pertemuan ke-8 alkanes & cycloalkane
TRANSCRIPT
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
1/38
Pharmacy Departement
Jenderal Soedirman University
Dr. Sri Sutji Susilowati, M.Si., Apt
M. Salman Fareza, M.Si.
!"A#$% %&'M$S(!) $!"A#$% %&'M$S(!) $
Al*anes + %ycloal*anesAl*anes + %ycloal*anes
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
2/38
$. %lasses o- ranic %ompounds
&ydrocar/ons 0% + & only1 &eteroatomic compounds
aliphatic aromatic
al*anes
al*enes
al*ynes
cyclic compounds
alcohols
ethers
aldehydes
*etones
car/o2ylic acids
esters
amines
amides
% %
% %
% %
! &
! !3
! %
&
! %
!3
! %
&
! %
!3
! %
#&
! #&,
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
3/38
4
$$. Al*anes
A. "eneral -ormula5 %n&n 6
%&7 methane 0natural as, swamp as1
%&4 8%&4 0%&91 ethane
%&4 8%& 8%&4 0%4&:1 propane 0;P"1
%&4%&%&%&4 0%7&?@:? %&7?@
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
4/38
7
$$. Al*anes
B. $somers5 normal and /ranched al*anes
n@/utane
Cstraiht chain
/ranched chain
iso/utane
%&4 %&, %&, %&4
%&4
%& %&4
%&4
& % % % % &
& &
& &
& &
& &
constitutional
isomers
%7&
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
5/38
?
$$. Al*anes
B. $somers5 normal and /ranched al*anes
%?&
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
6/38
9
$$. Al*anes
B. $somers5 normal and /ranched al*anes
uestion @
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
7/38
>
$$. Al*anes
B. $somers5 normal and /ranched al*anes
Answer @
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
8/38
:
$$. Al*anes
B. $somers5 normal and /ranched al*anes
(ypes o- car/ons5
%&4 %&
%&4
%& %&4
methyl car/ons
methylene car/on
methine car/on
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
9/38
E
$$. Al*anes
%. Structure@property relationships
$ntermolecular attractions5 ;ondon 0or van der Gaals1 -orces 0wea*1 /.p.
%&7 @
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
10/38
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
11/38
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
12/38
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
13/38
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
14/38
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
15/38
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
16/38
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
17/38
$. %hemical Properties o- Al*anes
Answer @9. Determine whether the -ollowin reactions will
/e o2idation, reduction, or neither. %hec* your answers /y clic*in
on the arrow.
Check Answer
&% %& 6 Br &% %&
Br Br
&,% %&, 6 &, %
&
&
&
%
&
&
&
2idation5 'ach car/on
chanes -rom a @ to a @
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
18/38
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
19/38
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
20/38
=
. %on-ormations o- Al*anes
B. Butane5 steric repulsions %&4 8%& 8%& 8%&4
%&4
%&4
%&4
&4%
%&4&4%
%&4%&4 %&4%&4
%&4
%&4
$
anti
0
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
21/38
<
. %on-ormations o- Al*anes
B. Butane5 steric repulsions
$ $$ $$$ $ $
=
7
9
∆G
4.9=.:
K9
=.:4.9
%&4
%&4
%&4
&4%
%&4&4%
%&4
%&4
%&4%&4
%&4
%&4
$ $$ $$$ $ $
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
22/38
$. %on-ormations o- %ycloal*anes
A. Sta/ilities o- cycloal*anes
!in strain L /ond anle strain
6 torsional strain 0eclipsin1
6 steric strain 0van der Gaals1
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
23/38
4
$. %on-ormations o- %ycloal*anes
A. Sta/ilities o- cycloal*anes∆ H com/
per %&
(otal
rin strain
.= 9.4
.4 E.9
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
24/38
7
$. %on-ormations o- %ycloal*anes
A. Sta/ilities o- cycloal*anes
&&
&&
& & poor overlap L bond angle strain
0i.e.,
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
25/38
?
$. %on-ormations o- %ycloal*anes
A. Sta/ilities o- cycloal*anes
&
&
&
&
&
&
&
&&
&
&
&
&&
&
&
planar, E=H /ut all eclipsed
Cpuc*ered, ::Hslihtly more anle strain,
/ut less eclipsin strain
%hem4D
planar,
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
26/38
9
$. %on-ormations o- %ycloal*anes
B. %on-ormations in cyclohe2ane
*cal
∆G K > *cal
%hem4D
Cskewed boat K
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
27/38
>
$. %on-ormations o- %ycloal*anes
B. %on-ormations in cyclohe2ane
. eRuatorial and a2ial positions
&
&&
&
&
&
&&
&
&&
&
&
&&
&
&
&
&&
&
&&
&
axial positions equatorial positions
4. chair@chair interconversion
&
&&
&
&
&
&&
&
&&
&
&
&&
&
&
&
&
&&
&&
&
E a K
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
28/38
:
$. %on-ormations o- %ycloal*anes
B. %on-ormations in cyclohe2ane
7. drawin cyclohe2ane chairs
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
29/38
E
$. %on-ormations o- %ycloal*anes
%. Su/stituted cyclohe2anes
%&4
%&4
&
&
&
%&4
&
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
30/38
4=
$. %on-ormations o- %ycloal*anes
%. Su/stituted cyclohe2anes
&
&
More pronounced e--ect with larer roups5
∆G K ?.? *cal
0EE.EE1 0=.=
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
31/38
4<
$. %on-ormations o- %ycloal*anes
D. Disu/stituted cyclohe2anes
%&4
%&4
%&4
%&4
trans@ cis@
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
32/38
4
$. %on-ormations o- %ycloal*anes
D. Disu/stituted cyclohe2anes
%&4
%&4
%&4%&4
&
&
%&4 &
%&4
&
%&4
%&4
∆G K 4.9 *cal
dieRuatorial
no repulsions
dia2ial
7
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
33/38
44
$. %on-ormations o- %ycloal*anes
D. Disu/stituted cyclohe2anes
%&4
%&4
&4% %&4
%&4
%&4
&
&
&
%&4
%&4
&
∆G L = *cal
eRuatorial@a2ial
2 =.E L
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
34/38
47
$. %on-ormations o- %ycloal*anes
D. Disu/stituted cyclohe2anes
%&4
%&4
%&4%&4
&
&
& %&4
%&4
&
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
35/38
4?
$. %on-ormations o- %ycloal*anes
D. Disu/stituted cyclohe2anes
%&4
%&4
%&4&4%
& %&4%&4
∆G K ?.7 *cal
no repulsions
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
36/38
49
$. %on-ormations o- %ycloal*anes
D. Disu/stituted cyclohe2anes
;arer roups predominate in determinin con-ormation5
%&4
%&4
t Bu
%&4
∆G K 4.> *cal
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
37/38
4>
$. %on-ormations o- %ycloal*anes
D. Disu/stituted cyclohe2anes
uestion 4@
-
8/18/2019 Pertemuan Ke-8 Alkanes & Cycloalkane
38/38
4:
$. %on-ormations o- %ycloal*anes
D. Disu/stituted cyclohe2anes
Answer 4@