Kimia Organik 2Semester Genap 2013
Enade P. Istyastono
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Aldehydes and KetonesAldehida dan Keton
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Aldehydes and Ketones
Page 276 - 304
Carbonyl Group: C=OGugus Karbonil: C=O
• The most important and widely occurring functional group in BOTH organic and biological chemistry.
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Carbonyl Group: C=OGugus Karbonil: C=O
• The most important and widely occurring functional group in BOTH organic and biological chemistry.
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Asam Etanoat - Asam AsetatEtanoic Acid - Acetic Acid
Carbonyl Group: C=OGugus Karbonil: C=O
• The most important and widely occurring functional group in BOTH organic and biological chemistry.
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Carbonyl Group: C=OGugus Karbonil: C=O
• The most important and widely occurring functional group in BOTH organic and biological chemistry.
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Carbonyl Group: C=OGugus Karbonil: C=O
• The most important and widely occurring functional group in BOTH organic and biological chemistry.
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Carbonyl Group: C=OGugus Karbonil: C=O
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Carbonyl Group: C=OGugus Karbonil: C=O
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Two Types of Carbonyl CompoundsDua Tipe Senyawa Karbonil
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Aldehida | Aldehyde
Keton | Ketone
Ester
Amida | Amide
Anhidrida asam | Acid anhydride
Asam karboksilat | Carboxylic acid
Klorida asam (!!!) | Acid chloride
Two Types of Carbonyl CompoundsDua Tipe Senyawa Karbonil
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Aldehida | Aldehyde
Keton | Ketone
Ester
Amida | Amide
Anhidrida asam | Acid anhydride
Asam karboksilat | Carboxylic acid
Klorida asam (!!!) | Acid chloride
Kenapa dibedakan?Clue => LG!!!
Two Types of Carbonyl CompoundsDua Tipe Senyawa Karbonil
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Aldehida | Aldehyde
Keton | Ketone
Ester
Amida | Amide
Anhidrida asam | Acid anhydride
Asam karboksilat | Carboxylic acid
Klorida asam (!!!) | Acid chlorideCANNOT!!!
Yes you CAN!!!
Naming Aldehydes and KetonesPenamaan Aldehida dan Keton
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Metanal | MethanalEtanal | EthanalPropanal…
Propanon | PropanoneButanon | Butanone3-Pentanon | 3-Pentanone2-Pentanon | 2-Pentanone2-Heksanon | 2-Hexanone3-Heksanon | 3-Hexanone…
Naming Aldehydes Attached to a RingPenamaan Aldehida Terikat Cincin
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Metanal | MethanalEtanal | EthanalPropanal…
Benzenakarbaldehida | Benzenecarbaldehyde
Sikloheksanakarbaldehida | Cyclohexanecarbaldehyde
2-Naftalenakarbaldehida | 2-Naphtalenecarbaldehyde
Common Names - Aldehydes and KetonesNama Trivial - Aldehida dan Keton
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
IUPAC Trivial | Common
Metanal | Methanal Formaldehida|Formaldehyde
Etanal | Ethanal Asetaldehida | Acetaldehyde
Propanal Propionaldehida|Propionaldehyde
Butanal Butiraldehida|Butyraldehyde
Pentanal Valeraldehida|Valeraldehyde
2-Propenal Acrolein
Benzenakarbaldehyde |Benzenecarbaldehyde
Benzaldehida | Benzaldehyde
Common Names - Aldehydes and KetonesNama Trivial - Aldehida dan Keton
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
IUPAC Trivial | Common
Metanal | Methanal Formaldehida|Formaldehyde
Etanal | Ethanal Asetaldehida | Acetaldehyde
Propanal Propionaldehida|Propionaldehyde
Butanal Butiraldehida|Butyraldehyde
Pentanal Valeraldehida|Valeraldehyde
2-Propenal Acrolein
Benzenakarbaldehyde |Benzenecarbaldehyde
Benzaldehida | Benzaldehyde
Aseton | Acetone
Asetofenon | Acetophenone
Benzofenon | Benzophenone
IUPAC Name ??? ======
Acyl - | Alkanoil -Asil - | Alkanoil -
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
R IUPAC TRIVIAL
H Metanoil | Methanoil Formil | Formyl
CH3 Etanoil | Ethanoil Asetil | Acetyl
… … …
C6H6 Benzoil | Benzoyl
If carbonyl considered as a “substituent” …Jika karbonil sebagai substituen …
• okso | oxo
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Metil 3-oksoheksanoat Methyl 3-oxohexanoate
Synthesis of Aldehydes and KetonesSintesis Aldehida dan Keton
• The best: the oxidation of alcohol!– Primary alcohols => Aldehydes
– Secondary alcohols => Ketones
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Note: PCC = pyridinium chlorochromate
Synthesis of Aldehydes and KetonesSintesis Aldehida dan Keton
• The best: the oxidation of alcohol!– Primary alcohols => Aldehydes
– Secondary alcohols => Ketones
– Tertiary alcohols => ?Competence – Conscience – Compassion
Konteks – Pengalaman – Refleksi – Aksi – Evaluasi
Oxydation of AldehydesOksidasi Aldehida
Asam karboksilat | Carboxylic acid Simplest method = menggunakan Tollens’ reagent (Ag+ in
dilute aqueous ammonia (NH4OH))
Kenapa keton tidak bisa? No removable “H” Oksidasi formadehida? -> asam metanoat -> CO2 +H2O Mekanisme reaksi? KO1? …
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Oxydation of AldehydesOksidasi Aldehida
Asam karboksilat | Carboxylic acid Simplest method = menggunakan Tollens’ reagent (Ag+ in
dilute aqueous ammonia (NH4OH))
Kenapa keton tidak bisa? No removable “H” Oksidasi formadehida? -> asam metanoat -> CO2 +H2O Mekanisme reaksi? KO1? …
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Nucleophilic Addition ReactionsReaksi Adisi Nukleofilik
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Nucleophilic Addition ReactionsReaksi Adisi Nukleofilik
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Nucleophilic Addition ReactionsReaksi Adisi Nukleofilik
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Some negatively charged :Nu =>• HO- (ion hidroksida | hydroxide ion) • H:- (ion hidrida | hydride ion)• R3C:- (karbanion | carbanion)• RO- (ion alkoksida | alkoxide ion)• N≡C:- (ion sianida | cyanide ion)
Some neutral :Nu =>• H2O (air | water)• R-OH (alkohol | alcohol)• H3N: (amonia | ammonia)• R-NH (amina | amine)
Nucleophilic Addition Reactions - ReductionReaksi Adisi Nukleofilik - Reduksi
• Example: Propanone =>
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Propanon | Propanone Ion 2-propoksida2-propoxide ion
2-Propanol
Nucleophilic Addition of Water - HydrationAdisi Nukleofilik Air - Hidrasi
• Example: Propanone =>
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Propanon | PropanoneHidrat propanon
Propanone hidrate
Nucleophilic Addition of Water - HydrationAdisi Nukleofilik Air - Hidrasi
• Dg katalis basa | Base-catalyzed:
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Nucleophilic Addition of Water - HydrationAdisi Nukleofilik Air - Hidrasi
• Dg katalis asam | Acid-catalyzed:
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Nucleophilic Addition of Water - HydrationAdisi Nukleofilik Air - Hidrasi
• Note:– Equilibrium reaction ~ depends on the structure.
Ex: acetone in water = 99.9% ketone 0.1% gem diol, but vice versa formaldehyde in water.
– Slow in pure water, catalyzes by acid/base. No change in equilibrium position.
– Differences in acid/base catalyzation:• Base: Hydroxide ion much better :Nu than water.• Acid: Protonate the carbonyl, makes it much better
electrophile.
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Nucleophilic Addition of AlcoholsReaksi Adisi Alkohol
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Some negatively charged :Nu =>• HO- (ion hidroksida | hydroxide ion) • H:- (ion hidrida | hydride ion)• R3C:- (karbanion | carbanion)• RO- (ion alkoksida | alkoxide ion)• N≡C:- (ion sianida | cyanide ion)
Some neutral :Nu =>• H2O (air | water)• R-OH (alkohol | alcohol)• H3N: (amonia | ammonia)• R-NH (amina | amine)
Nucleophilic Addition of AlcoholsReaksi Adisi Alkohol
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
R = H, aldehydesR = alkyl, ketones
Asetal | Acetal
Nucleophilic Addition of AlcoholsReaksi Adisi Alkohol
• Note: Useful for the following condition, which is NOT unusual …
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
?
Nucleophilic Addition of AlcoholsReaksi Adisi Alkohol
• LiAlH4 ?
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
?
LiAlH4
Nucleophilic Addition of AlcoholsReaksi Adisi Alkohol
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
• So … use acetal as a protecting group
Nucleophilic Addition of AminesReaksi Adisi Amina
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Some negatively charged :Nu =>• HO- (ion hidroksida | hydroxide ion) • H:- (ion hidrida | hydride ion)• R3C:- (karbanion | carbanion)• RO- (ion alkoksida | alkoxide ion)• N≡C:- (ion sianida | cyanide ion)
Some neutral :Nu =>• H2O (air | water)• R-OH (alkohol | alcohol)• H3N: (amonia | ammonia)• R-NH (amina | amine)
Nucleophilic Addition of Amines: Imine FormationsReaksi Adisi Amina: Pembentukan Imina
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
R = H, aldehydesR = alkyl, ketones
Imina | Imine
Nucleophilic Addition of Grignard ReagentsReaksi Adisi Reagen Grignard
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Some negatively charged :Nu =>• HO- (ion hidroksida | hydroxide ion) • H:- (ion hidrida | hydride ion)• R3C:- (karbanion | carbanion)• RO- (ion alkoksida | alkoxide ion)• N≡C:- (ion sianida | cyanide ion)
Some neutral :Nu =>• H2O (air | water)• R-OH (alkohol | alcohol)• H3N: (amonia | ammonia)• R-NH (amina | amine)
Grignard ReagentsReagen Grignard
• Apa itu reagen Grignard? KO1!
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Grignard ReagentsReagen Grignard
• Apa itu reagen Grignard? KO1!
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Grignard ReagentsReagen Grignard
• Apa spesialnya reagen Grignard?
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Nucleophilic Addition of Grignard Reagents – Alcohols FormationsReaksi Adisi Reagen Grignard – Pembentukkan Alkohol
• Apa spesialnya reagen Grignard? Karbanion!
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
R = H, aldehydesR = alkyl, ketones Alkohol| Alcohol
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Nucleophilic Addition of Grignard Reagents (GR) – Alcohols FormationsReaksi Adisi Reagen Grignard – Pembentukkan Alkohol
• Note:– GR + Formaldehyde -> 10 alcohols– GR + Other Aldehydes -> 20 alcohols– GR + Keton -> 10 alcohols
• Weakness: – Can’t be prepared from organic halides that has
other reactive functional groups: Br-Molecule-FG• FG: -OH, -NH, -SH, -COOH } The GR can be protonated• FG: aldehyde, ketone, amide, nitrile, nitro, sulphon }
The GR adds to these groups.
Conjugate Nucleophilic Addition ReactionsReaksi Adisi Nukleofilik Konjugasi
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Direct (1,2) addition:
Conj. (1,4) addition:
α,β-UnsaturatedR = H, aldehydesR = alkyl, ketones
Ion enolat | Enolate ion
Aldehida/Keton jenuhSaturated aldehyde/ketones
Some Biological Nucleophilic AdditionReaksi Adisi Nukleofilik Biologis
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Some Biological Nucleophilic AdditionReaksi Adisi Nukleofilik Biologis
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Serahkan pada biokimia (sem 4?) …
Competence – Conscience – CompassionKonteks – Pengalaman – Refleksi – Aksi – Evaluasi
Next … Carboxylic Acids and Derivatives
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