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INTRODUCTION :

CARBONIL COMPOUND

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Understanding Organic Reactions

Kinds of Organic Reactions

• A substitution is a reaction in which an atom or a group of atoms is


replaced by another atom or group of atoms.
• In a general substitution, Y replaces Z on a carbon atom.
Understanding Organic Reactions
Kinds of Organic Reactions
• Substitution reactions involve  bonds: one  bond breaks and another
forms at the same carbon atom.
• The most common examples of substitution occur when Z is a hydrogen
or a heteroatom that is more electronegative than carbon.
Understanding Organic Reactions
Kinds of Organic Reactions

• Elimination is a reaction in which elements of the starting material


are “lost” and a  bond is formed.
Understanding Organic Reactions
Kinds of Organic Reactions
• In an elimination reaction, two groups X and Y are removed from a
starting material.
• Two  bonds are broken, and a  bond is formed between adjacent atoms.
• The most common examples of elimination occur when X = H and Y is a
heteroatom more electronegative than carbon.
Understanding Organic Reactions
Kinds of Organic Reactions

• Addition is a reaction in which elements are added to the starting


material.
Understanding Organic Reactions
Kinds of Organic Reactions
• In an addition reaction, new groups X and Y are added to the
starting material. A  bond is broken and two  bonds are formed.
Understanding Organic Reactions
Kinds of Organic Reactions
• Addition and elimination reactions are exactly opposite. A  bond
is formed in elimination reactions, whereas a  bond is broken in
addition reactions.
Understanding Organic Reactions
Bond Making and Bond Breaking
• A reaction mechanism is a detailed description of how bonds are broken
and formed as starting material is converted into product.
• A reaction can occur either in one step or a series of steps.
Understanding Organic Reactions
Bond Making and Bond Breaking
• Regardless of how many steps there are in a reaction, there are only two
ways to break (cleave) a bond: the electrons in the bond can be divided
equally or unequally between the two atoms of the bond.
Understanding Organic Reactions
Bond Making and Bond Breaking

• Homolysis and heterolysis require energy.


• Homolysis generates uncharged reactive intermediates with unpaired
electrons.
• Heterolysis generates charged intermediates.
Understanding Organic Reactions
Bond Making and Bond Breaking

• To illustrate the movement of a single electron, use a half-headed curved


arrow, sometimes called a fishhook.
• Full headed curved arrows show the movement of an electron pair.
Understanding Organic Reactions
Bond Making and Bond Breaking
• Homolysis generates two uncharged species with unpaired
electrons.
• A reactive intermediate with a single unpaired electron is called a
radical.
• Radicals are highly unstable because they contain an atom that does
not have an octet of electrons.
• Heterolysis generates a carbocation or a carbanion.
• Both carbocations and carbanions are unstable intermediates. A
carbocation contains a carbon surrounded by only six electrons, and
a carbanion has a negative charge on carbon, which is not a very
electronegative atom.
Understanding Organic Reactions
Bond Making and Bond Breaking
Understanding Organic Reactions
Bond Making and Bond Breaking
• Radicals and carbocations are electrophiles because they contain an
electron deficient carbon.
• Carbanions are nucleophiles because they contain a carbon with a lone
pair.
Understanding Organic Reactions
Bond Making and Bond Breaking
• Bond formation occurs in two different ways.
• Two radicals can each donate one electron to form a two-electron bond.
• Alternatively, two ions with unlike charges can come together, with the
negatively charged ion donating both electrons to form the resulting two-
electron bond.
• Bond formation always releases energy.
Understanding Organic Reactions
Bond Making and Bond Breaking

• A number of types of arrows are used in describing organic reactions.


Carbonyl Compounds: Why need to be
studied by students of pharmacy?
• Carbonyl group is an important group in organic
chemistry. Almost every process synthesis (drug and
non-drug) utilizing the carbonyl group.
• Most important bioactive molecules (including drugs)
contains a carbonyl group.
• Physiologic mechanisms (eg visual mechanism)
involves the reaction of the carbonyl group.
• Many natural compounds / synthetic are important in
everyday life contain a carbonyl group.

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Contoh Sintesis Aspirin
O

O C CH3
OH
O O O
+ +
H3C C O C CH3 H3C C OH

anhidrida asetat COOH asam asetat


COOH
Asam salisilat Asam asetilsalisilat
(aspirin)

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Examples of carbonyl compounds
important
H O OH
O C
N O
C C O O
H3C OH C
CH3
Asam asetat HO CH3
(asam cuka) Asetaminofen Asam asetil salisilat
(analgesik, antipiretik)
(analgesik, antipiretik)

O
H2
H
C C
O C )
O H2 n
( O
C
Retinal Dakron
O
(suatu polimer sintetik)

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Examples of carbonyl compounds
important
O
O
O
O O OH CH
NH O H C OH

O HO C H

OH O H C OH
H
HO O H C OH
O
O CH2OH
O
Paklitaksel (Taxol)
Glukosa
(anti kanker yang kuat)

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Examples of carbonyl compounds important
O

O
O
1,4-benzokuinon
(kuinon)
CH3

Vitamin K

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Formaldehida
• Preservatives biological samples, reagents,
deodorizing to wick lamps / candle.
• Stored as a solution in water (formalin), polymers
(paraformaldehyde) or trimer (trioxane).
Formalin (HCHO + H2O)
kalor

O
kalor
CH2OCH2OCH2OCH2O C
paraformaldehida H H
kalor metanal
H2 (formaldehida)
C gas
O O
H2C CH2
O
t.l. 62 oC
trioksan 23
Asetaldehida
• Intermediates for the synthesis of acetic
acid and acetic anhydride
• Saved as a trimer (paraldehida) or tetramer
(metaldehyde).
H3 C
H3C O CH3 O CH O
CH CH CH3
kalor kalor O CH
O O C
H3C H CH O
CH H3C
etanal O CH
CH3 (asetaldehida)
o CH3
paraldehida t.d. 20 C metaldehida
zat sedatif dan hipnotik umpan bekicot
t.d. 125 oC t.l. 246 oC

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Kinds of carbonil compounds
O O O
C C C
R H R R' R O H

Aldehida Keton Asam karboksilat

O
O O O
C
R X C C C
X = halogen R O R' R O R'
Halida asam Anhidrida asam Ester
(Asil halida)

O
O O
C
C C C N
C O R N

Lakton Laktam
Amida (amida siklik)
(ester siklik) 25
Two general categories of carbonyl compounds
Aldehida (RCHO) Acyl groups bound to the
Keton (RCOR’) substituent (-H or -R) that can not
stabilize the negative charge and
therefore can not act as a leaving
group. Properties and reactions of
aldehydes and ketones are
similar.
Asam karboksilat (RCOOH) Acyl groups bound to the
Ester (RCOOR’) substituent can stabilize the
Klorida asam (RCOCl) negative charge that can act as a
leaving group. Properties and
Anhidrida asam (RCOOCOR’) reactions of these compounds are
Amida (RCONH2) similar.
O

R C 26
Asil atau alkanoil
Elektronic structural of carbonil group

Oksigen karbonil
mempunyai 2 PEB

Due to differences in electronegativities, the carbonyl group


is polarized. The carbon atom has a partial positive charge,
and the oxygen atom has a partially negative charge.
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Consequences polar carbonyl group: the
reactivity

 Oksigen bersifat nukleofil,


O bereaksi dengan asam dan elektrofil
 C
Karbon bersifat elektrofil,
bereaksi dengan basa dan nukleofil

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• The presence of the lone pairs (PEB) and
the high electronegativity O atoms, making
the carbonyl group of aldehydes and
ketones is a weak base.

+  _
C O

H+

Serangan Nu:
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• Nucleophile attacks the carbonyl C atom
becomes easier when the O atom is
protonated first (with acid catalyst) which
resulted in the C atom becomes more
positive...

R
C O + H+ C OH
R'

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The Main Reaction of The Carbonyl
Group
• Nucleophilic additions reaction
• Carbonyl condensation reaction
• Reduction reaction
• Oxidation reaction

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Reaksi Adisi Nukleofilik
• Addition is the addition of certain
compounds in the unsaturated compounds.

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  Nu:- Nu
C O + H+ C OH C OH C OH

karbokation terstabilkan resonansi

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Nukleofil
HO (ion hidroksida)

H (ion hidrida)
Nukleofil bermuatan negatif R3C (karbanion)
Nu
RO (ion alkoksida)

N C (ion sianida)

HOH (air)

Nukleofil netral ROH (alkohol)


Nu H H3N (amonia)

RNH2 (amina)
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Condensation Reaction
• The condensation reaction is the reaction of merging two or
more molecules of the same or different with or without
spending a simple compounds, such as H2O.

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rEdoX REACTION
• Redox reaction = Reduction or oxidation reactions.
• The oxidation reaction :
 Electron release reaction
 The reaction of the increase of oxidation number
 Reaction of substances with oxygen (O)
• The reduction reaction :
 Electron capture reaction
 The reaction of decreasing the oxidation number
 The reaction of taking O from a compound
rEdoX REACTION
• Contoh reaksi reduksi :
Cu2+ + 2e- Cu(s)
Fe2O3 + 2 Al 2 Fe + Al2O3

 Contoh reaksi oksidasi :


Zn(s) Zn2+ (aq) + 2e-
4 Fe + 3O2 2 Fe2O3

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