Sintesis Obat - 01 Karbonil

8/2/2019 Sintesis Obat - 01 Karbonil

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Reaksi-Reaksi Substitusi

Alfa Karbonil


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Karbonil

Aldehide Ketone Amide

Asam Kaboksilat Enone

Karbonil


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Reaktivitas

Oxygen is more electronegativethan carbon, and thus morereactive with nucleophiles

The alpha hydrogensis 1000

times more acidic than atypical C-H bond.

Amides are the most stable of thecarbonyl couplings due totheir high resonance

stabilization between thenitrogen-carbon and carbon-oxygen bonds.

Carbonyls would be alkylatedby nucleophilic attack byorganometallic reagentssuch asorganolithiumreagents andGrignard

reagents.

Carbonyls also may bealkylated by enolates as inaldol reactions
http://media/wiki/Nucleophilehttp://media/wiki/Alpha_hydrogenhttp://media/wiki/Alkylationhttp://media/wiki/Nucleophilic_attackhttp://media/wiki/Organometallichttp://media/wiki/Organolithiumhttp://media/wiki/Grignard_reagenthttp://media/wiki/Grignard_reagenthttp://media/wiki/Grignard_reagenthttp://media/wiki/Grignard_reagenthttp://media/wiki/Organolithiumhttp://media/wiki/Organometallichttp://media/wiki/Nucleophilic_attackhttp://media/wiki/Alkylationhttp://media/wiki/Alpha_hydrogenhttp://media/wiki/Nucleophilehttp://media/wiki/Nucleophile


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Reaksi-ReaksiPenting

Wittig Reaction, to create analkene

Wolff-Kishner reduction

Clemmensen reduction

Conversion into thioacetals

Hydrationhemiacetalsandhemiketals to acetals andketals

Reaction with ammonia andamines to form imines

Reaction with hydroxylamines toform oximes

Reaction with cyanide aniontofom cyanohydrins

Oxidation with oxaziridinestoacyloins

Reaction with Tebbe's reagentand phosphonium ylidestoalkenes

Perkin reaction and aldolreaction

Aldol condensation

Cannizzaro reaction

Tishchenko reaction
http://media/wiki/Wittig_Reactionhttp://media/wiki/Wolff-Kishner_reductionhttp://media/wiki/Clemmensen_reductionhttp://media/wiki/Thioacetalhttp://media/wiki/Hydration_reactionhttp://media/wiki/Hemiacetalhttp://media/wiki/Hemiketalhttp://media/wiki/Acetalhttp://media/wiki/Ketalhttp://media/wiki/Ammoniahttp://media/wiki/Aminehttp://media/wiki/Iminehttp://media/wiki/Hydroxylaminehttp://media/wiki/Oximehttp://media/wiki/Cyanidehttp://media/wiki/Cyanohydrinhttp://media/wiki/Oxaziridinehttp://media/wiki/Acyloin%23Enolate_oxidation_by_sulfonyloxazirineshttp://media/wiki/Tebbe%2527s_reagenthttp://media/wiki/Phosphonium_ylidehttp://media/wiki/Alkenehttp://media/wiki/Perkin_reactionhttp://media/wiki/Aldol_reactionhttp://media/wiki/Aldol_reactionhttp://media/wiki/Aldol_condensationhttp://media/wiki/Cannizzaro_reactionhttp://media/wiki/Tishchenko_reactionhttp://media/wiki/Tishchenko_reactionhttp://media/wiki/Tishchenko_reactionhttp://media/wiki/Cannizzaro_reactionhttp://media/wiki/Cannizzaro_reactionhttp://media/wiki/Aldol_condensationhttp://media/wiki/Aldol_condensationhttp://media/wiki/Aldol_reactionhttp://media/wiki/Aldol_reactionhttp://media/wiki/Aldol_reactionhttp://media/wiki/Perkin_reactionhttp://media/wiki/Alkenehttp://media/wiki/Alkenehttp://media/wiki/Phosphonium_ylidehttp://media/wiki/Tebbe%2527s_reagenthttp://media/wiki/Acyloin%23Enolate_oxidation_by_sulfonyloxazirineshttp://media/wiki/Acyloin%23Enolate_oxidation_by_sulfonyloxazirineshttp://media/wiki/Oxaziridinehttp://media/wiki/Cyanohydrinhttp://media/wiki/Cyanohydrinhttp://media/wiki/Cyanidehttp://media/wiki/Oximehttp://media/wiki/Oximehttp://media/wiki/Hydroxylaminehttp://media/wiki/Iminehttp://media/wiki/Iminehttp://media/wiki/Aminehttp://media/wiki/Ammoniahttp://media/wiki/Ketalhttp://media/wiki/Ketalhttp://media/wiki/Acetalhttp://media/wiki/Hemiketalhttp://media/wiki/Hemiacetalhttp://media/wiki/Hydration_reactionhttp://media/wiki/Thioacetalhttp://media/wiki/Thioacetalhttp://media/wiki/Clemmensen_reductionhttp://media/wiki/Clemmensen_reductionhttp://media/wiki/Wolff-Kishner_reductionhttp://media/wiki/Wolff-Kishner_reductionhttp://media/wiki/Wolff-Kishner_reductionhttp://media/wiki/Wittig_Reaction


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,-Unsaturated carbonylcompounds

,-Unsaturated carbonylcompounds are an importantclass of carbonyl compoundswith the general structureC

=C

(C=O)

Examples of unsaturatedcarbonyls are acrolein(Propenal)mesityloxideacrylic acid andmaleicacid. Unsaturated carbonyls

can be prepared in an aldolreaction and Perkin reaction

As a general rule withunsymmetric electrophiles,hydrogen attaches itself atthe -position in anelectrophilic addition

Since ,-unsaturatedcompounds areelectrophiles, many ,-unsaturated carbonylcompounds are toxic,

mutagenic andcarcinogenic. DNA Canattack the carbon andthus alkylated. However,the endogenous scavengercompound glutathione

naturally protects fromtoxic electro hiles in the
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KarakteristikSpektra

Spectroscopy Infrared

the C=O double bond absorbsinfrared light at wavenumbersbetween 1600-1900 cm-1. The exactlocation of the absorption iswell understood with respectto the geometry of themolecule. This absorption isknown as the "carbonylstretch" when displayed on an

infrared absorption spectrum

NMR (Nuclear MagneticResonance)

the C=O double-bond exhibitsdifferent resonancesdepending on surroundingatoms, generally adownfield shift. The 13CNMR of a carbonyl carbonis in the range of 160-220ppm.
http://media/wiki/Infraredhttp://media/wiki/Wavenumberhttp://media/wiki/Wavenumberhttp://media/wiki/Infrared


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Kondensasi Aldol

An aldol condensation is anorganic reaction in which anenol or an enolate reacts witha carbonyl compound to forma -hydroxyaldehide or -hydroxyketone, followed by a

dehydration to give aconjungated enone

Aldol condensations areimportant in organicsynthesis providing a goodway to form carboncarbonbonds
http://media/wiki/Organic_reactionhttp://media/wiki/Organic_synthesishttp://media/wiki/Organic_synthesishttp://media/wiki/Carbon%25E2%2580%2593carbon_bondhttp://media/wiki/Carbon%25E2%2580%2593carbon_bondhttp://media/wiki/Carbon%25E2%2580%2593carbon_bondhttp://media/wiki/Carbon%25E2%2580%2593carbon_bondhttp://media/wiki/Carbon%25E2%2580%2593carbon_bondhttp://media/wiki/Carbon%25E2%2580%2593carbon_bondhttp://media/wiki/Carbon%25E2%2580%2593carbon_bondhttp://media/wiki/Carbon%25E2%2580%2593carbon_bondhttp://media/wiki/Carbon%25E2%2580%2593carbon_bondhttp://media/wiki/Organic_synthesishttp://media/wiki/Organic_synthesishttp://media/wiki/Organic_reaction


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Reaksi SederhanaAldol

M k i
http://media/wiki/Carbon%25E2%2580%2593carbon_bondhttp://media/wiki/Carbon%25E2%2580%2593carbon_bondhttp://media/wiki/Carbon%25E2%2580%2593carbon_bond


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Mekanisme-Mekanisme dalam

Reaksi AldolThe first part of this reaction is analdol reaction, the second part adehydrationan elimination reaction. Dehydration may beaccompanied by decarboxylation when an activated carboxyl group

is present. The aldol addition product can be dehydrated via twomechanisms; a strong base like potassium t-butoxide , potassium

hydroxide or sodium hydride in an enolate mechanism, or in an acid-

catalyzed enol mechanism.
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Mekanisme ReaksiEnol-Aldol
http://media/wiki/Carbon%25E2%2580%2593carbon_bondhttp://media/wiki/Carbon%25E2%2580%2593carbon_bond


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Mekanisme ReaksiEnolat-Aldol
http://media/wiki/Carbon%25E2%2580%2593carbon_bondhttp://media/wiki/Carbon%25E2%2580%2593carbon_bond

Sintesis Obat - 01 Karbonil

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