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NAMA : REZA PAHLEVI NIM : 03101003039 JURUSAN : TEKNIK KIMIA FAKULTAS : TEKNIK UNIVERSITAS SRIWIJAYA ANGKATAN 2010-2011 REAKSI-REAKSI PADA ALDEHID DAN KETON 1. OKSIDASI ALDEHID DAN KETON A. Suatu keton tidak mudah dioksidasi O

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Page 1: 039 REZA PAHLEVI

NAMA : REZA PAHLEVI

NIM : 03101003039

JURUSAN : TEKNIK KIMIA

FAKULTAS : TEKNIK

UNIVERSITAS SRIWIJAYA

ANGKATAN 2010-2011

Page 2: 039 REZA PAHLEVI

REAKSI-REAKSI PADA ALDEHID DAN KETON

1. OKSIDASI ALDEHID DAN KETON

A. Suatu keton tidak mudah dioksidasi

O ║ KMnO4

CH3CCH3 → Tidak ada reaksi yang terjadi Aseton

B. Suatu Aldehida O O

║ KMnO4, H+ ║ a. CH3(CH2)5CH → CH3(CH2)5COH

Heptanal H2O asam heptanoat

2. ADISI PADA GUGUS KARBONIL

A. Adisi Pada Aldehid dan Keton menghasilkan suatu hemiasetal

a. Aldehid

O OH ║ |

CH3CH2CH2CH + C2H5OH ⇌ CH3CH2CH | OC2H5

Butanal Etanol 1-Etoksi-1-Propanol

Keton

O OH

║ | CH3CCH3 + CH3OH ⇌ CH3CCH3

|OCH3

2-propanon Metanol 2-Metoksi-2-Propanol O OH ║ |

CH3CH2CCH2CH3 + CH3CH2OH ⇌ CH3CH2CCH2CH3 | OCH3CH2

3-Pentanon etanol 3-etoksi-3-Pentanol

Page 3: 039 REZA PAHLEVI

B. Aldehid dan Keton berlebih direaksikan dengan alcohol berlebih dengan adanya katalis asam akan menghasilkan ASETAL. Asetal adalah 2 gugus alkil yang terikat pada satu atom sama.

a). Pada Aldehid

O OCH3

║ | CH3CH + 2CH3OH ⇌ CH3CH + H2O

| OCH3

Propanal Etanol Dietoksi Propana Air

O OC3H7

║ |

C3H7CH + 2 C3H7OH ⇌ C3H7CH+ H2O |

OC3H7

Butanal Propanol Dipropoksi Butana Airb). Pada Keton

O OCH3

║ | CH3CCH3 + 2CH3OH ⇌ CH3CCH3 + H2O

| OCH3

2-Propanon Metanol 2,2-dimetoksi Propana Air

O OC2H5

║ | C2H5CC2H5 + 2C2H5OH ⇌ C2H5CC2H5 + H2O

| OC2H5

2-Pentanon Etanol 3,3-dietoksi Pentana Air

ADISI DENGAN SENYAWA ORGANOMETALIK

a. Pada Aldehid

1). O OMgI OH ║ | H2O |

CH3CH + CH3MgI→ CH3CH → CH3CH + Mg(OH)I | | CH3 CH3

Etanal metil magnesium iodida Magnesium Hidroksi iodida

2). O OMgCl OH ║ | H2O |

C2H5CH + C2H5MgCl→ C2H5CH → C2H5CH + Mg (OH) Cl | | C2H5 C2H5

Propanal Etil Magnesium klorida Magnesium Hidroksi klorida

Page 4: 039 REZA PAHLEVI

b. Pada Keton

1).

O OMgCl OH ║ | H2O |

CH3CCH3+ CH3MgCl → CH3CCH3→ CH3CCH3 + Mg(OH)Cl | |

CH3 CH3

2-propanon metil Magnesium Magnesium Hidroksi Klorida Klorida

REAKSI-REAKSI DENGAN TURUNAN AMONIAK

1). ∖ ∖C=O + H2N-Y → C=N-OH + H2O

∕ ∕

A. Pada Aldehid

CH3 CH3

∖ ∖ C=O + H2N-OH → C=N-OH + H2O ∕ ∕

H HEtanal Hydroxylamine Etena Oxime Air

CH3CH2 CH3CH2

∖ ∖ C=O + H2N-OH → C=N-OH + H2O ∕ ∕

H HPropanal Hydroxylamine Propena Oxime Air

B. Pada Keton

CH3 CH3

∖ ∖ C=O + H2N-OH → C=N-OH + H2O ∕ ∕

CH3 CH3

Propanon Hydroxylamine Propena Oxime Air

CH3CH2 CH3CH2

Page 5: 039 REZA PAHLEVI

∖ ∖ C=O + H2N-OH → C=N-OH + H2O ∕ ∕

CH3CH2 CH3CH2

Pentanon Hydroxylamine Pentena Oxime Air

2). ∖ ∖C=O + H2N-NH2 → C=N-NH2 + H2O

∕ ∕

A). Pada Aldehid

CH3 CH3

∖ ∖ C=O + H2N-NH2 → C=N-NH2 + H2O ∕ ∕

H HEtanal Hydrazine Etena Hydrazone Air

CH3CH2CH2 CH3CH2CH2

∖ ∖ C=O + H2N-NH2 → C=N-NH2 + H2O ∕ ∕

H HButanal Hydrazine Butena Hydrazone Air

B). Pada Keton

CH3 CH3

∖ ∖ C=O + H2N-NH2 → C=N-NH2 + H2O ∕ ∕

CH3 CH3

Propanon Hydrazine Propena Hydrazone Air

CH3CH2 CH3CH2

∖ ∖ C=O + H2N-NH2 → C=N-NH2 + H2O ∕ ∕

CH3 CH3

2-butanon Hydrazine Butena Hydrazone Air

3). ∖ ∖C=O + H2N-NH- → C=N-NH-

Page 6: 039 REZA PAHLEVI

∕ ∕

A). Pada Aldehid

CH3 CH3

∖ ∖ C=O + H2N-NH- → C=N-NH-

∕ ∕ H H

Etanal Phenylhydrozine Etena Phenylhydrazone

CH3CH2CH2 CH3CH2CH2

∖ ∖ C=O + H2N-NH- → C=N-NH-

∕ ∕ H H

Butanal Phenylhydrozine Butena Phenylhydrazone

B). Pada Keton

CH3 CH3

∖ ∖ C=O + H2N-NH- → C=N-NH-

∕ ∕ CH3 CH3

Propanon Phenylhydrozine Propena Phenylhydrazone

CH3CH2 CH3CH2

∖ ∖ C=O + H2N-NH- → C=N-NH-

∕ ∕ CH3CH2 CH3CH2

Pentanon Phenylhydrozine Pentena Phenylhydrazone

NO2

4). ∖ ∖ ∖C=O + H2N-NH- -NH2 → C=N-NH- -NO2

∕ ∕

A). Pada Aldehid

CH3 CH3 NO2

Page 7: 039 REZA PAHLEVI

∖ ∖ ∖ C=O + H2N-NH- -NH2 → C=N-NH- -NO2

∕ ∕ H H

Etanal 2,4-Dinitrophenylhdrazine 2,4-Dinitrophenylhdrazone Etena

CH3CH2CH2 CH3CH2CH2 NO2

∖ ∖ ∖ C=O + H2N-NH- -NH2 → C=N-NH- -NO2

∕ ∕ H H

Butanal 2,4-Dinitrophenylhdrazine 2,4-Dinitrophenylhdrazone Butena

B). Pada Keton

CH3 CH3 NO2

∖ ∖ ∖ C=O + H2N-NH- -NH2 → C=N-NH- -NO2

∕ ∕ CH3 CH3

Propanon 2,4-Dinitrophenylhdrazine 2,4-Dinitrophenylhdrazone Propena

CH3CH2 CH3CH2 NO2

∖ ∖ ∖ C=O + H2N-NH- -NH2 → C=N-NH- -NO2

∕ ∕ CH3 CH3

2-Butanon 2,4-Dinitrophenylhdrazine 2,4-Dinitrophenylhdrazone Butena

5).

O ∖ ∖ //

C=O + H2N-NH-C-NH2 → C= H2N-NH-C-NH2

∕ ∕

A. Pada Aldehid

Page 8: 039 REZA PAHLEVI

CH3 CH3 O ∖ ∖ // C=O + H2N-NH-C-NH2 → C= H2N-NH-C-NH2

∕ ∕ H H Etanal Semicarbazine Semicarbazone Etena

CH3 CH2 CH2 CH3 CH2 CH2 O ∖ ∖ // C=O + H2N-NH-C-NH2 → C= H2N-NH-C-NH2

∕ ∕ H H Butanal Semicarbazine Semicarbazone Butena

B. Pada Keton

CH3 CH3 O ∖ ∖ // C=O + H2N-NH-C-NH2 → C= H2N-NH-C-NH2

∕ ∕ CH3 CH3

Propanon Semicarbazine Semicarbazone Propena

CH3CH2 CH3CH2 O ∖ ∖ // C=O + H2N-NH-C-NH2 → C= H2N-NH-C-NH2

∕ ∕ CH3CH2 CH3CH2

Pentanon Semicarbazine Semicarbazone Pentena

6). ∖ ∖ C=O + H2N=R → C= N-R

∕ ∕

A. Pada Aldehid

CH3 CH3

∖ ∖ C=O + H2N=CH3 → C= N-CH3

∕ ∕ H H

Etanal Primaryamine imine etena CH3CH2CH2 CH3CH2CH2

∖ ∖ C=O + H2N=CH3 → C= N-CH3

∕ ∕

Page 9: 039 REZA PAHLEVI

H H

Butanal Primaryamine imine butena

B. Pada Keton

CH3 CH3

∖ ∖ C=O + H2N=CH3 → C= N-CH3

∕ ∕ CH3 CH3

Propanon Primaryamine imine propena

CH3CH2 CH3CH2

∖ ∖ C=O + H2N=CH3 → C= N-CH3

∕ ∕ CH3 CH3

2-butananon Primaryamine imine butena