Systematic Characterization of Oxygen-Bearing Organic Compounds

Quintero, Christian Paul D., Ramos, Jandra Natanie C., Rapacon*, Mark Giane Dave V.,
Recto, Chris Vincent A.
College of Science, University of Santo Tomas, Manila, Philippines
__________________________________________________________________________________________

Abstract
Qualitative Chemical Analysis makes use of qualitative data for interpretation of compound identity. The
reference oxygen-bearing compoundsn-propanol, 2-propanol, t-butanol, formaldehyde and acetone
were subjected to the different classification tests. Positive results for Dichromate test classified npropanol, 2-propanol and formaldehyde as reducing agents; the Tollens test showed high specificity to
formaldehyde; the Lucas test classified n-propanol, 2-propanol and t-butanol based on their reaction
rates, with t-butanol being the most reactive; the DNPH test detected the carbonyl groups from
formaldehyde and acetone; and the Iodoform test identified the oxidation of 2-propanol and acetone.
Identification of two unknown oxygen-bearing compounds was based from the reactions of the reference
standards. The functional class of Unknown A was known to be a secondary alcohol, while Unknown B
was identified to be an aldehyde.

I. Introduction
Oxygen-bearing compounds, from the name itself, are
organic compounds that contain one or more oxygen. The
known oxygen-bearing organic compounds are alcohol,
phenol, ether, aldehyde, ketone, carboxylic acid, ester, and
an anhydride (Solomons, Fryhle & Snyder, 2014).
An alcohol is an organic compound with hydroxyl (
OH) group as its characteristic functional group. The

hydroxyl group is attached to an sp 3-hybridized carbon atom. Alcohols could be

classified as primary (1O), secondary (2O), or tertiary (3O) alcohol.
A primary (1O) alcohol is an alcohol whose hydroxyl
group is attached to a primary carbon, a carbon that has only
one other carbon attached to it (Solomons, Fryhle & Snyder,
2014). A 1O alcohol of particular interest in the experiment is
n-Propanol (CH3CH2CH2OH) (Fig.1). The IUPAC name for nPropanol is 1-Propanol. It is a colorless liquid, with molar
mass of 60.09 g/mol, and a polar solvent. It is used as a
cleaning

fluid,

adhesive

and

stain

remover, and

as

preservative (Pavia, 2007).

A secondary (2O) alcohol is an alcohol whose hydroxyl
group is attached to a secondary carbon, a carbon that bears
two other carbon atoms (Solomons, Fryhle & Snyder, 2014).
A

2O

alcohol

of

particular

interest

is

2-Propanol

(CH3CH(OH)CH3) (Fig. 2). It is commonly known as isopropyl

alcohol. Isopropyl alcohol is colorless, flammable chemical
compound with a strong odor, has a molar mass of 60.1
g/mol and a boiling point of 82.6

C. It is typically

commercialized as antiseptic (Pavia, 2007).

A tertiary (3O) alcohol is an alcohol whose hydroxyl
group is attached to a tertiary carbon, a carbon that bears
three other carbon atoms (Solomons, Fryhle & Snyder, 2014).

A 3O alcohol of particular interest in the experiment is t-butanol

((CH3)3COH) (Fig. 3). With its IUPAC name 2-methyl-2-propanol,

and

Figure
commonly called tert-butyl alcohol, it is a clear liquid (or a colorless
solid,10.
depending on
Anhydride Example

the ambient temperature) with a camphor-like odor. It has a molar mass of 74.12 g/mol
and

boiling

point

ethanol denaturant, paint

of

83

C.

tert-Butyl

remover ingredient,

alcohol
and

is

gasoline

used

as

solvent,

octane booster

and

oxygenate (Pavia, 2007).

Phenol (Fig.4) is an alcohol whose hydroxyl group is attached to a benzene ring.
However, they differ from simple alcohols with their relative acidity, separating them as
distinct functional group. Ethers (Fig.5) have the general formula ROR or RO
R, where R could be an alkyl (or phenyl) group different from R (Solomons, Fryhle &
Snyder, 2014).
Moreover, aldehyde is a functional group that contains a carbonyl group(C=O).
The carbonyl group of an aldehyde is bonded to one hydrogen and one carbon atom.
One exception, and is of particular interest, is the formaldehyde (CH 2O) (Fig. 6) which is
the only aldehyde bearing two hydrogen atoms (Solomons, Fryhle & Snyder, 2014).
Commonly known as formalin, it is gas at room temperature, colorless and has a
characteristic pungent, irritating odor. It has a molar mass of 30.031 g/mol and a boiling
point of -19 OC. It is commonly used in embalming, as nail hardener or nail varnish
(Pavia, 2007).
Another organic compound are the ketones; like aldeydes, ketones also contain
carbonyl group. However, the carbonyl group in ketones is bonded to two carbon atoms
(Solomons, Fryhle & Snyder, 2014). A ketone of particular interest is acetone

((CH3)2CO) (Fig. 7). Its IUPAC name is 2-propanone; it is the simplest ketone. Being a
polar solvent, it is colorless, volatile, flammable liquid. It has a molar mass of 58.08
g/mol and a boiling point of 56 OC. Acetone is used as active ingredient in nail polish
remover and as paint thinner (Pavia, 2007).
In addition, carboxylic acids(Fig.8) have a carbonyl group bonded to a hydroxyl
group (RCO2H). Esters(Fig.9), on the other hand, have a carbonyl group bonded to an
alkoxyl (OR) group (RCO2R). Lastly, organic acid anhydride (Fig.10) is a compound
that has two acyl (R bonded to carbonyl) groups bonded to the same oxygen atom
(Solomons, Fryhle & Snyder, 2014).
The systematic characterization of organic compounds is known as qualitative
organic analysis, which chemists often shorten to qual organic. Qual organic is
typically used to identify a compound that has been obtained by a process whose
outcome is uncertain, or from a natural product or other source whose composition is
unknown (Lehman, 2010).
Five classification tests were used in the course of experiment. Thus, five
reference standard organic compounds were used: three alcohols, aldehyde, and a
ketone. The first chemical test was Dichromate Test. Dichromate Test, also known as
Jones Oxidation Test, is mainly used to distinguish between primary, secondary, and a
tertiary alcohol based on their oxidation reactions. It is a functional-class test for
alcohols and aldehydes. Positive visible result is the presence of intense blue-green
solution (Pavia, Lampman, Kriz, & Engel, A microscale
laboratory techniques, 2013).

approach

to

organic

The second test is Tollens Test. It is also called Silver-Mirror Test. It is used to
distinguish between an aldehyde and a ketone, a functional class test for aldehydes
based on their oxidation reactions. Positive visible result is the formation of silver-mirror
coating in the test tube (Pavia, Lampman, Kriz, & Engel, A microscale

approach to

organic laboratory techniques, 2013).

Thirdly, the Lucas Test is used to classify alcohols in accordance with their
reactivity. It is both a functional-class test and chemical test that provides structural
information of alcohols. Positive Visible result yields a turbid solution (Pavia, Lampman,
Kriz, & Engel, A microscale approach to organic laboratory techniques, 2013).
The

fourth

test

is

DNPH

Test.

This

test

is

further

called

2,4-

dinitrophenylhydrazine test. This chemical test is used to detect the carbonyl group
functionality in aldehydes and ketones basing from condensation reaction; therefore, it
is a functional-class test for aldehydes and ketones. Positive visible result yields to
formation of red-orange precipitate (Pavia, Lampman, Kriz, & Engel, A microscale
approach to organic laboratory techniques, 2013).
Lastly, the Iodoform Test is mainly used to identify methyl ketones. This test
provides structural information not only for ketones, but also for alcohols basing from
the oxidation reactions. Positive visible result yields a yellow precipitate (Pavia,
Lampman, Kriz, & Engel, A microscale approach to organic laboratory techniques,
2013).
In this experiment, the different structural features of oxygen-bearing compounds
were identified. Qualitative chemical analyses characterized the identity of each oxygenbearing organic compounds based from their chemical reactions. Also, the structural

feature and identity of an unknown compound was deduced. Lastly, chemical equations
involved in each test were derived.

II. Methodology
The materials needed were prepared first. Twenty-six small-sized (13x100 mm)
test tubes were first prepared. The following reagents were procured from the laboratory
technician: 10% potassium dichromate (10% K 2Cr2O7), 6M sulfuric acid (6M H 2SO4),
Tollens Reagent, concentrated hydrochloric acid (HCl), anhydrous zinc chloride (ZnCl 2),
DNPH Reagent, 10% potassium iodide (10% KI), and 5% aqueous sodium hypochlorite
(5% NaClO). Alongside with the reagents were the reference standardsformaldehyde,
acetone, n-Propanol, 2-Propanol, t-butanoland the two unknown sample compounds,
A and B. Parallel chemical testing was followed all throughout the whole experiment.
Five chemical tests were conducted:
Dichromate Test
The reference standards and samples used were n-propanol, 2-propanol, tbutanol, formaldehyde, acetone, and the two unknown samples. Eight drops of the
standards and the samples were placed and mixed with two drops of 10% K 2Cr2O7 and
five drops 6M H2SO4 in separate test tubes assigned for each substance. The results
were observed and recorded.
Tollens Test
The reference standards and samples used were formaldehyde, acetone, and
the two unknown samples. Ten drops of the standards and the samples were placed

and mixed with 40 drops (2 mL) of Tollens Reagent. The chemical reactions were timed
five minutes. The results were observed and recorded.
Lucas Test
The reference standards and samples used were n-propanol, 2-propanol, tbutanol, and the two unknown samples. Ten drops of the standards and the samples
were placed and mixed with 20 drops of concentrated HCl in separate test tubes
assigned for each substance. The test tubes were shaken well and turbidity was
observed. If no turbid solution was observed, anhydrous ZnCl 2 was added. The results
were observed and recorded.
DNPH Test
The reference standards and samples used were t-butanol, formaldehyde,
acetone, and the two unknown samples. Ten drops of the standards and the samples
were placed and mixed with 20 drops of DNPH Reagent in separate test tubes assigned
for each substance. The results were observed and recorded.
Iodoform Test
The reference standards and samples used were 2-propanol, t-butanol, ,
acetone, and the two unknown samples. Ten drops of the standards and the samples
were placed and mixed with 20 drops of 10% KI and 20 drops 5% NaClO (aq) in separate
test tubes assigned for each substance. The results were observed and recorded.

III. Results and Discussion

Table 1. Data of Results of the Chemical Tests for the Reference Standards. The gray cells indicate
that standards were not subjected to a particular test.

Standards

n-propanol

2-propanol

Dichromate
Test

Tollens
Test

Blue-green
solution
(+)

Chemical Tests
Lucas Test
Before
After
DNPH Test
adding
adding
ZnCl2
ZnCl2
Clear
Clear
solution
solution

Iodoform
Test

(-)

Blue-green
solution
(+)

Clear
solution

Yellowish
white
precipitate
turned to
yellow

Slightly
turbid

(+)

(+)

t-butanol

Formaldehyde

Acetone

Orange
solution

Turbid
Solution

(-)

Turbid
Solution

(+)

Orange
solution,
Precipitate
absent

(-)

Silver-mirror
precipitate
formed

Yellow
precipitate
formed

Orange
solution

Clear
Solution

(-)

(-)

Orange
precipitate
formed

Blue-green
solution

(+)

(+)

Yellow
solution

(-)

(+)

(+)

Yellow
precipitate
formed

(+)

Table 2. Data of Results of the Chemical Tests for the Unknown Samples.

Standards

Unknown A

Unknown B

Dichromate
Test

Tollens
Test

Blue-green
solution
(+)

Clear
Solution

Blue-green
solution
(+)

(-)

Silver-mirror
precipitate
formed

(+)

Chemical Tests
Lucas Test
Before
After
DNPH Test
adding
adding
ZnCl2
ZnCl2
Yellow
solution,
Clear
Slightly
Precipitate
solution
turbid
absent

(-)

Clear
solution

Clear
solution

Yellow
precipitate
formed

(+)

Iodoform
Test
Yellowishwhite
precipitate
formed

(+)

Red-orange
solution

(-)

Table 1shows the results of the following chemical reactions on the reference
standards. For the dichromate test (Jones Oxidation Test), n-propanol, 2-propanol, and
the formaldehyde resulted positive for the test (formation of blue-green solution). Since
n-propanol is a primary alcohol, the reaction of the standard with K 2Cr2O7 and H2SO4
produces this balanced chemical equation:
20 CH3CH2CH2OH+ 6 K2Cr2O7 + 24 H2SO4 6 Cr2(SO4)3 + 6 K2SO2 + 15 CH3CH2CH2COOH + 44 H2O
The reaction between n-propanol being a primary alcohol with the two other
reactants yields the formation of butanoic/butyric acid (CH 3CH2CH2COOH) which is a
carboxylic acid. A 1O alcohol oxidizes first to an aldehyde (partial oxidation), which is
further oxidized into a carboxylic acidbutanoic acid in this case. The partial oxidation
to aldehyde does not take so long because the oxygen from the dichromate easily
further oxidizes the aldehyde, specifically the hydrogen attached to the carbonyl group
of the aldehyde. The full oxidation to a carboxylic acid takes place. The intense bluegreen color of the solution is due to the presence of Chromium (III) Sulfate (Cr 2(SO4)3)
which is an essential product in the reaction. It gives the solution the distinctive bluegreen color. The chromium is oxidized from a +3 state (orange solution) to a +6 state
(blue-green solution) (Shriner, Fuson, Curtin, Hermann &Morrill, 1997).
The reaction of 2-propanol, on the other hand, produces this balanced chemical
equation:
3 CH3CHOHCH3 + K2Cr2O7 + 4 H2SO4 3 CH3COCH3 + Cr2(SO4)3 + 7 H2O + K2SO4
A 2O alcohol, like 2-propanol, that reacts with K 2Cr2O7 and H2SO4 yields the
formation of acetone (CH3COCH3) which is a ketone, and also the chromium (III) sulfate

(Cr2(SO4)3). Again, the blue-green color is due to the presence of the Cr 2(SO4)3 as a
product of oxidation from Cr3+ to Cr6+. However, once the 2-propanol was oxidized to
acetone, no further oxidation reaction happens. The reason behind this is the absence
of terminal hydrogen attached directly to the carbonyl group (which is present on
aldehydes). In aldehydes, further oxidation happens because the hydrogen attached to
the carbonyl could be easily oxidized, rendering the compound a great reducing agent.
With the absence of that hydrogen in the acetone (ketone), therefore it could not be
further oxidized (Lehman, 2010).
Also, the reaction of the formaldehyde produces this balanced chemical
equation:
3CH3OH + 2K2Cr2O7 + 8H2SO4 = 3HCOOH + 2K2SO4 + 2Cr2(SO4)3 + 11H2O
Again, oxidation of an aldehyde is favored because of the presence of the
hydrogen attached to the carbonyl group. In the case of formaldehyde, the R group is
also hydrogen, which means that two hydrogens are attached to carbonyl group, thus, it
is easily oxidized into a formic acid (HCOOH) which is a carboxylic acid. Aliphatic
aldehydes react more quickly than aromatic aldehydes. Aldehydes, however, react more
slowly than alcohols. The blue-green coloration is due to the presence of Cr2(SO4)3 as
one of the products (Lehman, 2010).
The orange solution as a negative result for both t-butanol and acetone is
because of the potassium dichromate (K2Cr2O7), which is an orange solution. It was
already stated that ketones do not undergo oxidation to lack of hydrogen to be oxidized.
Thus, the color of the oxidizing reagent is retained due absence of oxidation reaction.

However, for a 3O alcohol like t-butanol, oxidation is not possible because oxidation only
happens when the oxidizing agent removes the hydrogen from the hydroxyl group, and
the hydrogen attached to the carbon where the hydroxyl group is attached. In the case
of t-butanol, a tertiary carbon does not have any hydrogen bonded to it, thus, oxidation
could not proceed (Shriner, Fuson, Curtin, Hermann &Morrill, 1997).
Tollens Test is a more specific classification test; it is highly specific to
aldehydes. The formaldehyde resulted positive in this test. The reaction produces this
balanced chemical equation:
HCOH + 2Ag(NH3)2OH 2Ag + HCOONH4 + H2O + 3NH3
Most aldehydes reduce ammoniacal silver nitrate solution to give a precipitate of
silver metal. As the formaldehyde, an aldehyde, is oxidized to an acid, the silver is
reduced from a +1 oxidation state of the diamminesilver(I) ion (Ag(NH 3)2+) to elemental
silver (Ag) and is deposited as a silver mirror or colloidal silver inside the test tube. The
Tollens reagent (Ag(NH3)2OH) oxidizes the formaldehyde to ammonium formate
(HCOONH4) which is an ammonium salt of carboxylic acid (formic acid). The presence
of the hydrogen atoms bonded to carbonyl group make aldehydes very easy to oxidize,
and act as strong reducing agents (Pavia, Lampman, Kriz & Engel, Introduction to
organic laboratory techniques: A microscale approach, 1995).
The acetone resulted negative because ketones, like acetone, do not have that
particular hydrogen atom; they are resistant to oxidation. Only very strong oxidizing
agents like potassium manganate (VII) solution (potassium permanganate solution)
oxidize ketones. However, they do it in a destructive way, breaking carbon-carbon

bonds. However, certain ketones such as -alkoxy- or -dialkylaminoketone result

positive in this test (Pavia, Lampman, Kriz & Engel, Introduction to organic laboratory
techniques: A microscale approach, 1995).
Under the Lucas
Test, only the t-butanol
and

the

2-propanol

produced turbid (slightly

turbid

for

the

latter)

Figure 11. SN1

solution among the three alcohols. The mechanism involved in this test is an SN 1
Nucleophilic Substituion Reaction (Fig.11). Zinc chloride (ZnCl2) is attracted to the
electrons of the oxygen (hydroxyl group). The leaving group, the alcohol-zinc chloride
complex, departs from the alkyl group because the positive charge of the oxygen that
was formed weakens the CO bond. Thus, a carbocation is formed. However, the
chloride ion (Cl-) from the hydrochloric acid (HCl) acts as the nucleophile and forms a
bond with the carbocation. Thus, an alkyl-chloride is produced. In addition, ZnCl 2 is a
catalyst for this reaction. The resultant alkyl chloride is insoluble in water and separates
from the Lucas reagent (ZnCl2 in concentrated HCl), forming a cloudy mixture (Lehman,
2010).
The reaction for t-butanol in this test is
(CH3)3COH + HCl

ZnCl

(CH3)3CCl + H2O

Tertiary alcohols, like t-butanol, are soluble in the Lucas reagent and should turn
the reagent cloudy almost immediately and soon form a separate layer of alkyl chloride

2-chloro-2-methylpropane ((CH3)3CCl). The acidity of the medium is increased by the

addition of the anhydrous ZnCl 2, which is a strong Lewis acid, and as a result, the
reaction rate is increased. The high reactivity of t-butanol is a consequence of the
relatively great stability of the intermediate carbocation; 3 O carbocation is the most
stable carbocation (Shriner, Fuson, Curtin, Hermann &Morrill, 1997).
The reaction for 2-propanol in this test is
CH3CH(OH)CH3 + HCl

ZnCl

CH3CH(Cl)CH3 + H2O

Secondary alcohols are intermediate in reactivity between primary and tertiary

alcohols. Although they are not appreciably affected by concentrated HCl alone, they
react with it fairly rapidly in the presence of anhydrous ZnCl 2. Also, the intermediate
carbocation formed in the reaction is secondary (2 O) carbocation, which is less stable
than 3O carbocation, but more stable than the primary (1 O) carbocation. That is the
reason why the solution turned a slightly turbid (Lehman, 2010).
Primary alcohol such as n-propanol did not react perceptibly with HCl even in the
presence of ZnCl2 at ordinary temperatures. Chloride ion (Cl -) is too poor to be a
nucleophilic agent to effect a concerted displacement reaction, and additionally, the 1 O
carbocation is too unstable to serve as an intermediate in the SN 1 mechanism. Also, npropanol is insoluble in Lucas reagent that is why no reaction occurred (Shriner, Fuson,
Curtin, Hermann &Morrill, 1997).
The DNPH (2,4-Dinitrophenylhydrazine) Test resulted
positive for formaldehyde and ketone. The DNPH test simply
tests condensation reaction, where DNPH condenses with

carbonyl-containing molecules specifically the aldehydes and

ketones (Pavia, Lampman, Kriz & Engel, A microscale approach to
organic laboratory techniques, 2013).
For

the

formaldehyde

and

acetone,

the

condensation reactions take place:

HCOH + 2,4-dinitrophenylhydrazine

H SO
2 4

(alcohol)

following
Figure 12. 2,4dinitrophenylhydraz
ine (DNPH)

Formaldehyde-2,4-dinitrophenylhydrazone

Figure 13.
Formaldehyde-2,4dinitrophenylhydraz
one

CH3COCH3 + 2,4-dinitrophenylhydrazine

H SO (alcohol)
2 4

Acetone -2,4-dinitrophenylhydrazone

Dinitrophenylhydrazones are insoluble in water.

Figure 14.
Acetone-2,4dinitrophenylhydraz
one

The

precipitate may be oily at first and become crystalline on standing. The color of 2,4dinitrophenylhydrazone gives an indication as to the structure of the aldehyde or ketone
from which it is derived. The color of the 2,4-dinitrophenylhydrazone (precipitate) formed
is often a guide to the amount of conjugation in the original aldehyde or ketone.
Unconjugated dinitrophenylhydrazones (carbonyl group is not conjugated with another

functional group) give yellow precipitates, whereas conjugated dinitrophenylhydrazones

(carbonyl with a C=C or a benzene ring) give orange to red precipitates. Compounds
that

are

highly

conjugated

give

red

precipitates.

However,

the

2,4-

dinitrophenylhydrazine reagent is itself orange-red, and the color of any precipitate must
be judged cautiously. Occasionally, compounds that are either strongly basic or strongly
acidic precipitate the unreacted reagent (Lehman, 2010).
Tert-butanol does not yield any positive result because primarily, it does not
contain any carbonyl group. There is a need for a carbony group in the substrate since
this carbony group will be condensed by the DNPH and produces the distinct part of the
2,4-dinitrophenylhydrazones. Also, the 2,4-dinitrophenylhydrazone gives the orange-red
color that precipitates from the solution (Shriner, Fuson, Curtin, Hermann &Morrill,
1997).
The last test would be the Iodoform Test. It detects the CH(OH)CH 3 and the
COCH3

groupings. Only 2-propanol and acetone resulted positive. The following

reactions contribute to the positive results of the two compounds:

CH3CH(OH)CH3 + I2 + 2 NaOH CH3COCH3 + 2 NaI + 2 H2O
CH3COCH3 + 3 I2 + 3 NaOH CH3COCI3 + 3NaI + 3H2O
CH3COCI3 + NaOH CH3COO- Na+ + CHI3 (s)
In the experiment, potassium iodide (KI) and Sodium hypochlorite (NaClO) are
used as reagents, in substitute with iodine and sodium hydroxide. However, it still
follows the same mechanism. The alcohol, 2-propanol (CH3CH(OH)CH3), is oxidized to
acetone (CH3COCH3), a methyl ketone, by the iodine bleach.

In the reactions above, the iodine reacts with the sodium hydroxide to produce
sodium iodate(I). This is an oxidizing agent (Pavia, Lampman, Kriz & Engel, Introduction
to organic laboratory techniques: A microscale approach, 1995).
In the experiment, the sodium hypochlorite (NaClO) acts as the oxidizing agent.
The sodium chlorate (I) solution is an oxidizing agent, and oxidizes the iodide ions in the
potassium iodide to iodine. As well as any possible precipitate, the typical reddish-brown
colour of iodine solution being formed during the reaction is present (Pavia, Lampman,
Kriz & Engel, A microscale approach to organic laboratory techniques, 2013).
Iodination occurs preferentially and completely on the methyl group of the
acetone. Cleavage and oxidation of the triiodo intermediate (CH3COCI3) produces the
sodium acetate (CH3COO- Na+), the sodium salt of acetic acid and iodoform (CHI3) in the
form of yellow solid. The test is positive for acetaldehyde, methyl ketones such as the
acetone, and methyl carbinols (alcohols that contain a CH(OH)CH 3 grouping) (Pavia,
Lampman, Kriz & Engel, Introduction to organic laboratory techniques: A microscale
approach, 1995).
In addition to the proof that using sodium hypochlorite will still follow the same
mechanism, sodium hypochlorite solution is alkaline and contains enough hydroxide
ions to carry out the second half of the reaction. Sodium hypochlorite is alkaline
because it reacts reversibly with water to form the weak acid chloric (I) acid together
with hydroxide ions (Lehman, 2010).
The established reaction mechanisms of the reference standards will help a
person identify and classify a certain unknown organic compound. Table 2 shows the
results of the different chemical tests the two unknown sample have undergone through.

Unknown A resulted positive for dichromate test; therefore, it could not be a ketone or a
tertiary alcohol. It means that it could be oxidized. Yet, a negative result for Tollens test
will deductively lead to either a primary or a secondary alcohol as the only possible
choices. The result suggests that it is not an aldehyde, thus, an alcohol. The results
from the Lucas and iodoform test confirms that the unknown A is actually a secondary
alcohol because a) Secondary alcohols could still undergo nucleophilic substitution but
slightly slower in reaction rate compared to tertiary alcohols and b) Only secondary
alcohols and methyl ketones yield positive results for iodoform test. Thus, unknown A is
a ketone.
For the unknown B, since it yielded positive for the dichromate test, the possible
choices could only be a primary and secondary alcohol or an aldehyde and could be
oxidized. The Tollens test suggests that since it is positive, it must be an aldehyde. The
results from DNPH and iodoform tests confirm the result because a) It is a carbonylcontaing compound and b) It could not form the iodoform. Therefore, unknown B must
be an aldehyde.
Qualitative Organic Analysis is an essential systematic procedure for the
identification of many unknown organic compounds. Results from the chemical tests
could be used to identify not only the functional-class of the compound, but may also
provide structural information about the compounds.

IV. Conclusion
The characterization of the oxygen-bearing reference standards n-propanol
(primary alcohol), 2-propanol (secondary alcohol), t-butanol

(tertiary alcohol),

formaldehyde (aldehyde) and acetone (ketone) could be done using the qualitative

organic classification tests: Dichromate Test, Tollens Test, Lucas Test, DNPH Test and
Iodoform Test. The dichromate test classified n-propanol, 2-propanol and formaldehyde
as

reducing

agents

(oxidized);

the

Tollens

test

identified

carbonyl-containg

formaldehyde; the Lucas test classified n-propanol, 2-propanol and t-butanol based on
their reaction rates; the DNPH test detected the carbonyl groups from formaldehyde and
acetone; and the Iodoform test identified the oxidation of 2-propanol and acetone. The
functional-class of the two unknown organic compoundsUnknown A and Unknown B
were identified to be a secondary alcohol and aldehyde, respectively.
V. References
Lehman, J. W. (2010). Multiscale operational organic chemistry: A problem-solving
approach to the laboratory course (2nd ed.). Upper Saddle River, NJ:
Pearson

Prentice Hall.

Pavia, D. L. (2007). Introduction to organic laboratory techniques: A microscale

approach. Belmont, CA: Thomson Brooks/Cole.
Pavia, D. L., Lampman, G. M., Kriz, G. S., & Engel, R. G. (1995). Introduction to organic
laboratory techniques: A microscale approach (2nd ed.). Orlando, FLO:
Saunders College Publishing.
Pavia, D. L., Lampman, G. M., Kriz, G. S., & Engel, R. G. (2013). A microscale
approach to organic laboratory techniques (5th ed.). Belmont, CA:
Brooks/Cole,

Cengage Learning.

Shriner, R. L., Fuson, R. C., Curtin, D. Y., Hermann, C. K., & T. C., Morrill. (1997). The
systematic identification of organic compounds (7th ed.). New York: John
Wiley &

Sons.

Solomons, T. G., Fryhle, C. B., & Snyder, S. A. (2014). Organic Chemistry International
Student Version (11th ed.). Singapore: John Wiley & Sons Singapore Pte. Ltd.