NAME:________________________ RATING:__________________

GROUP #:_____________________ DATE:____________________

EXPERIMENT NO. 19
KETONES: PREPARATIONS AND PROPERTIES

OBJECTIVES
1. To prepare ketones by reacting secondary alcohols
2. To differentiate the properties of ketones from other hydrocarbon derivatives
3. To observe and discuss the different reactions of ketones

INTRODUCTION

Ketones like aldehydes are characterized also by the presence of the “carbonyl group” (–C=O), perhaps
the most important functional group in organic chemistry. The carbon atom of a carbonyl group must form
two (2) other bonds in addition to the carbon oxygen double bond in order to have four bonds. The nature
of these two additional bonds determines the type of carbonyl containing compound it is. Ketones are the
organic compounds that have two other carbon groups connected to the carbonyl carbon atom. The
two other carbon atoms must be a part of an alkyl, cycloalkyl or aromatic group. The general formula of
a ketone is R – CO – R’, where the R and R’ could be both or a combination of either an alkyl, cycloalkyl
or aryl group.

The polarity of the carbonyl group strongly influences the physical and chemical properties of both
aldehydes and ketones. Aldehydes and ketones contain a polar carbonyl group (carbon–oxygen double
bond), which has a partially negative oxygen atom and a partially positive carbon atom. Because the
electronegative oxygen atom forms hydrogen bonds with water molecules, aldehydes and ketones with
one to four carbons are very soluble. However, aldehydes and ketones with five or more carbon atoms
are not soluble because longer hydrocarbon chains, which are nonpolar, diminish the solubility effect of
the polar carbonyl group. Chemically, ketones tend to be less chemically active than aldehydes of similar
molecular size.

Ketones are often used in perfumes and paints to stabilize the other ingredients so that they don’t degrade
as quickly over time. They also have other uses in surface coatings, adhesives, thinners, printing inks, and
cleaning agents, in tanning, as solvents, as preservatives, in hydraulic fluids and as intermediates in the
chemical industry.

In our bodies, ketones like acetone, acetoacetate, and beta-hydroxybutyrate (called ketone bodies) are
important biological components for metabolic processes. They are generated from carbohydrates, fatty
acids and amino acids. Ketones are elevated in blood after fasting including a night of sleep and also during
starvation. The brain cells rely heavily on ketone bodies as a substrate for lipid synthesis and for energy
during times of reduced food intake.

MATERIALS & REAGENTS

A. Materials
Test tubes, Test tube Rack, Test Tube holder, Test tube brush, Pasteur pipettes, Watch zglass,
Evaporating dish, 250 mL Beaker, Splinters, Bunsen Burner, Wire gauze, Tripod, pH papers, Litmus
papers

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B. Reagents
Acetone, Acetaldehyde, 95% Isopropanol, K2Cr2O7 Solution, Conc. H2SO4, 2,4 – DNPH in Methanol,
0.5% Sodium Nitroprusside Solution, Conc. NaOH, Benedict’s Reagent, Fehling’s A & B Reagents,
Distilled water

RUBRICS FOR SCORING

For Procedures:
➢ 2 points is given for every short procedure done that requires an immediate written observation
o 1 point for doing the procedure correctly
o 1 point for the answer
➢ An extra 3 points may be given for long procedures that requires 5 – 15 minutes to perform;
➢ An extra 5 points for procedures that require 16 – 30 min. to perform on the average
➢ An extra 8 points for procedures that require 31 – or more minutes to perform on the average
➢ 3 points is given for every generalization or conclusion made
o 1 point is to be deducted from the score for every mistake identified by the instructor
➢ 1 point is given for items that do not require performing a procedure

For Questions for Research:

➢ 1 point is given for each correct answer to an enumeration.
➢ 2 points is given to every correct definition answer.
o 1 point is to be deducted from the score for every mistake identified by the instructor
➢ 4 points is given for other questions.
o 4 – excellent – 1 mistake or missing concept identified
o 3 – Good – 2 mistakes or missing concepts identified
o 2 – Fair – 3 mistakes or missing concepts identified
o 1 – Poor – 4 mistakes or missing concepts identified
o 0 – The answer is totally different from the expected response

PROCEDURES & OBSERVATIONS:

A. PREPARATION OF KETONES
1. Get two (2) clean and dry test tubes and label them as test tube 1 (TT1) and test tube 2 (TT2)
respectively.
➢ To test tube 1 (TT1), place 1 mL of Isopropyl alcohol
➢ To test tube 2 (TT2), place 1 mL of Isoamyl alcohol
2. Add 3 drops of K2Cr2O7 solution to each solution in the test tube
3. Acidify with 3 drops of conc’d. H2SO4 and with constant swirling of the test tubes to mix the
contents. Observe the reactions and write your results below.

Observations _________________________________________________________________

_____________________________________________________________________________

4. Write the equation for the above reactions in the boxes below.

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B. CHEMICAL PROPERTIES

1. Brady’s Test

a. Place 1 mL of acetone in a clean and dry test tube

a. Add 1 mL of 2, 4 – Dinitrophenyl Hydrazine solution to the acetone
b. Acidify with 3 drops of conc’d sulfuric acid with caution (check acidity using BLP).
c. Observe for any changes in the color of each aldehyde solutions.

____________________________________________________________________

____________________________________________________________________

d. Is Brady’s test also positive for Ketones like aldehydes? Reason out your answer.

___________________________________________________________________

____________________________________________________________________

2. Legal’s Test

a. Place 2 mL of acetone in a clean and dry test tube

b. Add 5 drops of 0.5% Sodium Nitroprusside and note all changes that occurred

Observation: ___________________________________________________________

c. Add 10 drops of concentrated NaOH solution (check alkalinity using RLP).

d. Observe for further changes in the solution and write your observations below.

Note: This test may also be used to detect the presence of ketone bodies in urine.

Observations: __________________________________________________________

_______________________________________________________________________

3. Reaction with a Strong Oxidizing Agent (O.A.)

a. Place 1 mL of acetone in a clean and dry test tube
b. Add 3 drops of 1% potassium dichromate solution
c. Cautiously acidify with 3 drops of conc’d sulfuric acid with caution.
d. Observe for any changes in color in each aldehyde solutions.

____________________________________________________________________

____________________________________________________________________

e. Write the equation for the reactions in the boxes below.

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4. Benedict’s Test
Get two (2) clean and dry test tubes and label them as test tube 1, and 2 respectively.
➢ To test tube 1 (TT1), place 1 mL of Acetaldehyde
➢ To test tube 2 (TT2), place 1 mL of Acetone
a. Add 2 mL of Benedict’s reagent to each of the solutions in the test tubes
b. Place the test tubes in a boiling water bath for 2-3 minutes
c. Observe for any color change or formation of a precipitate.

TABLE 1: Results and Observations

Color of Solution Upon addition Results after the Hot water

Test Solutions of Benedict’s Reagents bath

Acetaldehyde

Acetone

Based on the results and observations of the above procedures:

In which solution was the Benedict’s test positive? ______________________________

What is the positive results for Benedict’s test? _________________________________

In which solution was the Benedict’s test came-out negative? Why? Explain your answer.

_______________________________________________________________________

_______________________________________________________________________

5. Fehling’s Test

a. Get two (2) clean and dry test tubes and label them as test tube 1, and 2 respectively.
➢ To test tube 1 (TT1), place 1 mL of Acetaldehyde
➢ To test tube 2 (TT2), place 1 mL of Acetone
b. Add 1 mL of Fehling’s reagent A and 1 mL of Fehling’s reagent B respectively to each of the
solutions in the test tubes. Carefully shake the test tubes to completely mix the contents.
c. Place the test tubes in a boiling water bath for 2-3 minutes
d. Observe for any color change or formation of a precipitate.

TABLE 2: Results and Observations

Color of Solution Upon addition Results after the Hot water

Test Solutions of Fehling’s Reagents A & B bath

Acetaldehyde

Acetone

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 Based on the results and observations of the above procedures:

In which solution was the Fehling’s test positive? ______________________________

What is the positive results for Fehling’s test? _________________________________

In which solution was the Fehling’s test came-out negative? Why? Explain your answer.

_______________________________________________________________________

_______________________________________________________________________

What can you say about the Benedict’s Test and Fehling’s test as to their results with both
aldehydes and ketones?

_______________________________________________________________________

_______________________________________________________________________

Can you use these tests to differentiate between an aldehyde and a ketone? __________

CONCLUSIONS

QUESTIONS FOR RESEARCH

1. In a tabulated form, enumerate the first four (4) member of the homologous series of ketones. (a) Write
their common name, (b) IUPAC name, (c) condensed structural formula, and (d) cite two of their uses
or importance.
2. Write the structural formula of (a) diphenyl ketone and (b) dibenzyl ketone. What are their IUPAC name?
and what are their uses or importance? Discuss each.
3. What are ketals and hemiketals? Explain briefly. Illustrate their mechanism of formation.
4. Cite two methods of preparing Ketones aside from the oxidation of secondary alcohols. Show by using
equations their mechanism of formation.
5. Describe the expected positive result of (a) Benedict’s test, (b) Fehling’s test, and (c) Tollen’s test?
Discuss also their applications.

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