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The simplest carbonyl compounds are ketones and aldehydes. A ketone has two
alkyl (or aryl) groups bonded to the carbonyl carbon atom. An aldehyde has one alkyl (or
aryl) group and one hydrogen atom bonded to the carbonyl carbon atom. Formaldehyde is
the simplest aldehyde, with two hydrogen atoms bonded to the carbonyl group.
Ketones and aldehydes are similar in structure, and they have similar properties.
There are some differences, however, particularly in their reactions with oxidizing agents
and with nucleophiles. In most cases, aldehydes are more reactive than ketones, for
reasons we discuss shortly.
The carbonyl carbon atom is hybridized sp2 and bonded to three other atoms
through coplanar sigma bonds oriented about 120° apart. The unhybridized p orbital
overlaps with a p orbital of oxygen to form a pi bond. The double bond between carbon
and oxygen is similar to an alkene C=C double bond, except that the carbonyl double
bond is shorter, stronger, and polarized.
IUPAC Names Systematic names of ketones are derived by replacing the final -e
in the alkane name with -one. The “alkane” name becomes “alkanone.” In open-chain
ketones, we number the longest chain that includes the carbonyl carbon from the end
closest to the carbonyl group, and we indicate the position of the carbonyl group by a
number. In cyclic ketones, the carbonyl carbon atom is assigned the number 1.
Systematic names for aldehydes are derived by replacing the final -e of the alkane
name with -al. An aldehyde carbon is at the end of a chain, so it is number 1. If the
aldehyde group is a substituent of a large unit (usually a ring), the suffix carbaldehyde is
used.
Common names of aldehydes are derived from the common names of the
corresponding carboxylic acids (Table 18-2). These names often reflect the Latin or
Greek term for the original source of the acid or the aldehyde. Greek letters are used with
common names of aldehydes to give the locations of substituents.
(Wade, J.R. 2013)
In general, aldehydes and ketones have higher boiling points than alkenes because
the dipole–dipole attractive forces between molecules are stronger. But they have lower
boiling points than alcohols because, unlike alcohols, two carbonyl groups can’t form
hydrogen bonds to each other.
The carbonyl oxygen of aldehydes and ketones can form hydrogen bonds with the
protons of OH groups. This makes them more soluble in water than alkenes, but less
soluble than alcohols.
To the synthetic chemist, the most important of these are the last two: the
oxidation of primary alcohols to aldehydes and secondary alcohols to ketones. Indeed,
when combined with reactions that yield alcohols, the oxidation methods are so versatile
that it will not be necessary to introduce any new methods for preparing aldehydes and
ketones in this chapter. A few examples will illustrate this point. Let’s first consider how
to prepare an aldehyde from a carboxylic acid. There are no good methods for going from
RCO2H to RCHO directly. Instead, we do it indirectly by first reducing the carboxylic
acid to the corresponding primary alcohol, then oxidizing the primary alcohol to the
aldehyde.
F. Lanes work :
1. Tollens Reagent Preparation
2 mL of AgNO3 1 %
Precipitate
Tollens Reagent
Reaction : 2 AgNO3 (aq) + 2 NaOH(aq) → Ag2O (s) + NaNO2 (aq) + H2O (l)
Test Tube 1 :
O
Test tube 4 :
O O
Result
Result
Reactions:
Test tube 1 :
O O
3. Bisulphite Addition
Reactions:
OH O
O
H3C C S O Na
OH O
OH O
H3C C S OH
H3C C S O Na
CH3 O
(aq) + HCl (aq) CH3 O (aq) + NaCl (aq)
4. Testing with Phenylhidrazine
Reactions:
O
C H
H H
H2N N N N C
H
(aq) + (aq) (aq) + H2O (l)
H H
H2N N N N
5. Haloform Reaction
Reactions:
CH3COCH3 (aq) + 3I2 + 4OH- → 2CHI3 (aq) + CHCOO- (aq) + 3H2O (l) + 3I-
CH3CH(CH3)OH (aq) + 3I2 + 4OH- → CH3COOCH3(aq) + 3I2 + 4OH- (aq) → 2CHI3
(aq) + CH3COO- (aq) + 3H2O (l) + 3I-(aq)
6. Aldol condensation
Reactions :
O O O
O
H2
H3C C C C H
H3C C H (aq) + -H2C C H (aq) H (aq)
O O
O
H2 H3C C C C
H3C C C C H H H
H (aq) + H2O panas H (aq)
7. Carboxylic identifications
15 ml of formic acid
Result
Reactions:
(aq) +
2Ag(NH3)2OH (aq) →
Test tube 4 :
O
H C H (aq) +
2Ag(NH3)2OH (aq) →
O
H C OH (aq) +
2Ag(s) + 2NH3 (aq) +
H2O (l)
2. Fehling Reagent Test Fehling A = light Fehling A+ Fehling 2KNaC4H4O4 (aq) + Formaldehyde
blue colour B = blue solution 2Cu2+ (aq) + 2OH- → oxydized while
C4(C4H2O6)2(aq) + ketone do not react
Fehling B = Fehling A+ Fehling Cu(OH)2 + 2Na+ +2K+ with fehling.
colourless B + Formadehyde +2H+ Indicated by the
= formed of red
Formaldehydes = There are two layer Test tube 1 : precipitation on
colourless . O aldehyde solution.
Upper layer = dark
Acetone = green solution H C H (aq) +
colourless Lower layer = blue 2Cu2+ (aq) + 2OH- →
solution O
Cyclohexanon =
colourless Fehling A, B + H C H + Cu2O (s)
Acetone = there are
+ 3H2O(l)
two layer white and
Test tube 2:
black layer O
Fehling A, B +
H3C C CH3 (aq)+
cyclohexanon =
form two layer. 2Cu2+ (aq) + 4OH- →
White and blue Test tube 3:
O
(aq) 2Cu2+
(aq) + 5OH- →
3. Bisulphite Addition Sodium Sodium bisulphate O From our experment
bisulphate = + acetone = turbid addition
turbid solution solution H3C C CH3 (aq) + nuchleophilic
(prescipitate and NaHSO3 (aq) reaction indicated by
Acetone = filtrate) the physical changes
colourless OH O from white turbid
Sodium bisulphate colourless solution.
+ acetone + ethanol H3C C S O Na
= turbid solution
CH3 O
H3C C S OH
CH3 O
(aq) + NaCl (aq)
4. Testing with phenylhidrazine Phenilhydrazine = Phenylhidrazine + O Benzaldehid and
yellow solution benzaldehid= two cyclohexanone
C H
layers. Upper = formed osazion
Benzaldehide = white crystall when reacted
colourless Lower= orange (aq) with fenilhidrazin.
precipitate + The melting point of
Cyclohexanone= benzaldehyde > he
colourless Phenylhidrazine + H melting point of
H2N N
Ethanol = benzaldehid + cuyclohexanone
colourless filterred = orange
(aq)
residu The melting point of
H benzaldehyde =
N N C
Residue + water + H 144oC
ethanol = orange The melting point of
residu cyclohexanone =
(aq) + H2O (l)
98oC
Phenylhidrazine + O
cyclohexanol = two
layer. Upper=
yellow oily (aq) +
Lower= colourless
H
H2N N
Phenylhidrazine +
cyclohexanol + (aq)
filtered = yellow
residue
Residue + water + H
N N
ethanol = yellow
residue
(aq) + H2O(l)
Melting point of The melting point of
benzaldehyde = phenylhydrazine
144oC benzaldehyde = 156oC
(Chemical book,2017)
Melting point of
cyclohexanone = The melting point of
98oC cyclohexanone
phenylhidrazinone = 78-
90oC
(P212121 company
information, 2018)
5. Haloform Reaction NaOH = NaOH 5% + CH3COCH3 (aq) + 3I2 + From this
colourless acetone + I2= 4OH- → 2CHI3 (aq) + experiment, ktone
turbid CHCOO- (aq) + 3H2O (l) given positive result
Acetone = (precipitated) + 3I- when reacted with
colourless haloform. Indicated
NaOH 5% + CH3CH(CH3)OH (aq) + with turbid
Isopropyl alcohol isopropyl alcohol + 3I2 + 4OH- → precipitation.
= colourless iodium= colourless CH3COOCH3(aq) + 3I2
+ 4OH- (aq) → 2CHI3 On reaction between
Iodium = yellow (aq) + CH3COO- (aq) + NaOH and acetone
solution 3H2O (l) + 3I-(aq) resulting white
precipitate.
On reaction between
NaOH and isopropyl
alcohol resulting
colourless solution.
6. Aldol Condensation NaOH = NaOH + O Aldol condensation
colourless Acetaldehyde = is reaction between
yellow grenish H3C C H (aq) + aldehyde and base.
Acetaldehyde= solution OH- Indicated with the
colourless rancid smell and
NaOH + O colourless solution.
Acetaldehyde + but from our
boiled = orange experiment formed
H3C C H (aq)
solution orange solution
O
Smell = rancid
H3C C H (aq) +
O
-
H2C C H (aq)
O
O
H2
H3C C C C H
H
(aq)
O
O
H2
H3C C C C H
H
(aq) H2O panas
O
H3C C C C
H H
H
(aq)
7. Carboxylic Identification Formic acid = Formic acid + 3HCOOH + KMnO4 → Formic acid oxidized
colourless KMnO4 = brown 2K+ + 2MnO2↓ + H2O + by KMnO4 formed
15 ml of formic acid solution blackish solution 3CO2 ↑+ 2OH- MnO2 (black
precipitate)
Poured into a test tube KMnO4 = purple Formic acid +
Added 3 mL of KMnO4 solution KMnO4 + cooled in Carboxylic can be
room temperature = identified with
Observed changes that occur
colourless solution reacting CH3COONa
CH3COONa = and black solution 10% with
Result colourless precipitate FeCl3 5% resulting
filtrate that
FeCl3 = yellow CH3COONa + CH3COONa (aq) contained Ferri ion
solution FeCl3 = red +FeCl3(aq) →
solution (CH3COO)3Fe (s) + NaCl It can be proved by
K4FeCN6 = light (s) the colour
yellow CH3COONa + comparation
FeCl3 + heated FeCl3 (aq) + between FeCl3 and
filtrate = orange K4FeCN6(aq) → KCl (aq) the filtrate colour
solution + Fe4[Fe(CN)6]3 (s) that added with
K4FeCN6
Residue = dark red
Filtrate + K4FeCN6
= dark blue
H. Analysis And Explanation
The title of this experiment is aldehyde, ketone, and carboxylic Acid Idetification.
The purpose of this experiment is to identified the aldehyde group in organic compound,
to indentified the ketone group in organic compound, to identified the carboxylic group in
organic compound, to differentiate the aldehyde group, ketone group and carboxylic group
that in organic compound. The experiment already started and done at Tuesday, 6 March
2018.
On this experiment there are seven flow chart that is tollens reagent preparation,
fehling or benedict reagent, bisulphite addition, testing with phenylhydrazine, haloform
reactions, aldol condensation and carboxykic identification.
1) Tollens Test
The purpose of the first experiment “Tollens Test” is to identified and
differentiate organic compound contained aldehyde and ketones group. The principal
of tollens test is aldehyde oxidized form carboxylic acid meanwhile Ag+ ion reduced
form Ag metal identificated with silver mirror. On this experiement the tester are
acetaldehyde, acetone, siclohexanon, and formaldehyde.
The first step is cleaned all of the tools. Then colourless 2 ml of AgNO3
entered into clean test tube, then added colourless 1 ml of NaOH 5% and shaken it
then formed black precipitate. The purpose of NaOH 5% addition is to form salt of Ag.
Then added some drops of colourless NH4OH 2% drop by drop while shaken until it
resoluble, the function of NH4OH 2% addition is to give base condition and dissolved
silver salt that have been formed. The reaction are,
AgNO3 (aq) + 2NaOH (aq) Ag2O (s) + NaNO3 (aq) + H2O (l)
Ag2O (s) + NH4OH (aq) Ag(NH3)2OH (aq)
The next step are entered 1 ml of tollens reagent into test tube A, test tube B,
test tube C and test tube D that have been washed, dried into oven. The purpose is to
sterilized the tools. On A tube added colourless acetaldehyde solution and resulted
colourless solution. Then heated on steam bath for 5 minutes. Acetaldehyde oxidized
by tollens reagent, indicated by the silver mirror formation. But from our experiment
the reaction between acetaldehyde and tollens reagent do not formed silver mirror. The
reason are there is impurities on test tube and the materials that have been used are
broken. From our experiment the result is yellow solution with brown precipitate. The
reaction are,
O O
For the second tube, it also formed 2 layers, but it has different color, the colors
are white for the upper layer, and blue for the lower layer.
The first experiment is Testing aldehyde and ketones group with tollens reagent.
The tube A is reaction between acetaldehyde and tollens reagent. The tube D is the reaction
between foemalin and tollens reagent. Our experiment unappropriate with the teory
because of there were impurities on test tube and the materials that have been used are
broken.
J. Conclusion
1. Acetaldehyde and formalin react with tollens formed silver mirror but from our on
acetaldehyde and formalin are not formed silver mirror. Acetone and cyclohexanone
do not react with tollens reagent.
2. Formaldehyde oxydized while ketone do not react with fehling. Indicated by the
formed of red precipitation on aldehyde solution.
3. From our experment addition nuchleophilic reaction indicated by the physical changes
from white turbid colourless solution.
4. From our experiment on benzaldehyde and cyclohexanone are formed osazon crystal
when reacted with phenylhydrazin. The melting point of benzaldehyde is higher than
the melting point of cyclohexanone. The melting point of pheylhydrazine benzaldehid
is 144˚C and the melting point of cyclohexanone phenylhydrazon is 98˚C.
5. From this experiment, ktone given positive result when reacted with haloform.
Indicated with turbid precipitation. On reaction between NaOH and acetone resulting
white precipitate. On reaction between NaOH and isopropyl alcohol resulting
colourless solution.
6. Aldol condensation is reaction between aldehyde and base. Indicated by rancid smell
and colourless solution. But from our experiment formed orange solution.
7. Formic acid oxidized by KMnO4 formed MnO2 (black precipitate). Carboxylic can be
identified with reacting CH3COONa solution 10% with FeCl3 5% resulting filtrate that
contained Ferri ion. It can be proved by the colour comparation between FeCl3 and the
filtrate colour that added with K4FeCN6
K. References
Carey, Franciss A. 1937. Organic Chemistry sevent edition (e-book). Virginia :
University of Virginia
McMurry, John. 2008. Organic Chemistry seventh edition. USA : Thomson Higher
Education
Wade JR, LG. 2013. Organic Chemistry eight edition (e-book). USA : United States of
America.
Tim Kimia Organik. 2017. Petunjuk Praktikum Kimia Organik. Surabaya : Universitas
Negeri Surabaya
L. Attachment
No. PICTURES NO PICTURES
1. AgNO3 + NAOH 5% 2. TOLLENS REAGENT