Chapter 6
Organic Chemistry
탄소에 의한 창조
Organic Chemistry• Organic 유기 -
– from living things (organism 유기체 )– 현대적 의미 - 탄소화합물
• polymers & plastics• petroleum• synthetic materials
• Over 13 million known organic compounds– accounts for more than 90% of all substances
Hydrocarbons 탄화수소hydrocarbons are made of carbon and hydrogen
메탄 methane, CH4
C H
H
H
H
hydrocarbons have the formula of CnH2n+2
Hydrocarbons
ethane, C2H6
propane, C3H8
butane, C4H10
C C
H
H
H
H
H
H
CH3CH3
C C
H
H
H
H
C
H
H
H
HCH3CH2CH3
Hydrocarbons
• Butane C4H10 CH3CH2CH2CH3
• Pentane C5H12 CH3CH2CH2CH2CH3
• Hexane C6H14 CH3CH2CH2CH2CH2CH3
• Heptane C7H16 CH3-(CH2)5-CH3
• Octane C8H18 CH3-(CH2)6-CH3
• Nonane C9H20 CH3-(CH2)7-CH3
• Decane C10H22 CH3-(CH2)8-CH3
Structure and ShapeMolecules with four pairs of electrons have fixed shapes = tetrahedral
단일결합을 가진 경우이다 .
이중결합을 가지고 있다면 ?
Structure and Shape
이중결합 = share two pairs of electron with another atom
formaldehyde, CH2O
C O
H
H
Structure and Shape
벤젠 - three double bonds in a ring
benzene, C6H6
H
H
H
H
H
H
발암물질
Structure and Shape
A cloud of electrons above and below the ring of atoms
benzene, C6H6
H
H
H
H
H
H
Robert Fulghum’s Credo• Share everything
• play fair
• don’t hit people
• put things back where you found them
• clean up your own mess
• don’t take things that aren’t yours
• say you’re sorry when you hurt somebody
• wash your hands before you eat
• warm cookies and cold milk are good for you
• live a balanced life - learn some and think some and draw and paint and sing and dance and play and work everyday some
• take a nap every afternoon
• Be aware of wonder.
• Goldfish and hamsters - they all die. So do we.
Organic Chemistry Credo
• Structure & function– 3 차원 구조가 기능을 나타낸다
• Reactivity– 유기화합물 분자는 체계적으로 , 예상할 수
있는 방법으로 반응한다 .
Boiling Points of Hydrocarbons
Water and Oil• Structure of water
– 극성 분자– 수소 결합
• Structure of oil– 비극성 탄소 - 수소결합
Like Likes
• 비슷한 것은 비슷한 것을 녹인다• 물오리의 익사
– 오리 깃털 = 비극성 밀납 코팅– 기름으로 오염된 물– 물
Oxygen additive in feul
• 휘발유에 산소를 공급하여 완전연소 유도• Methanol CH3-OH
• Ethanol CH3CH2-OH
• MTBE (methyl t-butyl ether)– CH3-O-C(CH3) 3
• ETBE (ethyl t-butyl ether)– C2H5-O-C4H9
Functional Groups
C COH
H H
H
HH
ethanol
C C OH
H
HH
O
acetic acid
OH
phenol
CH 3
toluene
OH
OCH3
O
aspirin
Structure and Function• Chemical Warfare Agents
– Soman (WW II) and Sarin(1995 Tokyo)
• Mimics Acetylcholine (neurotransmitter)– blocks receptors and interrupts nervous system
H3C P
O
F
O CH
H3C
C
CH 3
CH 3
CH 3
H3C N+
H3C
H2C
H2C O C
O
CH 3
H3C
Hormones• Hormones acts as chemical messengers,
regulate body functions and determine gender
• Estradiol and Testosterone
OHH3C
HO
OHH3C
O
CH 3
Hormones Mimics
O
OH
HO
OHO O
OH
Coumestrol
Equol
Environmental estrogens
Steroid
• 필수 천연화학물질• 호르몬 요법
– 표 6.5– 예제 6.6
Polymers
Polymers• Polymers 고분자
– long chains of repeating units– polymers are made from monomers 단량체
C C C C
H
H
H
H
H
H
H
Hn
C C
H
H
H
H
Polymerization• Radical Polymerization, 첨가 반응
– Step-wise addition of monomers– Monomers have double bonds ( 불포화 )– Polymers have carbon chain backbone ( 유기 )
• Condensation Polymerization, 축합반응– Generate a small molecule ( 탈수 등 )– Polymer can grow from both ends– Polymers have oxygen or nitrogen in backbone
Polyethylene
Radical polymerization
Monomer Polymer Applications
Polyethylene Plastic bags, bottles, toys
Polypropylene Carpeting, bottles
Poly(vinyl chloride) Vinyl siding, indoor plumbing
C C
H
H
H
H
C C
CH 3
H
H
H
C C
Cl
H
H
H
Polymers and Their Uses
Monomer Polymer Applications
Polymers and Their Uses
Polystyrene Insulation, outdoor furniture
Polyacrylonitrile Yarns, fabrics, wigsC C
C
H
H
H
N
C C
H
H
H
O
OHHO
HNH
NH
HO
n
n
O
HO
O
n NH
NH
HnH
NH
NH
Hn
HNH
NH
nOO
n NH
NH
Hn
H2O
H2O
Condensation Polymerization
Condensation PolymersMonomers Polymers
HOOH
O
O
NH 2
H2N
adipic acid & hexyldiamine Nylon-66
terephthalic acid &phenylenediamine
Kevlar
terephthalic acid ðylene glycol
Dacron
NH
O
NH
O6
NH
O
4
n
Kevlar(R) - Strong Fiber
• 방탄조끼의 원료• 윈드서핑 돛
• http://www.lbl.gov/MicroWorlds/Kevlar/index.html
Comparision of fibers
Proteins
H2N CH C
CH 3
OH
O
H2N CH C
H
OH
O
H2N CH C
CH 2
OH
O
SH
Amino Acids
H2N CH C
CH 2
OH
O
C
OH
O
H2N CH C
CH 2
OH
O
HN
H2N CH C
CH 3
OH
OHN CH C
CH 2
OH
O
SH
H
ProteinsProteins are polymers of amino acids
H2N CH C
CH 3
OHN CH C
CH 2
O
SH
NH
CH C
CH 2
OH
O
C
OH
O
HN CH C
CH 2
OH
O
C
OH
O
H
Peptide bond
Biological Polymers• Proteins
• DNA & RNA
• Starch (Amylose & Amylpectin)– polymer of -glucose
• Cellulose– polymer of -glucose
Glucose
Two Form of Glucose
-glucose for cellulose
-glucose
• Amylose– 1,4 glycosidic bond– natural organic polymer
• amylopectin– mostly amylose – 1,6 glycosidic bond– 분말형태
• 16 장 참조
Enzyme
• 옥수수를 읽으면서 신문을 먹는다 ?
• Amylase– enzyme for starch into glucose
• cellulase– enzyme for cellulose into glucose
Natural Polymer• Latex (Rubber Tree)
– isoprene H2C C
HC CH 2
CH 3
H2C C
HC
H2C
H2C C
CH 3
H2C
HC
CH 3
n
Homework
• 교과서 225 쪽 연습문제– 6, 8, 9 번– 마감 1/7 ( 월 ) 시험 시작 전까지
• 1/7 ( 월 ) 9 시 15 분부터 중간시험– 범위 서문부터 6 장 탄소에 의한 창조 까지– 계산기 준비
• 중간시험 후 수업 합니다 .
References• Robert Fulghum,
– All I really need to know I learned in Kinergarten, Villard Books, NY (1990)
• http://www.lbl.gov/MicroWorlds/Kevlar/index.html
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