nomenklatura, własności fizyczne,...
TRANSCRIPT
Slajd 1
Wstęp do chemii organicznej
Nomenklatura, własności fizyczne, struktura
eter mapa potencjału elektrostatycznego
cząsteczki eteru etylowego
hybrydyzacja sp3
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Slajd 2
• Alkany to węglowodory zawierające wyłącznie wiązaniapojedyncze o ogólnym wzorze: CnH2n+2
nazwa wzór Kekulego wzór półstrukturalny model kulkowy
metan
etan
propan
butan
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Slajd 3
• Izomery konstytucyjne mają ten sam wzór sumarycznyale różnią się sposobem połączenia atomów
butan
izobutan fragment struktury
„izo”
pentan
izopentan neopentan fragment struktury
„neo”
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Slajd 4
Nazewnictwo podstawników alkilowych
grupa metylowa grupa etylowa grupa propylowa grupa butylowa
dowolna grupa alkilowa
alkohol metylowy etyloamina bromek propylu chlorek butylu
jodek metylu alkohol etylowy propyloamina alkohol butylowy
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Slajd 5
metyl
etyl
izopropyl
izobutyl izopentyl
Nazwy wybranych grup alkilowych
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Slajd 6
• Związek może posiadać więcej niż jedną nazwęale nazwa może odpowiadać tylko jednemu związkowi
Związek o wzorze C7H16 może mieć jedną z następujących struktur:
3-metyloheksan 2,3-dimetylopentan 2,4-dimetylopentan
2,2,3-trimetylobutan
3,3-dimetylopentan 3-etylopentan2,2-dimetylopentan
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Slajd 7
Rzędowość atomu
pierwszorzędowy pierwszorzędowy drugorzędowy trzeciorzędowy
grupa butylowa grupa izobutylowa grupa sec-butylowa grupa tert-butylowa
pierwszorzędowy trzeciorzędowy drugorzędowy
atomy wodoru
alkohol butylowy lub
n-butanol
alkohol izobutylowy alkohol sec-butylowy lub
s-butanol
alkohol tert-butylowylub
t-butanol
pierwszorzędowy trzeciorzędowy drugorzędowy
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Slajd 8
Nazewnictwo alkanów1. Określić liczbę atomów węgla w najdłuższym łańcuchu
CH3CH2CH2CH2CHCH2CH2CH3
CH3
12345678CH3CH2CH2CH2CHCH2CH3
CH2CH2CH3
45678
123
CH3CH2CH2CHCH2CH2CH3
CH2CH2CH2CH3
1234
5 6 7 8
2. Podstawniki powinny posiadać jak najniższe numery
CH3CHCH2CH2CH3
CH3
1 2 3 4 5
2-methylpentane
CH3CH2CH2CHCH2CH2CH2CH3
CHCH3
CH3
1 2 3 4 5 6 7 8
4-isopropyloctane
CH3CHCH2CH2CH3
CH3
common name: isohexanesystematic name: 2-methylpentane
2-metylopentan4-izopropylooktan
2-metylopentan(izoheksan)
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Slajd 9
3. Podstawniki należy numerować tak aby otrzymały jaknajniższe numery
CH3CH2CHCH2CHCH2CH2CH3
CH3 CH2CH3 5-ehtyl-3-methyloctanenot
4-ethyl-6-methyloctanebecause 3<4
podstawniki wymieniane są w kolejności alfabetycznej
4. Wszystkie podstawniki powinny mieć jak najniższe numery
CH3CH2CHCH2CHCH3
CH3 CH3
2,4-dimethylhexane
CH3CH2CH2C
CH3
CH3
CCH2CH3
CH3
CH3
3,3,4,4-tetramethylheptane
CH3CH2CHCH2CH2CHCHCH2CH2CH3
CH2CH3
CH2CH3 CH2CH3
CH3
3,3,6-triethyl-7-methyldecane
5-etylo-3-metylooktan a nie
4-etylo-6-metylooctan
ponieważ 3<4
2,4-dimetyloheksan 3,3,4,4-tetrametyloheptan 3,3,6-trietylo-7-metylodekan
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Slajd 10
5. Jeśli numerowanie w obu kierunkach prowadzi do przydzielenia tego samego numeru o kierunku numerowania decydujeniższy numer kolejnego podstawnika
CH3CHCH2CHCH3
CH3
CH3 CH3
2,2,4-trimethylpentanenot
2,4,4-trimethylpentanebecause 2<4
CH3CH2CHCHCH2CHCH2CH3
CH3
CH3 CH2CH3
6-ethyl-3,4-dimethyloctanenot
3-ethyl-5,6-dimethyloctanebecause 4<5
6. Jeśli numerowanie w obu kierunkach prowadzi do przydzielenia tego samego numeru mniejszy podstawnik otrzymuje niższy numer
CH3CH2CHCH2CHCH2CH3
CH3
CH2CH3
3-ethyl-5-methylheptanenot
5-ethyl-3-methylheptane
CH3CH2CHCH3
Cl
Br
2-bromo-3-chlorobutanenot
3-bromo-2-chlorobutane
2,2,4-trimetylopentannie
2,4,4-trimetylopentanponieważ 2<4
6-etylo-3,4-dimetylooktannie
3-etylo-5,6-dimetylooktanponieważ 4<5
2-bromo-3-chlorobutannie
3-bromo-2-chlorobutan
3-etylo-5-metyloheptannie
5-etylo-3-metyloheptan
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Slajd 11
7. Jeśli numerowanie łańcucha węglowego w różnych kierunkachnależy wybrać taki sposób numerowania aby liczba podstawników była jak największa
CH3CH2CHCH2CH2CH3
CHCH3
CH31
2
3 4 5 6
3-ethyl-2-methylhexane (two substituents)
CH3CH2CHCH2CH2CH3
CHCH3
CH3
1 2 3 4 5 6
3-isopropylhexane (one substituent)
8. Niektóre nazwy zwyczajowe są używane również wnomenklaturze IUPAC
CH3CH2CH2CH2CHCH2CH2CH3
CHCH3
CH3
4-isopropyloctaneor
4-(1-methylethyl)octane
CH3CH2CH2CH2CHCH2CH2CH2CH2CH3
CH2CHCH3
CH3
5-isobutyldecaneor
5-(2-methylpropyl)decane
3-etylo-2-metyloheksan(dwa podstawniki)
3-izopropyloheksan(jeden podstawnik)
4-izopropylooktanlub
4-(1-metyloetylo)oktan
5-izobutylodekanlub
5-(2-metylopropylo)dekan
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Slajd 12
Nazewnictwo cykloalkanów1. Nie numeruje się podstawników w monopodstawionych
pierścieniach
CH3
methylcyclopentane
CH2CH3
ethylcyclohexane
CH2CH2CH2CH2CH3
1-cyclobutylpentane
2. Podstawniki wymienia się w kolejności alfabetycznej
H3CCH2CH2CH3
1-methyl-2-propylcyclopentane
H3CH2C
CH3
1-ethyl-3-methylcyclopentane
CH3
CH3
1,3-dimethylcyclohexane
metylocyklopentan etylocykloheksan 1-cyklobutylopentan
1-metylo-2-propylocyklopentan 1-etylo-3-metylocyklopentan 1,3-dimetylocykloheksan
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Slajd 13
3. Co wtedy kiedy jest więcej niż jeden podstawnik?
CH3CH2CH2
H3C CH2CH3
4-ethyl-2-methyl-1-propylcyclohexanenot
1-ethyl-3-methyl-4-propylcyclohexanebecause2<3
not 5-ethyl-1-methyl-2-propylcyclohexane
because 4<5
CH3
CH3
CH3
1,1,2-trimethylcyclopentanenot
1,2,2-trimethylcyclopentanebecause1<2
not1,1,5-trimethylcyclopentane
because 2<5
4-etylo-2-metylo-1-propylocykloheksannie
1-etylo-3-metylo-4-propylocykloheksanponieważ 2<3
nie5-etylo-1-metylo-2-propylocykloheksan
ponieważ 4<5
1,1,2-trimetylocyklopentannie
1,2,2-trimetylocyklopentanponieważ 1<2
nie1,1,5-trimetylocyklopentan
ponieważ 2<5
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Slajd 14
Nazewnictwo halogenków alkiluCH3Cl CH3CH2F
CH3CHI
CH3
CH3CH2CHBr
CH3chloromethane fluoroethane2-iodopropane 2-bromobutane
W nomenklaturze IUPAC halogenki alkilu nazywane są tak jakpodstawione alkany
CH3CH2CHCH2CH2CH2CH3
CH3
Br
2-bromo-5-methylheptane
CH3CH2CHCH2CH2CH2Cl
CH3
CH3
1-chloro-5,5-dimethylhexane
CH2CH3
I
1-ethyl-2-iodocyclopentane
Br
Cl
CH3
4-bromo-2-chloro-1-methylcyclohexane
chlorometan fluorometanfluorometan2-jodopropan 2-bromobutan
2-bromo-5-metyloheptan 1-chloro-5,5-dimetyloheksan
1-etylo-2-jodocyklopentan 4-bromo-2-chloro-1-metylocykloheksan
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Slajd 15
Różne typy halogenków alkilu
atom węgla pierwszorzędowy
atom węgla drugorzędowy
atom węgla trzeciorzędowy
halogenek pierwszorzędowy halogenek drugorzędowy halogenek trzeciorzędowy
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Slajd 16
Struktura halogenków alkiluDługość i moc wiązania w halogenkach alkilu
długośćwiązania
siła wiązaniakcal/mol kJ/mol
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Slajd 17
• Im większe siły przyciągania cząsteczek tym wyższa temperatura wrzenia związku
Siły przyciągania
siły van der Waalsa
oddziaływania dipol–dipol
wiązanie wodorowe
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Slajd 18
Siły van der Waalsa
Temperatura wrzenia substancji rośnie wraz ze wzrostem sił van der Waalsa
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Slajd 19
Oddziaływanie dipol–dipol
Oddziaływanie dipol–dipol jest silniejsze niż van derWaalsa ale słabsze niż wiązanie jonowe lub kowalencyjne
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Slajd 20
• Wiązanie wodorowe jest specyficznym oddziaływaniemdipol–dipol
wiązanie wodorowe
wiązanie wodorowe w wodzie
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Slajd 21
Porównanie temperatur wrzenia alkanów i halogenków alkilu (°C)
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Slajd 22
Podobne rozpuszcza podobne• Związki polarne rozpuszczają się w polarnych rozpuszczalnikach
• Niepolarne rozpuszczają się w niepolarnychrozpuszczalnikach
solwatacja polarnej cząsteczki przez cząsteczki wody
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Slajd 23
Konformacje alkanów:rotacja wokół wiązania podwójnego
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Slajd 24
• Oddziaływania torsyjne: oddziaływanie wiążących parelektronowych
• Naprzemianległy konformer jest bardziej stabilny niżnaprzeciwległy
Konformacje etanu
ener
gia
pote
ncja
lna
stopień obrotu
położenie naprzeciwległe
położenie naprzemianległe
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Slajd 25
Konformacje n-butanu• Oddziaływanie steryczne: oddziaływanie pomiędzychmurami elektronowymi atomów lub podstawników
ener
gia
pote
ncja
lna
kąt dwuścienny
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Slajd 26
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Slajd 27
Cykloalkany: naprężenia w pierścieniu
• Naprężenia kątowe są wynikiem różnicy wartości kątaod wartości preferowanej 109.5°
dobre nakładaniesilne wiązanie
(a)
słabe nakładaniesłabe wiązanie
(b)
wiązanie bananowe
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Slajd 28
• Konformacja krzesłowa cykloheksanu nie powodujenaprężeń kątowych
konformacja krzesłowacykloheksanu
projekcja Newmanacykloheksanu
model kulkowykonformacji krzesłowej
cykloheksanu
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Slajd 29
Odwrócenie pierścienia w cykloheksanie
atom węgla wędruje na dół
atom węgla wędruje do góry
odwrócenie pierścienia
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Slajd 30
Rysowanie cykloheksanu
wiązanie aksjalnewiązanie ekwatorialne
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Slajd 31
Konformacje cykloheksanu i ich energie
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Slajd 32
Konformacje monopodstawionegocykloheksanu
odwrócenie pierścienia
bardziej stabilnakonformacja krzesłowa
mniej stabilnakonformacja krzesłowa
grupa metylowa jest w położeniu anti do atomu węgla C-3
grupa metylowa jest w położeniu anti do atomu węgla C-5
grupa metylowa jest w położeniu ekwatorialnym
grupa metylowa jest w położeniu ekwatorialnym
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Slajd 33
Oddziaływanie 1,3-diaksjalne w metylocykloheksanie
oddziaływanie 1,3-diaksjalnemodel kulkowy
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Slajd 34
Keq = [konformer ekwatorialny]/[konformer aksjalny]
• Im większy jest podstawnik w pierścieniu cykloheksanutym bardziej uprzywilejowana jest konformacja, w którejułożony jest on ekwatorialnie
Stałe równowagi wybranych monopodstawionych pochodnych cykloheksanuw temperaturze 25°C
podstawnik aksjalny ekwatorialny podstawnik aksjalny ekwatorialny
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Slajd 35
H
CH3H
CH3 cis-1,4-dimethylcyclohexane
H
H3C
CH3
Hring-flip
Konformery krzesłowe cis-1,4-dimetyolcykloheksanu
cis-1,4-dimetylocykloheksan
odwróceniepierścienia
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Slajd 36
H
CH3H3C
H trans-1,4-dimethylcyclohexane
CH3
H
CH3
Hring-flipodwróceniepierścienia
trans-1,4-dimetylocykloheksan
Konformery krzesłowe trans-1,4-dimetyolcykloheksanu
Ta konformacja krzesłowa macztery oddziaływania 1,3-diaksjalne
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Slajd 37
1-tert-butylo-3-metylocykloheksan
trans-1-tert-butylo-3-metylocykloheksan
bardziej stabilna mniej stabilna
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