Alcoholes y Fenoles
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• Los alcoholes pueden considerarse losderivados orgánicos del agua, donde unode los hidrógenos es sustituido por un
grupo orgánico: H-O-H pasa a ser R-OH.
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Fórmulaestructural
Nombre Peso molecular p.eb. (°C) solubilidad enagua
CH3OH metanol 32 5 in!nita
CH3CH3 etano 3" #$% insolu&le
CH3CH2OH etanol 4 '$ in!nitaCH3CH2CH3 propano 44 #42 insolu&le
CH3CH2CH2OH (#propanol " %' in!nita
CH3CH2CH2CH3 &utano 5$ " insolu&le
CH3CH2CH2CH2OH (#&utanol '4 ((' $ g)(""g
CH3CH2CH2CH2CH3 pentano '2 3 insolu&le
CH3
CH2
CH2
CH2
CH2OH
(#pentanol $$ (3$ 2.3g)(""g
HOCH2CH2CH2CH2
OH
(,4#&utanodiol %" 23" in!nita
CH3CH2CH2CH2CH2
CH3
he*ano $ % insolu&le
Puntos de ebullición y solubilidades en agua de cinco grupos de alcoholes e hidrocarburos de peso molecular similar
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Los alcoholes pequeños
son muy solubles en
agua.
En los alcoholes grandes,
la cadena carbonada
dificula la formaci!n de
puenes de hidr!geno,
pro"ocando que elfen!meno sea
desfa"orable
energ#icamene.
Muy poco soluble en agua
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$
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• Los alcoholes se nom&ran en elsistema -/0 como derivados delalcano principal, usando el su!1o -ol :
• e elige la cadena de car&ono máslarga ue contenga al grupo hidro*ilo, se determina el nom&re principal
reemplaando la terminación -o delalcano correspondiente por -ol 6o &ienla terminación -ano por -anol 7.
%
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• e numera la cadena del alcanocomenando por el e*tremo máspró*imo al grupo hidro*ilo.
• e numeran todos los sustituentescon8orme a su posición en la cadena, se escri&e el nom&re con los
sustituentes en orden al8a&9tico.
("
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• Los nom&res comunes de losalcoholes incluen la pala&raalcohol , se nom&ra el grupo
aluilo unido al grupo -OH con laterminación ico. 0 continuación seincluen los nom&res -/0C , entre
par9ntesis, los nom&res comunes delos ocho alcoholes de peso molecularmás &a1o.
((
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(2
CH3OH
metanol
alcohol metílico
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(3
CH3CH2OH
etanol
alcohol etílico
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(4
CH3CH2CH2OH
1-propanol
alcohol n-propílico« Chem3D Embed »« Chem3D Embed »
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(5
CH3
2-propanolalcohol isopropílico
C$
C$3
%$
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(
alcohol n-butílico
C$3
C$&
C$&
C$&
1-butanol
%$
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('
alcohol isobutílico
C$33 C$&
C$&
'
2-metil-1-propanol
%$
C$3
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($
alcohol sec-butílico
C$3( C$&
3
C$&
2-butanol
%$
C$3
'
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(%
2-metil-2-propanol
alcohol t-butílico
C&
C$3
C$33
C$3
'
%$
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2"
ciclohexanol
alcohol ciclohexílico
%$
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2(
fenilmetanol
alcohol bencílico
C$&
%$
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• Los (, 2 dioles 6diolesvecinales7 son llamados
glicoles.• Los nom&res comunes de
los glicoles usan el nom&redel alcano &ase.
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CH2CH2
OH OH
',&)eanodiol
eilenglicol
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CH2CH2CH3
OH OH',&)propanodiol
propilenglicol
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%$
C$&
'
C$
&
%$
C$&
3
%$
1,2,3-propanotriol
glicerol
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2
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2'
CH3CH2CH2OH + KMnO4 CH3CH2CHO CH3CH2COOK + MnO2 H2O
1-propanol propanal !ci"o propanoico
#CH2OH+
KMnO4 # C
O
H
#COO-K MnO2 H2O
alcohol 1o$ al"ehí"o !ci"o carboxílico
frio
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2$
CH3CHCH3 + KMnO4
%$
CH3CCH3
%
+ MnO2 KOH
2-propanol propanona
frio
* C$
%$
* KMnO4 * C
%
* MnO2 KOH
alcohol 2o$ cetona
frio
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2%
• ;l reactivo de Lucas 6HCl6c7 <nCl27 identi!ca
alcoholes terciarios secundarios.
* C
%$
*
* HCl %nCl2 * C
Cl
*
* H2O
*eacci!n
inmediaa +lcohol 3
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3"
*eacci!n
m-s lena
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3(
o hay reacci!n
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C$& C$
%$
C$3 H2&O4
1'()+ H2O* C$& C$ C$&* C$ C$ C$3*
alcohol 2o
al*ueno menossustitui"o
al*uenos m!ssustitui"o
pro"ucto principal
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• &on compuestos org!nicos *ue resultan "esustituir un !tomo "e hi"r+geno uni"o a unanillo arom!tico por un grupo hi"roxilo, − OH
33
OH
OH CH3
enol o-metilfenol m-clorofenol
OH
Cl
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3
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3'
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3$
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• &on compuestos org!nicos en los *ue un !tomo "e oxígeno une "os ra"icalescarbona"os
• &e nombran .en la nomenclatura com/n0 por or"en alfabtico, los ra"icales uni"osal − O −, segui"os "e la palabra #
3%
CH3
− CH2
− O − CH2
− CH3
CH3 − CH2 − O − CH3CH3
− O − CH3
"imetil ter etilmetil ter "ietil ter
n la nomenclatura 56789, se nombra el ra"ical m!s sencillo .con la palabra O:60,segui"o sin gui+n "el nombre "el hi"rocarburo "el *ue "eri;a el ra"ical m!s
comple<oCH3 − CH2 − O − CH3
metoxietano
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4"
%C$3 C$&
C$3
'
C$33
2-metoxipropano
ter isopropilmetílico
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4(
%
C$&
C$3
C$&
C$3
ter "ietílico
etoxietano
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% C$3
metoxibencenoter fenilmetílico
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/ropiedades de los 8enoles
=O>?@; p8 AC pe ACsolu&ilidadg)("" g H2O
8enol 43 ($( %.3
o#cresol 3" (%( 2.5
m#cresol (( 2"( 2.5
p#cresol 3 2"( 2.3
catecol ("5 245 45
resorcinol ((" 2$( (23
hidrouinona ('" 2$ $
45
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• Los tioles, R-H, son análogos au8rados de los alcoholes.Los tioles se nom&ran por medio del sistema ue se usapara los alcoholes, con el su!1o -tiol en lugar de -ol. ;l grupo#H mismo se conoce como grupo mercapto.
4
C$3
C$&
/$
etanotiol
etilmercaptano
C$3 /$
metanotiol
metilmercaptano
• La propiedad m-s caracer0sica de un iol es su olor, La ra1a humana es
muy sensible a esos compuesos pudiendo deecar su presencia a ni"eles
2,2& pares de iol en mil millones de pares de aire. El olor de los 1orrillos
se debe, principalmene, a algunos ioles sencillos.
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4'
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4$
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