Alkohol Eter 56x56
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Alkohol dan Eter Ikatan tunggal Karbon ke Oksigen
Tata Nama: AlKohol
OH ditunjukkan oleh akhiran ol Rantai induk adalah rantai terpanjang yang mengandung COH Karbon dinomori dari ujung rantai yang terdekat –OH
Contoh OH
OH H3C CH2 CH
CH2 CH CH3
CH3 5-methyl-3-hexanol
HO
3-(1-methylpropyl)-2-heptanol
F CH3 (1R,3S,4S)3-fluoro-4-methylcyclohexanol, or (1R,3S,4S)3-fluoro-4-methyl-1-cyclohexanol OH
hex-5-en-2-ol or 5-hexen-2-ol (Note that the OH takes precedence over the pi bond in detemining the numbering.)
Tata Nama: Eter
Eter sederhana : nama dua gugus karbon sebagai substituen, diikuti dengan eter Sistematik: nama sebagai alkoksi alkana
Contoh CH3 CH2 O CH2 CH3 diethyl ether or ethyl ether (If both alkyl groups are the same, the "di" is often not used.)
O
O
phenoxycyclopentane or cyclopentyloxybenzene CH2-CH3
5-ethoxy-2-methylheptane
Gugus Fungsional Alkohol Tiga lokasi dimana kimia bisa terjadi
. . .. O
H
•Lokasi kaya elektron? •Lokasi miskin elektron?
The Ether Functional Group Same as Alcohols, but no O-H
O C
C
Reactions of the C-O Bond Does this happen? Nuc:
-
+
.. .. O
H
Nuc
+
OH
NO. The C-O is inert toward heterolytic cleavage. Why? OH--is too basic to be a leaving group.
Ikatan C-O putus pada kondisi asam Br
.. .. O
+
H
+
+
H
+
Br
Substitution OH H
+
H
Elimination
+
H2O
H2O
Kenapa ikatan C-O putus pada kondisi asam? H H
H
: O ..
H
OSO3H H
H : O ..
O ..
+
H
+
HSO4-
H H
OSO3H
O ..
+
H
Alkohol adalah basa lemah, bereaksi dengan asam kuat (Bronsted or Lewis).
+
HSO4-
C-O dari alkohol terprotonasi bisa putus .. . . O
H
H
+
.. + O
HA
H
+
H
.. + O
+
+
H
_ A
slow
+
+
A
•Suatu reaksi substitusi nukleofilik •Air sebagai gugus lepas •SN2 jika primer uncrowded •SN1 (seperti terlihat)
H2O
A
Ether Chemistry is C-O Chemistry --Just Like Alcohol C-O Chemistry O
O
H
+
+
H-X
H-X
X
X
H
+
O
H
+
O
H
Identical Mechanisms, Too. Protonation of the O, then Nucleophilic Substitution
O
X
+
O
H
H-X O
H
H-X
H + O
H
X
H
+
O
H
X X
+
O
H
Predicting the Products
Ether cleavage is not usually selective; both sets of cleavage products are to be expected. In methyl ethers, the X preferentially attacks the methyl group. In excess HX, both C-O are cleaved, producing water and two C-X bonds. In phenyl ethers, the benzene ring is not attacked, even in excess HX.
Ether Cleavage Reactions CH3 CH O CH2 CH3 CH3
+
H-I excess O
O
CH3
H-I excess
+
H-I excess
+
H-I one equivalent O
O
+
+
H-I excess
Alcohol Reactions Not Involving C-O Cleavage Electron-rich oxygen The O-H
Reactions of the O-H Water has the same functional group .. .. O
H
+
:Base
The H is electron-poor. Are alcohols acids? Learn from water’s chemistry
The Acidity of Alcohols
H-O-H pKa = 15.7
R-O-H pKa = 15 to 16
R-NH2 pKa = 34
CH3 CH2 OH
+
CH3 CH2 OH
+
HO
H2N
CH3 CH2 O
CH3 CH2 O
+
+
H2O
NH3
Reaction with active metals R O H
+
M.
R O M
+2
M can be Na or K K OH
OK
Na OH
ONa
H2
Other Ways to Convert the OH to a Good Leaving Group: Halides OH
+ PBr3 OH
+
SOCl2
Reactions Using the Lone Electron Pairs of Oxygen Base? Nucleophile?
Alcohols and Ethers are Weakly Basic
They are protonated in strong H + H acids.O H O +
H2SO4
H
O
CH3
+
H2SO4
O+ CH3
All oxygenated organic compounds are protonated by strong acids
Alcohols are Nucleophiles …but not very strong ones. C
X R O
+ C
H With methyl and primart halides, this probably happens by an SN2 mechanism
+
R O C
R O C
H
Note that the nucleophile is NOT alkoxide! Like water, alcohols are not strong acids, so there is no R-O - present. The nucleophile is the whole alcohol molecule.,
There is no alkoxide (RO-) in alcohol!!
Conversion to Sulfonates Nucleophilic Substitution by Alcohol at Sulfur!! SO2Cl OH
O SO2
+
OH
+
O Ts
Ts-Cl
H OH H3C
CH3 CH3
H OTs
+
Ts-Cl
H3C
CH3 CH3
Sulfonate is a Good Leaving Group As good as or better than bromide OTs
S-CH3
+
Na-SCH3
+
CH3
CH3
H OTs H3C
CH2 CH3
Ts O
I
+
NaI
H3C
H CH2 CH3
+
Ts O
Oxidation of Alcohols: Preparation of C=O bonds OH H OH CH3CH2CH2
C CH3 H CH2-OH
CH2-OH
O oxidize
HCrO3
CrO3 pyridine
HCrO3
Three Ways to Make the Alcohol Carbon More Electrophilic
Convert to a better leaving group
Oxidize
H
OH
X
OH
OTs
OH
O
DEHIDRASI ALKOHOL
Alcohols in Synthesis Nu
OTs
Nu: Nu
TsCl OH
X
HX, or SOCl2 or PBr3 H+, heat
Mg Strong base
oxidize O
etc.
MgX
Reaksi Pembukaan cincin Epoksida • The three-membered ring of epoxides is highly strained and undergoes ring-opening reactions with a variety of nucleophiles, as shown below.
Reaksi berkatalisis asam
Tata Nama: AlKohol
OH ditunjukkan oleh akhiran ol Rantai induk adalah rantai terpanjang yang mengandung COH Karbon dinomori dari ujung rantai yang terdekat –OH
Contoh OH
OH H3C CH2 CH
CH2 CH CH3
CH3 5-methyl-3-hexanol
HO
3-(1-methylpropyl)-2-heptanol
F CH3 (1R,3S,4S)3-fluoro-4-methylcyclohexanol, or (1R,3S,4S)3-fluoro-4-methyl-1-cyclohexanol OH
hex-5-en-2-ol or 5-hexen-2-ol (Note that the OH takes precedence over the pi bond in detemining the numbering.)
Tata Nama: Eter
Eter sederhana : nama dua gugus karbon sebagai substituen, diikuti dengan eter Sistematik: nama sebagai alkoksi alkana
Contoh CH3 CH2 O CH2 CH3 diethyl ether or ethyl ether (If both alkyl groups are the same, the "di" is often not used.)
O
O
phenoxycyclopentane or cyclopentyloxybenzene CH2-CH3
5-ethoxy-2-methylheptane
Gugus Fungsional Alkohol Tiga lokasi dimana kimia bisa terjadi
. . .. O
H
•Lokasi kaya elektron? •Lokasi miskin elektron?
The Ether Functional Group Same as Alcohols, but no O-H
O C
C
Reactions of the C-O Bond Does this happen? Nuc:
-
+
.. .. O
H
Nuc
+
OH
NO. The C-O is inert toward heterolytic cleavage. Why? OH--is too basic to be a leaving group.
Ikatan C-O putus pada kondisi asam Br
.. .. O
+
H
+
+
H
+
Br
Substitution OH H
+
H
Elimination
+
H2O
H2O
Kenapa ikatan C-O putus pada kondisi asam? H H
H
: O ..
H
OSO3H H
H : O ..
O ..
+
H
+
HSO4-
H H
OSO3H
O ..
+
H
Alkohol adalah basa lemah, bereaksi dengan asam kuat (Bronsted or Lewis).
+
HSO4-
C-O dari alkohol terprotonasi bisa putus .. . . O
H
H
+
.. + O
HA
H
+
H
.. + O
+
+
H
_ A
slow
+
+
A
•Suatu reaksi substitusi nukleofilik •Air sebagai gugus lepas •SN2 jika primer uncrowded •SN1 (seperti terlihat)
H2O
A
Ether Chemistry is C-O Chemistry --Just Like Alcohol C-O Chemistry O
O
H
+
+
H-X
H-X
X
X
H
+
O
H
+
O
H
Identical Mechanisms, Too. Protonation of the O, then Nucleophilic Substitution
O
X
+
O
H
H-X O
H
H-X
H + O
H
X
H
+
O
H
X X
+
O
H
Predicting the Products
Ether cleavage is not usually selective; both sets of cleavage products are to be expected. In methyl ethers, the X preferentially attacks the methyl group. In excess HX, both C-O are cleaved, producing water and two C-X bonds. In phenyl ethers, the benzene ring is not attacked, even in excess HX.
Ether Cleavage Reactions CH3 CH O CH2 CH3 CH3
+
H-I excess O
O
CH3
H-I excess
+
H-I excess
+
H-I one equivalent O
O
+
+
H-I excess
Alcohol Reactions Not Involving C-O Cleavage Electron-rich oxygen The O-H
Reactions of the O-H Water has the same functional group .. .. O
H
+
:Base
The H is electron-poor. Are alcohols acids? Learn from water’s chemistry
The Acidity of Alcohols
H-O-H pKa = 15.7
R-O-H pKa = 15 to 16
R-NH2 pKa = 34
CH3 CH2 OH
+
CH3 CH2 OH
+
HO
H2N
CH3 CH2 O
CH3 CH2 O
+
+
H2O
NH3
Reaction with active metals R O H
+
M.
R O M
+2
M can be Na or K K OH
OK
Na OH
ONa
H2
Other Ways to Convert the OH to a Good Leaving Group: Halides OH
+ PBr3 OH
+
SOCl2
Reactions Using the Lone Electron Pairs of Oxygen Base? Nucleophile?
Alcohols and Ethers are Weakly Basic
They are protonated in strong H + H acids.O H O +
H2SO4
H
O
CH3
+
H2SO4
O+ CH3
All oxygenated organic compounds are protonated by strong acids
Alcohols are Nucleophiles …but not very strong ones. C
X R O
+ C
H With methyl and primart halides, this probably happens by an SN2 mechanism
+
R O C
R O C
H
Note that the nucleophile is NOT alkoxide! Like water, alcohols are not strong acids, so there is no R-O - present. The nucleophile is the whole alcohol molecule.,
There is no alkoxide (RO-) in alcohol!!
Conversion to Sulfonates Nucleophilic Substitution by Alcohol at Sulfur!! SO2Cl OH
O SO2
+
OH
+
O Ts
Ts-Cl
H OH H3C
CH3 CH3
H OTs
+
Ts-Cl
H3C
CH3 CH3
Sulfonate is a Good Leaving Group As good as or better than bromide OTs
S-CH3
+
Na-SCH3
+
CH3
CH3
H OTs H3C
CH2 CH3
Ts O
I
+
NaI
H3C
H CH2 CH3
+
Ts O
Oxidation of Alcohols: Preparation of C=O bonds OH H OH CH3CH2CH2
C CH3 H CH2-OH
CH2-OH
O oxidize
HCrO3
CrO3 pyridine
HCrO3
Three Ways to Make the Alcohol Carbon More Electrophilic
Convert to a better leaving group
Oxidize
H
OH
X
OH
OTs
OH
O
DEHIDRASI ALKOHOL
Alcohols in Synthesis Nu
OTs
Nu: Nu
TsCl OH
X
HX, or SOCl2 or PBr3 H+, heat
Mg Strong base
oxidize O
etc.
MgX
Reaksi Pembukaan cincin Epoksida • The three-membered ring of epoxides is highly strained and undergoes ring-opening reactions with a variety of nucleophiles, as shown below.
Reaksi berkatalisis asam
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