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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