O5*$1ø.#.ø0<$ Orhan BÜLBÜL +ø'52.$5%21/$5 YalnÕzFD#NDUERQ### &#
# YH# KLGURMHQ# ## +#
# DWRPODUÕQGDQ# oOXúPXú# ELOHúLNOHUH# +ø'52.$5%21/$5 ODUGD# NDUERQ#DWRPODUÕ#VS PÕú#RODELOLUOHU# +DONDOÕ# DOkDQODUÕQ# DGODQGÕUÕOPDVÕQGD# LVH# ]LQFLU# úHNOLQGH# RODQ#DGÕQÕQ#| QQH#³ciklo” denir. Hidrokarbonya da “siklo” ön eki getirilir. CH2 H2C CH2 CH2 CH2 3 , sp2 , ve sp#KLEULWOHúPHOHULQH#X÷UaH2C CH2 CH2 H2C H2C C 2H6 CH4 C 2H4 ve ELOHúLNOHU#KLGUokarbonlara C 2H2 Siklopropan Siklobütan H2C CH2 Siklopentan örneNWLU##+LEULWOHúPHOHUH#|UQHN#LVH# $/.$1/$5'$#ø=20(5ø Düz zincirli alkanlardaki izomeriye 67(52# ø=20(5ø (yer izomeri) denir. AlkDQGDNL#NDUERQ#DWRPODUÕ#Xo#XFD#HNOHQesp3 sp3 sp2 UHN# G]# ]LQFLUOL# ELU# IRUPO# ROXúWXUDFD÷Õ# JLEL## KHU# LNL# XoWDNL# karbonlar hariç zincir içindeki karbonlara da yeni karbon DWRPODUÕ# ED÷ODQDUDN# GDOODQPÕú# ELU# IRUPO# ROXúWXUDELOLUOHU## øúWH# NDSDOÕ# IRUPOOHUL# D\QD# DQFDN# DoÕN# IRUPOOHUL# IDUNOÕ# RODQ# EX# WU# ELOHúLNOHUH# ø=20(5# %ø/(ùø./(5 sp denir.# =LQFLU# \DSÕOÕ#
alkanlarda izomeri 4 kDUERQOX# EWDQGDQ# EDúODU## 0HWDQ# etan YH#SURSDQÕQ#L]RPHUL# \RNWXU##$ONDQODUGD# NDUERQ#VD\ÕVÕ# DUWWÕNoD# L]RPHU# VD\ÕVÕ# GDKD# GD# oRN# DUWDU## 0HVHOD# +HN]DQÕQ# #&6 +ø'52.$5%21/$5 $/ø)$7ø.# +ø'52.$5%21/$5 $520$7ø. +ø'52.$5%21/$5 H14) 5 WDQH##GHNDQÕQ###&10 H22) 75 tane, C25H52#QLQ#\DNODúÕN####PLO\RQ# (zincir ya GD#KDONDOÕ
(Arenler) WDQH#L]RPHUL#YDUGÕU# ø]RPHUOHUGH#IRUPO#\D]ÕOÕUNHQ# '2<08ù# +ø'52.$5%21/$5 '2<0$0,ù +ø'52.$5%21/$5 W D]# ]LQFLUOL# RODQÕQ# EHOLUWLOPHVLQGH# GDOODQPDPÕú# \aSÕGD###QRUPDO
#ROGX÷XQX#EHOLUWPHN#LoLQ###n – ) ön eki ( Alkanlar) ALKENLER $/.ø1/(5 W W getirilir. En uzun zincirdeki 2. karbona bir alkil grubu ba÷# ODQPÕú#LVH#( izo – ) |Q#HNLQL#DOÕU# neo – )#|Q##HNLQL#DOÕU# ALKANLAR (Parafinler) 'R\PXú# KLGURNDUERQODU# RODUDN# ELOLQLU## $lkanlarda En uzun zincirdeki 2. karbona iki alkil grubu ba÷# ODQPÕú#LVH#( C–H 3 ve C –#&#ED÷ODUÕ#VLJPD###/
#ROXS#EX#NDUERQ#DWRPODUÕQD#EDúND# DWRPODU# ED÷ODQDPD]## 0ROHNOGH# EWQ# NDUERQ# DWRPODUÕ# VS KLEULWOHúPHVLQH#X÷UDPÕúWÕU##$lNDQODUÕQ#]LQFLU#úHNOLnde QÕQ# JHQHO# IRUPOOHUL# &n ùLPGL#EWDQÕQ###&4 H10#
#L]RPHUOHULQL#\D]DOÕP: olanlarÕ# CH3 - CH2 - CH2 - CH3 n- bütan CH3 - CH - CH3 CH 3 2 - metil propan ( izo - bütan ) ùLPGL#SHQWDQÕQ###&5 H2n+2 dir. Bu genel formülde “n” pozitif WDP#VD\ÕODUGÕU####Q ################«#JLEL
# CH4 , C2H6 , C3H8# «# # %X# IRUPOOHUGH# J|UOHFH÷L# JLEL# ELU# birini takip eden iki alNDQ#IRUPO# DUDVÕQGD# &+2# IDUNÕ# EXOXnPDNWDGÕU##
#L]RPHUOHULQL#\D]DOÕP# H8 formülüne CH2 yi eklersek C4H10 moleküOQ# EXOXUX]## %LU# ELULQL# E|\OH# VDELW# ELU# IDUNOD# L]OH\HQ# VÕUD\D# HOMOLOG SIRA denir. AlNDQODUÕQ#$GODQGÕUÕOPDVÕ# AlNDQODUÕQ#DGODQGÕUÕOPDVÕQGD#PROHNOGHNL#NDUERQ#VD\ÕVÕ# QÕQ#VRQXQD##–an#HNL#JHWLULOHUHN#DGODQGÕUÕOÕU# CH3 - CH2 - CH2 - CH2 - CH3 n - pentan CH3 CH3 CH3 - C - CH3 CH3 - CH - CH2 - CH3 CH3 izo - pentan neo - pentan tetra metilmetan 2, 2 di metilpropan 4 METAN CH C2H6 ETAN 38 PROPAN CH C4H10 BÜTAN 5 12 PENTAN CH 6 14 HEKZAN CH 7 16 HEPTAN CH C8H18 OKTAN C9H20 NONAN C10H22 DEKAN 11 24 UNDEKAN CH 12 26 DODEKAN
CH # - 1-
O5*$1ø.#.ø0<$ $ONLO#*UXSODUÕ %LU# DONDQ# PROHNOQGHQ# ## KLGURMHQ# DWRPX# oÕNDUÕOPDVÕ# VRQXFX#JHULGH#NDODQ#NÕVPD GHQLU## $ONLO# JUXSODUÕ# ùLPGL#DúD÷ÕGDNL#| UQHNOHUL#LQFHOH\HOLP# Orhan BÜLBÜL CH 3 - C H - C H - CH 2 - CH 3 I I alkil grubu (kök) ya da 5$'ø.$/ R – ile gösterilir. Genel formülleri -il eki CH 3 CH 3 2,3 – dimetilpentan C nH2n + 1 - # úHklindedir. AlkanÕQ# –an eki yerine getirileUHN#DGODQGÕUÕOÕU##ùLPGL#|UQHNOHUL#LQFHOH\HOLP# CH 3 CH 3 C2 H5 CH 3 - C - C H - C - CH 2 - CH 3 CH 3 I I I I I H H-CCH3 metil HH H-C-CHH C2H5 etil HHH H-C-C-CHHH C3H7 propil Br 4-brom, 4-etil, 2,2,3-trimetilhegzan H +$/.$/,#'2<08ù#+ø'52.$5%21/$5 ( Sikloalkanlar) +LGURNDUERQODUGD# +DONDOÕ# EX# DONDQODUD NDUERQ# ]LQFLUL# KDOND# ROXúWXUDELOLU## Sikloalkanlar GHQLU## %XQODUÕQ# JHQHO# Metan ve eWDQGDQ# KDQJL# KLGURMHQ# oÕNDUÕOÕUVD# oÕNDUÕOVÕQ# ROXúDQ DONLO# JUXEX# D\QÕGÕU## $QFDN# SURSDQGD# GXUXP# IDUNOÕGÕU## 8oWDNL# NDUERQODUGDQ# ELU# KLGURMHQ# oÕNDUÕOÕUVD# Q# formülü CnH2n# GLU## 6LNORDONDQODUÕQ# LON# \Hsi 3 karbonlu VLNORSURSDQ¶GÕU##%X# ELOHúLNOHUGH#WP#NDUERQ# DWRPODUÕQD### WDQH# KLGURMHQ# DWRPX#
ED÷ODQGÕ÷ÕQGDQ# IRUPOOHUL# oRNJHQOHU# LOH# GH# –#SURSLO#ROXúXU## – 2UWDGDNL#NDUERQGDQ#ELU#KLGURMHQ# oÕNDUÕOÕUVD# ROXúDQ# DONLOH#L]R# gösterilebilir. propil denir. AONDQODUÕQ#$GODQGÕUÕOPDVÕ 8OXVODUDUDVÕ# .LP\D# %LUOL÷L# # CH2 CH2 H2C H2C H2C CH2 CH2 CH2 IUPAC
# WDUDIÕQGDQ# DONDQODUÕQ#DGODQGÕUÕOPDVÕ#\|QWHPL#ú|\OH#EHOLUOHQPLúWLU# H2C • Alkan molekülündeki en uzun karbon zinciri esas DOÕQÕU## %X# NDUERQ# ]LQFLULQGHNL# HQ# E\N# QXPDUDOÕ# NDUERQXQXQ#VD\ÕVÕ#HVDV#DOÕQÕU. Siklopropan Siklohekzan • =LQFLUGHNL# NDUERQ# DWRPODUÕQD# QXPDUD# YHULOLU## $QFDN# EX# QXPDUD# YHUPH# LúL# UDVWJHOH# ROPD]## =LQFLUH# ED÷OÕ# RODQ# JUXSODU# KDQJL# XFD# GDKD# \DNÕQVD# R# XoWDNL# NDrSikloalkanlara birden fazla grup ya GD# DWRP# ED÷OÕ# LVH## bunlar en küçük numara\Õ#DODFDN#úHNLOGH#GDKD#|QFHNL#NXUDOODU# GD#J|]#|QQGH#EXOXQGXUXODUDN#DGODQGÕUÕOÕU# bon atomuna 1 numara verilerek zincirdeki tüm NDUERQODU#QXPDUDODQÕU# CH3 -) metilsiklopentan CH3 CH3 1,2-dimetilsiklopentan • *UXEXQ# ED÷OÕ# ROGX÷X# NDUERQ# QXPDUDVÕ# \D]ÕOÕS# ## oHNLOGLNWHQ#VRQUD#JUXEXQ#DGÕ#\D]ÕOÕU##$UD#YHULOPHGHQ# #ELWLúLN# RODUDN
# |QFHGHQ# EHOLUOHQPLú# DONDQÕQ# #X]XQ# NDUERQ# ]LQFLULQLQ
# DGÕ# \D]ÕOÕU## 0ROHNOQ# DGÕQÕQ# WaPDPÕ#WHN#V|]FN#JLEL#NDEXO#HGLOPHNWHGLU# $ONDQODUÕQ#(OGH#Edilme Yöntemleri rafinerilerde petrol Sanayide alkanlar petrolden elde edilir. Petrol bir alkan birNDUÕúÕPÕGÕU## $\UÕPVDO# GDPÕWPD# \|QWHPL\OH D\UÕúWÕUÕOÕU# /DERUDWXDUODUGD# LVH# DONDQODU# oHúLWOL# \|QWHPOHU# LOH# HOGH# HGLOLU##%XQODUÕ#ú|\OH#VÕUDOayabiliriz… • 8]XQ# NDUERQ# ]LQFLULQGH# D\QÕ# DONLO# JUXSODUÕQGDn GHQ# ID]OD# YDUVD# WHNUDU# VD\ÕVÕ# GL## WUL## WHWUD## SHQWD«# GL\H#\D]ÕOÕU# • 8]XQ# NDUERQ# ]LQFLULQGH# IDUNOÕ# DONLO# JUXSODUÕ# YDUVD# \XNDUÕGD# GHGL÷LPL]# LúOHP# D\QHQ# X\JXODQÕU## $QFDN# JUXSODUÕQ#DGODUÕ#DOIDEHWLN#VÕUD\D#J| UH#\D]ÕOÕU##0HVHOD# PHWLO# YH# HWLO# JUXSODUÕ# YDUVD# |nce JUXEX#\D]ÕOÕU# I. Wurtz Sentezi Bu yöntemde alkilhalojenür ( R – X ) ün metalik sodyum “etil” sonra “metil” ##1D#
#LOH#WHSNLPHVLQGHQ#DONDQ#ROXúXU##*HQHO#WHSNLPH#ú|\OHGLU# • 8]XQ# NDUERQ# ]LQFLULQGH# DONLO# JUXSODUÕ# GÕúÕQGD# EDúND# JUXSODU# \D# GD# DWRPODU# YDUVD# \XNDUÕGD# EHOLUWLOHQ# VDVODU#J|]#|QQH#DOÕQÕU# eR - X + 2 Na + R - X R - R + 2 NaX ALKAN # CH 3 − Cl + 2 Na + CH 3 - Cl CH 3 - CH 3 + 2 NaCl
metilklorur metilklorur ETAN
#
#
#
# - 2-
O5*$1ø.#.ø0<$ • • Wurtz sentezi ile metan elde edilemez. $ONLOKDORMHQUOHU# ELUELULQLQ# D\QÕVÕ# LVH# DONLOOHULQ# \DSÕ# VÕQGD# EXOXQDQ# NDUERQODUÕQ# WDPDPÕ# NDGDU# VDI# DONDQ# HOGH#HGLOLU###\XNDUÕGDNL#| UQHNWH#ROGX÷X#JLEL
Orhan BÜLBÜL ve benzen gibi organik çözücülerde çözünürler. Molekül içi ED÷ODUÕ#oRN#JoOü#ROGX÷XQGDQ#NROD\#NROD\#WHSNLPH#YHUPH]OHU## Ancak C –# +# ED÷ODUÕ# NRSDUÕOÕS# KLGURMHQLQ# \HULQH# EDúND# DWRP# \D# GD# DWRP# JUXSODUÕ# ED÷ODQDELOLU## %X# WU# WHSNLPHOHUH# GH# \HU# GH÷LúWLUPH#WHSNLPHOHUL##VEstitüsyon) • • AlkiOKDORMHQUOHU# IDUNOÕ# LVH# R# ]DPDQ# VDI# DONDQ# HOGH# HGLOPH]##$QFDN#ELU#DONDQ#NDUÕúÕPÕ#HOGH#HGLOHELOLU# $ONLOKDORMHQUOHUGH## KDORMHQOHU# Xo# NDUERQODUD# ED÷OÕ# GH÷LOVH# R# ]DPDQ# KDORMHQOHU# KDQJL# NDUERQODUGDQ# NRSPXú#LVH#R#NDUERQODU#ELUELULQH#ED÷ODQÕU# denir. b) I. Kimyasal Özellikleri
# Grignard bil. # metan CH 4 + Cl 2 CH 3 - Cl + HCl metilklorür hµ hµ
# *ULJQDUG#ELOHúL÷L#VX#LOH#WHSNLPH\H#JLUHUVH#DONDQ#ROXúXU# R - Mg - X + H - OH R - H + Mg(OH)X *ULJQDUG#ELOHúL÷L#+;#LOH#WHSNLPH\H#JLUHUVH#DONDQ#ROXúXU# # ALKAN CH 3 − Cl + Cl 2
CH 2 - Cl 2 + HCl
# metilklorür
# diklormetan
# # R - Mg - X + H - X R - H + MgX 2 ALKAN *ULJQDUG# ELOHúL÷L# DONLOKDORMHQU# LOH# VDI# HWHU# LoLQGH# WHSNi#
# diklormetan CH 2 - Cl 2 + Cl 2
CH - Cl 3
hµ + HCl triklormetan hµ meye girerse alkan oluúXU# R - Mg - X + R − X 'R\PDPÕú#KLGURNDUERQODUGDQ
R - R + MgX 2
# triklormetan II. CH - Cl 3 + Cl 2 CCl 4 + HCl tetraklormetan ' SAF ETER ' Yanma tepkimeleri $ONDQODU#\HWHUL#NDGDU#RNVLMHQ#JD]Õ###22
#LOH#\DNÕOGÕNODUÕQGD# 'R\PDPÕú# KLGURNDUERQODU# NDWDOL]|U# \DUGÕPÕ\OD# KLGURMHQ# JD]Õ##+2 ) ile doyurularak alkanlan elde edilir. Ni ürün olarak CO2 ve H22#ROXúXU##$ONDQODUÕQ#\DQPD#WHSNLPHleri DúD÷ÕGDNL#JLELGLU# Alkenlerin 1 molune 1 mol H2#NDWÕODUDN#DONDQ#HOGH#HGLOLU# Cn H 2n + H 2 2n + 2
Cn H
# ALKEN ALKø/ ALKAN
#
ALKAN
# 3n + 1 6 H 2 O
Cn H 2n + 2 +
O2
n CO2 + (n + 1) H 2 O 2 C5 H12 + 8 O2
5 CO2 +
Alkinlerin 1 molüne, 2 mol H2#NDWÕODUDN#DONDQ#HOGH#HGLOLU Cn H 2n - 2 + 2H 2 n H 2n + 2 IV. 2UJDQLN#$VLW#7X]ODUÕQGDQ
C
# Ni ALKENLER (Olefinler) 0ROHNOQGH# oLIW# ED÷# #=) bulunduran hidrokarbonlara Organik asit sodyum# WX]ODUÕQÕQ# ## 5# –# &221D
## GHULúLN# 1D2+#LOH#VÕFDNWDNL#WHSNLPHVLQGHQ#DONDQ#ROXúXU# ALKEN# GHQLU## %LU# WDQH# oLIW# ED÷# EXOXQGXUDQ# DONHQOHULQ# JHQHO# formülü CnH2n# úHNOLQGHGLU## $ONHQOHU# R - COONa + NaOH R - H + Na2 CO3 $ONDQODUÕQ#g]HOOLNOHUL # ALKAN R - C = H 2 ya da R -C =C - R 2 # úHNOLQGH# J|VWHULOLUOHU## dLIW# ED÷Õ# WDúÕ\DQ# NDUERQ# DWRPODUÕ# VS # KLEULWOHúPHVLQH# X÷UDPÕúWÕU## $GODQGÕUÕOPDODUÕQGD# a) Fiziksel özellikleri VDQ# GHU# :DDOV# ED÷ODUÕ# YDUGÕU## .DUERQ# DWRPODUÕ# VS 3 alkandaki -an eki yerine –en eki getirilerek ya da –ilen eki getirilerek DGODQGÕUÕOÕrlar. C2 H 6 $ONDQ# PROHNOOHUL# DSRODU# PROHNOOHUGLU## 0ROHNOOHU# DUDVÕ# \DOQÕ]FD# KLEULWOHúPHVL# \DSPÕúWÕU## *HQHO# RODUDN# HULPH# YH# ND\QDPD# QRNWDODUÕ# GúNWU## $QFDN# PROHNO# E\GNoH# HULPH# YH# NDyQDPD# QRNWDODUÕ# DUWDU## $ONDQODU# DSRODU# PROeNOOHUGHQ# ROGX÷Xn# C2 # etan etilen
H4
C3 H8 (eten ) C3 H 6 propan propilen (propen ) # # C4 H10
C4 #
#
H8 bütan
bütilen (büten ) dan su gibi polar çözücülerde çözünmezler. Aseton, dietileter, # - 3-
O5*$1ø.#.ø0<$ Alkenlerin AdlDQGÕUÕOPDVÕ ,83$&# VLVWHPLQH# J|UH# DONHQOHULQ# DGODQGÕUÕOPaVÕ## DONDQODUD# EHQ]HU## $QFDN# EXUDGD# oLIW# ED÷ODUÕ# WDúÕ\DQ# HQ# X]XQ# NDUERQ# ]LQFLUL#HVDV#DOÕQÕU## %X#NXUDOODUÕ#ú|\OH#VÕUDOD\DELOiriz. Orhan BÜLBÜL c) *HRPHWULN#ø]RPHUL $ONHQOHUGH#oLIW#ED÷#WDúÕ\DQ#NDUERQ#DWRPODUÕQD# ED÷OÕ# RODQ# DWRP# \D# GD#JUXSODU#oLIW# ED÷ÕQ#D\QÕ# WDUDIÕQGD#\D GD#IDUNOÕ# WDUaIÕQGD# RODELOLUOHU# EX# GXUXPGD# RODQ# DONHQ# PROHNOOHUL# IDUNOÕ# 1. 2. 3. dLIW#ED÷ODUÕ#WDúÕ\DQ#HQ#X]XQ#NDUERQ#]LQFLUL#VHoLOLU# dLIW# ED÷ODU# KDQJL# XFD# \DNÕQ# LVH# R# XoWDQ# EDúODQDUDN# ]LQFLUGHNL#NDUERQ#DWRPODUÕQD#QXPDUD#YHULOLU# =LQFLU# GÕúÕQGDNL# JUXSODU# DOIDEHWLN# VÕUD\D# J|UH bileúLNOHU# ROXúWXUXUODU## dLIW# ED÷# WDúÕ\DQ# NDUERQ# DWRPODUÕQD# ED÷OÕ#RODQ#EX#DWRP#\D#GD#JUXSODUÕ##oLIW#ED÷ÕQ#D\QÕ#WDUDIÕQGD#LVH# ve cis –#|Q#HNLQL#DOÕU##IDUkOÕ#WDUDIÕQGD#LVH#trans –#|Q#HNLQL#DOÕU# A C B cis CH 3 C Cl C Cl Cl CH3 CH 3 C C CH 3 ba÷OÕ#EXOXQGXNODUÕ#NDUERQ#QXPDUDODUÕ#HVDV#DOÕQDUDN# ya]ÕOÕU# 4. 5. $\QÕ# JUXSODU# WHNUDU# HGL\RUVD# WHNUDU# VD\ÕVÕ# GL## WUL## A C B A C B trans C B tetra gibi rakamlar ile belirtilir. dLIW#ED÷ODUÕQ#\HUi#EHOLUOHQLUNHQ##oLIW#ED÷ODUÕQ#ED÷OÕ#RlGX÷X# NDUERQODUGDQ# NoN# QXPDUDOÕ# NDUERQXQ# QuPDUDVÕ# \D]ÕOÕU## dLIW# ED÷ÕQ# WHNUDU# VD\ÕVÕ# ODWLQFH# \azÕ# OÕU# A Cl 6. 8]XQ# ]LQFLUGHNL# HQ# E\N# QXPDUDOÕ# NDUERQXQ# VDyÕ# VÕQD# NDUúÕOÕN# JHOHQ# DONan# DGÕQGDNi –an eki yerine – cis - 2,3- diklorbüten $ONHQLO#*UXSODUÕ
trans - 2,3- diklorbüten en#HNL#JHWLULOHUHN#DONHQLQ#DGÕ#EHOLUOHQLU# ùLPGL#DúD÷ÕGDNL#|UQHNOHUL#LQFHOH\HOLP# Alkenlerden bir hidrojen çÕNDUWÕOPDVÕ\OD# gruplara $/.(1ø/ $/.(1ø/ DGÕ#YHULOLU# HOGH# HGLOHQ# CH 3 − CH 2 − CH = CH 2
1
büten
# I CH 2 − CH = CH - CH 3
büten
# 2ADI ÖRNEK CH 2 CH 3 CH 3 I CH - C H − C = CH − C H − CH 2 − CH 3
5
etil,
-
2,3 dimetil, 3 - hepten #
Cl I I CH 2CH 3 CH2 = Metilen Metilensiklopentan Cl I I I CH2 = CH – CH3CH = CH – Etilen ( Vinil) Propenil (Allil) CH2 CH Vinilklorür Cl CH 3 − C H = C H − C = C − CH 2 − CH 3 CH 3
−
dimetil,32,4
heptedien
#
CH
2,3 diklor,4,5 − CH3CH = CH – Br Allilbromür
# 2,4 - dihepten +DONDOÕ#$ONHQOHU $ONHQOHU#GH#DONDQODU#JLEL#KDONDOÕ#\DSÕGD#RODELOLUOHU####WDQH# oLIW# ED÷# WDúÕ\DQ# KDONDOÕ# DONHQLQ# IRUPO# &n UÕOPDVÕQGD# LVH# KDONDOÕ# DONDQÕQ# Alkenlerde ø]RPHUL a) Yer izomeri dallanma sonucu Bunu bir örneNOH#DoÕNOD\DOÕP# CH3CH2 CH Cl 3-klor,2-penten 2-klor,2-penten H2n – 2 dir. adlandÕ# – an eki yerine –en# HNL# \D]Õl$ONDQODUGD# ROGX÷X# JLEL# DONHQOHUGH# GH# ROXúDQ#\HU#L]RPHUOHUL#YDUGÕU# PDVÕ#\HWHUOLGLU# +DONDGD# ## WDQH# oLIW# ED÷#YDUVD# DGODQGÕUPD# |UQHNWHNL# JLEL# \DSÕOÕU# CH3CH2 CH CH CH3 CH Cl CH3 siklobüten siklopropen siklohekzen b)
QXPDUDODUÕ#LOH# EHOLUOHQLU##dLWI# ED÷ÕQ# WHNUDU# VD\ÕVÕ#GL## WUL## WHWUD«# GL\H#\D]ÕOGÕNWDQ#VRQUD#sikloalken CH CH propen CH3 siklopropan diye yazÕOÕU# # - 4-
O5*$1ø.#.ø0<$ Orhan BÜLBÜL CnH2n −2 + H2 1 1 2 6 CH3 2
CnH2n
# Alkin
# ALKEN l l Alkenlerin Kimyasal Özellikleri .DWÕOPD#Tepkimeleri 5 3 4 4 3 Cl 1,2- disiklobüten Cl 4 3 5 - klor, 2 - metil, 1,3- disiklohekzen Alkenlerin kimyasal tepkimeleri genellikle − C = C− fonksiyonel grXEXQGDNL#]D\ÕI#RODQ#SL##
#ED÷ODUÕQÕQ#LNL#NDUERQ# ]HULQH# DoÕOPDVÕ# LOH# EXUDODUD# \DEDQFÕ# DWRP# \D# GD# JUXSOaUÕQ# 5 Cl ED÷ODQPDVÕ# LOH# JHUoHNOHúLU## %X# úHNLOGH# ROXúDQ# WHSNLPHOHUH# .$7,/0$# 7(3.ø0(/ (5ø# GHQLU## .DWÕOPD# WHSNLPHOHULQGH# 2 1 4,5-diklor, 1,2- disiklopenten EDúOÕFD#|QHPOL#RODQODUÕ##+2 VÕGÕU# , halojen (X2), H22#YH#+;#NDWÕOPaAlkenlerin Elde Edilme Yöntemleri I. Alkil Halojenürlerden Alkil halojenürlerden bir hidrojen (H) ve bir halojen (X) oÕNDUÕOPDVÕ# LOH# DONHQ# ROXúXU## %X# WHSNLPHQLQ# ROPDVÕ# LoLQ# .2+# W Hidrojen (H2 )#.DWÕOPDVÕ Bir alkene H2#NDWÕOÕUNHQ#QLNHO##1L
#\D#GD#SODWLQ##3W
#JLEL#Natalizörler kullanmak gerekir.alkenin 1 molünde kaçtane oLIW#ED÷#YDUVD#D\QÕ#PRO#VD\ÕVÕQGD#+2 #NDWÕODUDN#DONHQ#GR\uUXOXU#YH#DONDQ#ROXúXU# ED]ÕQÕQ#DONROGHNL#GHULúLN#o|]HOWLVL#NXOODQÕOÕU# Alkol R − CH 2 − CH 2 − Br + KOH
R − CH = CH 2 + KBr + H 2 O
# Alkil Halojenür
# Alken
# ALKEN W Halojen (X CnH2n + H2 2
CnH2n + 2
#.DWÕOPDVÕ Ni ya da Pt
# ALKAN $ONHQOHUH# NROD\OÕNOD# KDORMHQOHU# NDWÕODELOLU## $QFDN# EX# WHSNiCH3 CH CH2 + KOH CH3 H Br Propilbromür CH CH2 +KBr + H2O Propen PHOHULQ#ROXúXP#KÕ]Õ#KDORMHQLQ#DNWLIOL÷L#LOH#GR÷UX#RUDQWÕOÕGÕU# $ONHQLQ###PROQGH# NDo#WDQH#oLIW# ED÷# YDUVD#NDWÕODFDN#RODQ# KDORMHQLQ#PRO#VD\ÕVÕ#GD#R#NDGDU#ROXr. Tepkimede KOH’ un sudaki çözeltisi kulODQÕOÕUVa alken yerine alkol oluúXU## %XUDGD# DONLO# KDORMHQUGHNL# KLGURMHQ# oÕNÕS# \HULQH#2+#JUXEX#ED÷ODQÕU# R − CH = CH 2 + X 2 R − CH − CH 2 l l X X ALKEN 1,2 - halojenalkan CH 3 − CH = CH 2 + Br2 CH 3 − CH − CH 2 l l Br Br Cn H 2n +1−Br + KOH Cn H 2n +1 − OH + KBr + H 2O II. Alkollerden 1#PRO#PRQR#DONROGHQ###PRO#VX#oHNLOLUVH#DONHQ#ROXúXU##%X# LúOHP#LoLQ#GHULúLN#+2 ÕVÕWÕOÕU# SU ALKOL
# W Propen 1,2 - dibrompropan +DORMHQOL#$VLW##+;
#NDWÕOPDVÕ $ONHQH#+;#JLEL#SRODU#ELU#PROHNO#ED÷ODQGÕ÷ÕQGD#SL#ED÷ÕQÕQ# DoÕOGÕ÷Õ# NDUERQODUGDQ# KDQJLVLQH# KDQJL# DWRPXQ# ED÷ODQaFD÷Õ# |QHPOLGLU## $QFDN# HWHQ# \D# GD# #-büten SO4#LOH#DONRO#NDUÕúWÕUÕOÕU#YH#####0C ye kadar gibi simetrik ile R − CH 2 − OH 0
R − CH = CH 2 + H 2 O 170 C
ALKOL
#
H 2 SO 4
ALKEN
#
DONHQOHUGH# EX# GXUXP# |QHPOL# GH÷LOGLr. Simetrik olmayan alkenlerde ise bu durum DúÕOPÕúWÕU# 0$5.2:1ø.29# .85$/, 2 4 CH 3 − CH 2 − CH 2 − OH
CH 3 − CH = CH 2 + H 2 O
PROPANOL
#
1− H SO
# PROPEN # 0$5.2:1ú.29# .85$/,## VLPHWULN# ROPD\DQ# DONHQOHUH# IDUNOÖ# DWRPODUGDQ# ROXüDQ# PROHNOOHU# NDWÖOÖUNHQ## SR]LWLI# L\RQODU# KLGURMHQL# oRN# RODQ# oLIW# EDù# NDUERQXQD# EDù# ODQÖU##1HJDWLI#L\RQODUGD#KLGURMHQL#D]#RODQ#oLIW#EDù#NDUERQX# QD#EDùODQÖU## %X# WHSNLPHGH# VÕFDNOÕN# #### &# FLYDUÕQGD# WXWXOXUVD# DONHQ# \HULQH#HWHU#ROXúXU# 0 III. Alkinlerin HLGURMHQ#øOH#'R\XUXOPDVÕQGDQ 1 mol alkin, 1 mol hidrojen (H2
# JD]Õ# LOH# GR\XUXOXUVD# Buna göre H-X molekülündeki H atomu R − C H = C H 2 1 2 DONHQ#ROXúXU# (2) nolu karbon atomuna, X atomu ise (1) nolu karbon atoPXQD#ED÷ODQÕU# # - 5-
O5*$1ø.#.ø0<$ Orhan BÜLBÜL R CH ALKEN CH2 + H X R CH X CH2 H c) Yanarlar ve H2O +DYDQÕ# RNVLMHQL\OH# \DQDUODU# YH# UQ# RODUDN# &22 ROXúXU# Alkil halojenür C n H 2n + 3ROLPHUOHúPH 3n O nCO + nH O
2 2 22
Tepkimeleri CH3 CH CH2 + H Cl Propen CH3 CH CH2 Cl H 2-klorpropan Bir alNHQ#PROHNOOHULQGHNL#SL#ED÷ODUÕQÕQ#DoÕOPDVÕ\OD#D\QÕ# DONHQ# PROHNOOHULQGHQ# ³Q´# WDQHVLQLQ# ELUELULQH# ED÷ODQPDVÕ# W CH3 sonucu oluúDQ# E\N# PROHNOH# 32/ø0(5 bu olaya da Su (H22
#.DWÕOPDVÕ 32/ø0(5/(ù0(# # GHQLU## 3ROLPHUOHúPH# ROD\ÕQGD# VUHNOL# $ONHQH#VX# NDWÕOPDVÕ#GD#0$5.2:1ø.29# NLUDOÕQD#X\DU## ## PRO#$ONHQH###PRO#VX#NDWÕOÕUVD#PRQR#DONRO#ROXúXU# tekrarlanan birim molekülleri monomer# SROLPHUOHúPHOHUH#|UQHN#YHUHOLP# GHQLU## ùLPGL# ED]Õ# CH Propen CH2 + H OH CH3 CH OH CH3 MONOMER YAPISI H C H C 32/ø0(5ø1 ADI izopropil alkol Yükseltgenme Tepkimeleri Alkenlerin yükseltgenme tepkimeleri yine fonksiyonel C C H C H Cl H C H H C H xn xn 32/ø(7ø/(1 #32/ø7(1
grup olan ]HULQGHQ# JHUoHNOHúLU## H H ETEN Cl C H C Alkenlerdeki yükseltgenme tepkimelerini iki grupta inceleyebiliriz. 1. a) 3L#ED÷ÕQÕQ#NRSWX÷X#WHSNLPHOHU: $ONHQ# VR÷XN# YH# VH\UHOWLN# .0Q24 C 32/ø9ø1ø/./25h5 ( PVC) çözeltisiyle tepkiH H MONOKLORETEN ##9ø1ø/./25h5
H PH\H#JLUHUVH#\DOQÕ]#SL#ED÷Õ#NRSDU#YH#GLRO#ROXúXU##*HQHOOikOH# \NVHOWJHQPH# WHSNLPHOHUL# \D]ÕOÕUNHQ# NXOODQÕODQ# PDGGH# H C C H C H yerine ok üzerine [O ] #\D]ÕOÕU# OH OH R CH CH2 Alken O R CH CH2 H C H xn 32/ø67ø5(1 H )(1ø/(7(1 #67ø5(1
diol OH OH CH2 F C F F C F NDXoXN## F C F ELU# F C F GLHQ# 32/ø7(75$)/25(7$1 PTFE (TEFLON) CH2 CH2 Etilen O CH2 W 1,2-etandiol (glikol) TETRAFLORETEN xn RODQ# L]RSUHQLQ# GR÷DGD# Bir ELOHúL÷LQ# DONHQ# ROXS# ROPDGÕ÷ÕQÕ# GD# EX# WHSNLPHGHQ# DR÷DO# anlayabiliriz. KMnO4# ELOHúL÷L# PHQHNúH# UHQNOL# ROXS# JOikol reQNVL]GLU## 7HSNLPH# EDúÕQGD# NDUÕúÕPÕQ# UHQJL# PeQHNúHGLU# ]DPDQOD# EX# UHQN# ND\EROXUVD# WHSNLPH\H# JiSROLPHUOHúPHVL#VRQXFX#ROXúXU# n ( CH2 C CH 3 izopren C H CH2 ) ren madde alkendir. b) $ONHQ##VÕFDN#YH#GHULúLN#.0Q24
çözeltisi ya da ozon CH2 JD]Õ# #23
# LOH# \NVHOWJHQLUVH# VLJPD# YH# SL# ED÷ODUÕ# ELUOLNWH# NRSDU# YH# DONHQ# oLIW# ED÷ÕQ# ROGX÷X# \HUGHQ# LNL\H# D\UÕOÕU## %uC CH3 C H CH 2 CH 2 C CH3 C H CH2 nun sonucunda aldehit, keton ya da karboksilli asit oluúXU# O C C O O ya da O COH asit ## Dogal Kauçuk $ONHQOHULQ#$\ÕUDFÕ# %URP#o|]HOWLVLQLQ#NÕUPÕ]Õ#UHQJLQLQ#ND\EROPDVÕ# 1. 2. C ya da CH keton aldehit KMnO4# PDVÕ o|]HOWLVLQLQ# PHQHNúH# UHQJLQLQ# ND\ERl# - 6-
O5*$1ø.#.ø0<$ Orhan BÜLBÜL ALKOL CH3CH2CHCH2 + 2KOH → CH3CH2C ≡ CH + 2kBr + H O 2 ll 1 - Bütin Br Br 1,2 - dibrombuta n $/.ø1/(5 Alkinler − C ≡ C− l l # IRQNVL\RQHO# JUXEXQD# VDKLS# GR\PDPÕú# KLGURNDUERQODUGÕU## $ONLQOHUGH# oO# ED÷Õ# #)
# WDúÕ\DQ# NDUERQ# DWRPODUÕ# VS# KLEULWOHúPHVLQH# X÷UDPÕúWÕU#
# II. $ONLQOHULQ#0HWDO#7X]ODUÕQGDQ $ONLQOHULQ# VRG\XP# WX]ODUÕ## DONLOKDORMHQUOHU# LOH# WHSNLPH\H# Bir alkin molekülünde ## \D# GD# GDKD# ID]OD# oO# ED÷# EXOXQDELOLU## ## WDQH# oO# ED÷# JLUHUVH#DONLQ#ROXúXU## bulunduran alkinlerin genel formülü CnH2n tür alkinler R − C ≡ CH ya da – 2# úHNOLQGHGLU## %X# * $ONLQOHUGH# EXOXQDQ# VRG\XP# #1D
# PHWDOL# oO# ED÷Õ# R −C ≡ C − R veya WDúÕ\DQ#NDUERQ#DWRPODUÕQGDki hidrojen atomunun yarinde olur. R − C ≡ C − R1 #úHNOLQGH#RODELOLU##$ONHQOHULQ#HQ#NoN#\HVLQLQ# 6RG\XP#DWRPX#GL÷HU#NDUERQ#DWRPODUÕQD#ED÷ODQPD]# formülü C2H2# ROXS# |]HO# DGÕ# asetilendir. Bunun sonucu olarak alkinlere asetilen sÕQÕIÕ#KLGURNDUERQODU#GD#GHQLU# Alkinlerin AGODQGÕUÕOPDVÕ $ONLQOHULQ# DGODQGÕUÕOPDVÕ# GD# DONHQOHUGH# ROGX÷X# JLELGLU## hoO# ED÷ÕODUÕ# WDúÕ\DQ# HQ# X]XQ# NDUERQ# ]LQFLUL# VHoLOLU## hoO# ED÷ODU#KDQJL#XFD#\DNÕQ#LVH#R#XoWDNL#NDUERQGDQ#LWLEDUHQ#]LQFLrGHNL# NDUERQ# DWRPODUÕQD# # QXPDUD# YHULOLU## =LQFLU# GÕúÕQGDNL# JUXpODU# DOIDEHWLN# VÕUD\OD# YH# ED÷OÕ# EXOXQGXNODUÕ# NDUERQ# QXPDUDODUÕ# EHOLUWLOHUHN# \D]ÕOÕU## 8]XQ# NDUERQ# ]LQFLULQLQ# DONan DGÕQÕQ#VRQXQGDNL##-an R − C ≡ C − Na + R' − X → R − C ≡ C − R' + NaX ALKø/ ALKø/ Na TUZU CH 3 − C ≡ C − Na + CH 3 − Br → CH −C ≡ C − 3
CH# + NaBr
3 2 − Bütin
#
# Alkinlerin Kimyasal Tepkimeleri .DWÕOPD#7HSNLPHOHUL $ONLQOHUGH# ## WDQH# SL# ED÷Õ# EXOXQGX÷XQGDQ# EX# SL# ED÷ODUÕ# DoÕODUDN##DoÕODQ#EX# SL# ED÷ODUÕQD# \HQL#DWRP# ODQDUDN#GR\PXú#KDOH#JHOLU# ya da gruplar ba÷# cinsinden eki yerine - in#HNL#JHWLULOHUHN#DONLQLQ#DGÕ# EHOLUOHQPLú# ROXU## $ONLQGH# ELUGHQ# ID]OD# oO# ED÷# YDUVD# DONLQ# DGÕQGDQ# | QFH# ED÷ODUÕQ# NoN# NDUERQ# QXPDUDODUÕ# YH# WHNUDU# VD\ÕODUÕ#\D]ÕOÕU##ùLmGL#DúD÷ÕGDNL#|UQHNOHUL#LQFHOH\HOLP. W Hidrojen (H2
#.DWÕOPDVÕ NDWDOL]|UO÷QGH# ## PRO# DONLQH# Nikel (Ni), platin (Pt) ya da alkan oluúXU# ## PRO# KLGURMHQ# NDWÕOÕUVD# DONHQ## ## PRO# KLGURMHQ# NDWÕOÕUVD# H −C ≡ C −H
# Etin (asetilen)
2
# − bütin CH 3 − C ≡ CH
Propin
# CH3
- bütinC
CH
− CH
≡
2 − # 1 CH3 R − C ≡ CH + H 2 → R − CH = CH 2 CH 3 − C ≡ C − CH 3
Alkin
#
#
Alkin
ALKEN
#
# ALKAN
# propen R − C ≡ CH + 2H 2 → R − CH 2 − CH 3 CH 3 CH3 C C C ÖRNEK: CH 3 − C ≡ CH + H 2 4,4-dimetil, 2-pentin CH3 CH3 H C C C CH CH3 4,5,5- trimetil, 1,2- dihekzin C CH3 CH3
# propin CH 3 − CH = CH 2 CH 3 − C ≡ CH
+
# propin W 2H 2 CH 3 − CH 2 − CH 3
propan
#
Alkinlerin Elde Edilme Yöntemleri I. Di Halojenli Alkanlardan øNL# KDORMHQOL# DONDQODU# .2+¶XQ# DONROGHNL# o|]HOWLVL\OH# UHDkVL\RQD# VRNXOXUVD# NRPúX# LNL# NDUERQGDNL# \D# GD# D\QÕ# NDUERQ# DWRPXQGDNL# LNL# KDORMHQ# LOH# ELUOLNWH# LNL# GH# KLGURMHQ# DWRPX# oÕNaUDN#DONLQ#ROXúXU# Halojen (X2) .DWÕOPDVÕ $ONHQOHUGH#ROGX÷X#JLEL#EXUDGD#GD#SL#ED÷ODUÕ#DoÕODUDN###PRO# alkine 2 mol halojen (X2
# NDWÕODUDN# DONLO# KDORMHQUOHU# ROuúXU##$ONHQOHU#GH#ROGX÷X#JLEL#EXUDGD#GD#EURP## %U2 ) çözeltiVLQLQ#NÕUPÕ]Õ#UHQJL#]DPDQOD#ND\EROXU##%X#EURP#o|]HOWLVL#LOH# oODQ#WHSNLPH#DONLQOHULQ#GH#D\ÕUDFÕGÕU# ALKOL R − CH − CH 2 + KOH →R − C ≡ CH + 2KX + 2H 2 O
alkan
# di halojenli ya da ALKOL l X l X
#
Alkin Br R − C ≡ CH + 2 Br2 → Alkin kirmizi l l Br l l Br
Br
#
1,1,2,2 - tetrabromalkan (renksiz) R − C − CH Cn H 2n X 2 + 2KOH # - 7-
C n H 2n − 2 + 2KX 2 + H 2 O
O5*$1ø.#.ø0<$ %U %U Orhan BÜLBÜL H − C ≡ C − H + 2 CuCl → Cu − C ≡ C − Cu + 2HCl KIRMIZI ÇÖKELEK 3 R − C C − H + CuCl NH NH 3
# &+####&############&+########%U#####################&+####&########&+ 3URSLQ %U %U ########WHWUDEURPSURSDQ KIRMIZI ÇÖKELEK 3 R − C C − R + CuCl R −C ≡ C − H
Tepkime olmaz
NH
# + HCl W +DORMHQOL#$VLW##+;
#.DWÕOPDVÕ 3ROLPHUOHúPH#7HSNLPHOHUL $ONLQOHU# GH# $ONHQOHU# JLEL# SL# ED÷ODUÕ# DoÕODUDN# SROLPHUOHúH$ONHQOHUGH# ROGX÷X# JLEL# 0DUNRZQLNRY# NXUDOÕQD# J|UH# ## PRO# DONLQLQ###WDQH# SL# ED÷Õ# DoÕODUDN###PRO#+;#DVLGL#NDWÕOÕU#YH# GL# halojenli aONDQ#ROXúXU# X R-C CH + 2 H - X R-C CH 3 bilirler. Yanma Tepkimeleri $ONLQOHU# GH# GL÷HU# KLGURNDUERQODU# JLEL# \DQGÕNODUÕQGD# &22 ve H22#ROXúWXUXUODU# Cn H 2n − 2 + 3n −1 O2 5 CO2 + 4 H 2 O CH3 $6(7ø/(1 Alkin X Dihalojenli alkan (2 ) Br CH3 - C CH + 2 H - Br propin CH3 - C Br 2,2-dibrompropan Devam edecek W Su (H22
nCO2 + (n − 1) H 2 O
C5 H8 + 7 O2
#.DWÕOPDVÕ VX# NDWÕOGÕ÷ÕQGD# DOGHKLW# \D# GD# NHWRQ# ROXúXU## $ONLQH# $ONLQOHULQ# LON# \HVL# DVHWLOHQH# VX# NDWÕOÕUVD# DVHWDOGHKLW# ROuúXU##$ONLQ###YH\D#GDKD#ID]OD#NDUERQOX#LVH#EX durumda keWRQ#ROXúXU##ùLPGL#DúD÷ÕGDNL#LNL#|UQH÷L#LQFHOH\HOLP# O H-C C - H + H2 O Asetilen Hg+2 H2SO4 CH3 - C H Asetaldehit O CH 3 C CH + H2O Propin Hg+2 H2SO4 CH3 C Aseton CH3 0HWDO#ø\RQODUÕ#øOH#
# NORUU# ## &X&O#
# ELOHúL÷LQLQ# DPRQ\DNOÕ# #1+3 ) çö]HOWLVL#DONLQ#LOH#WHSNLPH\H#JLUHUVH#EDNÕUÕQ#DONLQOL#WX]X#ROXúXU#EX# WX]XQ#UHQJL#NÕUPÕ]ÕGÕU# # - 8-