Slajd 1

Alkeny:

Struktura, nazewnictwo,

Termodynamika i kinetyka

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 2

Węglowodory te zawierają wiązanie podwójne

C C

double bondthe functional group

center of reactivity

Alkeny

wiązanie podwójnegrupa funkcyjna

centrum reaktywności

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 3

Łańcuchowe alkeny:CnH2n

Pierścieniowe alkeny:CnH2n–2

Molecular Formula of Alkene

CH3CH2=CH2

alken alken cykliczny alken cykliczny alken

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 4

Nazewnictwo systematyczne alkenów•Należy wybrać najdłuższy łańcuch węglowy zawierającygrupę funkcyjną

1-buten 2-buten 2-heksen

2-propylo-1-heksen

najdłuższy łańcuch węglowy zawiera 8 atomów węgla ale najdłuższy łańcuch zawierający grupęfunkcyjną zawiera 6 atomów węgla stąd właściwa nazwa to heksen.

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 5

•Podstawniki wymienia się w kolejności alfabetycznej

•Nazwę należy tworzyć tak aby grupa funkcyjna oraz podstawniki miały jak najniższy numer

3,6-dimetylo-3-oktan 5-bromo-4-chloro-1-heptan

2,5-dimetylo-4-oktannie

4,7-dimetylo-4-oktanponieważ 2<4

2-bromo-4-metylo-3-heksannie

5-bromo-3-metylo-3-heksanponieważ 2<3

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 6

•W cyklicznych alkenach nie ma potrzeby podawania numeru określającego położenie grupy funkcyjnej

3-etylocyklopenten 4,5-dimetylocykloheksen 4-etylo-3-metylocykloheksen

1,6-dichlorocykloheksennie

2,3-dichlorocykloheksenponieważ 1 < 2

5-etylo-1-metylocykloheksennie

4-etylo-2-metylocykloheksenponieważ 1 < 2

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 7

Dodatkowe nazewnictwowęgiel winylowy

węgiel allilowy

grupa winylowa grupa allilowa

nazwa systematyczna: chloroetan 3-bromopropennazwa zwyczajowa: chlorek winylu bromek allilu

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 8

Struktura alkenów

sześć atomów węglależy w jednej płaszczyźnie

nałożone bocznie orbitalep tworzą wiązanie π

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 9

Izomeria alkenów

cis-2-buten trans-2-buten

Związki te nie mają izomerów cis-trans ponieważ podstawniki przy tym samym atomie węgla o hybrydyzacji sp2 są takie same

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 10

Moment dipolowy izomerów alkenów

cis-2-buten trans-2-buten cis-1,2-dichlorobuten trans-1,2-dichlorobuten

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 11

Izomeryzacja alkenów wymaga rozerwania wiązaniaπ pomiędzy atomami węgla o hybrydyzacji sp2

cis-2-penten trans-2-penten

izomer cis izomer trans

zerwane wiązanie π

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 12

Izomeryzacja cis-trans pod wpływem światła

rodopsyna metarodopsyna II(trans-rodopsyna)

wiązanie ciswiązanie trans

światło

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 13

Izomery E i Z

Który to izomer cis, a który trans?

izomer Z izomer E

wyższy priorytet wyższy priorytet

niższy priorytet niższy priorytet

wyższy priorytet

wyższy priorytetniższy priorytet

niższy priorytet

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 14

Zasady stosowania oznaczeń E i ZZasada 1: Określić liczbę atomową atomów

bezpośrednio związanych z atomamiwęgla o hybrydyzacji sp2.

izomer Z izomer E

wyższy priorytet wyższy priorytet

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 15

Zasada 2: Jeśli pierwszy atom nie rozstrzyga,należy rozpatrywać kolejne atomypowiązane z bezpośrednio sąsiadującym.

izomer Z izomer E

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 16

Zasada 3: Wiązanie wielokrotne traktowane jestjak kilka atomów połączonychwiązaniami pojedynczymi.

izomer Z izomer E

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 17

Zasada 4: O pierwszeństwie izotopów decydujewiększa liczba masowa.

izomer Z izomer E

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 18

Alkeny są związkami, których cząsteczki sąbogate w elektrony

Nukleofil: bogaty w elektrony atom lub cząsteczka, która dzieli elektrony z elektrofilem

Przykłady nukleofili:

Są nukleoflami

To są nukleofile, bo mają parę elektronów,którą mogą uwspólnić

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 19

Nukleofile przyciągają atomy lub cząsteczkiposiadające deficyt elektronów (elektrofile)

Przykłady elektrofili:

To elektrofile, ponieważ mogą przyjąćparę elektronów

To elektrofile, ponieważposzukują elektronu

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 20

Addycja elektrofilowa HBr do alkenów

karbokation 2-bromobutanhalogenek alkilu

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 21

Zakrzywione strzałki w mechanizmachreakcji

Przesunięcie pary elektronów

Przesunięcie jednego elektronu

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 22

Wykorzystanie strzałek

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 23

Diagram przebiegu reakcji

W stanie przejściowym wiązania są częściowo uformowaneProdukty pośrednie mają w pełni uformowane wiązania

postęp reakcji

Ener

gia

swob

odna

energia swobodna substratów

stan przejściowy:

najwyżejenergetyczny

stanreakcji

energia swobodna produktów

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 24

Termodynamika opisuje własności układu w stanie równowagi

produktysubstraty

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 25

Parametry termodynamiczne

Zmiana standardowej swobodnej energii Gibbsa (∆G°)

Entalpia (∆H°): ciepło oddawane lub absorbowanepodczas reakcji

Entropia (∆S°): miara nieuporządkowania

∆G° = ∆H° – T∆S°

Jeśli ∆S° jest małe w stosunku do ∆H°, to ∆G° ~ ∆H°

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 26

Reakcja egzoenergetyczna–∆G°

Reakcja endoenergrtyczna+∆G°

postęp reakcji postęp reakcji

Ener

gia

swob

odna

substrat

substratprodukt

produkt

reakcjiaegzoenergetyczna∆G° ujemna, Keq > 1

reakcjiaendoenergetyczna

∆G° dodatnia, Keq < 1

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 27

Addycja elektrofilowa HBr do 2-Butenu

W reakcjach wieloetapowych o szybkości reakcjidecyduje jej najwolniejszy etap

Ener

gia

swob

odna

postęp reakcji

produkt pośredni

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 28

Solwatacja: oddziaływanie pomiędzy rozpuszczalnikiem a cząsteczkami lub jonamizwiązku rozpuszczonego

solwatacja ładunku dodatniego przez cząsteczki wody

solwatacja ładunku ujemnego przez cząsteczki wody

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 29

Reakcje alkenów

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 30

Addycja elektrofilowa do alkenów

wiązanie podwójne skała się z wiązania σ i wiązania π

wiązanie π uległo rozerwaniu powstało nowe wiązanie σ

elektrofil nukleofil

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 31

Addycja halogenowodoru

eten chlorek etylu

2,3-diemtylo-2-buten 2-bromo-2,3-dimetylobutan

cykloheksen jodocykloheksan

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 32

Jaki produkt powstanie?

2-metylopropen chlorek tert-butylu chlorek izobutylu

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 33

O kierunku reakcji decyduje tworzenie karbokationu

kation tert-butylowy

kation izobutylowy

chlorek tert-butylujedyny produkt

chlorek izobutylunie powstaje

bardziej stabilnykarbokation

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 34

Stabilność karbokationów

trzeciorzędowy drugorzędowy pierwszorzędowy kation metylowy

rosnąca stabilność

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 35

Grupy alkilowe rozpraszają ładunek dodatni stabilizując karbokation

Mapy potencjału elektrostatycznego

kation tert-butylowy kation izobutylowy kation etylowy kation metylowy

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 36

Delokalizacja elektronów

hiperkoniugacja

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 37

W reakcjach regioselektywnych jeden z izomerów konstytucyjnychjest głównym lub jedynym produktem

Reguła MarkovnikovaElektrofil przyłącza się do atomu węgla o hybrydyzacjisp2 do którego przyłączonych jest więcej atomów wodoru

2-metylopropen

jedyny produkt

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 38

Addycja halogenu do alkenów

jon bromoniowy1,2-dibromoetan

wicynalny dibromek

jon bromoniowyetenu

jon bromoniowycis-2-butenu

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 39

mniej stabilny

bardziej stabilny

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 40

Tworzenie rodników

nadtlenek alkilu rodnik alkoksylowy

rodnikbromkowy

światło

lub

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 41

Addycja rodnikowa do alkenów

rozpoczęcie reakcji

rozwinięcie reakcji

zakończenie reakcji

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 42

Względna stabilność rodnikówalkilowych

rosnąca stabilność

trzeciorzędowy drugorzędowy pierwszorzędowy rodnik metylowy

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 43

Addycja wodoru do alkenów

2-buten butan

2-metylopropen 2-metylopropan

cykloheksen cykloheksan

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 44

Katalityczne uwodornienie alkenów

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 45

Energia potencjalna izomerów pentenu

ener

gia

pote

ncja

lna

najtrwalszynajmniej trwały

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 46

Względna stabilność podstawionychalkilami alkenów

rosnąca stabilność

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 47

Zawada steryczna w alkenach

cis-2-buten trans-2-buten

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________

Slajd 48

Względna stabilność dialkilopodstawionych alkenów

rosnąca stabilność

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________________________________________________

___________________________________