ALKOHOL

Oleh : Alvan Febrian Shalas, S. Farm., Apt

STRUKTUR ALKOHOL

The functional roup of an alcohol is an !OH

roup bon"e" to an sp# h$bri"i%e" carbon

bon" anles about the h$"ro&$l o&$en atom are

appro&imatel$ '().*+

O&$en is sp# h$bri"i%e"

t,o sp# h$bri" orbitals form sima bon"s to

carbon an" h$"roen

the remainin t,o sp# h$bri" orbitals each contain

an unshare" pair of electrons
108.9
O
C
H
H
H
H
-O./-KLATUR

0U1A2 names

the parent chain is the lonest chain that 2ontains the OH

roup

number the parent chain to ive the OH roup the lo,est

possible number

chane the suffi& !ana to !ol

2ommon names

name the al3$l roup bon"e" to o&$en follo,e" b$ the

,or" al3ohol
-O./-KLATUR

2ompoun"s containin more than one OH roup are

name" "iol, triol, etc.
CH
3
CHCH
2
HO OH
CH
2
CH
2
OH OH
1,2-Etanadiol
(Ethylene glycol)
1,2-Propanadiol
(Propylene glycol)
-O./-KLATUR

Unsaturate" alcohols

sho, the "ouble bon" b$ chanin the infi& from !an! to

!en!

sho, the the OH roup b$ the suffi& !ol

number the chain to ive OH the lo,er number

1
2 3
4 5
6
(E)-2-Hexene-1-ol
(t rans-2-Hexen-1-ol)
HO
-O./-KLATUR

For c$clic alcohols, the carbon bearin the OH is

numbere" as 4'.5

1henols are name" after the parent compoun"

phenol6 the 2 bearin the OH is numbere" as
4'.5
Latihan....
',7,#!propana"iol
#!metilsi3lohe3sanol
p-propilfenol
#!fenil!7!propanol
SIFAT FISIKA

H$"roen bon"in: ,hen the positive en" of

one "ipole is an H bon"e" to F, O, or - 8atoms
of hih electroneativit$9
SIFAT FISIKA
SIFAT FISIKA

:ecause alcohols h$"roen bon" to each other, the$ have

hiher boilin points than al3anes of the same molecular
,eiht

The boilin point of alcohols increases as the molecules

become larer
SIFAT FISIKA
SIFAT FISIKA
Alcohols are polar compoun"s

the$ interact ,ith themselves an" ,ith other polar compoun"s b$

"ipole!"ipole interactions
;ipole!"ipole interaction: the attraction bet,een the positive en" of one
"ipole an" the neative en" of another
SIFAT FISIKA

The O<H bon" is therefore a polar bond, an" an$

molecule ,hich contains an O<H bon" 8li3e an alcohol9
is a polar molecule.

Since the OH roup ma3es alcohols polar, the$ ,ill mi&

,ith polar solvents li3e ,ater < as lon as the carbon
chain is fairl$ short 8The loner the carbon chain, the less
soluble the alcohol is9
SIFAT FISIKA
K/ASA.A- ALKOHOL

0n "ilute a=ueous solution, alcohols are ,ea3l$ aci"ic

CH
3
O H
:
H O
H
[ CH
3
OH]
[ CH
3
O
-
] [H
3
O
+
]
CH
3
O:

O
H
H H
+
+
= 10
- 15.5
pK
a
= 1 5.5
K
a
=
+
( CH
3
)
3
COH
( CH
3
)
2
CHOH
CH
3
CH
2
OH
H
2
O
CH
3
OH
CH
3
COOH
HCl
15.5
15.7
15.9
17
18
4.8
Hydrogen chloride
Acetic acid
Methanol
ater
!thanol
2-"ro#anol
2-Methyl-2-#ro#anol
$tr%ct%ral
&or'%la
$tronger
acid
ea(er
acid
)Al*o gi+en ,or co'#ari*on are #K
a
+al%e* ,or -ater.
acetic acid. and hydrogen chloride.
/o'#o%nd
#K
a
-7
K/ASA.A- ALKOHOL
KLASIFIKASI ALKOHOL
ALKOHOL
S-7
>R0>-AR;
R/;UKS0
KAR:O-0L
H0;RAS0
ALK/-A
PEMBUATAN ALKOHOL
PEMBUATAN ALKOHOL
A. SN2 dari Alkilhalida
HO
-
H
3
C
H
H
3
CH
2
C
Br
HO
H CH
3
CH
2
CH
3
Br
H
3
C
H
H
3
CH
2
C
Br
(S)-2Broo!"tane
#ran$ition State
% HO
-
CH
3
H
CH
2
CH
3
HO
(&)-2-B"tanol
%
Br
-
PEMBUATAN ALKOHOL
SN2 dari Alkilhalida
PEMBUATAN ALKOHOL
:. Rea3si >R0>-AR; "ari 3arbonil
PEMBUATAN ALKOHOL
PEMBUATAN ALKOHOL
2. R/;UKS0 KAR:O-0L
REUKTOR ! Na"ri#$ borohidrida
Li"i#$ al#$#ni#$hidrida
PEMBUATAN ALKOHOL
PEMBUATAN ALKOHOL
;. H0;RAS0 ALK/-A
%The rea&"ion o' alkene( )i"h dil#"e a*#eo#( a&id
lead( "o Marko+niko+ addi"ion o' )a"er,
PEMBUATAN ALKOHOL
ALKOHOL
/L0.0-AS
0
SU:ST0TU
S0
OKS0;AS0
REAKSI ALKOHOL
REAKSI ALKOHOL
%SUBSTITUSI,
A. '+ alcohols react ,ith H? b$ an S-7 mechanism
S"ep -: rapi" an" reversible proton transfer
S"ep 2: "isplacement of HOH b$ hali"e ion
RCH
2
-OH
:
H
H
H O RCH
2
- O
H
H
:
H
H
O
+
ra#id and
re+er*i0le
1
+
+
Br:
-
RCH
2
-O
H
H
RCH
2
-Br
:
H
H
O
+
+
S
N
2
+
*lo-. rate
deter'ining
REAKSI ALKOHOL
%SUBSTITUSI,
:. For '+ alcohols ,ith e&tensive !branchin

S-' is not possible because this path,a$ ,oul"

re=uire a '+ carbocation

S-7 is not possible because of steric hin"rance

create" b$ the !branchin

These alcohols react b$ a concerte" loss of HOH an"

miration of an al3$l roup

S"ep -: proton transfer ives an o&onium ion

S"ep 2: concerte" elimination of HOH an" miration of a

meth$l roup ives a #+ carbocation
+
O
H
O
H
H H
+
ra#id and
re+er*i0le
+
O H
H
2.2-2i'ethyl-1-
#ro#anol
An oxoni%' ion
O
H
H
+
O
H
H
*lo- and
rate deter'ining
(concerted)
O
H
H
1
A 3 car0ocation
inter'ediate
REAKSI ALKOHOL
%SUBSTITUSI,
REAKSI ALKOHOL
%SUBSTITUSI,
S"ep .: reaction of the carbocation interme"iate 8an electrophile9
,ith hali"e ion 8a nucleophile9 ives the pro"uct
2-/hloro-2-'ethyl0%tane
Cl
-
1
,a*t
Cl
REAKSI ALKOHOL
%SUBSTITUSI,
2. 7+ an" #+ alcohols react ,ith H? b$ an S-' mechanism
S"ep -: proton transfer to the OH roup ives an o&onium
ion
S"ep 2: loss of H7O ives a carbocation interme"iate
CH
3
CH
3
CH
3
-C-OH
:
H
H
H O
O
H
H
CH
3
-C
CH
3
CH
3
:
H
H
O
+
+
ra#id and
re+er*i0le
1
1
O
H
H
CH
3
-C
CH
3
CH
3
CH
3
CH
3
CH
3
- C+
:
H
H
O
+
A 3 car0ocation
inter'ediate
*lo-. rate
deter'ining
S
N
1
+
REAKSI ALKOHOL
%SUBSTITUSI,
S"ep .: reaction of the carbocation interme"iate 8an
electrophile9 ,ith hali"e ion 8a nucleophile9 ives the
pro"uct
CH
3
CH
3
CH
3
- C+
:Cl CH
3
- C- Cl
CH
3
CH
3
2-/hloro-2-'ethyl#ro#ane
(t ert-4%tyl chloride)
,a*t
+
REAKSI ALKOHOL
%SUBSTITUSI,
;. An alternative metho" for the s$nthesis of '+ an" 7+
bromoal3anes is reaction of an alcohol ,ith
phosphorus tribromi"e
PBr
3
H
3
PO
3
"ho*# horo%*
acid
+
+
2-Methyl-1-#ro#anol
(5*o0%tyl alcohol)
"ho*#hor%*
tri0ro'ide
1-4ro'o-2-'ethyl#ro#ane
(5*o0%tyl 0ro'ide)
OH
Br
REAKSI ALKOHOL
%SUBSTITUSI,
S"ep -: formation of a protonate" "ibromophosphite converts
H7O, a poor leavin roup, to a oo" leavin roup
S"ep 2: "isplacement b$ bromi"e ion ives the al3$l bromi"e
Br O PBr
2
R-CH
2
H
P Br Br
Br
R-CH
2
-O-H
1 1
a good lea+ing gro%#
1

Br
-
O PBr
2
R-CH
2
H
&-CH
2
-Br HO-PBr
2
1
+
+
S
N
2

An alcohol can be converte" to an al3ene b$ aci"!catal$%e"

"eh$"ration 8a t$pe of !elimination9
'+ alcohols must be heate" at hih temperature in the presence of
an aci" catal$st, such as H7SO@ or H#1O@
7+ alcohols un"ero "eh$"ration at some,hat lo,er
temperatures
#+ alcohols often re=uire temperatures at or slihtl$ above room
temperature
Ahere isomeric al3enes are possible, the al3ene havin the
reater number of substituents on the "ouble bon" 8the more
stable al3ene9 usuall$ pre"ominates 8Baitsev rule9
2arbocation rearranement is possible
REAKSI ALKOHOL
%ELIMINASI,
REAKSI ALKOHOL
%ELIMINASI,
1'()C
CH
3
CH
2
OH
H
2
SO
*
CH
2
+CH
2
% H
2
O
1*()C
Cyclohe,anol Cyclohe,ene
OH
% H
2
O
H
2
SO
*
CH
3
COH
CH
3
CH
3
H
2
SO
*
CH
3
C+CH
2
CH
3
%
H
2
O
-()C
2-.ethyl-2-propanol
(tert- B"tyl alcohol)
2-.ethylpropene
(/$o!"tylene)
REAKSI ALKOHOL
%ELIMINASI,
Step ': proton transfer to the !OH roup ives an o&onium
ion
Step 7: loss of H7O ives a carbocation interme"iate
A 2 car0ocation
inter'ediate
O
H H
+
*lo-. rate
deter'ining
H
2
O +
REAKSI ALKOHOL
%ELIMINASI,
Step #: proton transfer from a carbon a"Cacent to the
positivel$ chare" carbon to ,ater6 the sima electrons of the
2!H bon" become the pi electrons of the carbon!carbon
"ouble bon"
ra#id and
re+er*i0le
O
H
H
H H
+
+
O
H
+
+
H
H
REAKSI ALKOHOL
%OKSIASI,
Ok(ida(i Alkohol pri$er
Ok(ida(i Alkohol (ek#nder
ETER dan EPOKSIA
ETHERS are compoun"s that have t,o oranic roups attache"
to o&$en
Eto0$i
etana
Etil eter
eto3siben%ena
/til fenil eter
ETER dan EPOKSIA

/thers are polar molecules, but because of steric

hin"rance, onl$ ,ea3 "ipole!"ipole attractive forces e&ist
bet,een their molecules in the pure li=ui" state

:oilin points of ethers are

D lo,er than alcohols of comparable .A an"
D close to those of h$"rocarbons of comparable
.A

/thers are more soluble in H7O than are h$"rocarbons

ETER dan EPOKSIA

EPOKSIA 8o3sirana9! three!membere" rin,

c$clic ethers6 the strain of the three!membere"
rin ma3es epo&i"es electrophilic
O0$irana
Epo0$ida
7!metilo3sirana
TIOL dan SULFIA

Tiol 8RSH9, are sulfur analos of alcohols

D -ame" ,ith the suffi& !"iol
D SH roup is calle" 4mercapto roup5 84capturer of
mercur$59
#iol
etanatiol
TIOL dan SULFIA

S#l'ide( 8RSRE9, are sulfur analos of ethers

-ame" b$ rules use" for ethers, ,ith sulfi"e in place

of ether for simple compoun"s an" alkylthio in place
of alkoxy
S"l1ida "imetilsulfi"a