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 &ethylene 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