Name Ilagan, Lineses
Maderazo, Mercado Group 3
POST- Properties of Alcohols, Aldehydes
LAB and Ketones Section Q1A2 Schedule Monday
5
Instructor Sir Edward Gonzales Date 04/12/19
Pre-laboratory Questions
1. Define the following:
a. Primary alcohol - Primary alcohols are those alcohols where the carbon atom of the hydroxyl
group(OH) is attached to only one single alkyl group. Some of the examples of these primary alcohols
include Methanol (, propanol, ethanol, etc. The complexity of this alkyl chain is unrelated to the
classification of any alcohol considered as primary. The existence of only one linkage among –OH
group and an alkyl group and the thing that qualifies any alcohol as a primary.
b. Secondary alcohol - Secondary alcohols are those where the carbon atom of the hydroxyl group is
attached to two alkyl groups on the either sides. The two alkyl groups present may be either
structurally identical or even different.
c. Tertiary alcohol - Tertiary alcohols are those which feature hydroxyl group attached to the carbon
atom which is connected to 3- alkyl groups. The physical properties of these alcohols mainly depend
on their structure. The presence of this -OH group allows the alcohols in the formation of hydrogen
bonds with their neighboring atoms. The bonds formed are weak, and this bond makes the boiling
points of alcohols higher than its alkanes.
2. Draw the structural formula for the following aldehydes and ketones:
a. Formaldehyde b. Propanone
c. Acetaldehyde d. 3-pentanone
3. Aldehydes and ketones can be prepared by oxidizing alcohols. What kind of alcohols can be used to
prepare aldehydes? What kind of alcohols can be used to prepare ketones?
Primary alcohols can be oxidized to either aldehydes or carboxylic acids depending on the
reaction conditions. In the case of the formation of carboxylic acids, the alcohol is first oxidized to an
aldehyde which is then oxidized further to the acid. Secondary alcohols are oxidized to ketones - and
that's it. For example, if you heat the secondary alcohol propan-2-ol with sodium or potassium
dichromate(VI) solution acidified with dilute sulfuric acid, propanone is formed.
4. Write the balance equation for the reaction of acetaldehyde with Benedict’s reagent.
CH3CHO + 2Cu{2+} + 4OH {-} CH3COOH + Cu2O + 2H2O
I. Introduction
In chemistry, an alcohol is any organic compound in which the hydroxyl functional group (–OH) is
bound to a carbon. The term alcohol originally referred to the primary alcohol ethanol (ethyl alcohol),
which is used as a drug and is the main alcohol present in alcoholic beverages.
Aldehydes and ketones are characterized by the presence of a carbonyl group, and their reactivity
can generally be understood by recognizing that the carbonyl carbon contains a partial positive charge
and the carbonyl oxygen contains a partial negative charge. Aldehydes are typically more reactive than
ketones.
A comparison of the properties and reactivity of aldehydes and ketones with those of the alkenes
is warranted, since both have a double bond functional group. Because of the greater electronegativity
of oxygen, the carbonyl group is polar, and aldehydes and ketones have larger molecular dipole moments
than do alkenes. The larger the dipole moment the greater the polar character of the carbonyl group. We
expect, therefore, that aldehydes and ketones will have higher boiling points than similar sized alkenes.
Furthermore, the presence of oxygen with its non-bonding electron pairs makes aldehydes and ketones
hydrogen-bond acceptors, and should increase their water solubility relative to hydrocarbons.
II. Objectives
To observe the different properties of alcohols, aldehydes and ketones.
To compare the properties of organic groups
III. Materials and Reagents
Test tube (16), cork (20), 5-mL pipet, test tube rack, 600-mL beaker, wire gauze, burner,
tripod, test tube holder
ethanol, 1-butanol, 1-pentanol, 1-hexanol, 1-octanol, acetone, distilled water, chromic acid,
propanal, 2-methyl propanal, heptanal, glucose, propanone (acetone), 2-heptanone, 2-
propanol, Benedict’s reagent
IV. Procedure
Label 11 test tubes 1 through
Add 10 drops of each
11, then place 1 mL of distilled water in
alcohol listed in the appropriate
each one.
tube:
After 5 minutes record
Seal each test tube with a observations. If the alcohol is
cork or plastic file and shake the insoluble in water, a cloudy
mixture vigorously. Then place mixture or two separate layers will
each in a test tube rack. appear.
Label four test tubes A Add 10 drops
through D, then place 1mL of of each alcohol listed
acetone in each one. in the appropriate
tube:
Seal each test tube with a
cork or plastic file and shake the
mixture vigorously. Then place
each in a test tube rack. After 5
minutes record observations.
Label 10 test tubes 1 Add 2 drops of each
through 10, then place 1 mL of alcohol listed in the appropriate
acetone in each one. tube. No alcohol will be added to
test tube
Thoroughly mix the
alcohol with the acetone, then add
Observe any color
one drop of chromic acid reagent
change. A color change from
to each test tube. (CAUTION:
orange to green or to blue-green
Handle the chromic acid reagent
within 5 seconds is a positive test
with care).
indicating alcohol had been
oxidized. Record observations.
Label 5 test tubes A Add 1 mL of each of the
through E and place 2 mL of following compounds to the
Benedict’s reagent in each. appropriate test tube.
Remove and place the
Seal each test tube with a test tubes in a test tube rack. As
cork and mix thoroughly. Place the test tubes cool, check for a
the labeled test tube in a boiling red, brown or yellow precipitate.
water bath for 10 minutes. Record the results.
V. Data and Results
A. Solubility in Water
Samples Soluble/Insoluble
1. Ethanol Soluble Out of the five samples, ethanol was the only
soluble sample since it is a polar compound. In
2. 1-butanol Insoluble
the other four samples, the solubility decreases
3. 1-pentanol Insoluble as the hydrocarbon chain length increases
therefore making 1-octanol the more insoluble
4. 1-hexanol Insoluble compared samples 2, 3, 4.
5. 1-octanol Insoluble
6. Formaldehyde Soluble Formaldehyde and 2-methylpropanal are soluble
in water due to them being a polar compound.
7. 2-methylpropanal Soluble
Meanwhile, 1-Heptanol is an alcohol with a seven
8. heptanal Insoluble carbon chain and is considered slightly soluble or
totally insoluble because as the carbon chain
increases, the solubility decreases.
9. Glucose Soluble
10. Propanone Soluble
11. 2-heptanone Insoluble
B. Solubility in Acetone
Samples Soluble/Insoluble
A. 1-butanol Soluble Acetone is an amphipathic substance meaning it
has both a polar end and a nonpolar end. That is
B. 1-pentanol Soluble
why it can dissolve both polar and non-polar
C. 1-hexanol Soluble compounds.
D. 1-octanol Soluble
C. Oxidation Reactions
Samples Positive/ Negative Color reactions
1. ethanol Positive Dark green
2. 1-butanol Positive Dark green
3. 2-butanol Positive Dark green
4. 2-methyl-2-propanol Positive Dark green
5. control – no alcohol Positive Dark green
6. propanone (acetone) Positive Dark green
7. 2-propanol Positive Dark green
8. formaldehyde Positive Dark green
9. 2-heptanone Positive Dark green
D. Benedict’s Test
Samples Positive/ Negative Color reactions
1. distilled water Negative No change
2. ethanol Negative No change
3. formaldehyde Negative No change
4. glucose Positive Orange - brown
5. propanone (acetone) Negative No change
VI. Discussion of Results
Solubility in water
Within the eleven samples mixed with water, only five were soluble which are ethanol,
formaldehyde, 2-methypropanol, glucose, and propanone. First reason for this is the polarity of the
given compounds. Polar compounds are soluble in water because water is also polar, thus the simple
rule “like dissolves like”. Another reason besides polarity is its molecular structure. The other organic
compounds that did not mix with water has long carbon chains and as the length of the hydrocarbon
chain increases, the solubility in water decreases. The decrease in solubility becomes visible as the
mixture forms two immiscible layers of liquid as observed in the experiment. The reason why the
solubility decreases as the length of hydrocarbon chain increases is because it requires more energy
to overcome the hydrogen bonds between the molecules as the molecules are more tightly packed
together as the size and mass increases. Typically, only those with four carbons or fewer can be
soluble in water.
Solubility in acetone
Sample A (1-butanol), Sample B (1-pentanol), Sample C (1-
hexanol) and Sample D (1-octanol) appears to all be soluble
in acetone. Acetone is an amphipathic substance meaning it
has both a polar end and a nonpolar end. In the molecular
structure of acetone, there is a negative charge on the
oxygen atom, a slight positive charge on the carbonyl group,
and it has two non-polar alpha carbons. Below is the
molecular formula of acetone:
The C=O bond provides polarity necessary for dissolving other polar molecules and the R groups or
the carbon chains are nonpolar and can dissolve nonpolar molecules. Thus, making acetone polar
but less polar than water making it capable of dissolving polar and nonpolar substances. This is why
acetone is consideres as a good solvent because it can be used for both polar and nonpolar.
Oxidation Reactions
Primary alcohols are converted either into an aldehyde if
carefully controlled conditions are used, or into a carboxylic acid if an
excess of oxidant is used. On the other hand, secondary alcohols are
converted into ketones on treatment with oxidizing agent. The chromic
acid test uses the Jones reactant to oxidize aldehydes and alcohols and
reduce the chromic acid, resulting in a color change. It is able to identify
aldehydes, primary alcohol, and secondary alcohol. Chromic acid has
an oxidation of 6+.
Chromic acid has several oxygens surrounding the chromium. These oxygens are able to act as
a source of oxidation for the aldehyde or alcohol. Since chromium loses an oxygen it's reduced to an
oxidation state of 3+. When chromium has an oxidation state of 6+ it's an orange color, but when it has
an oxidation state of 3+ it's a green-blue color. A positive test for aldehydes and primary or secondary
alcohols consists the production of blue-green color and in the case of this experiment, all samples turned
dark green or dark blue-green color. Compounds that are easily oxidized causes the solution to turn
green because of the formation of Cr3t ion.
Benedict’s Test
In the experiment conducted, only sample D which contains glucose came out positive determined
by its change of color into orange brown. Commonly, Benedict’s test is used for testing simple
carbohydrates, reducing sugars, monosaccharides and disaccharides. A reducing sugar is any sugar that
is capable of acting as a reducing agent because it has a free aldehyde group or a free ketone group.
When Benedict’s reagent and reducing sugars are heated together, the solution changes its colors. the
Copper (II) ions in Benedict’s solution are reduced to Copper (I) ions, which causes the color change.
Benedict’s reagent test is also commonly used to test for the presence of glucose precisely why sample
D reacted immediately. Though in this experiment, the purpose of Benedict’s reagent is to oxidize
aldehydes which is indicated by a precipitate in color red, orange or brown. And for ketones there will be
no change in the blue solution.
Questions to answer:
1. What tests would differentiate an alcohol from an aldehyde and a ketone?
Jones's Test is an organic reaction for the oxidation of alcohols to carboxylic acids and ketones.
This oxidation is very rapid and exothermic with high yields. Tollen's Reagent was used to determine
whether a substance is an aldehyde or ketone, which shows that aldehydes are easily oxidized while
ketones are not.
2. Give the sources and uses of aldehydes and ketones
So far we all know that formaldehyde is an aldehyde that can be used in embalming fluid and that
acetone is a ketone used in nail polish remover. Formaldehyde also has other uses, from killing pests on
plants to tanning animal hides. The most common ketone is acetone which is an excellent solvent for a
number of plastics and synthetic fibers. In the household, acetone is used as a nail paint remover and
paint thinner. In medicine, it is used in chemical peeling and for acne treatments.
3. How can alcohol be formed from aldehyde and from ketone?
Solid sodium tetrahydridoborate is added to a solution of the aldehyde or ketone in an alcohol
such as methanol, ethanol. The alcohol formed can be recovered from the mixture by fractional
distillation.
VII. Conclusion
Polar molecules interact through dipole–dipole intermolecular forces and hydrogen bonds.
Polarity underlies a number of physical properties including surface tension, solubility, and melting
and boiling points .Polar compounds are soluble in water because water is also polar, thus the simple
rule “like dissolves like”. The other organic compounds that did not mix with water has long carbon
chains and as the length of the hydrocarbon chain increases, the solubility in water decreases.
Acetone is an amphipathic substance meaning it has both a polar end and a nonpolar end. Primary
alcohols are converted either into an aldehyde if carefully controlled conditions are used, or into a
carboxylic acid if an excess of oxidant is used. On the other hand, secondary alcohols are converted
into ketones on treatment with oxidizing agent. Chromic acid has several oxygens surrounding the
chromium. These oxygens are able to act as a source of oxidation for the aldehyde or alcohol.
Benedict’s test is used for testing simple carbohydrates, reducing sugars, monosaccharides and
disaccharides.
VIII. Reference
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