NOTRE DAME OF DADIANGAS UNIVERSITY
Marist Avenue, General Santos City
Physico-chemical Properties of Carbonyl and
Activity Hydroxyl Compounds, and Carboxylic acid and
Derivatives
No.5 Title of the Activity
Name: Bea M. Rada_____ Date: July 21, 2021
Instructions:
1. Watch the video below and answer the questions:
a. https://www.youtube.com/watch?v=4yPjkRLcauI
b. https://www.youtube.com/watch?v=mAZqGzFbGQE
c. https://www.youtube.com/watch?v=Z2AdINwT8W0
d. https://www.youtube.com/watch?v=yjLB_ntM324
e. https://www.youtube.com/watch?v=7I-y3I3VzM8
f. https://www.youtube.com/watch?v=Fn3q4y6_F7g
g. https://www.youtube.com/watch?v=2eEjAONin9E
2. Complete the table by providing theoretical results.
3. All questions and answers should be typewritten. Font: Arial, size 12 and justified
paragraph.
4. Questions in black color and your answers in red color.
5. Submit as pdf file not later than 12 midnight of July 21, 2021.
6. FILE NAME should be: Act5_ph20_SURNAME
CARBONYL AND HYDROXYL COMPOUNDS
Procedure:
I. Lucas Test
Preparation of reagent: Dissolve 16 g of anhydrous zinc chloride in 10 mL of
conc. HCl. Allow the mixture to cool.
1. Add about 50mg (2-3 drops) of the sample to 1 mL of the reagent in a
small vial. Cap the vial and shake vigorously for a few seconds.
2. Allow the mixture to stand in room temperature.
3. Observe the rate of formation of the cloudy suspension or the formation of
2 layers.
II. Chromic Acid Test (Jones Oxidation)
Preparation of reagent: Dissolve 20 g chromium trioxide in 60 mL of cold water in
a beaker. With stirring, slowly and carefully add 20 mL of conc. Sulfuric acid to
the solution. This reagent should be prepared fresh each time.
1. Dissolve 1 drop of liquid or small amount of the solid sample in 1 mL of
acetone in a small vial.
2. Add 5 drops of chromic acid reagent, one drop at a time, while shaking the
mixture.
3. Place the test tubes in a 60degC water bath for 5 minutes. Note the color
of each solution.
III. 2,4-dinitrophenylhydrazine (or 2,4-DNP) Test
Preparation of reagent: add a solution of 3 g of 2,4-dinitrophenylhydrazine in 15
mL of conc. Sulfuric acid slowly while stirring to a mixture of 20 mL of water and
70 mL of 95% ethanol. Stir and filter.
1. Place a drop of a liquid sample into a small test tube.
2. Add 5 drops of 95% ethanol. Shake well.
3. Add 3 drops of reagent. If no yellow or orange-red precipitate forms, allow
the solution to stand for at least 15 minutes.
4. Perform this test on acetone and benzaldehyde. Describe the result.
IV. Fehling’s test
1. Into each test tube, place 1 mL of Fehling’s reagent.
2. Add 3 drops of the sample to be tested.
3. Place the tubes in a beaker of boiling water and observe the changes
which occur within 10-15 minutes. Perform test on acetone and
benzaldehyde.
V. Tollen’s Silver Mirror test
Preparation of reagent: to 2 mL of 5% silver nitrate solution, add 2 drops of 5%
sodium hydroxide solution and mix thoroughly. Then add drop by drop, and with
stirring, only enough 2% ammonium hydroxide (conc. Ammonium hydroxide is
28%) to dissolve the precipitate. The test will fail if excess ammonia is added.
1. Prepare 2 test tubes with 1 mL of tollen’s reagent.
2. Add 2 drops of the sample separately: acetone and benzaldehyde.
3. Shake the mixture. Allow it to stand for 10 minutes. If no reaction has
occurred, place the tube in a beaker of warm water (35-50 degC) for 5
minute. Record your observations.
VI. Iodoform Test
1. Place 2 drops of each sample (acetone, benzaldehyde and isopropyl
alcohol) into its own vial.
2. Add 20 drops of 10% KI solution.
3. Add slowly while shaking, 20 drops of fresh chlorine bleach (5% sodium
hypochlorite) of each tube and mix.
4. Note the formation of yellow precipitate.
Questions:
Substance Tests
Lucas Chromic 2,4- Fehling’s Tollen’s Iodoform
(Visible acid DNP (Visible (Visible (Visible
Result) (Visible (Visible Result) Result) Result)
Result) Result)
Ethanol Colorless Blue- No No No Yellow
(No green reaction reaction reaction precipitat
reaction) Solution e
Benzaldehyde Colorless Blue- Yellow Brick-red Silver Red
(No green Precipit precipitat Solution precipitat
reaction) Solution ate e e with
globules
Acetone Turbid Orange Yellow Blue Colorles Yellow
(Cloudy)S Solution Precipit Solution s precipitat
olution ate Solution e
within 3-5
minutes
Isopropyl Turbid Blue- No No Yellow
alcohol (Cloudy)S green No reaction reaction crystal
olution Solution reaction precipitat
within 3-5 e
minutes
1. Differentiate the three types of alcohol. Give example for each.
In primary alcohols, the carbon atom of the hydroxyl group (OH) is connected to only
one alkyl group. Examples include methanol, propanol, ethanol, and other major
alcohols. Secondary alcohols contain the carbon atom of the hydroxyl group. There
are two alkyl groups on each side. Rubbing alcohol, which comes in a 70% solution,
is the most prevalent form of isopropyl alcohol. Anti freezes, glass cleaners, jewelry
cleaners, stain removers, deicers, home disinfectants, and hand sanitizers all
contain this ingredient. In tertiary alcohols, the hydroxyl group is connected to the
carbon atom. It is a member of the 3-alkyl group. This alcohol is used to make
alcoholic beverages such as wine, beer, and liquor.
2. Differentiate aldehydes from ketones based on chemical structure.
Aldehydes have an alkyl bond on one side and a hydrogen atom on the other,
whereas ketones have double alkyl bonds on both sides due to the substitution of a
R group for the hydrogen. Aldehydes are also commonly found at the ends of a
carbon chain. They are written as (R-(C=O)-H), with R denoting the alkyl group and
H denoting the hydrogen atom. Ketones are denoted by the letters R-(C=O)-
R'.where R and R’ are alkyl groups present on each side of the compound.
3. How do structure and number of carbons affect the solubility of alcohols in
water?
As the carbon chain lengthens, the polar OH group becomes a smaller component
of the molecule, and the molecule begins to resemble a hydrocarbon (non-polar) and
less like water (polar). As a result, the longer an alcohol's carbon chain is, the lower
its solubility in polar solvents such as water and the higher its solubility in nonpolar
solvents.
4. Based on the compounds, which alcohol:
a. Is most readily oxidized? Why do you think this is so?
Primary alcohol is easily converted to an aldehyde, which can then be
converted to carboxylic acids. Because secondary alcohols have a stronger
steric effect than primary alcohols, they will react more slowly. Tertiary
alcohols, on the other hand, cannot be oxidized at all. When comparing the
ease with which primary, secondary, and tertiary alcohols oxidize, the first
oxidizes the most quickly, while the third oxidizes the slowest.
b. Immediately forms 2 layers with the Lucas test? Why do you think this is
so?
Between Ethanol, a primary alcohol, and Isopropyl alcohol, a secondary
alcohol, the formation of two layers in the latter is more immediate (within 3-5
minutes based on the results) because primary alcohols are generally
nonreactive unless heated. They form two layers because a secondary
alcohol has one more carbon in its chain and that makes it more non-polar
and less soluble in polar solvents like water. When the reaction between
isopropyl alcohol and Lucas reagent occurs, a cloudy solution forms quickly,
followed by two layers. The top layer is clear, but the bottom layer is hazy.
5. Which chemical test/s help/helps differentiate between aldehydes and
ketones? Explain your answer.
The Jones reactant is used to oxidize aldehydes and alcohols while reducing
chromic acid, producing in a color shift. Aldehydes, primary alcohol, and secondary
alcohol can all be detected. The Fehling's test, like the Chromic acid test, can
distinguish an aldehyde from a ketone based on its capacity to be oxidized.
Aldehydes are oxidized, giving a positive result (precipitation of red copper
(I)oxide),but ketones do not react unless it is an alpha-hydroxy- ketones and instead,
remain as a blue solution.
CARBOXYLIC ACID AND DERIVATIVES
Procedure:
I. Hydrolysis of Acid Derivatives
a. Acyl halides and Acid anhydrides
1. Place 1 ml of water in a test tube. Cautiously add dropwise 10 drops of the
sample. Note for a warming effect.
2. Divide the resulting mixture in #1 inti 2 portions. To the 1st, add 1ml of 2%
AgNO3. Observe for precipitation. To the 2nd portion, add 1 mL of saturated
NaHCO3. Note for the evolution of gas.
b. Esters
1. Add 2 mL of 25% NaOH solution to 1 mL of ethyl acetate. Cover mouth of the
test tube with a marble and heat the test tube in a boiling water bath for 5
minutes.
2. Neutralize the mixture with 10% HCl solution. With wafting motion, take note
of the odor.
II. Alcoholysis: Schotten-Baumann Reaction
a. Acetic acid
Warm a mixture of 10 drops of acetic acid, 1 mL ethanol, and 5
drops of conc. Sulfuric acid over a water bath for 2 minutes. Note the odor
of the ester formed.
b. Acyl halides and Acid anhydrides
In another test, place 0.5 mL ethanol, 1 mL water, and 0.2 mL of
acetic anhydride sample. Add 2 mL 20% NaOH solution. Plug the test
tube with a cork stopper or parafilm and shake mixture for several
minutes. Note the odor and the layers of the ester formed.
c. Aminolysis: Anilide Formation
Add a few drops of acetyl chloride or acetic anhydride sample to
0.5 mL aniline. Transfer the mixture into new test tube containing 5 mL
water. Describe precipitate formed.
III. Hydroxamic Acid Test
Preliminary test: mix 2 drops of the sample, 1 mL of 95% ethanol and 1 M
HCl. Note color produced when 1 drop 5% FeCl3 solution is added to the mixture.
If a color other than yellow is obtained, the test cannot be used. Otherwise, the
test is conducted as follows:
Add 2 drops of the samples to 2 mL of alcoholic NH2OH.HCl and 1 mL of 1M
KOH. Heat in a boiling water bath for 2 minutes. Cool the mixture. Add 1 mL of
5% FeCl3. Note the color of the solution.
Questions:
I. Hydrolysis of Results
Acid Derivatives
Acyl halides and Acid Warming effect addition of 2% addition of
anhydrides AgNO3 saturated
NaHCO3
I.A. Acetyl chloride Slightly warm White precipitate
No precipitate
White gas
I.A.Acetic anhydride No temperature No precipitate
change (room No precipitate
temperature)
White gas
I.B.Ester:Ethyl acetate Odor: Plastic balloon-like or thinner-like odor
II. Alcoholysis: Schotten- Results
Baumann Reaction
Acetic acid Odor: Fruity odor/Plastic balloon-like odor
Acyl halides and acid anhydrides Odor Formation of Layers
Acetyl chloride Vinegar-like odor Formation of two
layers
Acetic anhydride Plastic balloon-like Formation of two
odor layers
III. Aminolysis: Anilide Formation Results
Acyl halides and acid anhydrides Appearance of Precipitate
Acetyl chloride White precipitate Formation of dark red
gel-like precipitate
Acetic anhydride White precipitate Formation of dark red
gel-like precipitate
IV. Hydroxamic Acid Test Result
Preliminary Test Upon addition of 5%
FeCl3
Ethyl acetate Yellow solution Deep burgundy color
1. Arrange the following in the order of decreasing reactivity towards a
nucleophile. (number them 1 – 5):
___5__ acid amide
___1__ acid halide
___3__ ester
__4___ carboxylic acid
___2__ acid anhydride
2. Rationalize the order of reactivity in #1.
The reactivity trend of carboxylicacid derivatives can be deduced by looking at the
leaving group's basicity (acylX group). It is advantageous for weaker bases to leave
groups. This increases the reactivity of a derivative. A more reactive carboxylic acid
derivative will be transformed to a less reactive derivative, but not the other way
around.
3. Draw the condensed structural formulas of the sample compounds.
ACID HALIDE ESTER
ACID ANHYDRIDE CARBOXYLIC ACID
ACID AMID
4. Write the equations involved in the chemical tests.
Hydrolysis of acetic anhydride
Hydrolysis of ethyl acetate
Alcoholysis of acetic acid
Alcoholysis of acetyl chloride
Alcoholysis of acetic anhydride
Aminolysis of acetyl chloride
Aminolysis of acetic anhydride
Hydroxamic acid test of ethyl acetate (General equation)
5. Why it is necessary to perform a preliminary test on the sample before doing
the hydroxamic acid tests?
Before performing a hydroxamic acid test, any phenols and enols that could
cause a false positive result when testing an unknown substance must be removed
by performing a preliminary test. Any color other than yellow will reject this test if
ferric hydroxamate is used.
6. Discuss the leaving group ability of chloride versus carboxylate in the
reaction of acid halide and an acid anhydride.
The ability of acyl derivatives to leave groups, which is influenced by acidity,
is a key element in determining their reactivity. In order for a leaving group to
leave, it must be able to accept electrons. A strong base wants to donate
electrons; therefore, the leaving group must be a weak base. Weak bases, such
as chlorides, leave better than strong bases, such as carboxylates, while a
species with a strong conjugate acid will leave better than one with a weak
conjugate acid.
