CARBONIL COMPOUND
1
Understanding Organic Reactions
18
Contoh Sintesis Aspirin
O
O C CH3
OH
O O O
+ +
H3C C O C CH3 H3C C OH
19
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)
20
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)
21
Examples of carbonyl compounds important
O
O
O
1,4-benzokuinon
(kuinon)
CH3
Vitamin K
22
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
24
Kinds of carbonil compounds
O O O
C C C
R H R R' R O H
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
28
• 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:
29
• 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'
30
The Main Reaction of The Carbonyl
Group
• Nucleophilic additions reaction
• Carbonyl condensation reaction
• Reduction reaction
• Oxidation reaction
31
Reaksi Adisi Nukleofilik
• Addition is the addition of certain
compounds in the unsaturated compounds.
32
Nu:- Nu
C O + H+ C OH C OH C OH
33
Nukleofil
HO (ion hidroksida)
H (ion hidrida)
Nukleofil bermuatan negatif R3C (karbanion)
Nu
RO (ion alkoksida)
N C (ion sianida)
HOH (air)
RNH2 (amina)
34
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.
35
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