1

KIMIA DASAR II
(KIMIA ORGANIK)

DOSEN PE NGAMPU:

d Ethers
T IRZA HAN UM
RIBUT S UGIHARTO
SAMS U U. NURDIN
Methyl Alcohol (Methanol)
ANW I KA UTAMI P UTRI
Methyl alcohol, with one carbon atom and one —OH group, is the simplest alcohol. This
colorless liquid is a good fuel for internal combustion engines. Since 1965 all racing cars
at the Indianapolis Speedway have been fueled with methyl alcohol (Figure 14.3). (Methyl
J urusan Tek n ologi Hasil Pe r t an i an

alcohol fires are easier to put out than gasoline fires because water mixes with and dilutes
Fakultas Pertanian Universitas Lampung

hers
methyl alcohol.) Methyl alcohol also has excellent solvent properties, and it is the solvent
s, of
andchoice
Ethers for paints, shellacs, and varnishes.
Methyl alcohol is sometimes called wood alcohol, terminology that draws attention
ethyl Alcohol
to an early method (Methanol)
for its preparation—the heating of wood to a high temperature in the
absence
Methylof air. Today, nearly all methyl alcohol is produced via the reaction between H2
ethyl alcohol,Alcohol
and CO. with one(Methanol)
carbon atom and one —OH group, is the simplest alcohol. This
lorless liquidalcohol,
Methyl is a good withfuel
onefor internal
carbon atomcombustion
and one —OH engines.
group, Since
is the1965 simplest all racing cars
alcohol. This
ZnO O Cr2O3
the Indianapolis
colorless liquidSpeedway
is a CO
goodhave
" fuel2 been
2H for fueled
internal with methyl
combustion
300°C ! 400°C, 200 atm
CH 3 alcohol
engines.
O OH (Figure
Since 1965 14.3). all (Methyl
racing cars
coholatfithe
res Indianapolis
are easier toSpeedway
put out than havegasoline fireswith
been fueled because
methyl water
alcohol mixes with 14.3).
(Figure and dilutes
(Methyl
2
DrinkingG. methyl
BEBERAPA alcohol is
toJENISvery dangerous.
ALKOHOL Within
firesthe
YANG humanwater
PENTING body,mixes methyl alcohol
ethylalcohol
alcohol.)fires are easier
Methyl alcohol putalsoouthas
than gasoline
excellent solvent because
properties, and it iswith the and dilutes
solvent
is oxidized
methyl by the liver
alcohol.) enzyme
Methyl alcohol
alcohol also dehydrogenase
has excellent to the toxic
solvent metabolites
properties, and it formal-
is the solvent
choice for paints,
1. shellacs,
Methanol and varnishes.
(Methyl Alcohol)
dehyde and formic
of choice acid. shellacs, and 14.5
for paints, varnishes.
Important Commonly Encountered that Alcohols 405
Methyl alcohol •isJenis
sometimes
alkohol called
palingwood alcohol,
sederhana, terminology
terdiri 1 atom Cdrawsdan 1attention
Methyl alcohol
an early method forgugus its is sometimes called
preparation—the of woodterminology
Owood alcohol,
heating toOa high temperature that draws in attention
the
~OH. B heating B to a high temperature in the
sencetoof anair.
early method
Today, for its
nearly
CHDigunakan all preparation—the
methyl
Alcohol
3OOH dehydrogenase
alcohol
HOpelarut is Furtherof wood
produced
C OH oxidation via
HOvernis)the reaction
C O OH dan bahan between H2
• sebagai (cat dan
absence of air. Today, nearly all methyl alcohol is produced via the reaction between H2
d CO.
and CO. bakar. DihasilkanFormaldehydedari mereaksikan COacid
Formic dan H2.
Phenols, and Ethers ZnO O Cr2O3
Formaldehyde can cause COblindness
" 2H2 (temporary ZnOorOpermanent).CH3O Formic
OH acid causes acidosis
" 300°C
COfeature2H2 on! 400°C, 200Cratm
2O3
CH OHas 1 oz (30 mL) of
(see the Chemical Connections page! 279).
300°C Ingesting
400°C, 200 atm as3O little
Drinking
methyl methyl
alcohol alcohol
can cause
Methyl •Alcohol is
optic very
nerve
(Methanol) dangerous.
damage. Within the human body, methyl alcohol
Drinking Sangat
methyl berbahaya,
alcohol bila diminum.
is very dangerous. WithinDithe dalamhuman tubuh,
body, methyl alcohol
oxidized by
is oxidized
the liver
by the
enzyme
methanol
liver
alcohol
dioksidasi
enzyme
dehydrogenase
alcohol oleh to
enzim alkohol
dehydrogenase
the
to
toxic
the toxic
metabolites
metabolites
formal-
formal-
Ethyl
hydedehydeAlcohol
Methyl
and formic (Ethanol)
alcohol,
acid. with
dehidrogenase
one carbon atom
menjadi
and one —OH
formaldehyd
group,
dan
is the
asam
simplest alcohol. This
and formic acid.
colorless liquid is a good fuel for internal combustion engines. Since 1965 all racing cars
Ethyl alcohol, format.
the two-carbon
at the Indianapolis monohydroxy
Speedway have been alcohol, with
is themethyl
alcohol present in alcoholic
O fueledOas alcohol or drinking
alcohol
O O
(Figure 14.3). (Methyl
beverages and isfires
alcohol commonly referred
to put outtothan
are easierAlcohol simply
Bgasoline fires becauseB water alcohol.
mixes with Likeand dilutes
B Further B
methyl alcohol,
methyl CH ethyl
3Oalcohol
OHMethyl
alcohol.)
CH OH is oxidized
AlcoholHin
alcohol Othe
also C HO
has human
HC O Hbody
excellent by
Further
HO
solvent the C
HO liverOH
properties,
C Oenzyme
OHand italcohol is the solvent
3O dehydrogenase
dehydrogenase
O oxidation
oxidation
O
dehydrogenase.
of choice for paints, shellacs, andFormaldehyde
varnishes. Formic acid acid
Formaldehyde Formic
Methyl alcohol is sometimes called wood alcohol, terminology that
J urusan Tek n ologi Hasil Pe r t andraws
i an attention
orO O
Fakultas Pertanian Universitas Lampung
ormaldehyde to ancan
Formaldehyde cause
early can blindness
cause
method for its (temporary
blindness (temporary
preparation—the B permanent).
or permanent).
heating Formic
of wood toBaacid
Formic high causes
acid causes
temperature acidosis
acidosis
in the
Alcohol Further
eeFigure
the(see
Chemical
the
14.4 CH
absence Connections
Chemical
OofCHair.
2O
An3experimental feature
Connections
OH setup
Today, nearly
for onmethyl
feature
all page
CH
preparing
dehydrogenase on
3O 279).
page
C
alcohol
ethyl Ingesting
279).
is produced
OHalcohol as3little
Ingesting
CH O asC OOH
via
by fermentation.
oxidation as reaction
little
the 1asoz
(a) A1small (30 mL)
oz between
(30 ofHof2
mL)
ethyl
amount alcohol
ofand
methyl yeastcan
hascause
CO.
alcohol been optic nerve
can cause
added optic damage.
to the nerve
aqueous damage.
Acetaldehyde
sugar solution in the flask. AceticYeast acid enzymes cata-
lyze the decomposition of sugar to ethanol and carbon dioxide, CO2. The CO2 is bubbling through
Acetaldehyde,
lime Ethyl
the, producing
first oxidation product,
2H2is 300°C
largely responsible
ZnO O Cr O for3the symptoms of hang-
thyl Alcohol Alcohol
(Ethanol)(Ethanol)
2 3
water, Ca(OH) 2
CO
calcium "
carbonate, CaCO . (b)200
! 400°C, More CH O OH
atm concentrated
3 ethanol is
over. The odors of both acetaldehyde and acetic acid are detected on the breath of someone
produced from the solution in the flask by collecting the fraction that boils at about 78"C.
who
hyl
(c) Ethyl
alcohol,
Concentrated Drinking
alcohol,
has consumed
the the methyl
a large
two-carbon
ethanol (50% alcohol
two-carbon
amount ofiswhen
monohydroxy
v/v) burns veryitdangerous.
monohydroxy
alcohol. Ethyl
alcohol,
is ignited. isWithin
alcohol,
alcohol
the thealcohol
human
isoxidation
the
alcohol body,
products
present inmethyl
present inless
are alcohol
alcoholic
alcoholic
verages than isthose
toxicbeverages
and oxidized
isand
of by commonly
is
methyl
commonly thealcohol.
liver enzyme
referred toalcohol
referred simply dehydrogenase
to simply as alcohol
as alcohol to the
or or toxic metabolites
drinking
drinking alcohol.
alcohol. formal-
LikeLike
dehyde
Long-term and ethyl
formic
excessive acid.
use
ethylmethyl
alcohol, alcohol,
ethyl alcohol isofoxidized
alcohol ethyl alcohol
in themay
is oxidized thecause
inhuman human undesirable
body body effects
by liver
by the the such
liver asalcohol
enzyme
enzyme cir-alcohol
rhosis of BEBERAPA
the liver,JENIS
dehydrogenase. lossALKOHOL
of memory,
……………… and strong physiological addiction. Links have also
hydrogenase.
e been established between certain birth defects andO O 3
B the ingestion of Bethyl alcohol by
or fortifi cation with alcohol obtained by the distillation of another fermentation product.
during2.pregnancy
EthanolCH (Ethyl Alcohol)
Alcohol Further
d women
with 3OOH
(fetal alcohol syndrome). H O COO H H O C O O
OH
dehydrogenase
Table 14.2 lists the alcohol content ofAlcohol common alcoholicO B beverages and Oof selected
oxidation B com-
Ethyl alcohol • can
CH Biasabe produced
disebut by
alkohol, B OCdari
yeast fermentation
terdiri
Formaldehyde Further found
of2sugars
C danFormic CHB3acid
1~OH. in plant extracts
mon household 3 O CHand
products 2 O OH Alcohol
over-the-counter
dehydrogenase
CH
drug OH
3 products.Further
oxidation
OC OOH
(see Figure CH14.4).
3 O CHThe 2 O OH synthesis of ethylCH
dehydrogenase 3OC OH
alcohol in this manner,
oxidation
CHfrom
3OC OOH grains such as
• Diproduksi
Formaldehyde
Denatured alcohol is ethyl
can secara
causealcohol
blindnessthatfermentasi
has Acetaldehyde
(temporary orgula
been rendered atauunfiproses
permanent). t to drink
Formic hidrasi
Acetic by
acidthe
acid addi-
causes acidosis
corn, rice, and barley, is the reason why ethyl alcohol is often called
Acetaldehyde grain
Acetic acid alcohol.
(see the
tion of small amounts etena
Chemical (alkohol
Connections
of toxic industri)
substances feature on page 279).
(denaturing Ingesting
agents). Almost as little
all ofas 1the
ozethyl
(30 mL) of
eated Acetaldehyde, the first oxidation product, is largely responsible for the symptoms of hang-
alcohol
cetaldehyde,
up
methyl
theover.used for alcohol
the fiindustrial
rstof canpurposes
oxidation causeproduct,
optic
is nerve
Yeast is damage.
denatured
largely alcohol.
responsible for2 the symptoms of someone
hang-
The odors C H12Oacetaldehyde
6both 2CH
and 3O CH
acetic 2 O OH
acid are " 2CO
detected on the breath of
lcohol
er. TheMost ethyl
odors ofalcohol
both used6 in Fermentation
acetaldehyde industry
and is prepared
acetic acid from
are ethene via
detected athe
hydration
onoxidationbreath reaction
of someone
lcohol who
(Section has consumed
Ethyl Alcohol
13.9). a large
(Ethanol)
Sugar amount of alcohol. Ethyl
Ethyl alcoholalcohol products are less
ho
the has consumed
toxic than those a large amount
of(glucose)
methyl of alcohol. Ethyl alcohol oxidation products are less
alcohol.
xic
e thatthan Ethylof
those alcohol,
Long-term methyl the two-carbon
alcohol. monohydroxy alcohol, is undesirable
the alcohol present in alcoholic
Fermentation is excessive
the process use ofHethyl
by!which O ethylalcohol
alcohol
Catalyst may for cause
alcoholic
OH beverages effects such
is produced. as cir-
ionLong-term
is beverages andCH is P CH
2commonly 2 2referred to CH 3O CH
simply O
as2undesirable
alcohol or drinking alcohol. Like
The rhosis
maximum of excessive
theconcentration
liver, loss use ofofmemory,
of ethyl
ethyl alcohol
alcohol may
and strong cause
obtainable physiological
by effects
addiction.
fermentation is such
Links
about as cir-
have
18% also
1.7. methyl alcohol, ethyl alcohol is oxidized in the human body by the liver enzyme alcohol
osis of
been
(v/v),
The theestablished
liver,
because
reaction •
yeast
producesloss
Bila ofproduct
enzymes
a memory,
dikonsumsi,
between cannot
that and
certain strong
ethanol
birth
function
is 95% physiological
dioksidasi
indefects
stronger
alcohol and and the
alcohol
5% addiction.
menjadi
ingestion
water.solutions.
In Links
of ethylhave
Alcoholic
applications bev-also by
alcohol
where
dehydrogenase.
en established
erages
water women
does duringbetween
withinterfere
a higher pregnancyitscertain
concentration
acetaldehyde
with thebirth
use,(fetal of defects
alcohol
alcohol
(ethanal)
mixture than and
this
is syndrome).
dan
treated the
acetic
with ingestion
areaprepared
acid
dehydrating byofeither
ethylto
agent alcohol
produce by
distillation
omen be during
to100% Ethyl
ethyl pregnancy
alcoholSuch
alcohol. can(fetal
be alcohol
produced
alcohol, withby syndrome).
allyeast
traces fermentation
of water
O of sugarsisfound
removed, O inabsolute
called plant extracts
ynol to B B
(seealcohol
Ethyl
alcohol. Figure can 14.4). be The
CH3produced
synthesis
O CH2 OOH
of
by yeast ethyl
Alcohol alcohol
fermentation
CH O C
inofthis
OH sugars manner,
Further found
CH
from
O in
C
grains
plant
OOH
such as
extracts
heir dehydrogenase 3 3
2.corn, rice,
ee Figure
only 14.4).and Thebarley, is the of
synthesis reason
ethylwhy ethyl in
alcohol alcohol
Acetaldehyde
isoxidation
this manner,often called grain alcohol.
from grains
Acetic acid
such as
rn,
re rice, andAlcohol
Isopropyl barley, is the reason why
(2-Propanol) ethyl alcohol is often called grain alcohol.
Yeast
d Acetaldehyde, theC6fiHrst
12oxidation product,2CH
O6 Fermentation is largely
3O CHresponsible
2 O OH for 2Universitas
the symptoms
J urusan Tek n ologi Hasil Pe r t an i an
" 2CO
Fakultas Pertanian Lampung of hang-
ough
Isopropylover. The is
alcohol odors
one of
ofboth
two acetaldehyde
Yeast
three-carbon and acetic acid
monohydroxy are detected
alcohols; theon the
other breath is of someone
propyl
y C6 H12O6SugarFermentation 2CH3O CH2 OEthyl OHalcohol
" 2CO2
alcohol. Awho 70% hasisopropyl
consumed a large amount
alcohol–30%
(glucose) of alcohol.
water solutionEthyl alcohol oxidation
is marketed as rubbingproducts
alcohol.are less
toxic Sugarof methyl alcohol.
than those Ethyl alcohol
IsopropylFermentation
alcohol’s rapid evaporation
is the process
(glucose)
rate
byofwhichcreates
ethyl a dramatic
alcohol cooling
for alcoholic effect when
beverages isitproduced.
is
applied to the Long-term
skin, henceexcessive
its use foruse ethyl
alcohol alcohol
rubs may cause
to combat undesirable
high body effectsItsuch
temperature. also as cir-
The maximum
Fermentation concentration
is the formulations
process of
liver, lossbyofwhich ethyl alcohol
ethylandalcohol obtainable
for by
alcoholic fermentation is about
have 18%
finds use rhosis of
in cosmetics memory,
such as stronglotion
after-shave and handbeverages
physiological addiction. is produced.
lotions. Links also
(v/v),been
because yeast enzymes
established between cannot
certainfunction
birth in stronger
defects and alcohol
the solutions.
ingestion of Alcoholic
ethyl bev-
he maximum
ated inIsopropylconcentration
alcohol has a bitterof ethyl alcohol
taste. obtainable
Its toxicity is twicebythatfermentation but it18%by
is about
of ethyl alcohol, alcohol
he erages with aduring
women higherpregnancy
concentration
(fetal of alcohol
alcohol than this are prepared by either distillation
syndrome).
/v), because
causes
stem
few yeast enzymes
fatalities becausecannot
it often function
induces in strongerand
vomiting alcohol solutions.
thus doesn’t stayAlcoholic
down longbev-
enough
ages Ethyl
withto abehigher alcohol can
fatal. concentration be
In the body it is produced by
of oxidized
alcohol toyeast
than fermentation
acetone. of sugars
this are prepared byfound
eitherindistillation
plant extracts
entury
50% (see Figure 14.4). The synthesis of ethyl alcohol in this manner, from grains such as
ill corn, rice, and barley, OHis the reason why ethyl alcohol O is often called grain alcohol.
 sopropylBeverages
Alcoholic alcohol is one of two three-carbon
beer monohydroxy alcohols; the other
3.2–9is propyl
Ethers A 70% isopropyl alcohol–30%wine
lcohol. (unfortifi
water ed) is marketed as rubbing
solution 12 alcohol.
sopropyl alcohol’s rapid evaporation brandy rate creates a dramatic cooling effect 40–45when it is
whiskey
pplied to the skin, hence its use for alcohol 45–55 It also
rubs to combat high body temperature.
rum 45
3. Isopropil
nds use in cosmetics Alcohol
formulations (2-Propanol,
such as 2-Propyl
after-shave lotion and handalcohol)
lotions. 4
Isopropyl alcohol
Flavorings has a bitter taste. Its 1~OH.
vanillatoxicity Volume
extract is twice that of ethyl 35Percent
alcohol, but it
Product Type • Terdiri dari 3C danProduct Biasanya pada konsentrasi
Ethyl Alcohol
auses almond
few fatalities because it often induces extract
vomiting and thus doesn’t stay50down
14.6 long
Physical Properties of Alcohols 407
70%, digunakan untuk kompress.
nough to
Alcoholicbe fatal.
BeveragesIn
Cough and Cold Remedies the body it is oxidized
beer to acetone.
Pertussin Plus 3.2–9
25
• Kalau dikonsumsi,
winedioksidasi
Nyquil (unfortified) menjadi aceton. 25
12
OH brandy O 40–45
A Glycerol (1,2,3-Propanetriol)
Dristan B 12
Volume Percent
Type CH3O CH OProduct
CH3 whiskey
VicksAlcohol
44 CH O CO CH3Ethyl Alcohol45–55
10
3
Glycerol, rum
dehydrogenase
which is DM
Robitussin, a45clear, thick liquid that has the consistency of
often also called glycerin, is1.4
Isopropyl alcohol Acetone
Beverages beer Itsvanilla
honey. molecular structure involves three 3.2–9
—OH 35 groups on three different carbon atoms.
Flavorings
Mouthwashes Listerineextract 25
arge amounts4.(about 150 mL) wine
of (unfortifi
ingested
almond ed)
isopropyl
extract alcohol can be 12 death
fatal; 50 occurs
Glycerol (Glycerin; 1,2,3-
Scope
CH40–45
18
brandy 2O CH O CH2
om paralysis
Cough of the
and Cold central nervous
Propanetriol)
Remedies system.
Colgate 100Plus
Pertussin A A 17
25 A
whiskey OH45–55
OH
Cepacol
Nyquil 1425 OH
• Terdiri dari rum3C dan 3~OH.
Lavoris
Dristan
45 5
12
14.6 Physical Properties of Alcohols 407

s • Sangat larut Glycerol

dalam
vanilla is normally
air,44banyak
Vicks
extract present in the human 35 body 10 because Glycerolit is a product of fat metabo-
(1,2,3-Propanetriol)
lism. It isRobitussin,
present,DM in combined form, in 50 all 1.4animalhoney. fats and vegetable oils (Section
Glycerol, which is often also called glycerin, is a clear, thick liquid that has the consistency of
digunakan almond extract
di farmasi dan Its molecular structure involves three —OH groups on three different carbon atoms.

6Mouthwashes
Glycerol is often called 19.4). In some Arctic species, glycerol functions as a “biological CH antifreeze” (see
kosmetik. Pertussin
O CH O CH
Listerine 25 25
2 2
A A A
d Cold Remedies Figure Plus
14.6). OH OH OH
hylene Glycol (1,2-Ethanediol)
ntifreeze. For survival in
Nyquil
and Propylene
Scope 25 18
• Berfungsi juga sebagai “biological
Glycerol is normally present in the human body because it is a product of fat metabo-
northern winters, many fish Because glycerol has a great affi nity for17water vapor (moisture),
lism. It is present, in combined form, it inisall animal
often added
fats and vegetable oils (Section
ycol (1,2-Propanediol)
including the common antifreeze” to Dristan
Colgate
pharmaceutical
100 Figure 14.6
preparations suchJ urusan 12
as Tekskin lotions
19.4). In some Arctic species, glycerol functions as a “biological antifreeze” (see
Glycerol is often called

Cepacol n ologi14 Pe r t an i an and soap. Florists sometimes use

Figure 14.6).
biological antifreeze. For survival in
Hasil
oduce large amounts of Vicks 44Lavoris 10 Universitas
Fakultas Pertanian Lampung
Because glycerol has a great affinity for water vapor (moisture), it is often added
Arctic and northern winters, many fish

hylene glycol and propylene glycol are on

glycerol thecut
twoflowers
simplestto alcohols possessing
help retain water andtwo —OHtoglycerol
5maintain freshness.
on cut flowers toIts
and insects, including the common
lubricative properties
pharmaceutical preparations such as skin lotions and soap. Florists sometimes use
housefly, produce large amounts of
t dissolve in their blood, Robitussin, DM 1.4 help retain water and maintain freshness. Its lubricative properties
oups. Besides being diols, theyalso
are also
makeclassifi ed asinglycols. glycol isand
shavingAcreams
glycerol that dissolve in their blood,
it useful a diol in whichalso
in applications for rectalsuch asofglycerol
administration medicines. It is usedsuppositories
make it useful in shaving creams and in applications such as glycerol suppositories
thereby lowering the freezing point of
in candies and icings as a retardant for

eering the freezing point

are of
the blood.
two —OH
shes groups on adjacent carbon
forListerine
rectal atoms.
administration of medicines. It 25
preventing sugar crystallization.
is used in candies and icings as a retardant for
Scope
preventing sugar crystallization. 18 14.6 PHYSICAL PROPERTIES OF ALCOHOLS
CH2OColgate
CH2 and
Ethylene Glycol (1,2-Ethanediol) 3O CH O CH2
CHPropylene
100 17
A A A A Alcohol molecules have both polar and nonpolar character. The hydroxyl groups present

Glycol (1,2-Propanediol) Cepacol

OH OH OH OH 14 14.12 are
Nomenclature for Phenols
polar, and the alkyl (R) group present is nonpolar.
419 Nonpolar portion q o Polar portion
EthyleneLavoris
glycol Propylene glycol 5
14.6arePHYSICAL
Ethylene glycol and propylene glycol PROPERTIES
the two simplest OF ALCOHOLS
alcohols possessing
CH O CH O CH OOH
two —OHThe physical properties of an alcohol depend on whether the polar or the nonpolar por-
3 2 2

oth of these
groups. glycols
Besides arediols,
being colorless, odorless,
they are high-boiling
also classifi liquidsAthat
ed as glycols. are is
glycol completely mis-tion
a diol in which of its structure “dominates.” Factors that determine this include the length of the
nonpolar carbon chain present and the number of polar hydroxyl groups present (see
ble
thewith water.groups
two —OH arePoly(vinyl
Their majoronuses are as
Alcohol
adjacent alcohol)
the
carbon main
moleculesisingredient
atoms. ahave
tough,bothinwhitish andpolymer
automobile
polar that
“year-round”
nonpolar can
character. beThe
Figure 14.7). formed hydroxyl intogroups strongpresent films,
tubes,
tifreeze and airplane and
“de-icers”
5. Ethylen Glycol fi
are bers
(Figure
polar, that
14.5)
and are
and
the
(1,2-Etanediol) highly
as
alkyla (R) resistant
starting material
group to
present hydrocarbon
foristhe manufac-
nonpolar. solvents.
5 Unlike
Solubilitiesmost organic
dan Propylene Glycol Figure 14.8a shows that the boiling point for 1-alcohols, unbranched-chain alcohols with
Boiling Points and Water
ere Glycol (1,2-Ethanediol)
of polyester fibers (SectionCH 2and
O CHPropylene CH3O CH O CH2
polymers, A16.18).
PVA A is water-soluble. A Water-soluble films andan sheetings areincreases
important
as the length of the PVA
2
(1,2-Propanediol) A —OH group on an end carbon, carbon chain increases.

1,2-Propanediol)
Ethylene glycol products.
is extremelyOH toxic
PVA OHwhen
has ingested.
oxygen-barrier
Nonpolar
OHIn OH
portion
the body, liver
q
properties enzymes
under oxidize
dry o Polar
This trend
conditions
portion
results from increasing London forces (Sections 7.13 and 12.16) with increasing
that are superior to
carbon chain length. Alcohols with more than one hydroxyl group present have signifi-

to oxalic acid. • Terdiri dari 2C dan

Ethylene glycol 3C dengan 2~OH
Propylene glycol (diol atau glycol).
CH3O CH2 O CH2OOH cantly higher boiling points (bp) than their monohydroxy counterparts.

glycol and propylenethose

Larutan of tidak
glycol any
are theother
twopolymer.
berwarna,simplest PVA
alcohols
tidak can
beraroma, be rendered
possessing
laruttwo insoluble in CHwater,
—OH
di air.
O CH O CH ifCHneeded,
A
O CH O CH
A A
CHby
A A use
O CH O CH
A
3 2 2 3 2 2 2

Both ofbeing
esides these diols,
glycols are
ofthey colorless,
chemical
are also odorless,
Theagents
classifi
physicaled high-boiling
that
as glycols.O
properties Aliquids
cross-link
of glycol
O
an that
is are
individual
alcohol completely
a depend
diolpolymer
in whichmis- OH OH OH
strands.the polar or the nonpolar por-
on whether
OH OH OH
bp ! 97°C bp ! 188°C bp ! 290°C

ciblegroups
with water.• Digunakan
Their major uses sebagai
are as antifreeze dan
B B “de-icers”, dan
—OH are on adjacent carbon itsthe
atoms. main ingredient in automobile “year-round”
Figure 14.7 Space-filling molecular
HO O CH tion2 OofOH
2 O CH(Figure
structure
Liver “dominates.”
CO OHFactors that determine this include the length of the
juga sebagai bahan baku andHO
as O
seratCO poliester.
models showing the nonpolar (green)
antifreeze and airplane “de-icers” 14.5)
enzymes a starting material for the manufac- and polar (pink) parts of methanol and
nonpolar carbon chain present and the number of polar hydroxyl groups present (see
1-octanol. (a) The polar hydroxyl func-

14.11
ture of polyester fibers
CH
A
2O CHSTRUCTURAL
Ethylene glycol
(Section
A
16.18).
Figure
2 CH 3O CH O CH
14.7). A
CHARACTERISTICS
A
2
Oxalic acid
OF PHENOLS
tional group dominates the physical
properties of methanol. The molecule

Ethylene glycol is extremely toxic when ingested. In the body, liver enzymes oxidize is completely soluble in water (polar)

xalic acid, as a calcium OHsalt,OHcrystallizes in the OHkidneys,OH which leads to renal problems. CH OH
but only partially so in hexane (nonpo-
lar). (b) Conversely, the nonpolar por-
it to oxalic acid. CH CH CH CH CH CH CH CH
tion of 1-octanol dominates its physical 3 OH 3 2 2 2 2 2 2 2

Propylene glycol, on the glycol

phenol
AEthylene other
is hand,
an is essentially
organic
Propylene compound
glycol nontoxic and hasanbeen
inSolubilities
which —OH usedgroup as a(a) Methanol
is attached (b) 1-to
properties; it is infinitely soluble in hex-
a carbon atom
Nonpolar Polar Nonpolar Polar

Boiling Points
lvent for drugs. Like ethylene glycol, it is oxidized by liver and Water Oenzymes;
ane and has limited solubility in water. Octanol

that is part of anhigh-boiling

aromatic carbon O ring system.however,mis- pyru-
cese glycols
acid, are colorless,
its oxidation product, odorless,
isFigure
a compound
14.8a normally
shows
Liver
liquids
that B that
found
the Binare
boilingthe completely
humanforbody,
point being unbranched-chain alcohols with
1-alcohols,
water. Their inmajorHO O CH
uses are2 OasCH OH enzymes
2 Omain
the ingredient HOO inCautomobile
O CO OH “year-round”
intermediate carbohydrate metabolism
an —OH (Chapter
group on an24). end carbon, increases as the length of the carbon chain increases.
and airplane “de-icers” (Figure 14.5)
Ethylene glycol and as a starting
Aromatic material
Oxalic
This trend results from increasing London
acid for theOH manufac-
forces Hydroxyl 7.13 and 12.16) with increasing
(Sections
lyester fi bers (Section 16.18). ring O
system O functional group
carbon chain
Oxalic acid, as a calcium salt, crystallizes in
Liver
length.
the kidneys,Alcohols
which with
leads more
to renal than one
problems. hydroxyl group present have signifi-
ene glycol
Propyleneis extremely
CHon
glycol, toxic
3 the
when
CHother
cantly ingested.
CHhand,
2 higher CH In3 the
is essentially
enzymes boiling C body,C (bp)
nontoxic
points liver
OHthan enzymes
and has
theirbeen oxidize
used as a counterparts.
monohydroxy
csolvent
acid. for drugs. Like ethylene glycol, it is oxidized by liver enzymes; however, pyru-
OH OH
vic acid, its oxidation product, is a compound CH
Propylene glycol 3O
normally CH O CH2in the CH
Pyruvic2found
acid human3O CH O CH
body, being2 CH2O CH O CH2
O A is Ar–OH, A Universitas
A Lampung A A A
J urusan Tek n ologi Hasil Pe r t an i an
The general
an intermediate in carbohydrate formula
metabolism forOBphenols
(Chapter 24).
B OH
where
Fakultas Pertanian
OH OH Ar represents
OH OH an aryl OH group. An aryl
oup (Ar) is Liver
group is an aromatic
HOO CH2 O CH2 O OH enzymes HOO bp carbon COringCO OH
! 97°C system from which
bp ! 188°C one hydrogen atom
bp ! 290°C has been removed.
of the O O
m alkyl Ethylene A hydroxyl
glycol group
Liver
is Oxalic
thus acid
the functional group for both phenols and alcohols. The
7 Space-filling molecular
CH3 CH CH2 enzymes CH3 C C OH
reaction chemistry for phenols is sufficiently 14.12 Nomenclature fordifferent Phenols from419 that for nonaromatic alcohols
wing
d, asthe nonpolarsalt,
a calcium (green)
crystallizes in the kidneys, which leads to renal problems.
ink) parts of methanol (Section
and 14.9)OHto justify discussing these compounds separately. Remember that phenols
OH
ylene glycol, on the other hand,
Propylene is essentially nontoxic
glycol and has been used as a
Pyruvic acid
) The polar hydroxylcontain
func- a “benzene ring” and that the chemistry of benzene is much different from that
r drugs. Like ethylene glycol, it is oxidized by liver enzymes; however, pyru-
pnyl alcohol) is aoftough, whitish polymer that canin be formed into strong
other unsaturated hydrocarbons (Section
human13.14). being films,
dominates the physical
ts oxidation product, is a compound normally found the body,
of methanol. The molecule
fiediate
bers inthat are highlyThe
carbohydrate resistant
following
metabolism to(Chapter
hydrocarbon
are examples
24). solvents.
of compounds Unlikeclassifi
most organic
ed as phenols.
y soluble in water (polar)
PVA is inwater-soluble.
tially so hexane (nonpo- Water-soluble films and sheetings are important PVA 6
VA has
versely, theoxygen-barrier
nonpolar por- PHE Nunder
properties OLOOH (FEN
O conditions
dry O L)thatOH are superior to OH
CH
Liver OH CH CH CH CH CH CH CH CH OH
yanolother polymer.
dominates CH PVACH
its3physical
CH can be rendered
3
CH3 insoluble
C C OHin water, if needed, by use
3 2 2 2 2 2 2 2
๏ Phenol
2 enzymes
t is infinitely soluble in hex-(fenol) adalah
Nonpolar bahan organik yang
Polar mengandung Polar
Nonpolar
agents that cross-link
limited solubilitygugus OH ~OH
in water.
individual
OH terikat
(a) Methanol
polymer strands.
pada rantai 6 atom Cl
karbon aromatik. CH3
(b) 1- Octanol
CH3
Propylene glycol Pyruvic acid
๏ Rumus umumnya: Ar-OH (Ar = Aryl group, 6 carbon
TRUCTURALaromatic
CHARACTERISTICS
14.12yang OF1PHENOLS
NOMENCLATURE
kehilangan FOR
atom H).PHENOLS
๏ Phenol = Phenyl dan Alkohol.
an organic๏ compound
Besides in
Penomoran
which
being
atom theC, —OH
anname forgroup
dimulai
is attached
a family
dari
to a carbon
of compounds,
C yang
atom
phenol
mengikat ~OH. is also the IUPAC-approved
of an aromatic carbon ring
name for thesystem.
simplest member of the phenol family of compounds.

Aromatic OH Hydroxyl
OH
ring system functional group

Phenol
neral formula for phenols is Ar–OH, where Ar represents an aryl group. An aryl
J urusan Tek n ologi Hasil Pe r t an i an
aromatic carbonAring
space-fi llingfrom
system model for the
which onecompound phenol
hydrogen atom hasis been
shownremoved.
in Figure 14.14. The name phenol Fakultas Pertanian Universitas Lampung

is derived
oxyl group is thus from a combination
the functional group for ofboththephenols
terms phenyl and alcohol.
and alcohols. The
emistry for phenols isThe IUPAC
suffi cientlyrules for naming
different phenols
from that are simply extensions
for nonaromatic alcohols of the rules used to name
benzene derivatives
.9) to justify discussing with hydrocarbon
these compounds separately.or halogen
Remember substituents (Section 13.12). The parent name
that phenols
benzene ring” andis phenol.
that theRing numbering
chemistry always begins
of benzene withdifferent
is much the hydroxyl
fromgroup
that and proceeds in the direc-
tion that gives
saturated hydrocarbons (Sectionthe lower
13.14).number to the next carbon atom bearing a substituent. The numerical
positionofofcompounds
lowing are examples the hydroxylclassifi
groupedis as
notphenols.
specified in the name because it is 1 by definition.

OH OHOH OH
OH OH
CH3 Br
 nol solutions, however, can cause
2 severe skin burns. Today, phenol has been largely
benzene derivatives with hydrocarbon or halogen substituents (Section 13.12). The parent name
replaced by more effective phenol derivatives such as 4-hexylresorcinol. The compound
is phenol. Ring numbering always begins
Phenol withphenoxide
Sodium the hydroxyl group and proceeds in the direc-
n antiseptic is a substance that kills 4-hexylresorcinol is an ingredient in many mouthwashes and throat lozenges.
tion that gives
icroorganisms on living tissue. A the lower number to the next carbon atom bearing a substituent. The numerical
positionthat
sinfectant is a substance of the
killshydroxyl group is not specified in the name because OH it is 1 by definition.
Phenols, and Ethers
icroorganisms on inanimate
bjects. OH OH OH 7
14.14 OCCURRENCE OF AND USES FOR PHENOLS
s, Phenols, and Ethers CH3 Br
Methyl and hydroxy derivatives of phenol have IUPAC-accepted OH common names.
Dilute (2%) solutions of phenol have long been used as antiseptics. Concentrated phe-
heing“parent”
model nameMethylphenols
for a benzene are called Clcresols. The name cresol CH applies
2 O(CH Brto allCHthree
2)4 O 3 isomeric
nol
ng solutions,
at bearing
has two however,
Methyl
hydroxyl can
and cause
groups hydroxy severe skin burns.
derivatives ofCH Today,have
phenol phenol has
IUPAC-accepted been largely
common names.
methylphenols. 2OCH3
4-Hexylresorcinol
eplaced by more
ctly totoa each
meta” other effective
is resorcinol phenol derivatives such as 4-hexylresorcinol.
Methylphenols are called cresols. The name cresol applies to all three isomeric
3-Chlorophenol 4-Ethyl-2-methylphenol
The compound
2,5-Dibromophenol
4-hexylresorcinol
ection 14.12). is an ingredient
methylphenols. inThe phenol
many derivativesOH
mouthwashes
(or meta-Chlorophenol)
OH o-phenylphenol
and throat lozenges.andOH2-benzyl-4-chlorophenol are the active ingre-
Methylphenol
dients in Lysol, a disinfectant= for Cresol
walls, floors, and furniture in homes and hospitals.
OHOH CH3 OH OH
OH
CH3
CH CH2
OH 3
OH CH3
CH3
ortho-Cresol
CH2 O(CH2)4 O CHmeta-Cresol
3
p ara-Cresol
CH3
4-Hexylresorcinol meta-Cresol
ortho-Cresol p ara-Cresol Cl
For hydroxyphenols, each of the three isomers has a different common name.
The Hydroxyphenol o-Phenylphenol 2-Benzyl-4-chlorophenol
e phenol derivatives o-phenylphenol
For hydroxyphenols, each ofand the2-benzyl-4-chlorophenol are the
three isomers has a different active name.
common ingre-
dients in Lysol, a disinfectant for walls,OH flAoors, and OHin homes and hospitals.
furniture OH
number of phenols possess antioxidant activity. An antioxidant is a substance
the OH
OHprotects OH OH oxidized by being oxidized itself in preference
, that other substances from being
OH
to the OH other substances. An antioxidant has a greater affinity for a particular oxidizing
dives. agent than do the CHsubstances
OHthe antioxidant is “protecting”; the antioxidant, therefore,
2
OH
vatives. reacts with the oxidizingOH agent first. Many foods sensitive to air are protected from
OH
J urusan Tek n ologi Hasil Pe r t an i an
ure 14.15 Many commercially oxidation
Catechol through Resorcinol
the use of phenolic antioxidants.
OH Two commercial
Fakultas Pertanian Universitas
Hydroquinone Lampung phenolic antioxidant
d goods contain the antioxidants food
Catecholadditives
Cl areResorcinol
BHA (butylatedHydroquinone
hydroxy anisole) and BHT (butylated hydroxy toluene)
and BHT to help prevent spoilage. (see Figure2-Benzyl-4-chlorophenol
o-Phenylphenol
14.15).

A number 14.13 PHYSICAL

of phenols possess AND CHEMICAL
antioxidant activity.PROPERTIES OH CH
An antioxidant A OF
3 is PHENOLS
a substance OH
14.13
hat protects other PHYSICAL
substances fromAND
beingCHEMICAL
oxidized by PROPERTIES
being oxidizedCOF itself
O CH PHENOLS
3in preference
A
o the otherPhenols
substances.are An antioxidant
generally has a greater
low-melting solidsaffiornity
oilyforliquids
a CH
particular
at roomoroxidizing
temperature.CH3 Most of
ithin the human body, natural
Phenols are generally low-melting solids or oily the liquids at3 room therefore,
temperature.A Most of
gent than do them
etary antioxidants
thealso
substances
are the antioxidant
only slightly
offer soluble iniswater.
“protecting”;
Many phenols antioxidant,
have antiseptic andCdisinfectant
O CH3
eacts with them
the are onlyagent
oxidizing slightly soluble
first. Many infoods
water.sensitive
Many phenols air have antisepticfromand disinfectant
otection properties.
against undesirable The simplest phenol, phenol itself,to are protected
Oisa acolorless
colorless solid Owith Aa medicinal
oxidation properties.
through the The simplest
use of phenolic phenol,
antioxidants.phenol itself, is solid with a medicinal
CH
xidizing agents. TheyIts
odor.
odor.
include
Its melting
melting point
point is
is 41!C, and
41!C, andTwoitisiscommercial
moresoluble phenolic
A soluble in antioxidant
water thanA
are3are
3
most other
tamin C (Section
ood additives 21.12),
are
phenols. BHA beta-
(butylated hydroxy anisole) itand more
BHT CH3
(butylated inhydroxy
water than CH
toluene) most other
rotene (Sectionphenols.
see Figure 14.15).21.13), vitamin E
ection 21.14), andWe flWe have
have previously
avonoids previously noted Synthetic
noted that the
that Antioxidants
thechemical
chemical properties
properties of
BHAof(2phenols
isomers)are are
phenols signifi
signifi 8
cantly
cantly
ection 23.11).different
differentfromfrom those
those of
of
CH alcohols
alcohols (Section
(Section 14.11).
14.11). The
The similarities
similarities andand differences
differences between
between
OH A 3 OH H3 C
these
thesetwotwo reaction
reaction chemistries
chemistries areare asasfollows:
follows: A OH CH A
3
C O CH3
A 3 CH OC C O CH
3
1.1.Both
Bothalcohols
alcohols and phenolsor
CHphenols areflflammable.
are ammable.CH3 A A
3 A Hphenols
3 Cphenols CHbe
,enols,
Phenols,
andand2.
2. Dehydration
Dehydration
Ethers
Ethers is
is a reaction
reaction of
of alcohols
alcohols but
but not
not
C O CH3ofof phenols;
phenols; cannot
cannot 3 be
dehydrated.
dehydrated. A
O O
ols, and Ethers3.3.Both
Both1! 1!and
andA 2!
2! alcohols
alcohols are oxidized
are oxidized CH
A bymild
by 3 oxidizing
mild oxidizingagents.
agents.CH
Tertiary (3!)(3!)
Tertiary
3 alcohols
alcohols
andphenols
and phenolsCH do
do not react
3 not react with
withthe CH
theoxidizing
oxidizing agents
agentsthat cause
that cause
BHT
1! andand
1! 2! alcohol
2! alcohol
A naturally
A naturally occurring
oxidation.occurring phenolic
phenolic
3
antioxidant
antioxidant that is
that is agents. 14.14
important
important Occurrence
in the of and Usesoffor
functioning thePhenols
of the human 421
oxidation. Phenols can
Phenols can be
BHAbe(2oxidized
oxidized
isomers)
bybystronger
strongeroxidizing
oxidizing agents. in the functioning human
A naturally
4.4.body
body isoccurring
Both
Both is vitamin
alcohols
vitamin
alcohols phenolic
and
E (Section
and phenols antioxidant
E (Section
phenols undergo
21.14).
undergo that
21.14). is important
halogenation
halogenation inin in the
which
which functioning
thethe
hydroxyl
hydroxyl of
group the
groupis human
is
body is vitamin
replacedEby
replaced (Section
by H21.14).
aa halogen
halogen atom in
3 C atom
aasubstitution
Natural
in substitution
CH reaction.
Antioxidants
reaction.
A OH A
3
CHCH OH
3 3 C O CH O"Na!
Acidityof
of Phenols
Phenols HOA CH3 3OC
CH 3
A
Acidity HO HOH3 C CH3 ! NaOH(aq ) ! H2O
One of the most important properties of phenols is their acidity. Unlike alcohols, phenols
One of theacids
are weak mostinimportant
solution. As properties of phenols
acids, phenols have Kisa values
their acidity.
(SectionUnlike
10.5) ofalcohols,
about 10phenols
" 10
.
are weak acids in solution. CH3 Phenol
Asthose
acids, phenols have Ka values (Section 10.5) 10" 10.
Such Ka values
H3C areH lower
H
C 3
O
than
C BHT
ofO O
most weak inorganic acids (10" 5 to 10" 10of). about
Sodium phenoxide
The acid
Such K values are 3
lower than those of most weak inorganic acids (10 " 5
to 10 " 10
). The acid
ionization
a reaction for
CHphenol itself is
CH
theCH
3
ionization
antioxidant reaction for in
that is important phenol itself
3 3is
functioning ofEthe human
Vitamin
OH Vitamin
O" Vitamin E E
4).
A number of phenols foundOHin plants are usedOas flavoring
"
agents and/or antibacte-
J urusan Tek n ologi Hasil Pe r t an i an

A14.14
number OCCURRENCE
of phenols inOF
Hfound in AND
plantsUSES
Hare # used FOR
as as PHENOLS
flavoring agents and/or antibacte-
Fakultas Pertanian Universitas Lampung
A number
rials. Included among of phenols
these phenolsfound
# are
2O
plants #are used
3O
flavoring agents and/or antibacte-
rials.
rials. Included
Included among
among these
these H2phenols
# phenols
O areare # H3O#
OH
Phenol PhenoxideOH
ion
Dilute (2%)H3C solutions
14.14 Occurrence ofOH
ofphenol
and Useshave long been
for Phenols 421
OH used as antiseptics. Concentrated phe-
Note that the negative ion
Phenol
produced
OHfrom the
Phenoxide ion OOCH3OH
ionization is called theburns.
phenoxide ion. phenol has been largely
nol solutions,Hhowever, H can cause severe skin Today,
Whenthat
Note phenol
the itself is reacted
negative ion C 3C sodium
with
3produced fromhydroxide
the (a base),isthecalled
ionization salt sodium
the OOCH
OOCH
phenoxide
phenoxide
3 3 ion.
replaced by more effective
is produced. CHO CH3 !
phenol derivatives such as 4-hexylresorcinol. The compound
When
OH phenol itself is reacted with sodium
Na hydroxidein(amany base), the salt sodium phenoxide
nce that kills 4-hexylresorcinol isA anO"ingredient
is produced. CH O CH P CH
mouthwashes and throat lozenges.
CH3 2 2
g tissue. A Vitamin E
! NaOH(aq ) !CHO
CHO O CH
H CH 3
3Eugenol
e that kills Thymol A A 2 OH
nd in plants are used as flavoring agents and/or CHCH CHCH O CH
2 O2CH P CH
P CH
mate 3antibacte-
3 2 2
Phenol OH
Sodium phenoxide OH
enols are Thymol
Thymol
Flavoring Agents
Eugenol
Eugenol 9
OOCH OOCH 3 3

H OH OHOH OHOH
OH
OOCH3 OO CH
OOCH3 3 OO OOCH
CH 3
RRENCE
benzene OF AND USES FORCH
PHENOLS
P CH O CH3
CH2 O(CH2)4 O CH3 3
CHPO
yl groups 4-Hexylresorcinol
Isoeugenol Vanillin
esorcinol
CHO CH
utions of phenol 3 have long been used as antiseptics. Concentrated phe-
A The phenol derivatives o-phenylphenol and 2-benzyl-4-chlorophenol are the active ingre-
owever,
CH3 can cause severe
CH2 Oskin
CH P burns. CHCH
CH2 Today, P CHP CH O CH
phenol
O CH 3has3 beenCHPOlargely
CHPO
Thymol,dients in Lysol,
obtained from thea disinfectant for walls,
herb thyme, possesses floors,
both and furniture
flavorant in homes and hospitals.
and antibacterial
e effective phenol derivatives
hymol such as 4-hexylresorcinol.
Eugenol Isoeugenol
Isoeugenol The compound Vanillin
Vanillin
properties. It is used as an ingredient in several mouthwash formulations.
ol is an ingredient in many
Eugenol is responsiblemouthwashes and
for the flavor of throat lozenges. OH used clove oil as
cloves. Dentists traditionally
H Mouthwash
OH Disinfectant
an antiseptic because of eugenol’s presence; they use it to a limited extentCH even today.
OOCH Thymol,
3 Thymol,
Isoeugenol,
obtained
OH obtained
OOCH
which differs
from
infrom thethe
3structure OHherb
herb
from
thyme,
thyme,
eugenol
possesses
possesses
only bothboth
in the location
flthe
avorant
fl2ofavorant and antibacterial
dou-and antibacterial
ble bond properties.
properties.
in the It It used
is is used
hydrocarbon as
an an
asside ingredient
ingredient
chain, in in
is responsible several
several mouthwash
formouthwash
the odor associated formulations.
formulations. with
- nutmeg (see Eugenol
Eugenol
Figure is is responsible
responsible
14.16). forforthethe flavor
flavor of of cloves.
cloves. Dentists
Dentists traditionally
traditionally used
used clove
clove oiloil
as as
h
an an
Vanillin, antiseptic
whichbecause
antiseptic because
gives
OH of of
vanilla itseugenol’s
flavor, is
eugenol’s presence;
extracted
presence; from
they they theuse
use dried
itClto it to seed a limited
a limited pods of extent
the
extent eveneven today.
today.
H P CH O CHorchid.
vanilla Natural supplies of vanillin are inadequate to meet demand forinthis
3
Isoeugenol, CHPO
Isoeugenol,
CH2 O(CH which
which differs
differs
2)4 O CH3
in structure
ino-Phenylphenol
structure fromfrom eugenol
eugenol only only
2-Benzyl-4-chlorophenol
theflthe
in avor-location
location of of
thethedou-dou-
uit. ing agent.
Isoeugenol ble Synthetic
bond in vanillin
Vanillin
the is produced by
hydrocarbon oxidation
side chain, of eugenol.
is responsible Vanillin is for an the unusual
odor associated with
A A ble bond in the hydrocarbon
4-Hexylresorcinol side chain, is responsible for the odor associated with
substance in that even though its odor can be perceived at extremely low concentrations,
sl,re-
is re- nutmeg nutmeg (see(see
A Figure
number
Figure 14.16).
of
14.16). phenols possess antioxidant activity.
J urusan Tek n ologi An
Hasil Pe r t an i an antioxidant is a substance
vatives the strength of its odor does not increase greatly asare
and which
2-benzyl-4-chlorophenol its the
concentration is increased.
witho-phenylphenol isactive ingre-
Fakultas Pertanian Universitas Lampung
ed
with Vanillin,
that
Vanillin, protects
which othergives
gives vanilla
substances
vanilla its flavor,
flfrom
itsantibacterial
avor, being
isFor extracted
oxidized
extracted from from
by thethe
being drieddried
oxidized seed
seed pods
itself
pods inof
of the
preference
the
e herb Certain
thyme, phenols
possesses exert
bothprofound
fl physiological
avorant and
ahedisinfectant for walls, floors, and furniture in homes and hospitals. effects. example, the irritating con-
vanilla
vanilla
stituents of to orchid.
the
orchid.
poison other
ivy Natural
Natural
and
redient in several mouthwash formulations. poison supplies
substances.
supplies
oak are An
of of vanillin
antioxidant
vanillin
derivatives are
of are inadequate
has
inadequate
catechol a greater
(Section to to
meet meet
affi
14.12). nity demand
demand
These for a
for for this
particular
this fl flavor-
avor- oxidizing
the flavor ofing
skin ing
irritants agent.
agent
agent.
cloves. Synthetic
haveSynthetic
15-carbon
than
Dentists doOH thevanillin
alkyl
vanillin substances
traditionally is
sideischains produced
produced
used with
the varying
clove by asoxidation
antioxidant
byoil degreesisof
oxidation of eugenol.
unsaturation
of“protecting”;
eugenol. Vanillin
(zero is is
anan
the antioxidant,
Vanillin unusual
unusual therefore,
to three double
substance
substance bonds).
in in
reacts that
with
that even
the
even though
oxidizing
though itseven
odor
agent ficanbe be
rst. perceived
Many foods at at extremely
sensitive tolow
air concentrations,
are protected from
ol’s presence; they use it to a limited CH 2 its odor
extent can
today. perceived extremely low concentrations,
OH
he
in structure
mercially thethe
from strength
strength
oxidation
eugenolof of its
itsonly
odor
through odor
OHdoes
in the
the does notnot
use
locationof increase
increase
of thegreatly
phenolic
OH greatly as as
antioxidants.
dou- its its concentration
concentration
Two commercial is is increased.
increased.
phenolic antioxidant
short-
rt- Certain phenols exert OH profound physiological
OH effects. For example, the irritating con-
sidethe Certain
food phenols
additives exert
are profound
BHA
chain, is responsible for the odor associated with physiological
(butylated hydroxy effects.
anisole) Forand example,
BHT the
(butylatedirritating
hydroxycon- toluene)
dntioxidants
r for
the
ent spoilage.
stituents
stituents of of
(see poison
poison
Figure ivy ivy
14.15).and and poison
poison oak oak are are derivatives
derivatives of of catechol
catechol (Section
(Section 14.12).
14.12). These
These
ia
and and Cl
t its flavor,
lla skinskin irritants
isirritants
extracted havehave
from 15-carbon
15-carbon
the dried alkyl
alkyl
seed sideside
pods Cchains
chains !31with
25with
15 Hthe
of varying
varying degreesdegrees of of unsaturation
unsaturation (zero
(zero
o-Phenylphenol 2-Benzyl-4-chlorophenol
to to three doubletobonds). OHthisCH
Catechol Poison ivy irritants
of vanillin three
are double bonds).
inadequate meet demand for flavor-
3 OH
 CH3 O OO CH3 CH3 O CH2 O OO
14.16 Nomenclature~105˚
for Ethers 423
The
10CH3 O OOtwo
CHgroups attached
CH 3 O CH2to
atomCHOthe
OOoxygen
of3 OO
an etO
E TWater
E R (HOH) 3
but they need not be so (second and third structures).
~105˚
O CH2 O OO
A. STRUKTUR DAN SIFAT ETER
CH3 OO O All ethers contain a C—O—C unit, which is the
•Water (HOH) senyawa organik dimana atom
Eter adalah
The two groups attached to the oxygen atom of an ether can be the s
oksigen terikat pada dua atom karbon butdengan
they need not be so (second and third structures).Ether functional group
ikatan tunggal.
gen atom of ~111˚ All ethers contain a C—O—C unit, which is the,ether C O O function
• anDalamethereter,
canatombe the same
karbon (firstterikat
yang structure),
pada O C,
hird structures).atom oksigen dapat dari gugus alkil, sikloalkil,
atau aril. Generalized formulas for ethers,
Ether functional group which depend
unit, which is thegroup
• Dua ether functional group.
~111˚ yang terikat pada atom oksigen the oxygen atom (alkyl , Cor OO aryl),
O C, include R—O—R
eter bisa sama Dimethyl ether
(struktur (CH3 OCH
primer), atau3 )tidak
sama (struktur sekunder atau tersier).
Ether functional group group different from R), R—O—Ar, and Ar—O—A
• Semua eter Figure 14.17 The
mengandung unitsimilar
C-O-C, Generalized
shapes
yang of formulas for ethers,
Structurally, which
an ether can depend on theastypes
be visualized o
a deriv
, C O O O Cmerupakan
, group
water fungsional
and dimethyleter.etherthe molecules.
Dimethyl ether (CH
oxygen atomgen (alkyl
atomsorhave
aryl), include
been replacedR—O—R, R—O—R!
by hydrocarbon (w
groups
3 OCH3ether
Dimethyl ) may beattached
viewed struc-
s, which depend on the types of groups to
group different 423 from R), R—O—Ar,
alcohols and phenols,and Ar—O—Ar.
ethers do not possess a hydrox
J urusan Tek n ologi Hasil Pe r t an i an

turally14.16 aNomenclature for Ethers water.

Fakultas Pertanian Universitas Lampung

Figure
clude 14.17 The
R—O—R, similar
R—O—R! as
shapesdialkyl
(where of derivative
R! is an of alkyl
Structurally, an ether can be visualized as a derivative of water i
water
, and and dimethyl ether molecules.
Ar—O—Ar. gen atoms have been replaced by hydrocarbon groups HO O O (see
H Figure
R O14
OO
Dimethyl ether may be viewed
ualized as a derivative of water in which struc- 14.16
both Nomenclature
hydro-for for Ethers 423
alcohols
14.16 Nomenclature and phenols,
Ethers 423ethers do not possess a hydroxyl Water (—OH)Angro eth
turally
CH
drocarbon as a
CH dialkyl
3 groups
O 2 O O O derivative of
(see Figure 14.17). water.
CH 3 OONote that unlike
O
14.16 Nomenclature for Ethers 423
possess a hydroxyl (—OH) group. HO O O H ROO OR
o the CH 3 O OO
oxygen CH3 of an
atom CHether3 O CH 2 Obe
can OOthe same (fiCH OO O
rst3 structure),
CH3 O OO CH3
OO Hand third
econd R Ostructures).
OOR
CH3 O CH2 O OO CH3 OO O 11
14.16 NOMENCLATURE Water FOR ETHERS
An ether

CH 14.16 Nomenclature OO for Ethers 423

C—O—C
o groups attached
Water unit, O
An3which toOthe
ether O CH isoxygen
the
3 etherCH3functional
atom O ofCH an2 Oether group.
can be the same CH3 OO (firstOstructure),
groups attached to the oxygen
y need not be so (second and third structures). atom
Line-angle of an ether
structural can be
formulas the same
for14.16
(fi Nomenclature
rst Commonfornames
structure), 423 always used for ethers w
Ethers are almost
eed not be so (second and third
selected structures).
simpleisethers:
lThe
ethers
thers two
contain
Ether
contain
groupsa
functional
aattached
C—O—C
C—O—C
group
to unit,
unit, the which
oxygen
which is theatomthe of 14.16
ether
ether functional
functional
an ether canNOMENCLATURE
be
group. thefewer
group. same carbon FOR ETHERS
atoms.
(first structure), There are two rules, one for unsym
, C O O O C , aryl groups) and one for symmetrical ethers (both alky
Hbut
3 they CH 3 O CH
need not2 O beOsoO(second Etherand
CH
third
3 OO structures).
O
O
ETHERS All ethers contain a Ether
C—O—C
functional
functional group
unit,
group
which is the ethernames
functional
for Line-angle
ethers, CHwhich structural
3 O O O CH3
depend formulas
on,C the for
types
OEthyl
CH O3OOCCH ,of2 O
methyl OCommon
groups
etherO attached toCHRule are group.
almost always used for ethers whose alkyl gr
3 OO1:O For unsymmetrical ethers, name both hydroca
or
dused selected
toaryl),
thefor oxygen simple
includeatom R—O—R,ethers: ,
of analkyl
C O
ether
O
R—O—R! O C ,
(methoxyethane)
can Ether
be the (where
same R!
fewer
(fi iscarbon
rst an alkyl
structure), atoms. Thereatom are two rules, one for unsymmetrical ether
eneralized
R—O—Ar,
ethers
formulas
and
whose
for ethers,
Ar—O—Ar.
groups
which dependcontain
functional
on the four
group types orof groups attached to in alphabetical order and add the word e
ralized
second formulas
and(alkyl for ethers, which depend on the aryl typesgroups)
of groups attached to symmetrical
les,
ygen
hecan
en two
atom
one
beatom forthird
groups
visualized
(alkyl or
structures).
unsymmetrical
or
attached
as
aryl), a O
aryl), to
derivative
include
ethers
include
the oxygen
of
R—O—R,
(two
R—O—R,, CO
water different
O
atom
inOO
R—O—R!
R—O—R!
C ,an
of
which alkyl/
both (where
ether
(where
and
can
hydro-
R!
R!
isbe
one
an
isthe for
an same
alkyl
space.
alkyl (fi Such
rst
ethersnames
ether
structure),
(bothhave
alkyl/aryl groups th
three separate w
adifferent
C—O—C unit,
from R), which
R—O—Ar, is the ether
and the functional
Ar—O—Ar. group.
lferent
ethers
tced
they by (both
need not
hydrocarbon
from
Generalized R), alkyl/aryl
Ethyl be
R—O—Ar, methyl
so
groups
formulas groups
ether
(secondand(see
for and
Figure
Ar—O—Ar.
ethers, same).
third
Diethyl
which Rule
Note1:that
structures).
ether
14.17). depend on For unsymmetrical
unlike
the types of groups attachedethers, to name both hydrocarbon groups bo
ructurally, an Ether ether can be
(methoxyethane)
functional visualized
group as a derivative of water in which both hydro-
(ethoxyethane) CH3 OO O CH2O CH3 CH3 O C
turally,
ers
the do
All an ether
not
oxygen
ethers possess
atom can (alkyl
contain be
a visualized
hydroxyl
a or
C—O—C aryl), as ainclude
(—OH) derivative
group.
unit, of water
R—O—R,
which is in which
R—O—R!
the ether
atom Note both hydro-
(where
functional
in alphabetical R! is an
group. alkyl
amehave
oms
sgroup
bothbeen
have been
hydrocarbon
replaced
replaced by by groups
hydrocarbon
hydrocarbon
bonded
groupsgroups to the
(see (see oxygen
Figure Figure 14.17).
14.17). Note that that
unlikeunlike order and add the word ether, separating
different from R), R—O—Ar, and Ar—O—Ar. space. Such ether names have three separate words within th
, C O O O C , J urusan Tek n ologi Hasil Pe r t an i an

ndand add the word separating the words with a group.

Fakultas Pertanian Universitas Lampung

ls
and phenols,
phenols, ethers ether,
ethers Odo
doether
not not
possesspossesshydroxyl
a Ether
O Rbe avisualized
hydroxyl
Ofunctional
(—OH) (—OH) group.
HO O O
Structurally, H an R OO can as group
a derivative of water in which both hydro- Ethyl methyl ether Eth
veas three
for ethers,separate which words
Diethyl depend within
ether on them.
the Dipropyl
types of groups attached to
ether
gen atoms have been replaced byH hydrocarbon Rgroups C ,(see Figure 14.17). Note that unlike
or aryl),Water , OC ROOO O R!
An ether
include HOHOO
R—O—R,
(ethoxyethane) OOHO R—O—R! R ORO O O(where
(1-propoxypropane) is an alkyl RuleCH 2: For symmetrical ethers, CHname the alkyl group
alcohols and phenols, ethers do not possess a hydroxyl (—OH) group. 3 OO O CH2O CH3 3 O CH2O O
, R—O—Ar, andformulas Ar—O—Ar. Water An ether
the word ether, separating the words with a sp
CHGeneralized
3 CH3 O CH2OO Waterfor ethers, which depend on the types of groups
An ether attached to
er can be visualized asOa derivative of water in which both hydro- separate
Ethyl methyl words
ether within them. Ethyl phenyl ether
e oxygen atom (alkyl or aryl), HOinclude
O O H R—O—R, R O O O R R—O—R! (where R! is an alkyl
URE
placedFOR ETHERS
by hydrocarbon Dipropyl
Ethyl phenyl groups
ether
ether (see Figure 14.17). Note that unlike
6oup
thers different
NOMENCLATURE
do not possess
NOMENCLATURE
from
FORaR),
FOR
(1-propoxypropane)
R—O—Ar,
hydroxyl
ETHERS ETHERS (—OH)and
Water Ar—O—Ar.
group.
An ether
Rule 2: For 12symmetrical ethers, nameCH the alkyl
3 OO O CHgroup,
3 add
CHthe prefi
3 O CH 2O x
ost Structurally, an ether can be xvisualized ascontain
aaddderivative of water in which both hydro-
A. TATANAMA SIFAT ETER
me always
the alkyl used
group,
1. Nama Umum:
for ethers
add the whose
prefi alkyl
di-, groups
and then four or
the word ether, separating the words Dimethylwith
ether a space. Such ethe Dieth
hennames
on
areatoms
names
twoare
words H have
O
are
rules,
with O
almost been
Oalmost
one
a Hspace.
for replaced
always RSuch
always O Oused
unsymmetrical
used by
R for
Oether
for hydrocarbon
ethers
ethers
names
ethers whose whose
(two
have groups
alkyl
different
alkyltwo groups (see
groups
alkyl/ Figure
containcontain
four 14.17).
four
or or Note that unlike
14.16 •Water
Rule No. 1
NOMENCLATURE FOR ETHERS separate words within them.
cohols
.arbon
ymmetrical
bon atoms. and
atoms. phenols,
There
ethers
There are
(both ethers
two rules,
alkyl/aryl do one not
for
groups possess
unsymmetrical
the same). a hydroxylethers (—OH)
(two differentgroup.
alkyl/ with more complex alkyl/aryl groups are
Ethers
• for symmetrical ethers (both alkyl/aryl groups the different
are two rules, one for unsymmetrical ethers (two alkyl/
An ether
Untuk eter yang tidak simetris, beri nama
oups) and one
ps) and one forkedua symmetrical ethers hidrokarbon
(both alkyl/aryl groups same).
the same). this CH system, ethers
alCommon
ethers, name both
kelompok
hydrocarbon groups bonded
yang terikat
to the oxygen 3 OO O CH3 are namedCH3 O CH as 2O substituted
O O CH2Ohydro CH3
CH O names
CH
pada
O are
atom
O O almost
CH
oksigen
O always
CH
dalam
H O used
O O for
urutan
H ethers
abjad
R O whose
dan
O O R alkyl groups contain four or
For
or unsymmetrical
unsymmetrical ethers,
ethers, name nameboth both hydrocarbon
hydrocarbon groups bonded to attachment
the oxygen and the oxygen atom are called an alkoxy
forgroups bonded
with ato the oxygen
3 2
tambahkan 2
kata 3
eter, pisahkan kata-kata
cal order
fewer carbonand addatoms. theThere
word ether,
are twoseparating
rules, the
onesemacam words
unsymmetrical (twoDimethyl
differentether Diethyl ether
itu the ethers alkyl/
TUREatom
tom
names
aryl
in FOR
in ETHERS
alphabetical
have three
groups)
dengan
alphabetical
and
Diethyl
memiliki
order spasi.
order
ether
separate
one for
and and
add
words
tigasymmetrical
kata
Nama
add
the the
wordether
word
Water
within
terpisah
ether,
dithem.
ethers
ether, separating
separating the
An ether words
(both alkyl/aryl groups the same).
dalamnya.
wordsa
with with
a a
substituent on the larger hydrocarbon group. An a
space. Such ether names have three separate words within them.
pace. Such ether names have three separate words withinEthers them. with more alkyl (orcomplex
aryl) alkyl/aryl groupstoare
group attached annamed
oxygenusing
atom.th
l/aryl
most groups
Rule always
1: For used are named
unsymmetrical using
for ethers ethers, the
whosename IUPAC
alkylboth groups system.
hydrocarbon
contain In groups
four
this system, ethers or bonded to the oxygen
are named as substituted hydrocarbons. The s
O O CH2O CH3 CH3 O CH2OO following:
ubstituted
re are twoatom hydrocarbons.
rules,
CH CH
3 OOin3 OO
alphabetical
one
O CHOfor2CH
O 2It
Ois The
order
possible
unsymmetrical
CH 3CH 3 CH smaller
andOto
3CH add
have
ethers
3O
CH 2CH
Ohydrocarbon
the
O word
2compounds
(two
O ether,
O different separating
thatalkyl/ the wordsatom
with aare called an alkoxy group, and this
4.16 NOMENCLATURE FOR ETHERS attachment and the oxygen
called an
ylsymmetrical alkoxy
space. Such
ethers group,
etherEthyl
(both andphenyl
contain
names this
alkyl/aryl both
have group
groupsthreeis
ether and considered
alcohol
separate
the same). words within them. CH3 OO O CH3 O CH2OO CH
methyl ether
EthylEthyl methyl
methyl etherether
functional
ether
groupsEthylEthyl
such
phenyl aassubstituent
phenyl
ether ether on the larger hydrocarbon group. An alkoxy group is
bon group. An alkoxy group is an —OR group, an Methoxy group Ethoxy group
cal ethers,
ommon
ethers, name name
names bothalmost
are
theethers,
alkyl hydrocarbon
group, always
add thegroupsused
prefi bonded
xadd for
di-, alkyltothen
ethers
and (or
the aryl) alkyl
oxygen
whose
add groupgroups
attached to an
contain fouroxygen
or atom. Simple alkoxy
Simple alkoxy groups include xthe
J urusan Tek n ologi Hasil Pe r t an i an

an oxygen
ForForsymmetrical
tical order atom.
symmetrical
and add
ethers,
CH
the
name name
3 OO
CH
C
word
the
OOthe
alkyl
CHCH
3 ether, 2alkyl
OO group,
CH
CH group,
3 O
separating CH add
CHthe
the 3O
O the
prefi
O
words
CH
Oprefi
O xOdi-,
di-, and and
Fakultas Pertanian Universitas Lampung
2CH
with a
thenthen
add add
following: haveThe general symbol for an alkoxy group is —O—R
2 2 3
parating
wer
he the carbon
wordword the words
atoms. with
There
separating
separating
ether,
ether, a space.
the are
the
words A Such
two
wordswith aether
rules,
with aone
space. names
space. for
Such Suchhave
ether twonames
unsymmetrical
ether
names ethers
have
two two (two different alkyl/
er
ithin It
names is
them. possible
have three to have
separate compounds
Ethyl words
methylOH within
ether that them. Ethyl phenyl ether The rules for naming an ether using the IUPAC
yl groups)
containand
eparate
separate words
bothone
wordswithin forthem.
them.
within
ether andsymmetrical
alcohol ethers (both alkyl/aryl groups CH theOsame). CH CH
CH2OO CH3 O CH2O CH2O O
4-Methoxy-2-b utanol 3 OO 3 O 2 O
O CH3 O CH2O CH2O
OORule
le
OO O
xy 1:
2:
group For
CH For
functional
OCH 3 OCH
CH symmetrical
groups
CH
3 OO
CH OCH
3O
unsymmetrical
3 OO OCH
CH such
3CH
2O
ethers,
O3 CH
Propoxy
as
Oethers,
OO
CH name
CH
O
3CH
group 3O
O2CHname
O the
2CH
OO 23 O
alkyl
O OCH
both O2CHgroup,
O CH
hydrocarbonadd
2O3 CH3
the Rule
prefix 1:
di-,
Methoxy and
groupSelect
then the
add
groups bonded to the oxygen longest
Ethoxy groupcarbon chain and use its
Propoxy na
group
2 3 3 2
the Dimethyl
word ether, separating
(Theether theDiethyl
alcohol words etherwith
functional a space. Such ether
ethergroup Rulenames have twothe -yl ending
CHatom
methyl ether
C 3O CH inO
separate
alphabetical
etherether
Dimethyl
CH 2 O CH
words
Diethyl
2O
within
orderO CHand
Opriority
them.
add
Diethylthe wordhas 2: the
ether, separating Changeof the other hydrocarb
words with a
The general symbol for an alkoxy group is —O—R (or —OR).
3 in
group is —O—R
Ethyl methyl ether
A (or —OR). higher
Ethyl phenyl ether IUPAC nomencla-
s with
hers withspace.
more Such
complex ether names
alkyl/aryl have
groups arethree
named separate
using thewords
IUPACInwithin
system. In alkoxy
them. group name; methyl becomes methoxy
mplex
using themore
OH complex
alkyl/aryl
IUPAC groups alkyl/aryl
are
system named
ture,
areso groups
theusing are
thenamed
compound IUPAC
is using the
system.
named
The as IUPAC
rules for system.
naming Inan ether using the IUPAC system are
 s have beeninreplaced by hydrocarbonaddgroups (seeether,
Figure 14.17). the
Note that unlike
ls andatom alphabetical
phenols, ethers doorder
not
H O
and
possess
O O H
the word
a hydroxyl
R O O O
separating
(—OH)
R group. words with a
and phenols, ethers do not possess a hydroxyl (—OH) group.
space. Such ether names have three separate words within them.
HO OWater
OH R O OAnOether
R
HO O O H ROO OR 13
1. Nama
CHUmum:
3 OO O CHWater
2O CH3 CHAn
3O CH2OO
ether
• Rule Ethyl
No. 2
Water
methyl ether
An ether
Ethyl phenyl ether
6 NOMENCLATURE
• Untuk eter FOR simetris,ETHERS
beri nama kelompok alkil,
tambahkan awalan di, lalu tambahkan kata
e 2: For symmetrical
6 ethers, name the alkyl group, add the prefix di-, and then add
NOMENCLATURE
NOMENCLATURE FORFOR
eter, pisahkan ETHERS
kata dengan spasi. Nama ether
ETHERS
mon names are almost always used forwith
the word ether,
semacamseparating
itu the words
memiliki akata
space.
ethers
dua Suchalkyl
whose ether
terpisah names have
digroups two four or
contain
separate words within them.
dalamnya.
carbon
on namesatoms. There are two rules, oneethers
for unsymmetrical ethers (two differentoralkyl/
names areare almost
almost always
always usedusedfor for
ethers whose whose alkylalkyl groups
groups contain
contain fourfour
or
roups) atoms.
carbon and one for
There symmetrical ethers (both alkyl/aryl groups the different
same). alkyl/
bon atoms. There areare
CH OO
3 two two
O rules,
CH
rules, 3 oneoneCHfor
for 3 Ounsymmetrical
CH2O
unsymmetricalO O CH 2Oethers
3 (two
CH(two
ethers different alkyl/
oups)
ps)Forandand
oneone
forfor symmetrical
Dimethyl ether
symmetrical ethers
ethers (both alkyl/aryl
(both Diethyl ether groups
the the same).
unsymmetrical ethers, name bothalkyl/aryl
hydrocarbongroups groups same).
bonded to the oxygen
For
atom
Ethers unsymmetrical
in alphabetical
with ethers,
order name
and both
add hydrocarbon
the word groups
ether, bonded
separating to the
to the oxygen
words with
In a
For
atom
satomspace.
system, in • more
unsymmetrical
Such
Ether
ethers
complex
ethers,
alphabetical
ether
are
dengan
order
names
named
alkyl/aryl
name
gugus
and
have
as
both
add
groups
alkil/aril
the
three
substituted word
are named
hydrocarbon groups
yang lebih
ether,
separate words
hydrocarbons.
using
separating
the IUPAC
bonded
kompleks
within
The the
them.
smaller
the
words
system.
oxygen
with a
hydrocarbon
in alphabetical
diberiorder
namaand add the
dengan word ether,sistem
menggunakan separating
IUPAC the words with a
space.
achment
Ethers
space. SuchSuch
and theether
ether names
oxygen
names atom
havehave
are three
called
three separate
an alkoxy
separate words
words group,
withinwithin
and them.
this
them. group is considered
ubstituent on the CHlarger hydrocarbon group.CH An O alkoxy
CH2Ogroup is an —OR group, an
3 OO O CH2O CH3 3 OJ urusan Tek n ologi Hasil Pe r t an i an

yl (or
Two aryl)
examplesgroup
of IUPAC
CH OO attached
Oether
CH to
O CHan oxygen
nomenclature, with
CH atom.
theOalkoxy
CH Simple
groups
O O alkoxy
present high-groups include the
Fakultas Pertanian Universitas Lampung

in each CH
3 O CH O2CH CH3 O3CH2OO
3 OOare:
3 2
ighted structure 2 3
owing: Ethyl methyl ether Ethyl phenyl ether
EthylCH
methyl
3OO O ether
CH2 O CH2O CH2 O CH 3 Ethyl phenyl
etherether
thers CHEthyl
OO methyl
O ether
CH O CH OO Ethyl phenyl CH O CH O CH OO
: For424 symmetrical3
14 ethers,
Chaptergroup
Methoxy Alcohols, name
3
the
2
1-Methoxybutane
Phenols,
Ethoxy
alkyl group,
groupand Ethers
3
add2 the prefi
Propoxy group
2
x di-, and then add
For
Forthe symmetrical
symmetrical
word ether, ethers,
ethers, name
separating
CH3O
name
CH O CH the
theO
the
O
alkyl
alkyl
words
O CH O
group,
group,
with
CH add
a add
the
space. the prefi
prefix
Such xether
di-, di-,
and and
thenthen
names add add two
have
2 2
Two word
the examples of IUPAC
ether, etherA nomenclature,
separating the words with the3 a
with alkoxy
space.groups
Suchpresent
etherhigh-
names have two
ethe word
general
separate
ighted ether,
symbol
in each separating
words
structurefor
are: the
an alkoxy
within CH them.
3
words
groupwith a space.(or
is —O—R Such ether names have two
—OR).
separate
The
separaterules words
for naming
words within
within anthem.
them. ether using the IUPAC
1-Ethoxy-2-methylpropane
system
Two examples areof IUPAC ether nomenclature, with the alkoxy groups present high-
CH OO O CH O CH O CH O CH
3 2 2 2 3
The simplest aromatic CH
ether OO
involves a methoxy group attached
lighted to
Oaeach
Obenzene ring. Thisare:
e 1: goes
Select O CH CHuse 3 Oits 2in
CHname O CHstructure
2O CH 3 14
by thethe longest
3 carbon chain and as
Othe
2O3base 3 name.
3
ether CH
CH3 OO
common OO O
3 O CH3 3
name CH
anisole. CH
1-Methoxybutane
CH3 O3CH2OOO CH 2OOOCH O2CH CH CH
2. Nama Dimethyl
Berdasarkan ether IUPAC: Diethyl ether CH3OOthe
O CH2 O CH2O CH2 O CH3
e 2: Change the -yl ending
CH
Dimethyl
Dimethyl 3O
ether CHof
ether
A
O CHthe Oother
2O OO CH CHhydrocarbon
3
CH3Diethyl
2 ODiethyl group to -oxy to obtain
etherether
a) Pilih rantai karbon terpanjang dan gunakan
thers alkoxy
withmore groupcomplex
more
CHname; methyl 3 becomes
alkyl/aryl methoxy,
groups are ethyl
named becomes
using ethoxy,
the etc. system. In
IUPAC
1-Methoxybutane
hers with namanya
complex sebagai
alkyl/aryl nama groupsdasar/nama
are named induk.
using the IUPAC system.
rs
eandwith
3: Ethers
Placemore the complex
alkoxy alkyl/aryl
name, groups
1-Ethoxy-2-methylpropane
with are
a locator number, named in using the
frontpendek
of the IUPAC
base system. In In
ystem,
ystem, Theethers
compound
ethers b) areare
Carilah named
responsible
named rantaias as
for substituted
the
hidrokarbon
Anisole
substituted hydrocarbons.
yang
hydrocarbons. lebih The The CHchain
smaller
smaller O CHname.
hydrocarbon
O CH2 O O O CH2 O CH3
hydrocarbon
em, ethers
The simplest are dan
aromatic
characteristic named
ether
odor of as
involves
atom anise substituted
a methoxy
and fen-anisoles,
oksigen
hydrocarbons.
group
yang
attached to
disebut
a The smaller hydrocarbon
benzene ring.
kelompok
This 3
A
ment
ther goes
nt and and
Derivatives
ment andthe
nel is
the
byofthe
oxygenoxygen
common
anisole
the oxygenare
alkoksi.
anethole,
name
named
atom
an
atom
atom
allyl are
dan
are
as substituted
anisole.
are
called called
called
kelompok
derivative an
of an an inalkoxy
alkoxy
alkoxy
ini
a mannergroup,
group,
group,
dianggap
similar
and andtoand
this this
sebagai
this
that for
groupgroupgroup
is is is3 considered
considered
considered
CH
ubstituted phenols (Section 14.12).ether
Anisole derivatives were
with encountered in Section 14.14
stituent
tituent
uent
when
Two
onon on
anisole.
the
considering the
examples
the larger
of IUPAC
larger
rantai
larger hydrocarbon
hydrocarbon
cabang
hydrocarbon
antioxidant
nomenclature,
pada
O
food additives:group.
BHAs
CHgroup.
group.
gugus
An
are
3 An
both An
the alkoxy
alkoxy
alkoxy
hidrokarbon
alkoxy
a phenol
groups
groupgroup
and an group
present
yang
is an
anisole. is
high-an
an —OR
is —OR —OR group,
group, group,
an an an
1-Ethoxy-2-methylpropane
lighted in each structure
lebih are:
besar.
(or
er
or
aryl) aryl)
nomenclature,
aryl) group
Ogroup
group withattached
the
attached
CHattached
alkoxy
to to antoan anoxygen
groups
oxygen oxygen
present
atom.atom.
The atom.
high-
Simple
simplest Simple
Simple alkoxy
alkoxy
aromatic alkoxy groups
groups
ether groups
include
include
involves ainclude
the the the
methoxy group attached to a benzene ring. This
3 CH3OOaOkCH
nols, and Ethersc) M e n g u b a h
wing:
ing:
g: Anisole
r aCH
h i2 O n 2OgCHu 2gOuCH
ether sgoes
a
3 lkoksi,
by the m e t i l name anisole.
common
menjadi metoksi, etil menjadi etoksi, dst.
1-Methoxybutane
OO O CH
Name the2 O
Derivatives ofCH
following CH
2 Oethers
anisole are2 O CH3 asIUPAC
utilizing
named nomenclature
substituted rules.
anisoles, in a manner similar to that for
CH 3CH
CHOO 3 OO
3 OOO OO14.12).
CHCH 3CH
3O 3CH
O 3OCH
2OCHO2O OO Owere
CH O CH O CH O O O CH O CH2CH3CH3 CH
O O32CH
CH OinCHCH
O2CHOO
2O 2CH
OO 2O O
O CH3
ubstituted
a. CH phenols (Section
3!CH2!O!CH2!CH2!CH3A
1-Methoxybutane Anisole b. 2CH23O OOCHO
derivatives CH32OCH
encountered 3
2Section 14.14
Two
Methoxy
Methoxy
when considering examples
group
Methoxy group
antioxidant of IUPAC
groupfoodEthoxy group
Ethoxy
Ethoxy
CH
additives:
3 BHAsether
group arenomenclature,
group both with
Propoxy
A a phenol and the
group
Propoxy
an group
Propoxy alkoxy
anisole.group groups present high-
1-Ethoxy-2-methylpropane CH3
CHO CHlighted
2CH
OO 2O in
CHeach
OCH OCH
2P structure
CH are:
e) Tempatkan nama alkoksi, dengan nomor
23
eral
eneral
eneral
A The symbol
symbol
symbolfor
simplest an
for
aromaticalkoxy
forananalkoxy
ether group
alkoxy
involvesgroupis —O—R
agroup is is
methoxy —O—R
—O—R
group (or —OR).
(or
attached —OR).
to(or —OR).
a benzene ring. This
OO by thelocator, di depan nama rantai dasar. Anisole
c. CH
CH 3Ogoes d.
CH Ethyl methyl
CHether CH
rules
he rulesfor
3ether
naming
for naming an
common ether
an using
ether
name using
anisole. the3OO
the O
IUPACIUPAC2O
system 2 O CH
system are O CH3
2 are
he rules for naming an ether using the IUPAC system are
1-Ethoxy-2-methylpropane
Name the following ethers utilizing IUPAC nomenclatureDerivatives
1-Methoxybutaneof
rules.
J urusan Tek n ologi Hasil Pe r t an i an

anisole are named as substituted anisoles, in a manner similar to that for

Fakultas Pertanian Universitas Lampung

O CH3
Select
a.
ves Select
CH thethe
!CH 2longest
a 3methoxy groupcarbon
longest
!O!CH carbon
2!CH chain
2!CH
attached to a and
3chain CHuse
b. and
benzene 3O its
use
OOCHOname
substituted
ring.its CHas
name
This the
2OCH base
phenols
as 3the name.
(Section
base name. 14.12). Anisole derivatives were encountered in Section 14.14
e Select the longest carbon chain and use its name as the base name.
Solution
CH3O CH O ACH O O CH2 O CH
nisole. when 2O
considering antioxidant
3 food additives: BHAs are both a phenol and an anisole.
:eChange thethe-yl ending of the other hydrocarbon group to -oxy to -oxy
obtain the
a. The base name is propane. An ethoxy group is attached CH
to carbon-1 of the propane
en- Change
Change
chain. the -yl
-ylending
ending ofof
the other
the other
Anisole
hydrocarbon
A 3
hydrocarbon groupgroup to -oxy
to to obtain
to the the
obtain
ofalkoxy CH
alkoxy group
Ogroupname; methyl becomes
CH3name; methyl becomes methoxy,
3
methoxy, ethyl becomes
ethyl becomes ethoxy, etc.
ethoxy, etc.
alkoxy
c. CH 3O OO group
Derivatives 1 name;
of anisole are methyl
2 named becomes
3 as substituted
methylmethoxy,
d. Ethyl1-Ethoxy-2-methylpropane
anisoles, ether
in a mannerethyl becomes
similar to that for ethoxy, etc.
Place
Placethe alkoxy
the
substituted
CH3OCH phenols
2OOOCH
name,
alkoxy2OCH name,
(Section with
2OCHwith
14.12).a locator number, in front
a locator number, in front of the base
Anisole derivatives were encountered of the
in base
Section chain
14.14 name.
chain name.
:les Place
when thesimplest
The alkoxy
considering
of IUPAC name,
aromatic
antioxidant
ether with
foodether
nomenclature,
3
a locator
involves
additives:
with BHAs
the are number,
a methoxy inandfront
group
both a groups
alkoxy phenol ofhigh-
attached
an the
anisole.
present
to base chainring.
a benzene name.
This
les of IUPAC
Solution
The IUPAC
ethername
Anisole ether
goes is bynomenclature,
the common name
1-ethoxypropane. withanisole. Name the
the alkoxy following
groups ethers
present utilizing IUPAC nomenclature rules.
high-
structure
b. The
are:
structure
a. The baseare: butane, asAn
name is propane. theethoxy
longestgroup
carbon chain contains
is attached four carbon
a. CH3!CH2!O!CH2!CH
to carbon-1 of the atoms.
propane b. CH3O OOCHO CH2OCH3
as chain.
substituted anisoles, in a manner similar to that for O CH3 15 2!CH3 A
2CH3OO 3 O 4CH2 O CH2 O CH2 O CH3
). Anisole derivatives
Name the following
CH3OO were
ethers
O CH encountered
utilizing
2 O CH IUPAC
2 O CHin2 Section
nomenclature
O CH 3 14.14
rules. CH 3
CH OOOCHOCH 1 OCH 2
1-Methoxybutane3
a.3 CH3!CH
d additives: BHAs are2 OCH
A 2!O!CH both3
aOCH
2!CH phenol
2!CH3and an
1-Methoxybutane anisole.
b. CH3O OOCHO CH2OCH3
CH OCH
3 OOOCH
1 2 CH 2 2 3 A 14.16 Nomenclature for Ethers 425
3 14.16 Nomenclature
Anisole for Ethers 425
CH 3 O CH O CH 2 O O O CH 2 O CH 3
c. CH CH33 O OO d. Ethyl methyl ether
The IUPAC CH nameO is A
1-ethoxypropane.
The base
IUPAC name3 is CH O CH2 O O O CH2 O CH3
b. The
c. CH
Derivatives
name A2-methoxybutane.
of anisole
is butane,
CH
OOis cyclohexane.
are carbon
as the longest namedchain as contains
substituted
d. Ethyl methyl
anisoles,
four carbon
ether
atoms.in a manner similar to that for
c. The base3Oname 3 The complete IUPAC name is methoxycyclohexane. No
substituted CH
phenols
3 the methoxy group since all ring carbon atoms arewere
(Section 14.12). Anisole derivatives encountered in Section 14.14
numbernomenclature
gc.IUPAC is needed
2 3 1-Ethoxy-2-methylpropane
to locate
rules.
4 d. Dimethyl ether equivalent
OOCH 1-Ethoxy-2-methylpropane c.
Solution OOCH d. Dimethyl ether
A when
3 considering antioxidant food additives: BHAs are both a phenol and an anisole.
to each
CH other. 3
3OOOCHOCH2OCH3 A
omatic
!CH
d. The ether
Solution
3 ether b. CH
structureO
A involves OOCHO
3 is CH3a—CH CH
methoxy
2—O—CH
OCH
2 group
3, and
3 the attached
IUPAC name to abase
isbenzene ring.
methoxyethane. This An ethoxy group is attached to carbon-1 of the propane
omatic ether 1 CH involves aA methoxy group attacheda. The to a benzenename is propane.
ring. This
e common name
a. The base name
3
anisole.
is propane. An ethoxy group is attached to
CH carbon-1 of the propane
chain.
e common chain.name anisole. 3
OOCH3 14.5
Practice
The IUPAC Exercise
name is 2-methoxybutane.
Ocomplete OOCH3
CH3 IUPAC name is methoxycyclohexane.
c. The
Name
Answers:
base name
Name
a. d.
the following isthe
Ethyl
cyclohexane.
following
ethers 1
utilizing
methyl
1-Propoxypropane;
2The
ethers
O 3 CH
IUPAC
b. ether utilizing IUPAC
nomenclature
1-Methoxy-2-methylpropane;
3 rules. nomenclature rules.1No
c. 1, 3-Dimethoxycyclohexane;
2 3
numberThe
CH is
3 contrast
needed
OCH
d. Methoxymethane 2 tobetween
OOOCH locate 2the
OCH IUPAC
methoxy
2OCH and
group
3 since all ring carbon
CH
Answers:3
atoms
OCH
a. 2
are equivalent OCH OCH
OOOCH
1-Propoxypropane;2 b. 1-Methoxy-2-methylpropane;
2 3 c. 1, 3-Dimethoxycyclohexane;
a. to
CHeach
3 OCHa. 2OCH
other.
common CHnames
3!CH
2 OOOCH 2!O!CH
for 2 OCH 2 OCH
ethers !CH
is 2as 3 2!CH b. CH
3 3OOOCH b. CH2OCHOCH
3OOOCHOCH 3 2OCH3
The IUPAC
d. The follows:
ether structurename is 31-ethoxypropane.
is CH d. Methoxymethane
—CH2—O—CH3, and the IUPAC name is methoxyethane.
A A
The IUPAC CHname CHis3 1-ethoxypropane.
b. The base name is butane, Anisole as the longest carbon chain contains
Anisole four carbon3
atoms.
IUPAC (one 4word) b. The base name is butane, as the longest carbon chain contains four carbon atoms.
nisole
thoxy areExercise
group
Practice named as 3substituted
is attached
2 14.5 to carbon-1 ofanisoles, in a manner similar to that for
the propane
nisole are named as substituted anisoles, in a manner similar to that for
J urusan Tek n ologi Hasil Pe r t an i an

ols (Sectionc. CH OOO

3 alkoxyalkane
14.12). Anisole d. Ethyl
2OCH3derivatives were encountered in 2
methyl
Section ether
Fakultas Pertanian Universitas Lampung

Name
CH3OOOCHOCH
the following 3 14.144
ols (Section Aethers
14.12). utilizing
Anisole IUPAC nomenclature
derivatives were rules.
encountered in Section 14.14
ga.antioxidant 1food
CH3 additives: BHAs are both a phenol
2-methoxybutane andOCHOCH
an anisole.2OCH3
CH3OOOCHOCH
g3antioxidant
CH 3OCH 2OCH food additives:
2 OOOCH BHAs
2 OCH 2 OCHare
3 both a phenol
b. CH 3OOOCH and
2 an anisole.
AA
3

c
Solution
OCH3 TheCommon IUPAC name (three or two words)
is 2-methoxybutane. 1 CHCH3 3

rs asc. General
The base name is cyclohexane. The complete IUPAC name is methoxycyclohexane. No
Anesthetics
a. The alkyl
base nameether
alkyl is propane. An ethoxy group is attached to carbon-1 of the propane
opane. number is needed to locate the methoxy group since all ring carbon atoms are equivalent
longestto eachchain.
carbon other.
chain
HEMICAL
ethyl IUPAC
methyl ether
contains four carbon atoms.
The IUPAC name is 2-methoxybutane.
wing ethers utilizing nomenclature rules.
wing d. The ether
ethers onnections
structure
utilizing IUPACis CH3—CH 2—O—CHEthers
nomenclature and thec.
3, rules. as
IUPAC General
Thename
baseisname isAnesthetics
cyclohexane. The complete IUPAC name is methoxycyclohexane. No
methoxyethane.
thoughts of hospital
!O!CH 2!CH2!CH3
op- b.1 until
orIt was not CH3the2 late 1950s
O OOCHO 3 andCH
early
2OCH
number 1960s
is3 that nonflam-
needed to locate the methoxy group since all ring carbon atoms are equivalent
!O!CH 2!CH
ponse derives from
CH32the!CH
OCH mable b. CH
general
23OOOCH2OCH 3O OOCHO
anesthetics
2OCH A 3 CH
became 2OCH
available. Anesthetic
3 non-
Practice
a general Indialkyl
Exercise
anesthetic. fl14.5 ether was achieved
ammability to each
byA incorporating other.
halogen atoms into