopental is still used in some places as a truth serum!
For example… 2-Amino-3-(1H-indol-3-yl)propanoic acid , better
known as Tryptophan
Turkey meat and drowsiness!
Novocaine
2-(diethylamino)ethyl 4-aminobenzoate
functional gps: (2 aminos, ester, benzene ring)
Mechanism:
inhibits sodium influx through voltage gated
sodium channels in the neuronal cell
membrane of peripheral nerves
action potential cannot arise
signal conduction inhibited
binds function of N-methyl-D-aspartate
(NMDA) receptors as well as nicotinic
acetylcholine receptors and the serotonin
receptor-ion channel complex
KNOWING NAMES...
Antifreeze
Ethylene glycol
1,2 - ethanediol
Esters
 formed from the Rx between alcohols and acids.
 word 'ester' alone implies that the acid is an organic
acid, but inorganic acids can also form esters.
-ATP is a well-known phosphate ester in biology!
-“halogenoalkanes” may be regarded as inorganic esters, of
alcohols and hydrochloric acid.
-We are focusing upon ORGANIC esters of organic acids
RCOOR' where R can be hydrogen or an organic group:
Esterification
Esters in the food industry
Esters are widely used for flavorings; many are 'nature-identical', that is
synthetic versions of the esters present in the fruit. Fruit flavors are very
complex, though, often arising from many different compounds, some of
which are present in small quantities.
Ethyl methanoate (ethyl formate): rum flavoring
Propyl pentanoate (n-propyl n-valerate): pineapple flavoring
Ethyl butanoate (ethyl butyrate): apple odor
Octyl ethanoate (n-octyl acetate): orange odor
Procedure
Obtain two test tubes, 150 x 80 capacity; two one-holed rubber
stoppers, #2; and two disposable Pasteur pipets, 2-mL vol, to act as
air condensers. After deciding what two esters you would like to
make, obtain the appropriate acids and alcohols
(refer to reactants list).
Formulations:
propionic acid (1.8 mL) + ethanol (1.5 mL)
butyric acid (1.0 mL) + isopentyl alcohol (1.5 mL)
acetic acid (2.0 mL) + isopentyl alcohol (2.8 mL)
acetic acid (2.0 mL) + n-butyl alcohol (2.8 mL)
acetic acid (1.0 mL) + octyl alcohol (2.0 mL)
salicylic acid (1.8 g) + methyl alcohol (1.0 mL)
butyric acid (1.0 mL) + methyl alcohol (0.8 mL)
trans-cinnamic acid (1.8 mL)+ ethyl alcohol (1.0 mL)
LIKE A DOG CHASING ITS TAIL…
CLEANING THINGS UP...
MORE RINGS...
RINGS MAY EXHIBIT “CIS” or “TRANS”
1,3,5 - cyclohexatriene (benzene)
O
Aromaticity...
How many bonds does each carbon atom
form? Remember carbon has 1s22s22p2…
but all bonds are to be equal!
C
sp2 hybridized
Nomenclature Hierarchy…
IS THIS… pentyl benzene
C-C-C-C-C-
O
O
-C-C-C-C-C-C-C-C-C
OR, IS THIS
phenyl nonane
“Special” Nomenclature
orthodichlorobenzene
metadichlorobenzene
paradichlorobenzene
“Special” Nomenclature
“Xylene” with methyl’s
ortho-
meta-
O
para-
Benzene Derivatives...
Methylbenzene (Toluene)
Chlorobenzene
Hydroxybenzene (phenol)
Benzoic Acid
Aminobenzene (aniline)…
where AMINES are R - NH2
O
Fibers, films, and bottles made of
polyester all contain…
SOAP MAKING
7.4 a and b Video Clips
CO
KID
C
H
SYL
C
H
C
H
-O-
H
C
VANIA