tema 6 alcanos
TRANSCRIPT
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CH3 CH2 CH2 CH3
CH3 CH CH3
CH3 ! " "
#
H2C CH2
CH2
H2C
H2C
$ # %
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/ "
0C
1 5 10 15
-100C
-200C
200C
100C
Punto de ebullicin
Punto de fusin
T (C)
nmero de carbonos
" " 0
1
$ 2 3
4 - -(5 3
" " #2
6 7 / 8 7 9 " : ;( &
, & ,
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$ < < (;< <
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B
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C C
HH
HH
H
H
C C
HH
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H
H
H
60
ALTERNADA ECLIPSADAH
H HH
HH HH
HH
HH
4 @ > "
@ 0
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0 60 120 180 240 300 360
Eclipsada
Alternada
E
Ekcal/mol
ngulo de torsin ()
60
H2H3
H1H
HH = 0
60
H2
H3 H1H
HH
60
H1H2
H3H
HH
H1
H2 H3H
HH
60
60
H3H1
H2H
HHH3
H1 H2H
HH
60
= 60 = 120
= 180 = 240 = 300
7 3 "
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60
HH
CH3CH3
HH = 0
60
H
H CH3CH3
HH
60
CH3H
HCH3
HH
CH3
H HCH3
HH
60
60HH3C
HCH3
HH
H
H3C HCH3
HH
60
= 60 = 120
= 180 = 240 = 300
ECLIPSADASINPERIPLANAR
ALTERNADASINCLINAL
ECLIPSADAANTICLINAL
ALTERNADASINCLINAL
ECLIPSADAANTICLINAL
ALTERNADAANTIPERIPLANAR
interaccingauche
interaccingauche
0, " , 3 #C D " , , (5
" . , , (-.. , , ;
.. ,: 5 <
2 " , " " * > , " " " , , .. 3 , .. " 3
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0 60 120 180 240 300 360
Ekcal/mol
ngulo de torsin ()
E=2.9E=3.6
E=0.9
E=3.8
E=4.5
60
HH
CH3CH3
HH = 0
60
H
H CH3CH3
HH
60
CH3H
HCH3
HH
CH3
H HCH3
HH
60
60HH3C
HCH3
HH
H
H3C HCH3
HH
60
= 60 = 120
= 180 = 240 = 300
ECLIPSADASINPERIPLANAR
ALTERNADASINCLINAL
ECLIPSADAANTICLINAL
ALTERNADASINCLINAL
ECLIPSADAANTICLINAL
ALTERNADAANTIPERIPLANAR
interaccingauche
interaccingauche
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+
+ ,,&
&
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,3 ,2 3 "
3
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E3
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(5 < F $ :
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"
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
HH
H
H
H
H
H
H
H
HH
HH
HH
H H
HH
H H
HH
H
SILLA(alternada)
BOTE(eclipsada)
E3
(5 < 3 * > ,3
,
* > ,
, * > ,
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+
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!%&
7
silla semisilla bote semisilla silla
silla
Ekcal/mol
E=10.8
E=5.5bote
silla
semisilla semisilla
,
3 "
&" "
@
"
Hax
Hek
Hax
Hek
Hek
Hax
Hax
Hek
Hax
Hek
Hax
Hek
Hax
HekHax
HekHax
HekHax
Hek
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+
+ ,,&
&
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#..
%& $$
* @
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2 , ,
H
H
H
CH3
H
H
H
H
H
H
H
H
H
H
H
H
HH
H
H
CH3
H
H
H
H
H
H
H
H
H
H
H
CH3
H
H
H
SILLAMe en ecuatorial BOTE
H
HH
HH
CH3H
HH
CH3H
HH
HH
H
H
HH
HCH3
CH3H
H
SILLAMe en axial
$ @ ,. > G
$ * > :
* @ # , 2
2 > " ,
-
+
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%& $$?
* @
0, (+
H
CH3
H
tBu
H
H
H
H
H
H
H
H
H
H
H
H
HH
H
HtBu
H
H
H
H
H
H
H
H
CH3
H
H
tBu
H
H
H
BOTE
H
HH
HH
tBuH
CH3H
tBuH
HH
HH
H
H
HH
HtBu
HCH3
H
SILLAtBu y Me en ecuatorial- Tensin de torsin: NO- CH3 - tBu gauche
- Tensin de torsin: SI
SILLA tBu y Me en axial
- Tensin de torsin: NO- CH3 - -CH2- gauche-
tBu - -CH2- gauche
(?
* @ -, " , " ,
0, (+
CH3
H
H
tBu
H
H
H
H
H
H
H
H
H
H
H
H
HH
H
HtBu
H
H
H
H
H
H
H
H
CH3
H
H
tBu
H
H
H
BOTE
H
HH
HH
tBuCH3
HH
tBuCH3
HH
HH
H
H
HH
HtBu
HH
CH3
SILLAtBu ecuatorial; Me axial- Tensin de torsin: NO- CH3 - tBu gauche- CH3 - -CH2- gauche
- Tensin de torsin: SI
SILLAtBu axial; Me ecuatorial- Tensin de torsin: NO- CH3 - tBu gauche-
tBu - -CH2- gauche
-
+
+ ,,&
&
* $
* $ -
-#
..
#..
%& $$
0, (+.
0, (+.
H
H
H
tBu
H
H
H
H
H
H
CH3
H
H
H
H
H
HH
H3CH
tBu
H
H
H
H
H
H
H
H
H
H
H3C
tBu
H
H
H
BOTE
CH3
HH
HH
tBuH
H H
tBuH
HH3C
HH
H
H
H3CH
HtBu
HH
H
SILLAtBu ecuatorial; Me axial- Tensin de torsin: NO- CH3 - -CH2- gauche
- Tensin de torsin: SI
SILLAtBu axial; Me ecuatorial- Tensin de torsin: NO-
tBu - -CH2- gauche
H
H
H
tBu
H
H
H
H
H
H
H
H3C
H
H
H
H
HH
H3CH
tBu
H
H
H
H
H
H
H
H
H
CH3
H
tBu
H
H
H
BOTE
H
H3CH
HH
tBuH
HH
tBuCH3
HH
H3CH
H
CH3
HH
HtBu
HH
CH3
SILLAtBu y Me en ecuatorial- Tensin de torsin: NO - Tensin de torsin: SI
SILLAtBu y Me en axial
- Tensin de torsin: NO- CH3 - -CH2- gauche-
tBu - -CH2- gauche
(? .
* @ -, " , " ,
-
+
+ ,,&
&
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* $ -
-#
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0, (+-
0, (+-
(? -
* @
, : 2
H
H
H
tBu
H
H
H
H
H
H3C
H
H
CH3H
H
H
HH
H
HtBu
H
H
H
H
H
CH3
H
H
H
H
H
tBu
H
H
H
BOTE
H
HH
H3CH
tBuH
HH
tBuH
HH
HH
CH3
H
HCH3
HtBu
HH
H
SILLAtBu y Me en ecuatorial- Tensin de torsin: NO - Tensin de torsin: SI
SILLAtBu y Me en axial
-Tensin de torsin: NO-
tBu - -CH2- gauche- Me - -CH2- gauche
H
H
H
tBu
H
H
H
H
CH3
H
H
H
H
H3C
H
H
HH
H
HtBu
H
H
H
H
H
H
H3C
H
H
H
H
tBu
H
H
H
BOTE
H
HCH3
HH
tBuH
H H
tBuCH3
HH
H3CH
H
H
HH
H3C tBu
HH
CH3
SILLAtBu ecuatorial; Me axial
- Tensin de torsin: NO- CH3 - -CH2- gauche
- Tensin de torsin: SI
SILLAtBu axial; Me ecuatorial
- Tensin de torsin: NO-
tBu - -CH2- gauche
-
+
+ ,,&
&
* $
* $ -
-#
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#..
!
C C
C
H
H
H
H
H
H
60
115 "
3
5 F ,3
" ,
$!
H
H
H
HH
H
HH
H
H
HH
H
HH
H
H "
3
(5 5 F ,3
!
H H
HH
H
H
H
H
H
HH H
HH
H
H
H
H
H
H
H "
3
(5 = F ,3
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#..
CH3 ClCH4 + Cl2 + HClh o
$ "
( 0, 3 " * #
Cl2h o Cl2
H " !
' (
& " 3 , 3 >
*
Cl + CH4 Cl H + CH3
CH3 + Cl2 CH3 Cl + Cl
. , 3
#* "
Cl + Cl Cl
CH3 + Cl CH3 Cl
Cl
CH3 + CH3 CH3 CH3
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0, :I7 8 " 3 # " 8
+
" " " " 3 ,
Cl2h o Cl2
ClCH4 +HClCH3 +
CH3ClCl +
CH4+Cl2
INICIACIN PROPAGACIN
Curso de la reaccin
GKcal/mol
/ ? 0
FJ .A ;= - .
& " 3 , " 1 F K ( / ? 0
J -. J .5 (= .-. JJ .J A. A ; (
- J.J J (5 . ; A (.
/ ,L
,L ? ,
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!7 7
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7 7 " " # ,
C R3
R1
R2
R1 CR2
R3
" .
H " 3
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FM D FM D "
. (5 ; .. < 5 .
! < = !. = A !"
! < -; !. = - !
!. < . !.. A !
L 6 L & L .
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6 7 ,
& "
CH3 CH2 CH3
CH3 CH2 CH2
CH3 CH CH3
+ CH3 CH2 CH2 Cl CH3 CH CH3Cl
+
REACTIVIDAD RELATIVA (a 25)
572
436
4
1
REACTIVIDAD TERICA:REACTIVIDAD EXPERIMENTAL (25C)REACTIVIDAD EXPERIMENTAL(600C)
6:243:573:1
REACTIVIDAD RELATIVA (a 600)
11
33
1
1
( . K (-;
$ " "
CH3 CH CH3 + +
REACTIVIDAD RELATIVA (a 25)
361
649
51
REACTIVIDAD TERICA:REACTIVIDAD EXPERIMENTAL (a 25C)REACTIVIDAD EXPERIMENTAL (a 600C)
9:164:3680:20
CH3
CH3 CH CH2CH3
CH3 C CH3CH3
CH3 CH CH2CH3
Cl CH3 C CH3CH3
Cl
! ! !./;F+3 ( ( (-;F+3 ( - ;? (;5 F+3 ( ; (A5 5
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1 7 *
3 ,
6 1 SO2Cl2
Iniciador radicalario
Cl+ SOCl2 + HCl
0 &,@ +" 8
0? H
H
H? H6 +H? 6
NBS =
Iniciador radicalario
Br+ N
O
O
H
NO O
Br
3 ,
, 3 "
, 3
Br2
hBr Br
Cl2
hCl
Cl
!7
Cl
O
OO
H
m-CPBA
H3C
O
OO
H
cido peractico
tBu-O-O-H
terc-butilhidroperxido
N NC C CH3CN
CH3H3C
CN
CH3
AIBN
-
+
+ ,,&
&
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#..
C5H12 + 8 O2 5 CO2 + 6 H2O +
@ #3 " 1+1>
Alcanos pequeos (mezcla compleja)
Alcano grande600C
$
600CPtO2 (kat.)
600CPd (kat.)
! )*(+
7 " + 1+
> " * # >
" 7
, %( " 8 " > " 1+ " * 3 , 2
!7
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600CNi (cat.)
H2, 1atm
Pd (cat.)
+ H2
' ( -$
/,&
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F
H%
N 7
I
B 3 + +
" " O .5 (- (
1 , 2
P " , .5 A5 ;A (5 (; 4 7
B 5 5 5 A( (5 (;
C 5 5 .5 5 ((= ;5
B , .5 5 -5 5 (5 (5 -5
! L -5 5 L 5 (5 A5 &