WPC
a ܲ֩ q$"c,"wxF6#
cw)1[T2oNÂN~ӔΉez0Om_*Hs;}wMJLUM8_2p[4 6W}<$NrTLmwd!hv" # ! 4
U
P U % 0 1
1 u 8 0
i 1 ^ w @ 4 m 0@ w % 1 1 # U > H 1 1
@ J o ? z @ J o i @
3) o =) @ J ) ? 7* @ J -+ o w+ ? +5 ? !6 o 7 ? @ @ J A o DB ? J @ J K o 0L ? U 1 V @ J nW 1 W 1 ?X o X ? Ga @ J ;b o b ? l @
&m o 0m ? m @ J n o 0o ? y @ J z o D ]z ? f a 1 1 H 1 υ 1 V D 3 ݆ A Q a 0 ' 0 D # 7 g @
o @ J X o I ? @ J o I 9 ? @
o B @ @
] o g 1 B D + @
0 0 N : D 3 B * 3 D 3 ] B * D 3 B 7 B 7 $ D 3 [ B D 5 D - D 3
B @ D / ] B D 3 B * ܩ D 3 B * 9 D 3 c C D 3 D 3 B D C 3 B - v o S S S S S S S S S S A C ƭ C C C C . C H C b C | C C A ʮ ʮ ʮ ʮ ʮ C e K y o c e r a M i t a F S - 1 0 1 0 K X 0 ( 9 Z 8 T i m e s N e w R o m a n S t a n d a r d X ( /I$ DEUS. , , , . .
T R V6& A 4 X3' L e t t e r 6& A 4 3' T$ P < ( C E Q ] i u A u t o L i s t 1 I . 1 . I . 1 . I . 1 . I . 1 . I . 1 . I . 1 . I . 1 . I . 1 . 3# 3 7 = C I Q Y a g 1 . a . i . ( 1 ) ( a ) ( i ) 1 ) a ) ( A %$ 2 I. 0
. 3
0 EC E K Q W ] c i o A u t o L i s t 2 I . a ) I . I . I . I . I . I . 0
_ _ _ _ E U 1 = 0 M L - 3| x U ( O ,$ 0 2 E a
)3
0 ` "" U C E K Q W ] c i o A u t o L i s t 3 I I a ) I I I I I I I I I I I I e C E K Q W ] c i o A u t o L i s t 4 I I a ) I I I I I I I I I I I I a u f g a b e n z u r n u c l e o p h i l e n s u b s t i t u t i o n _ 0 1
*
' $ J o h a n n e s H a m m $ 0 J o h a n n e s H a m m
.
( 9 Z & T i m e s N e w R o m a n uC E K Q W ] c i o A u t o L i s t 5 I . a ) I . I . I . I . I . I . (ڽC E K Q W ] c i o A u t o L i s t 6 a ) a ) a ) a ) a ) a ) a ) a ) C : \ E I G E N E ~ 1 \ C H E M S K 5 0 \ 2 - B R O M ~ 1 . P C X WPC e f f f e ?b b!R `!b `1 bA b` BB A` 7`^ ?b ? b bR `O /// q ¼ h | Ұj u б @@@ " / 1 @ O @ / R" OOO A @ @ B b a O / ! !! A b! ___ b b B @ _ "" ` A /" 1 11 `B @ rrr @ @ " / 2? @# B BB B ` ` @ @@ @ @A `< ` bb ? A A @" A ` `` P A A b A b A b % "Y + " " " AA 5 @p @ B @ B A ! B @@ ` ` _ b ` a R @ A ? B B A2 t q 5 ҿ f } 5ҿ @ D C : \ E I G E N E ~ 1 \ C H E M S K 5 0 \ 2 - B R O M ~ 1 . P C X C : \ E i g e n e D a t e i e n \ c h e m s k 5 0 \ 2 - b r o m - 2 - m e t h y l p r o p a n . p c x \ |Ф Τ "` sG` W d #GGd lϤ Ϥ | pе C : \ E I G E N E ~ 1 \ C H E M S K 5 0 \ 2 - B R O M ~ 2 . P C X WPC U V V V U ?b b!R `!b `1 bA b` BB A` 7`^ ?b ? b bR `O /// q ¼ h | Ұj u б @@@ " / 1 @ O @ / R" OOO A @ @ B b a O / ! !! A b! ___ b b B @ _ "" ` A /" 1 11 `B @ rrr @ @ " / 2? @# B BB B ` ` @ @@ @ @A `< ` bb ? A A @" A ` `` P A A b A b A b % "Y + " " " AA 5 @p @ B @ B A ! B @@ ` ` _ b ` a R @ A ? B B A2 t q 5 ҿ V }B B B B WPC s U 5 1 3 + % . 1 + ` My ` y ` My - + % y y # C : \ E I G E N E ~ 1 \ C H E M S K 5 0 \ 1 - B R O M ~ 2 . P C X @ D C : \ E I G E N E ~ 1 \ C H E M S K 5 0 \ 1 - B R O M ~ 1 . P C X C : \ E i g e n e D a t e i e n \ c h e m s k 5 0 \ 1 - B r o m - p e n t a n . p c x uy? I? > |Ф Τ "D sGD W Ջ #GGՋ lϤ C : \ E I G E N E ~ 1 \ C H E M S K 5 0 \ 1 - B R O M ~ 1 . P C X WPC 2 3 3 3 2 ?b b!R `!b `1 bA b` BB A` 7`^ ?b ? b bR `O /// q ¼ h | Ұj u б @@@ " / 1 @ O @ / R" OOO A @ @ B b a O / ! !! A b! ___ b b B @ _ "" ` A /" 1 11 `B @ rrr @ @ " / 2? @# B BB B ` ` @ @@ @ @A `< ` bb ? A A @" A ` `` P A A b A b A b % "Y + " " " AA 5 @p @ B @ B A ! B @@ ` ` _ b ` a R @ A ? B B A2 t q 5 ҿ a 3 }Z Z @ D C : \ E I G E N E ~ 1 \ C H E M S K 5 0 \ 1 - B R O M ~ 1 . P C X C : \ E i g e n e D a t e i e n \ c h e m s k 5 0 \ 1 - B r o m - p e n t a n . p c x uyxҍ I\ҍ \э |Ф Τ "l sGl W hǍ #GGhǍ lϤ @ D C : \ E I G E N E ~ 1 \ C H E M S K 5 0 \ 2 - B R O M ~ 2 . P C X C : \ E i g e n e D a t e i e n \ c h e m s k 5 0 \ 2 - B r o m - p e n t a n . p c x uyt IX X |Ф Τ "h sGh W r #GGr lϤ WPC E F F F E ?b b!R `!b `1 bA b` BB A` 7`^ ?b ? b bR `O /// q ¼ h | Ұj u б @@@ " / 1 @ O @ / R" OOO A @ @ B b a O / ! !! A b! ___ b b B @ _ "" ` A /" 1 11 `B @ rrr @ @ " / 2? @# B BB B ` ` @ @@ @ @A `< ` bb ? A A @" A ` `` P A A b A b A b % "Y + " " " AA 5 @p @ B @ B A ! B @@ ` ` _ b ` a R @ A ? B B A2 t q 5 ҿ F }4 # " "#4 @ D C : \ E I G E N E ~ 1 \ C H E M S K 5 0 \ 1 - B R O M ~ 2 . P C X C : \ E i g e n e D a t e i e n \ c h e m s k 5 0 \ 1 - B r o m - 3 - m e t h y l b u t a n . p c x L |Ф Τ "\ sG\ W #GGlϤ Ϥ | p & C : \ E I G E N E ~ 1 \ C H E M S K 5 0 \ 2 - B R O M ~ 1 . P C X WPC e f f f e ?b b!R `!b `1 bA b` BB A` 7`^ ?b ? b bR `O /// q ¼ h | Ұj u б @@@ " / 1 @ O @ / R" OOO A @ @ B b a O / ! !! A b! ___ b b B @ _ "" ` A /" 1 11 `B @ rrr @ @ " / 2? @# B BB B ` ` @ @@ @ @A `< ` bb ? A A @" A ` `` P A A b A b A b % "Y + " " " AA 5 @p @ B @ B A ! B @@ ` ` _ b ` a R @ A ? B B A2 t q 5 ҿ f } 5ҿ % @ D C : \ E I G E N E ~ 1 \ C H E M S K 5 0 \ 2 - B R O M ~ 1 . P C X C : \ E i g e n e D a t e i e n \ c h e m s k 5 0 \ 2 - b r o m - 2 - m e t h y l p r o p a n . p c x $f |Ф Τ "4l sG4l W ܐ #GG ܐ lϤ Ϥ |e pе ) C : \ E I G E N E ~ 1 \ C H E M S K 5 0 \ 2 - B R O M ~ 3 . P C X WPC g h h h g ?b b!R `!b `1 bA b` BB A` 7`^ ?b ? b bR `O /// q ¼ h | Ұj u б @@@ " / 1 @ O @ / R" OOO A @ @ B b a O / ! !! A b! ___ b b B @ _ "" ` A /" 1 11 `B @ rrr @ @ " / 2? @# B BB B ` ` @ @@ @ @A `< ` bb ? A A @" A ` `` P A A b A b A b % "Y + " " " AA 5 @p @ B @ B A ! B @@ ` ` _ b ` a R @ A ? B B A2 t q 5 ҿ h }9 9 47 9 9 ʀ5ҿ ( @ D C : \ E I G E N E ~ 1 \ C H E M S K 5 0 \ 2 - B R O M ~ 3 . P C X C : \ E i g e n e D a t e i e n \ c h e m s k 5 0 \ 2 - B r o m - 3 - m e t h y l b u t a n . p c x p|Ф Τ "sGW /#GG /lϤ Ϥ | p (C E K Q W ] c i o A u t o L i s t 7 a ) a ) a ) a ) a ) a ) a ) a ) / C : \ E I G E N E ~ 1 \ C H E M S K 5 0 \ 1 - B R O M ~ 3 . P C X (h C E K Q W ] c i o A u t o L i s t 8 I I I I I I I I I I I I I I I I (h C E K Q W ] c i o A u t o L i s t 9 I I I I I I I I I I I I I I I I WPC ) * * * ) ?b b!R `!b `1 bA b` BB A` 7`^ ?b ? b bR `O /// q ¼ h | Ұj u б @@@ " / 1 @ O @ / R" OOO A @ @ B b a O / ! !! A b! ___ b b B @ _ "" ` A /" 1 11 `B @ rrr @ @ " / 2? @# B BB B ` ` @ @@ @ @A `< ` bb ? A A @" A ` `` P A A b A b A b % "Y + " " " AA 5 @p @ B @ B A ! B @@ ` ` _ b ` a R @ A ? B B A2 t q 5 ҿ . * }4 4 , @ D C : \ E I G E N E ~ 1 \ C H E M S K 5 0 \ 1 - B R O M ~ 3 . P C X C : \ E i g e n e D a t e i e n \ c h e m s k 5 0 \ 1 - B r o m - B u t a n . p c x :uyT}I8} 8||Ф Τ "HsGHW #GGlϤ 2 C : \ E I G E N E ~ 1 \ C H E M S K 5 0 \ 1 - B R O M ~ 4 . P C X WPC a b b b a ?b b!R `!b `1 bA b` BB A` 7`^ ?b ? b bR `O /// q ¼ h | Ұj u б @@@ " / 1 @ O @ / R" OOO A @ @ B b a O / ! !! A b! ___ b b B @ _ "" ` A /" 1 11 `B @ rrr @ @ " / 2? @# B BB B ` ` @ @@ @ @A `< ` bb ? A A @" A ` `` P A A b A b A b % "Y + " " " AA 5 @p @ B @ B A ! B @@ ` ` _ b ` a R @ A ? B B A2 t q 5 ҿ
b }!
! ! 1 @ D C : \ E I G E N E ~ 1 \ C H E M S K 5 0 \ 1 - B R O M ~ 4 . P C X C : \ E i g e n e D a t e i e n \ c h e m s k 5 0 \ 1 - B r o m - 2 , 2 - d i m e t h y l p r o p a n . p c x Τ "sGW #GG lϤ Ϥ |xpеϤ 5 WPC 5 1 3 + % . 1 + ` g = ag = g - + % q cg 4 @ D C : \ E I G E N E ~ 1 \ C H E M S K 5 0 \ 2 - B R O M ~ 1 . P C X C : \ E i g e n e D a t e i e n \ c h e m s k 5 0 \ 2 - b r o m - 2 - m e t h y l p r o p a n . p c x pa|Ф Τ "gsGgW X#GGXlϤ Ϥ | apе 8 C : \ E I G E N E ~ 1 \ C H E M S K 5 0 \ 1 - B R O M ~ 2 . P C X WPC E F F F E ?b b!R `!b `1 bA b` BB A` 7`^ ?b ? b bR `O /// q ¼ h | Ұj u б @@@ " / 1 @ O @ / R" OOO A @ @ B b a O / ! !! A b! ___ b b B @ _ "" ` A /" 1 11 `B @ rrr @ @ " / 2? @# B BB B ` ` @ @@ @ @A `< ` bb ? A A @" A ` `` P A A b A b A b % "Y + " " " AA 5 @p @ B @ B A ! B @@ ` ` _ b ` a R @ A ? B B A2 t q 5 ҿ F }4 # " "#4 7 @ D C : \ E I G E N E ~ 1 \ C H E M S K 5 0 \ 1 - B R O M ~ 2 . P C X C : \ E i g e n e D a t e i e n \ c h e m s k 5 0 \ 1 - B r o m - 3 - m e t h y l b u t a n . p c x |Ф Τ " sG W #GGlϤ Ϥ |p ; C : \ E I G E N E ~ 1 \ C H E M S K 5 0 \ 1 - B R O M ~ 5 . P C X WPC O P P P O ?b b!R `!b `1 bA b` BB A` 7`^ ?b ? b bR `O /// q ¼ h | Ұj u б @@@ " / 1 @ O @ / R" OOO A @ @ B b a O / ! !! A b! ___ b b B @ _ "" ` A /" 1 11 `B @ rrr @ @ " / 2? @# B BB B ` ` @ @@ @ @A `< ` bb ? A A @" A ` `` P A A b A b A b % "Y + " " " AA 5 @p @ B @ B A ! B @@ ` ` _ b ` a R @ A ? B B A2 t q 5 ҿ P }> > > : @ D C : \ E I G E N E ~ 1 \ C H E M S K 5 0 \ 1 - B R O M ~ 5 . P C X C : \ E i g e n e D a t e i e n \ c h e m s k 5 0 \ 1 - B r o m - 2 - m e t h y l - b u t a n . p c x w|Ф Τ "}sG}W #GGlϤ Ϥ |@wpе8 T A B E L L E A (գ E G M S Y _ e k q A u t o L i s t 1 0 I I I I I I I I I I I I I I I I ( E G M S Y _ e k q A u t o L i s t 1 1 I I I I I I I I I I I I I I I I JE G M S Y _ e k q A u t o L i s t 1 2 a ) a ) a ) a ) a ) a ) a ) a ) E G M S Y _ e k q A u t o L i s t 1 3 I I a ) I I I I I I I I I I I I W W W W ' d x d E F Z G C C << C S t u f e 1 S t u f e 2 S t u f e 3 S t u f e 4 S t u f e 5 ( 3$
/I! DEUS. , , , . .
T R W6& A 4 X3' L e t t e r 6& A 4 3' T$ P < ( $$ 1
-
F " DEUS. , , , . .
$ P < _
X X ChemieArbeitsblatt# X4' X
# __Klasse___Name:__________________________Datum:__.__.__ J WPC s U 5 1 3 + % . 1 + ` My ` y ` My - + % y y L C : \ E I G E N E ~ 1 \ C H E M S K 5 0 \ 2 - B R O M ~ 4 . P C X WPC a b b b a ?b b!R `!b `1 bA b` BB A` 7`^ ?b ? b bR `O /// q ¼ h | Ұj u б @@@ " / 1 @ O @ / R" OOO A @ @ B b a O / ! !! A b! ___ b b B @ _ "" ` A /" 1 11 `B @ rrr @ @ " / 2? @# B BB B ` ` @ @@ @ @A `< ` bb ? A A @" A ` `` P A A b A b A b % "Y + " " " AA 5 @p @ B @ B A ! B @@ ` ` _ b ` a R @ A ? B B A2 t q 5 ҿ b }0 0 . ) 0 0 K @ D C : \ E I G E N E ~ 1 \ C H E M S K 5 0 \ 2 - B R O M ~ 4 . P C X C : \ E i g e n e D a t e i e n \ c h e m s k 5 0 \ 2 - B r o m - 2 - m e t h y l b u t a n . p c x |Ф Τ "(sG(W #GGlϤ Ϥ |p O C : \ E I G E N E ~ 1 \ C H E M S K 5 0 \ 2 - B R O M ~ 4 . P C X WPC a b b b a ?b b!R `!b `1 bA b` BB A` 7`^ ?b ? b bR `O /// q ¼ h | Ұj u б @@@ " / 1 @ O @ / R" OOO A @ @ B b a O / ! !! A b! ___ b b B @ _ "" ` A /" 1 11 `B @ rrr @ @ " / 2? @# B BB B ` ` @ @@ @ @A `< ` bb ? A A @" A ` `` P A A b A b A b % "Y + " " " AA 5 @p @ B @ B A ! B @@ ` ` _ b ` a R @ A ? B B A2 t q 5 ҿ b }0 0 . ) 0 0 N @ D C : \ E I G E N E ~ 1 \ C H E M S K 5 0 \ 2 - B R O M ~ 4 . P C X C : \ E i g e n e D a t e i e n \ c h e m s k 5 0 \ 2 - B r o m - 2 - m e t h y l b u t a n . p c x |Ф Τ "sGW -#GG-lϤ Ϥ |p R WPC 5 1 3 + % . 1 + ` g :g g - + % q <g d U WPC 5 1 3 + % . 1 + ` g U y g U g - + % g z g E G M S Y _ e k q A u t o L i s t 1 4 I I a ) I I I I I I I I I I I I d ' d x d w ( 3$
/I! DEUS. , , , . .
T R W6& A 4 X3' L e t t e r 6& A 4 3' T$ P < ( # $ Abbildung 1
S t u f e 1 S t u f e 2 S t u f e 3 S t u f e 4 S t u f e 5 ^ ^ ^ ^ ' d x d & p d P d ` ` ` ` ' d x d & p P d d b c b c ' d x d 3 + 0 d d d 3 + 0 d d d e e e e ' d x d d W W W W W ' d x d W ' d x d i i i i ' d x d d k k ' d x d P P d m m m m ' d x d & 0 d d o o o o ' d x d & P d d S S S S ' d x d d k k k k ' d x d t t t t ' d x d d v v v v 7 H a a r f e i n d x d ) H a a r f e i n d WPC s U 5 1 3 + % . 1 + ` My ` y ` My - + % y y S t u f e 1 S t u f e 2 S t u f e 3 S t u f e 4 S t u f e 5 y X Z e i c h e n & o b j e k t <<= 8 C HK K K K d d (d 2d V! "" "" # U ! ! U # U ! ! U # X4' X ! U # U ! X X4' bungenzur_ Nucleophilen_ ԀSubstitution# U ! ! Uk # # X4' X ! U # x 0 X F X X0 L E 3 L % - X F ` X X- %m 2 E I
.3
0 F FormulieredieStrukturformelnderfolgendenVerbindungeninjederGruppeundordnedie VerbindungennachihrerReaktivittbeiSN2Reaktionen: %m
F"F" Ќ , , 0 F 2 E a
)3
0 F"F" 2Brom2methylbutan,1Brom pentan,2Brompentan , ; x
"" Ќ , ,& 0 F 2 E b
)3
0 F"F" 1Brom3methylbutan,2Brom2methylbutan,2Brom3methylbutan ,& Q d "" Ќ , ,A 0 F 2 E c
)3
0 F"F" 1Brom butan,1Brom2,2_ dimethylpropan_ ,1Brom2methylbutan,1Brom3 P methylbutan. ,A l
"" Ќ L @ ( L II.0 F StelleeineReaktivittsreihef rdieVerbindungenjederGruppebeiSN1Reaktionenauf: P F"F" L A J( (@ L , , 0 F 2 J a
)3
0 F"F" 2Brom2methylbutan,1Brom pentan,2Brompentan , <
"" Ќ , , 0 F 2 J b
)3
0 F"F" 1Brom3methylbutan,2Brom2methylbutan,2Brom3methylbutan , &
( "" Ќ , , 0 F 2 J c
)3
0 F"F" 1Brom butan,1Brom2,2_ dimethylpropan_ ,1Brom2methylbutan,1Brom3 methylbutan. , K
"" Ќ L B (A L III.0 F NimmalsBeispieleinbeliebigesAlkylhalogenidundNaOHinwssrigerLsung. VergleichebeideMechanismen,indemDueineTabellemiteinerSpaltef rdieSN1undeineranderenf rdieSN2Reaktionanfertigst,hinsichtlichfolgenderKategorien:
F"F" , ,# 0 F 2 a
)3
0 F"F" derStereochemie ,# N ` "" Ќ , , 0 F 2 b
)3
0 F"F" derReaktionsordnung , 9 L "" Ќ , , 0 F 2 c
)3
0 F"F" derrelativenGeschwindigkeitvonCH3X,C2H5X,_ iso_ ԄC3H7Xund_ tert_ .C4H9X. , ( 8t "" Ќ , , 0 F 2 d
)3
0 F"F" derrelativenGeschwindigkeitvonRCl,RBrundRI. , $` "" Ќ , , 0 F 2 e
)3
0 F"F" desEinflusseseinerVerdoppelungderKonzentrationvonRXaufdie L Reaktionsgeschwindigkeit ,
"" Ќ , ,. 0 F 2 f
)3
0 F"F" desEinflusseseinerVerdoppelungderKonzentrationvonOH aufdie $ Reaktionsgeschwindigkeit ,. Y
"" Ќ , , 0 F 2 g
)3
0 F"F" desEinflussesderErhhungdesWassergehaltesderLsungaufdie Reaktionsgeschwindigkeit ,
"" Ќ ( &( f U ! X X4' U ! ! U H 8 4 l ~8
X
` EX X X H 8 4 l ~8 b 4 H
` E^b4H 4H ^b4H Q r b ^ j ~8X `
p @ @ @"
I E` vr Lsungen # U ! ! U* # # X4' X ! U # L u B L % % 2 u I
.3
0 F Formulieredie Strukturformeln derfolgendenVerbindungeninjederGruppeundordne /( dieVerbindungennachihrer ReaktivittbeiSN2Reaktionen: % F"F" Ќ , p K < , ( ` ~0 f
` E f f cc p K H 8 4 l ~0 &
` E|& & |& ||"" ,i 0 F 2 u a
)3
0 F|F" 2Brom2methylbutan,1Brom pentan,2Brompentan , "" Ќ , , 0 F 2 u b
)3
0 F"F" 1Brom3methylbutan,2Brom2methylbutan,2Brom3methylbutan , "" Ќ , N > : h ~0 B t
` @ H EL B t t @ 6 , 0 F 2 u c
)3
0 F"F" 1Brom_ butan_ ,1Brom2,2_ dimethylpropan_ ,1Brom2methylbutan,1Brom3 @ @ "" methylbutan. ,i |" Ќ N > : h ~0C n
` @ H E4n
(b
8 || N > : h ~0M x
z
` @ H Ex
z z l
L ڽ( L % %" 2 ڽ a
)3
0 F N > : h ~0 z
` @ H Ez z N > : h ~0m
` @ H E^ R8 r b ^ j ~0n s p s @ @ @" ( ) [ s Eu
s s {*
I r b ^ j ~0! s p s @ @ @" ( ) [ s E(
s s 5 Y r b ^ j ~0l s p s @ @ @" ( ) [ s E
s s A
"" DieReaktivittnimmtf r SN2Reaktionenab: zunehmende sterischeHinderung erschwert
SN2.DieReaktivittnimmtf r SN1Reaktionzu: zunehmendeStabilisierungdurchden +IEffekt s
l derMethylgruppen.SterischeHinderungund+IEffektergnzensichundbeg nstigenSN1. c\
UnterschiedeinderRGbei SN2Reaktionen sindhauptschlichauf sterischeFaktoren und OH
nichtaufelektronischeFaktorenzur ckzuf hren.Jegr erdieAnzahlderSubstituentenandemKohlenstoffist,derdasHalogentrgt,destokleinerwirddieReaktivittgegen bereinerSN2Reaktion.UnterschiedeinderRGbei SN1Reaktionen sindhauptschlichauf elektronischeFaktoren und nichtauf sterischeFaktoren zur ckzuf hren. b)0 F 1Brom3methylbutan,2Brom2methylbutan,2Brom3methylbutan F"F" p < , ( ` ~0 ,
` E , ,
p p ( < , ( ` ~0 X
` EHX X L p p % < , ( ` ~0 f
` E f f p p % < , ( ` ~0# f
` E> f f W p p ( < , ( ` ~0 8 X
` E8X X IL p p N < , ( ` ~0 V R
` EVR R p "" p ( < , ( ` ~0 B X
` EBX X cL p cc SN2Reihenfolge: cccc p < , ( ` ~01 ( ,
` E(, , p I 9 5 l ~01 ( , 0 E(, , (, cc 4 r b ^ j ~0 p @ @ @"
I EZ
i e "" 0 F 0 F"F" 0 "" Reaktivittf rSN2nimmtab0 p " " 0 p"p" f rSN1zu C < "" / ( zunehmendesterischeHinderungerschwertSN2zunehmender+IEffektbeg nstigtSN1 L + ( ( L % %6 2 c
)3
0 F 1Brom butan,1Brom2,2_ dimethylpropan_ ,1Brom2methylbutan,1Brom3methyl ! " butan. %6 ?6
F"F" Ќ Reihenfolgef rReaktionsgeschwindigkeitnach SN2 zunehmend: $"% p 1 < , ( ` ~0
:* < p
` E:*<p <p ) p p : < , ( ` ~0 ) " p
` E )"p "p I ) p p 7 < , ( ` ~03 b*
` Eb* w* p p , < , ( ` ~0 + Z
` E +Z Z a * p p 1 < , ( ` ~0{ & < p
` EP&<p <p & p p 1 < , ( ` ~0{ & < p
` EP&<p <p & p ""
p , < , ( ` ~0 & Z
` E &Z Z u &
p p 7 <
, ( ` ~0 &
` E"& & p p 7 < , ( ` ~0 &
` E"& &
p
p : < , ( ` ~0 & " p
` E &"p "p & p p : < , ( ` ~0 & " p
` E &"p "p & p
p , < , ( ` ~0 '
` E* ' ='rb p
""
T r
b ^ j ~0Z )
p @ @ @"
I E
#+ * e
abnehmendesterischeHinderungdurchdieMethylGruppenbeg nstigtSN2abnehmende+I nEffekterschwertSN1:der+IEffektistabernichtstarkvorhanden:dasReaktionszentrumistimmereinprimresCAtom. /-1 L V (+ L III.0 F NimmalsBeispieleinbeliebigesAlkylhalogenidundNaOHinwssrigerLsung. VergleichebeideMechanismen,indemDueineTabellemiteinerSpaltef rdieSN1undeineranderenf rdieSN2Reaktionanfertigst,hinsichtlichfolgenderKategorien:
F"F" , ,%B 0 F 2 II3
0 F"F" , ,7C 0 F 2 a
)3
0 F"F" derStereochemie ,7C bC "" Ќ , ,'D 0 F 2 b
)3
0 F"F" derReaktionsordnung ,'D RD "" Ќ , ,E 0 F 2 c
)3
0 F"F" derrelativenGeschwindigkeitvonCH3X,C2H5X,_ iso_ ԄC3H7Xund_ tert_ .C4H9X. ,E AE "" Ќ , ,F 0 F 2 d
)3
0 F"F" derrelativenGeschwindigkeitvonRCl,RBrundRI. ,F F "" Ќ , ,G 0 F 2 e
)3
0 F"F" desEinflusseseinerVerdoppelungderKonzentrationvonRXaufdie {t Reaktionsgeschwindigkeit ,G G
"" Ќ , ,H 0 F 2 f
)3
0 F"F" desEinflusseseinerVerdoppelungderKonzentrationvonOHaufdie S
L Reaktionsgeschwindigkeit ,H "I
"" Ќ , ,BJ 0 F 2 g
)3
0 F"F" desEinflussesderErhhungdesWassergehaltesderLsungaufdie + $
Reaktionsgeschwindigkeit ,BJ mJ
"" Ќ * = W > d d d X d d X d d X "" , d d ,
d d , d d +
* q
*
Kriterien
A q , ! ?8 q A
6 , ! ?8 q 6 SN1
A q , ! ?8 " q A
6 , ! ?8 " q 6 SN2 - # ! ?8 " q - Stereochemie
InversionundRetention:_ Racemisierung_
' " ' vollstndigeInversion:_ Waldensche_ ԀUmkehr " Reaktionsordnung
+$ Reaktion1.Ordnung
' +$ " ' Reaktion2.Ordnung +$ " relativeGeschwindigkeitvon:Alkylstruktur
CH3XC2H5X>_ iso_ Ԅ C3H7X>_ tert_ .C4H9X. " relativeGeschwindigkeit:Abgangsgruppe
# RCl ><RBr ><RI .Reaktivitt>zunehmend
' % " ' RCl ><RBr < >RI.Reaktivitt>zunehmend ' " RGVerdoppelungvonc(_ RY_ )
[ T) Verdoppelungvonc(RX)verdoppeltdieRG
' [ T+ " ' Verdoppelungvonc(RX)verdoppeltdieRG [ T- " RGVerdoppelungvonc(OH)
/ Verdoppelungvonc(OH) 0 spieltkeineRolle
' 1 " ' Verdoppelungvonc(OH) 2 verdoppeltdieRG 3 " RGErhhungdesWassergehalts
3!, 5 ErhhungdesWassergehaltssteigertdieRG
' 3!, 7 " ' ErhhungdesWassergehaltsbeeinflusstnichtwesentlichdieRG" " : "
"