300 107 300 107 LIFE & ENVIRONMENTAL II LIFE & ENVIRONMENTAL II “Introduction to Organic Chemistry” “Introduction to Organic Chemistry” e-mail: [email protected]mail: [email protected]อ. . ชนกพร เผาศิริ ชนกพร เผาศิริ (http://chemsci.kku.ac.th/chanokbhorn/)
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300 107300 107
LIFE & ENVIRONMENTAL IILIFE & ENVIRONMENTAL II
“Introduction to Organic Chemistry”“Introduction to Organic Chemistry”
(Ib f )2 Acetyloxybenzoic acid(Aspirin, Bayer Aspirin) (Ibuprofen)
OH
N-(4-Hydroxyphenyl)acetamide(A t i h T l l)
HNC
CH3
(Acetaminophen, Tylenol) The Painkillers
O
O
NH +CNO- H N C NHNH4 CNOAmmonium cyanate
H2N C NH2
UreaAmmonium cyanate Urea
Organic CompoundOrganic Compound
Electron ConfigurationsElectron Configurations
Classification of Chemical Bonds
Difference in Difference in Electronegativity B t B d d At Type of BondBetween Bonded Atoms Type of Bond
less than 0.5 nonpolar covalentless than 0.50.5 to 1.9
nonpolar covalentpolar covalent
greater than 1.9 ionic
Molecular Representationsp
(Line-Angle Formula)
Provide Lewis Structures for these compounds.f p
(CH3CH2)2CO( 3 2)2
HCOCH2CH2OH
HCONH2HCONH2
CH3CH2CHCHCCH
Classes of Compounds
Classification based on functional group
Three broad classes
Hydrocarbons
Compounds containing oxygen
Compounds containing nitrogen
Functional GroupsFunctional GroupsFunctional groupFunctional group: an atom or group of atoms
within a molecule that shows a characteristic t f h i l d h i l tiset of physical and chemical properties
Functional groups are important for threeFunctional groups are important for three reason; they arethe units by which we divide organic compounds
into classesinto classes
the sites of characteristic chemical reactions
the basis for naming organic compounds
Hydrocarbonsy Alkane/ Cycloalkane: single bonds.
Alkene/ Cycloalkene: double bonds.
Alkyne: triple bonds.
Aromatic: contains a benzene ring.
An oil spill is the release of a liquid petroleum
hydrocarbon into the environment due to human
i i d i f f ll i Th f activity, and is a form of pollution. The term often
refers to marine oil spills, where oil is released into refers to marine oil spills, where oil is released into
the ocean or coastal waters. The oil may be a variety
of materials, including crude oil, refined petroleum
products (such as gasoline or diesel fuel) or by-
products ships' bunkers oily refuse or oil mixed in products, ships' bunkers, oily refuse or oil mixed in
waste. Spills take months or even years to clean up. p y p
(From Wikipedia, the free encyclopedia)
Natural gas 90-95% methane
PetroleumPetroleum
C1-C2: gases (natural gas)
C3-C4: liquified petroleum (LPG)
C5 C8: gasolineC5-C8: gasoline
C9-C16: diesel, kerosene, jet fuel
C17-up: lubricating oils, heating oil
Origin: petroleum refining
CoalCoal
GasolineGasoline
•• Octane ratingOctane rating: the percent 2 2 4 trimethylpentane•• Octane ratingOctane rating: the percent 2,2,4-trimethylpentane (isooctane) in a mixture of isooctane and heptane that has equivalent antiknock properties
1000 Americans die each year from unintentional CO poisoning
Symptoms of CO poisoning
* Slight headache, dizziness, drowsiness.* Weakness, mental confusion, nausea.* Rapid pulse and respiration, fainting.R p p p , f g* Possibly fatal coma.
Chlorination of Methane
Cl Cl + photon (h) Cl + Cl
H H
photon (h) Cl + Cl
CH
H
H Cl+ CH
H
+ H Cl
H H
H HCH
H
+ Cl Cl CH
H
Cl + ClH
C
H
H H + Cl Cl C
H
H ClCH
H
H + Cl Cl CH
H
Cl + H Cl
ChlorofluorocarbonsChlorofluorocarbons
Cl h ClC ClFCl h
CFCl
+ ClC ClFF
CFF
Cl
Chlorine radicals : Damage Ozone Layer
Cl + O3 ClO + O2Cl + O3 ClO + O2
ClO + O3 Cl + 2 O2ClO + O3 2
Chemistry for ThoughtChemistry for Thought
Would you expect a molecule urea produced in the bodyto have any different physical or chemical properties to have any different physical or chemical properties from a molecule of urea prepared in a laboratory?
Why might the study of organic compounds be important to someone interested in the health or life sciences?f
AlkeneAlkene
Alkene:
CnH2n CH3CH=CH23 2
Cyclic alkene:
CnH2n–2n 2n–2
CHEMISTRY IN VISION
Improve your Eye Sight with Vitamin A
- carotene is converted into vitamin A.
p y y g
carotene is converted into vitamin A.
-carotene
OH
Vitamin A
vitamin A is converted into retinal.
cis-retinal reacts with opsin.
Ocis-Retinal
HC N OpsinHC
Rhodopsin
N Opsin
Common Names
Usually used for small molecules.y f
Examples:pCH3
CH2 CH2
ethylene
CH2 CH CH3
propylene
CH2 C CH3
isobutyleneethylene propylene isobutylene
Naming these compounds
CH2 CH CH2 CH3CH2 CH CH2 CH3
CHCH2CH31-butene
CH3 C CH CH3
CHCH2CH3H3C
CH3
2 methyl 2 butene
2-sec-butyl-1,3-cyclohexadiene
CH3
2-methyl-2-butene
CH3
3 l 1 h3-methylcyclopentene
3-n-propyl-1-heptene
Isomers of Alkenes
CH3H BrBrC C
CH3
H
H
CH CHC C
Br
H
Br
HHCH3CH2
t 2 t
HH
i 1 2 dib thtrans-2-pentene cis-1,2-dibromoethene
Hydration of AlkenesHydration of Alkenes
H OHC C + H2O
H+
C
H
C
OH
2
alkene alcoholalcohol
Reverse of dehydration of alcohol
U d l l f dUse very dilute solutions of H2SO4 or H3PO4 to drive