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EFN-313 Lífræn efnafræði 11. kafli. “ The most important hypothesis in all of biology…is that everything that animals do, atoms do. In other words, there.

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Presentation on theme: "EFN-313 Lífræn efnafræði 11. kafli. “ The most important hypothesis in all of biology…is that everything that animals do, atoms do. In other words, there."— Presentation transcript:

1 EFN-313 Lífræn efnafræði 11. kafli

2 “ The most important hypothesis in all of biology…is that everything that animals do, atoms do. In other words, there is nothing that living things do that cannot be understood from the point of view that they are made of atoms acting according to the laws of physics.” Richard Feynman ( )

3 Lífræn efni byggjast öll á kolefni C, CO, CO 2 og CO 3 teljast ólífræn Önnur C sambönd kallast lífræn Annaðhvort sameindir eða sameindajónir Óendanlega mörg lífræn efni til, á öllum formum með mismunandi eiginleika.

4 C-atóm eru einstök Mynda óskautað samgild tengi við Vetni Mynda samgild tengi sín á milli og mynda langar keðjur Mynda samgild tengi við aðra málmleysingja t.d. P,O,N,S og halogena C-C og C-H tengi eru óskautuð (nonpolar)

5 Fjögur sp 3 hybridised orbitals mynda ferflötung sp 3 hybridised orbitals frá 2 C atómum geta skarast og myndað C-C σ-tengi C-C  bond Each sp 3 orbital contributes one electron to form C-C [C.. C] Raun lögun etan sameindar

6 sp 3 svigrúmablanda (rafeindir) flýr eins langt frá kjarnanum og hægt er og tengist í þær áttir.

7 Carbon sp 3 orbitals can overlap with Hydrogen 1s orbitals to form Carbon-Hydrogen  bonds  bonds: symmetrical about the bond axis Each sp 3 orbital contributes one electron; each s orbital contributes one electron to form C-H [C.. H]

8 C-C N-N O-O Bond Dissociation Energy (kJ mol -1 ) Carbon-Carbon bonds: especially Sterk samgild tengi Kolefni: Einstakt, myndar catenate [Keðjur] Forms molecules composed of C-C bonds Línulaga/Linear Greinótt/Branched Hring/Cyclic

9 Organic molecules = Carbon-based molecules Organic chemistry = Chemistry of carbon-based molecules Some properties of organic molecules Stability: composed of stable C-C covalent bonds Defined molecular structures Defined three-dimensional shapes

10 Organic chemicals are universal OrganicChemicals Biological matter Plants Animals Microbes Geological matter Fossil Fuels Other Atmospheric and cosmic matter Manufactured products

11 Biological organic chemicals Sugars Proteins Fats & oils Vitamins DNA & RNA Wood Natural rubber Essential oils Natural fibres Antibiotics Fermentation products Natural flavours Natural fragrances Plant & microbial products Bio-matter

12 Organic chemicals in manufactured products Bio-active products Medicines Veterinary medicines Herbicides Pesticides Fungicides Plant growth hormones Imaging agents Fertilizers Antiseptics Disinfectants

13 Organic chemicals in manufactured products Materials Fibres & clothings Plastics Coatings & lacquers Packaging Paper Films Medical implants Wound dressings

14 Organic chemicals in manufactured products Foods Sugars Fats & Oils Anti-oxidants Colourants Flavourings Vitamins Dietary supplements Fibre Fuels “Petrol” “Diesel” LPG Natural gas Coal Peat/Turf Methanol/Ethanol

15 Organic chemicals in manufactured products Miscellaneous Lubricants Cosmetics Fragrances Pigments Dyes Inks Adhesives Explosives Detergents Surfactants Emulsifiers Coolants Photographic agents Anti-scalants Forensic chemicals Liquid crystal displays

16 Hydrocarbons - Kolvetni Kolvetni eru einföldustu lífrænu efnin Kolvetni eru gerð úr Kolefni og Vetni Kolvetni þar sem öll tengi milli atóma eru einföld kallast ALKANar Öll eintengi eru sigmatengi (σ-bonds) og um þau frjás snúningur. Einföldustu: CH 4, C 2 H 6, C 3 H 8

17 Um kolvetni Mettað kolvetni (Saturated hydrocarbon):Mettað kolvetni (Saturated hydrocarbon): Kolvetni eingöngu með eintengi Alkane:Alkane: Mettuð kolvetni þar sem kolefnin raða sér í opna keðju. Aliphatic hydrocarbon:Aliphatic hydrocarbon: Annað nafn á alkan

18 Hydrocarbons

19 Bygging Lögun –Ferflötungslaga –Öll horn tengja um 109.5°

20 Drawing Alkanes Nokkrar aðferðir við að teikna byggingu –Endi og horn eru kolefnisatóm (line-angle)

21 IUPAC International Union of Pure and Applied Chemistry Látum nægja að læra utanað upp í 10 en allt ofar þarf að kannast við. Sjá annars töflu 11.1 í bók.

22 Línulaga - Beinkeðjualkanar Nafn# Kolefni Byggingaformúla Methane1CH 4 Ethane2CH 3 CH 3 Propane3CH 3 CH 2 CH 3 Butane4CH 3 CH 2 CH 2 CH 3 Pentane5CH 3 CH 2 CH 2 CH 2 CH 3

23 IUPAC NAMES Nafn # C-atóma Byggingaformúla Hexane 6 CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 Heptane 7 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 Octane 8 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 Nonane 9 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 Decane 10 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3

24 Dæmi A. Hver er byggingaformúla… H H H H H C C C C H H H H H B. Hver er mólikúlformúlan? C. Hvert er nafnið?

25 Lausn A.CH 3 CH 2 CH 2 CH 3 B. C 4 H 10 C.butane

26 Nafnakerfi - IUPAC Forskeyti/Prefix segir fjölda C-atóma

27 Nöfn: Greinóttra alkana 1.Finndu lengstu kolefniskeðjuna. 2.Númera keðjuna, byrja þaðan sem styst er í fyrstu hliðargrein. 3.Nefnið hliðarhópa og notið númer á C sem staðsetningu. 4.Raðið hliðarhópum (substituents) í stafrófsröð. 5.Notið di-, tri-, ef sami hópur kemur oft fyrir. 

28 Lengsta keðjan 6.Fjöldi kolefnisatóma í lengstu keðju ræður orðstofni/Nafni 7.Ef það eru tvær keðjur jafnlangar velst sú keðja sem hefur fleiri hliðarhópa. =>

29 Númera C -atóm Byrjið við endann næst fyrsta hliðarhóp. Ef tveir hl.hópar eru jafn langt frá skoðið þá aðra hópa =>

30 Nöfn hliðarhópa – ALKYL hópar CH 3 -, methyl CH 3 CH 2 -, ethyl CH 3 CH 2 CH 2 -, n-propyl CH 3 CH 2 CH 2 CH 2 -, n-butyl =>

31 Alphabetize Raðið í stafrófsröð. Ignore di-, tri-, í stafrófsröðinni. 3-ethyl-2,6-dimethylheptane =>

32 Flóknari hliðarhópar Ef greinin er greinótt, númerið C in frá tengi við aðalkeðju. Nefnið og númerið hliðarkeðju í hliðarkeðju. Setjið sviga utanum flókna hliðarhópinn methyl-3-(1,2-dimethylpropyl)cyclohexane =>

33 Nomenclature - IUPAC Parent name:Parent name: the longest carbon chain Substituent:Substituent: a group bonded to the parent chain –alkyl group: –alkyl group: a substituent derived by removal of a hydrogen from an alkane; given the symbol R-

34 Nomenclature - IUPAC 1.The name of a saturated hydrocarbon with an unbranched chain consists of a prefix and suffix 2. The parent chain is the longest chain of carbon atoms 3. Each substituent is given a name and a number 4. If there is one substituent, number the chain from the end that gives it the lower number

35 Nomenclature - IUPAC 5. If there are two or more identical substituents, number the chain from the end that gives the lower number to the substituent encountered first –indicate the number of times the substituent appears by a prefix di-, tri-, tetra-, etc. –use commas to separate position numbers

36 Nomenclature - IUPAC 6. If there are two or more different substituents, –list them in alphabetical order –number from the end of the chain that gives the substituent encountered first the lower number

37 Nomenclature - IUPAC 7. The prefixes di-, tri-, tetra-, etc. are not included in alphabetization –alphabetize the names of substituents first and then insert these prefixes

38 Nomenclature - IUPAC Alkyl groups

39 Nomenclature - Common The number of carbons in the alkane determines the name –all alkanes with four carbons are butanes, those with five carbons are pentanes, etc. –iso- indicates the chain terminates in -CH(CH 3 ) 2 ; neo- that it terminates in -C(CH 3 ) 3

40 Propyl Groups H n-propylisopropyl H A primary carbon A secondary carbon =>

41 Butyl Groups n-butylsec-butyl H H A primary carbon A secondary carbon =>

42 Isobutyl Groups H H A primary carbon A tertiary carbon => isobutyltert-butyl

43 Alkyl Groups Branches on carbon chains H H C CH 3 methyl H H H H C C CH 3 CH 2 ethyl H H

44 Branched Alkanes CH 3 CH 3 CHCH 3 methyl groups CH 3 CH 3 CH 3 CHCH 2 CHCH 3

45 Naming Branched Alkanes CH 3 methyl branch CH 3 CH 2 CH 2 CHCH 2 CH Count

46 Naming Branched Alkanes CH 3 methyl branch CH 3 CH 2 CH 2 CHCH 2 CH Count 3-Methylhexane on third C CH 3 six carbon chain group

47 Naming Summary 1. Count the C’s in the longest chain 2. Name each attached group 3 Count the longest carbon chain to give the first attached group the smallest number 4. Name and locate each group

48 Dæmi A. CH 3 CH 3 CH 3 CHCH 2 CHCH 3 B. CH 3 CH 3 CH 3 CH 2 CHCH 2 CCH 2 CH 3 CH 3

49 Svör A. CH 3 CH 3 CH 3 CHCH 2 CHCH 3 2,4-dimethylpentane B. CH 3 CH 3 CH 3 CH 2 CHCH 2 CCH 2 CH 3 CH 3 3,3,5-trimethylheptane

50 Dæmi Write a condensed structure for A. 3,4-dimethylheptane B. 2,2-dimethyloctane

51 Solution Alk5 A. 3,4-dimethylheptane CH 3 CH 3 CH 2 CHCHCH 2 CH 2 CH 3 CH 3 B.2,2-dimethyloctane CH 3 CH 3 CCH 2 CH 2 CH 2 CH 2 CH 2 CH 3 CH 3

52 Constitutional/structural Isomerism Byggingaisomerur:Byggingaisomerur: Efni með sömu mólikúlformúlu en ólíka byggingaformúlu t.d. : C 4 H 10

53 Byggingaisomerur 11.6 –Eru þetta byggingaisomerur? –Finndu lengstu keðjuna –Númerið að fyrsta hliðarhóp –Berið saman lengd og greinar

54 Constitutional Isomerism World population is about 6,000,000,000

55 Learning Check Alk6 Write 3 isomers of C 5 H 12 and name each.

56 Solution Alk6 CH 3 CH 2 CH 2 CH 2 CH 3 pentane CH 3 CH 3 CHCH 2 CH 3 2-methylbutane CH 3 CH 3 CCH 3 2,2-dimethylpropane CH 3

57 Dæmi Write a condensed structure for A. 3,4-dimethylheptane B. 2,2-dimethyloctane

58 Svör A. 3,4-dimethylheptane CH 3 CH 3 CH 2 CHCHCH 2 CH 2 CH 3 CH 3 B.2,2-dimethyloctane CH 3 CH 3 CCH 2 CH 2 CH 2 CH 2 CH 2 CH 3 CH 3

59 Dæmi Write 3 isomers of C 5 H 12 and name each.

60 Svör CH 3 CH 2 CH 2 CH 2 CH 3 pentane CH 3 CH 3 CHCH 2 CH 3 2-methylbutane CH 3 CH 3 CCH 3 2,2-dimethylpropane CH 3

61 Cycloalkanes Hringmyndanir (CH 2 groups) Formula: C n H 2n Óskautaðir og óleysanlegir í vatni eins og alkanar Bræðslu, suðumörk og flestir eiginleikar svipaðir og hjá samsvarandi alkönum =>

62 Nafnakerfi Sykloalkanar eru venjulega orðstofninn Hringur á hvorki upphaf né endi – en sé hliðarhópur þarf að númera…. Raða í stafrófsröð. Stöku sinnum finnast cyklo sem hliðarhópar eins og syklopentyl. =>

63 Cycloalkanes Hringir með 5 og 6 C algengastir Structure and nomenclature –if two substituents, number from the substituent of lower alphabetical order –if three or more substituents, number to give them the lowest set of numbers and then list substituents in alphabetical order

64 Cycloalkanes Teiknaðir –Lína er C-C bond –Horn og lína þýðir C

65 Cycloalkanes Example:Example: name these cycloalkanes

66 Bicycloalkanes Bicycloalkane:Bicycloalkane: an alkane that contains two rings that share two carbons Bicyclo[4.4.0]decane (Decalin) Bicyclo[4.3.0]nonane (Hydrindane) Bicyclo[2.2.1]heptane (Norbornane)

67 Bicycloalkanes Nomenclature –parent is the alkane of the same number of carbons as are in the rings –number from a bridgehead, along longest bridge back to the bridgehead, then along the next longest bridge, etc. –show the lengths of bridges in brackets, from longest to shortest

68 Chair Conformer =>

69 Boat Conformer =>

70 Conformational Energy =>

71 Axial and Equatorial Positions =>

72 Monosubstituted Cyclohexanes =>

73 1,3-Diaxial Interactions =>

74 Disubstituted Cyclohexanes =>

75 Cycloalkanes Cyclopropane CH 2 CH 2 CH 2 Cyclobutane CH 2 CH 2 CH 2

76 More Cycloalkanes Cyclopentane CH 2 CH 2 CH 2 CH 2 Cyclohexane CH 2

77 Naming Cycloalkanes with Side Groups Number of Naming side groups OneSide group name goes in front of the cycloalkane name. TwoNumber the ring in the direction that gives the lowest numbers to the side groups.

78 Cycloalkanes with Side Groups

79 Dæmi

80 Lausn

81 Chapter 11.8 Alkenes and Alkynes Alkenes and Alkynes Geometric Isomers / rúmísomerur Alkena Alken hefur C=C tvítengi Alkýn hefur C  C

82 Mettuð/Saturated og ómettuð/Unsaturated Mettuð kolvetni hafa mesta mögulega fjölda vetnisatóma. C n H 2n+2 fyrir alkan Ómettuð kolvetni hafa færri vetnisatóm en mettuð Ómettuð kolvetni hafa tví eða þrítengi milli C atóma Milli tví og þrítengja er enginn snúningur

83 ALKEN  C=C tvítengi  Endar á EN H 2 C=CH 2 ethen (ethylen) H 2 C=CH-CH 3 propen (propylen) cyclohexen

84 Alkyn  Carbon-carbon triple bonds  Endar á -yn HC  CHethyn (acetylen) HC  C-CH 3 propyn Alken mun algengari en alkyn

85 Nafnakerfi alken/alkyn Þegar keðja hefur 4 eða fleiri C, þá númera keðju þaðan sem styst er í tvítengi án tillits til alkýl hliðarhópa CH 2 =CHCH 2 CH 3 1-buten eða But-1-en CH 3 CH=CHCH 3 2-buten eða But-2-en CH 3 CH  CHCH 3 2-butyn eða But-2-yn

86 Dæmi Ritið nöfn þessara efna: A.CH 3 CH 2 C  CCH 3 CH 3 B. CH 3 C=CHCH 3 C.

87 Lausn IUPAC nöfnin eru: A.CH 3 CH 2 CH=CHCH 3 2-pentyne CH 3 B. CH 3 C=CHCH 3 C. 3-methyl-2-butene 3-methylcyclopentene

88 Þar sem engin snúningur er um tvítengi geta myndast rúmísomerur (geometric isomers) Rúmisomerur geta myndast ef keðja er 4C eða lengri. Rúmisomerur myndast á C no. 2 eða ofar Sömu megin úr tvítengi er CIS Sitthvoru megin úr tvítengi er Trans

89 Cis and Trans Isomers  Efnið er 2-buten  Cis/trans eru mögulegar CH 3 CH 3 CH 3 CH = CH CH = CH cis trans CH 3

90 Cis/trans Cis/trans isomerur hafa mikil áhrif á lögun sameinda Náttúran notar oftast Cis í lífverum og allar fitusýrur í náttúrunni eru Cis Cis og trans hafa líka ólík bræðslu og suðumörk

91 Trans fitusýrur - ómettaðar

92 Sömu ómettuðu – CIS

93

94 12.8 Alkenar och Alkynar π orkumeira, Léttara brjóta - hvargjarnara  Stöðugra, orkulægra óhvarfgjarnt

95 Nafnareglur Liknar det för alkaner –en -yn 1. Namnge den kolkedja som innehåller längsta kedja med dubbel trippel bindning 2. Numrera kedjan från den ände som ger dubbel trippel bindning lägst siffra. 3. Placera siffra och namnet på substituenter framför alken- alkyn namn 2-etyl-1-buten

96 Cykloalkanar, þar er talið yfir tvíbinding til hliðarhóps Hefur efnið tvo tvíbindinga kallast það DÍEN Hexatrien Butadien

97 Cis-trans isomer stereoisomeri,cis-trans Almennt er trans stöðugra

98 Cis-trans isomer Cis och trans isomeri kräver att de grupper som binder till kolet är OLIKA

99

100 11.9 Aromatic Compounds  Aromatic compounds innihalda benzene.  Benzene C 6 H 6 has 6 C atoms and 6 H Atoms  Two possible ring structures show benzene.

101 Benzene Structure The structures for benzene are also written as one formula with a circle within the ring to represented the alternating double bonds. Benzene structure

102 Aromatic Compounds in Nature and Health Many aromatic compounds are common in nature and in medicine.

103 Naming Aromatic Compounds Aromatar hafa Bensen sem orðstofn og hliðarhópar settir fyrir fram. (stundum!!!!). methylbenzenechlorobenzene

104 Þegar bensen er tvískipt (tveir hliðarhópar) er hringur númeraður þannig að hóparnir fái sem lægst númer. Forskeytin ortho (1,2), meta (1,3-) and para (1,4-) eru einnig notuð.

105 Aromatar hafa verslunarnöfn (common name). Ef tvískipt, þá oft með ortho-, meta-, para-.

106 Dæmi Select the names for each structure: 1. Chlorocyclohexane 2. Chlorobenzene 3. 1-chlorobenzene 1. Meta-methyltoluene 2. Meta-dimethylbenzene 3. 1,3-dimethylbenzene

107 Svör Select the names for each structure: 2. Chlorobenzene 1. Meta-methyltoluene 2. Meta-dimethylbenzene 3. 1,3-dimethylbenzene

108 Dæmi Ritið byggingaformúlur: A. 1,3-dichlorobenzene B. Ortho-chlorotoluene

109 Svör Byggingaformúlurnar: A. 1,3-dichlorobenzene B. Ortho-chlorotoluene

110 Learning Check Alk11 Identify the organic family for each:

111 Solution Alk11 Identify the organic family for each: alkane cycloalkane aromatic

112 Fused Benzene Rings

113 Carcinogens Fused ring of benzene cause cancer Contain four or more fused rings Present in tobacco smoke, auto exhaust, and burned food The more a person smokes, the greater the risk of developing cancer

114 Unsaturated Fatty Acids Fatty acids in vegetable oils are omega-6 acids (the first double bond occurs at carbon 6 counting from the methyl group) A common omega-6 acid is linoleic acid CH 3 CH 2 CH 2 CH 2 CH 2 CH=CHCH 2 CH=CH(CH 2 ) 7 COOH 6 linoleic acid, a fatty acid

115 Trans Fats  In vegetable oils, the unsaturated fats usually contain cis double bonds.  During hydrogenation, some cis double bonds are converted to trans double bonds (more stable) causing a change in the fatty acid structure  If a label states “partially” or “fully hydrogenated”, the fats contain trans fatty acids.

116 Trans Fats  In the US, it is estimated that 2-4% of our total Calories is in the form of trans fatty acid.  trans fatty acids behave like saturated fatty acids in the body.  Several studies reported that trans fatty acids raise LDL-cholesterol. Some studies also report that trans fatty acid lower HDL- cholesterol  The trans fatty acids controversy will continue to be debated.

117 Fats and Atheroschlerosis Inuit people of Alaska have a high fat diet and high blood cholesterol levels, but a very low occurrence of atherosclerosis and heart attacks. Fat in the Intuit diet was primarily from fish such as salmon, tuna and herring rather than from land animals (as in the American diet).

118 Omega-3 Fatty Acids Fatty acids in the fish oils are mostly the omega-3 type (first double bond occurs at the third carbon counting from the methyl group). linolenic acid 18 carbon atoms CH 3 CH 2 CH=CHCH 2 CH=CHCH 2 CH=CH(CH 2 ) 7 COOH  eicosapentaenoic acid (EPA) 20 carbon atoms CH 3 CH 2 (CH=CHCH 2 ) 5 (CH 2 ) 2 COOH

119 Atherosclerosis Plaques of cholesterol adhere to the walls of the blood vessels Blood pressure rises as blood squeezes through smaller blood vessels Blood clots may form Omega-3 fatty acids decrease the “sticking” of blood platelets (fewer blood clots) Omega-3 fatty acids can increase bleeding time

120 Learning Check HA6 (1) Ture or (2) False A. ____ There are more unsaturated fats in vegetable oils. B. ____ Vegetable oils have more omega-3 oils than found in fish. C. ____ Hydrogenation of oils converts some cis-double bonds to trans- double bonds. D. ____ Animal fats have more saturated fats.

121 Solution HA6 (1) True or (2) False A. _T__ There are more unsaturated fats in vegetable oils. B. _F__ Vegetable oils have more omega-3 oils than found in fish. C. _T__ Hydrogenation of oils converts some cis-double bonds to trans- double bonds. D. _T__ Animal fats have more saturated fats.


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