EXPERIMENT NO.
CARBONYL COMPOUNDS: PROPERTIES OF ALDEHYDES AND KETONES
Purpose : Investigate the different properties of aldehydes and ketones.
Carry out simple chemical test to distinguish between aldehydes and
ketones.
Apparatus: test tubes, test tube holder, water bath, Bunsen burner, wire gauze,
dropper, and graduated cylinder
Materials : formaldehyde, acetaldehyde, benzaldehyde, acetophenone, isopropyl
alcohol, ethanol, acetone, Tollen’s reagent, Fehling’s reagent,
phenylhydrazine, sodium bisulfite, glacial acetic acid, saturated NaCl,
H2CrO4, conc. NaOH, I2 in KI, dil. NaOH, and litmus paper.
Discussion:
Aldehydes and ketones are somewhat similar in their structure as both
contain the C=O or known as Carbonyl group. All aldehydes contain at least one
hydrogen bonded directly to the C=O whereas ketones always have two organic
(alkyl) groups bonded to the C=O.
Aldehydes are compounds of the general formula RCHO, while ketones are of
the general formula R-CO-R’. The groups R and R’ could be aliphatic or aromatic.
The double bond in the carbonyl group is very susceptible to chemical
reactions. It is the carbonyl group that largely determines the chemistry of
aldehydes and ketones
https://www.ch.ic.ac.uk/local/organic/tutorial/DB_Carbonylnotes1.pdf
Naming Aldehydes in the IUPAC
Find the longest chain containing the CHO group, and change the -e ending of
the parent alkane to the suffix -al.
If the CHO group is bonded to a ring, name the ring and add the suffix –
carbaldehyde or benzaldehyde.
Number the chain or ring to put the CHO group at C1.
Examples:
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Common Names for Aldehydes
The common names of aldehydes are derived from the names of the
corresponding carboxylic acids by replacing –ic acid by –aldehyde.
Greek letters are used to designate the location of substituents in common names.
The carbon adjacent to the CHO group is the alpha(α) carbon, and so forth down
the chain.
Common names of the first 10 aldehydes
No. Acid name Aldehyde name No. Acid name Aldehyde name
of C of C
1 formic formaldehyde 6 caproic caproaldehyde
2 acetic acetaldehyde 7 enanthic enanthaldehyde
3 propionic 8 caprylic
4 butyric 9 pelargonic
5 valeric 10 capric
Naming Ketones in the IUPAC System
Find the longest chain containing the carbonyl group, and change the -e
ending of the parent alkane to the suffix -one.
Number the carbon chain to give the carbonyl carbon the lower number. Apply
all of the other usual rules of nomenclature.
Example:
3 – methyl -2 - pentanone
Common Names for Ketones
Most common names for ketones are formed by naming both alkyl groups on
the carbonyl carbon.
Arrange them alphabetically, and add the word ketone.
Example:
1.
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2.
Three widely used common names for some simple ketones do not follow
this convention:
Physical properties:
Aldehydes and ketones are polar compounds due to the polarity of
carbonyl group and hence they have higher boiling points than non-polar
compounds of comparable molecular weight.
But they have lower boiling points than comparable alcohols or
carboxylic acids due to the intermolecular hydrogen bonding.
The lower aldehydes and ketones are soluble in water, because of
hydrogen bonding between carbonyl group and water, also they are soluble in
organic solvents.
Chemical Properties:
The difference in the bonding, is the factor that affects the chemical
properties of aldehydes and ketones. This makes the aldehydes very easily to be
oxidized. Ketones don't have any hydrogen atom bonded to the carbonyl group, thus,
they are highly resistant to oxidation. They can only be oxidized by powerful
oxidizing agents which are capable of breaking the carbon-carbon bonds.
https://www.ch.ic.ac.uk/local/organic/tutorial/DB_Carbonylnotes1.pdf
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I. Physical Properties of Carbonyl Compounds
Procedures:
1. Prepare five (5) clean and dry test tubes and label as 1, 2, 3, 4, and 5.
2. To each tube, pour 1 mL of the carbonyl compounds listed in the table and take
note the color and odor. Save the solution for procedure number 3.
3. To each tube in number 2, add equal amount of water and shake vigorously.
4. Take note the miscibility of the carbonyl compounds.
5. Record your observations in the table below.
Carbonyl Compounds Color Odor Miscibility in H2O
Tt#1: Formaldehyde
Tt#2: Acetaldehyde
Tt#3: Acetone
Tt#4: Benzaldehyde
Tt#5: Acetophenone
II. Chemical Properties of Aldehydes and Ketones
1. Oxidation:
Aldehydes and ketones behave differently toward oxidizing agents. Because
aldehydes have hydrogen atom directly bonded to the carbonyl carbon it makes them
more reactive to oxidation than ketones.
(aldehyde) RCHO (O) RCOOH (carboxylic acid)
strong oxidizing agent
Ketones, which have no hydrogen attached to the carbonyl carbon atom, may
be oxidized to a carboxylic acid only under more severe conditions (stronger reagents
and higher temperatures), because their oxidation to an acid requires the rupture of
a carbon-carbon bond.
A. Silver Mirror Test (Tollen’s Test)
Tollen’s test, perhaps is the most distinctive qualitative test for
aldehydes in which silver ion [as the complex ion Ag(NH 3)+2] oxidizes the aldehydes
to the corresponding carboxylic acid, and in turn, is reduced to metallic silver which
is deposited on the walls of the test-tube as a mirror (hence frequently referred to as
the Silver Mirror Test). Ketones are not usually oxidized by the reagent.
A: negative result B: positive result
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B. Fehling’s Test
Fehling’s solution is restricted to the detection of aliphatic aldehydes. The
reagent is a deep-blue, alkaline solution containing a complex cupric ion. Upon
reaction with an aliphatic aldehyde, the cupric ion is reduced to form cuprous oxide
which is deposited as an orange to brick red precipitate.
NaOH
RCHO + Cu++ RCOO- Na+ + Cu2O
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procedure-and-result-interpretation/
Aromatic aldehyde, because of the additional resonance stabilization arising from
conjugation of the carbonyl group with the benzeneoid ring is insensitive to this
reagent (the oxidation-potential of cupric ion is less than that of silver ion).
Simple ketones, alcohols, and alkenes compounds are not affected,
compounds such as α –hydroxy ketones are oxidized almost as easily as aldehydes;
both these tests find wide application in carbohydrate chemistry for the detection of
reducing sugars. Fehling’s test is the basis of a quantitative determination for
“blood sugar” levels.
C. Chromic Acid (H2CrO4)
Chromic acid is a strong oxidant. Aldehydes are oxidized to carboxylic acids
by chromic acid. The Cr 6+ in the chromic acid which is orange, then is reduced to
Cr3+ which is green/blue-green/blue. Ketones are not oxidized by chromic acid.
D. 2,4-dinitrophenylhydrazine (DNP Test or Brady’s Reagent)
Most aldehydes and ketones reacts very readily with this reagent to give the
bright yellow or orange 2,4-dinitrophenylhydrazones. The conversion of aldehydes
and ketones into hydrazone is an example of the addition-elimination reaction
occurring at the unsaturated carbonyl group.
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2. Iodoform Test
Iodoform test is used to check the presence of carbonyl compounds with the
structure R-CO-CH3 or alcohols with the structure R-CH(OH)-CH 3 in a given unknown
substance. The reaction of iodine, a base and a methyl ketone gives a yellow
precipitate along with a strong medicinal or antiseptic smell.
https://byjus.com/chemistry/iodoform-test/
3. Schiff’s Test:
Fuschin (roseaniline hydrochloride) is a red-pink triphenylmethane dye that is
converted to a colorless compound upon reaction with sulfurous acid. The sulfurous
acid reacts with the dye via an electrophilic addition to generate a colorless reagent
called Schiff’s reagent. Reaction of the Schiff’s reagent with an aldehyde results in
loss of the sulfurous acid and generation of a different dye that has a magenta red
color. A color change from pink or colorless to violet-purple/magenta red indicates
the presence of aldehyde functional group.
4. Cannizaro Reaction
In the presence of concentrated alkali, aldehydes containing no α-hydrogen
undergo self-oxidation and reduction to yield a mixture of an alcohol and a salt of a
carboxylic acid. This reaction is known as the Cannizzaro reaction.
https://ypen.com/the-cannizzaro-reaction/
5. Addition of Alcohols (Acetal Formation):
Aldehydes and ketones react with two equivalents of alcohol to form
acetals. In an acetal, the carbonyl carbon from the aldehyde or ketone is now
singly bonded to two OR" (alkoxy) groups.
https://www.studocu.com/en-us/document/drexel-university/organic-chemistry-
laboratory-i/other/lab-report-5-cannizaro-and-aldol-reaction/1987316/view
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Procedures:
1. Prepare 36, clean and dry test tubes for each of the following compounds;
Tube # 1- 6: 1 mL of unknown A
Tube # 7-12: 1 mL of unknown B
Tube # 13-18: 1 mL of unknown C
Tube # 19-24: 1 mL of unknown D
Tube # 25-30: 1 mL of unknown E
Tube # 31-36: 1 mL of unknown F
2. To test tubes 1,7,13,19,25, and 31 add 1 mL of Tollen’s reagent and place in
a boiling water bath for at least 3 minutes and observe.
3. To test tubes 2,8,14,20,26,and 32 add 1 mL of Fehling’s reagent and place in
a boiling water bath for at least 3 minutes and observe.
4. To test tubes 3,9,15,21,27,and 33 add 1 mL of K 2Cr2O7 and 5 drops of dilute
H2SO4 and place in a boiling water bath for at least 3 minutes and observe.
5. To test tubes 4,10,16,22,28,and 34 and 5 drops of DNP, 10 drops of glacial
acetic acid and 1 mL of saturated NaCl solution, mix thoroughly and then
heat in a water bath for at least 10 minutes. After 10 minutes remove from
the water bath and immerse in an ice bath until crystals are formed.
6. To test tubes 5,11,17,23,29 and 35 add 3 drops of 6N NaOH solution and
iodine in KI solution and warm in a water bath for at least 3 minutes and
observe.
7. To test tubes 6,12,18,24,30, and 36 add 2 drops of Schiff’s reagent and
observe any change in color.
8. Tabulate results in the table below.
Tests Done
X Tollen’s Fehling’s K2Cr2O7 + DNP I2 in KI Schiff’s
Test Test dil. H2SO4 soln. test
A + + + + + +
_ _ _ _
B + +
C _ _ _ + _ +
_ _ _ _
D + +
_ _ _ _
E + +
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Output 1:
1. What can you say about the miscibility of carbonyl compounds in water?
________________________________________________________________
2. What property of aldehydes is shown in the different tests done?
________________________________________________________________
3. Do all carbonyl compounds exhibit the same property to the different tests above?
_________________________________________________________________
4. Explain your answer in number 3.
__________________________________________________________________
5. Which of the following is __________?
a) ____________*an aldehyde
b) ____________*a ketone
c) ____________*not a carbonyl compound
6. What class of organic compound you think unknowns A, B and C belongs?
__________________________________________________________________
7. Support your answer in number 6.
__________________________________________________________________
8. What class of organic compound you think unknowns D and E belongs?
__________________________________________________________________
9. Support your answer in number 8.
__________________________________________________________________
10. Which of the following is the (a) reduced product (b) oxidized product in the
following tests?
1. Tollen’s test
a)________________ b) _______________
2. Fehling’s test
a)________________ b)_______________
3. Chromic acid test (K2Cr2O7 + dil. H2SO4)
a)_________________ b)_______________
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