Exercise No.

7: Solubility
Classification
Introduction

Determination of the solubility characteristics of an organic compound can

give an important information on the structural composition of the compound
one can gather valuable information about possible functional groups
through the use of solubility classification. There is no sharp distinction
between the solubility and insolubility of organic compounds in a particular
solvent and so arbitrary ratio of solute to solvent must be selected. We
suggest that a compound is considered soluble if its solubility is greater than
30 mg/mL. Five common reagents for solubility tests are water; 2.5 M (9%)
NaOH; 0.6 M (5%) NaHCO3, 1.4 M (5%) HCl and concentrated (96%) H2SO4.
Except in the case of water, solubility experiments probe the acid-base
properties of organic compounds. If a compound is an acid, you can obtain a
relative measure of its acid strength by testing it against the weak base
sodium bicarbonate and strong base sodium hydroxide. By using hydrochloric
acid and powerful acid sulfuric acid, you can determine how basic the
compound is if it is a base at all. Naturally, any organic compound that is
soluble in water will probably also be soluble in 0.6 NaHCO3, 1.5 M HCl and
2.5 M NaOH solution. These solutions are composed largely of water, so
water-soluble compounds may also be soluble in them, revealing virtually
nothing about the acid-base properties of the unknown.

Learning Outcomes

1. To evaluate the solubility of different organic compounds using

different solvent systems.
2. To test the acidity or basicity using litmus paper.
 st
For instructional purposes only • 1 Semester SY 2020-2021 29

Figure 12 The Solubility Test Flowchart

Materials

 Test tube 2.5M NaOH Phenol

 Test tube rack 1.5M HCl Salicylic acid
 Medicine dropper 5% NaHCO3 Sulfanilic acid
 Spatula Conc. H2SO4 α- napthol
 50 mL beaker Alanine Hexane
 cyclohexane aniline Chlorobenzene

Procedure

1. For solid sample, weigh about 30mg and evaluate the solubility of this
sample by adding 20 drops of the solvent. Determine the extent of
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 30 CHEM 120.1: Organic Chemistry Laboratory

dissolution using the following notations: +++ = completely soluble ++

partially soluble, + slightly soluble; and (-) = insoluble. Since there are
seven solvent systems, you are going to use seven test tubes for each
sample. To facilitate the weighing process, just weigh one solid
sample and then approximate the weights of the other samples.

2. For liquid sample, place 2 drops into a test tube and add 20 drops of
the solvent. Determine the extent of dissolution using the following
notations: +++= completely miscible, ++ = partially miscible; x =
immiscible.

3. Fill up the table in the data sheet.

Guide questions and instructions on how to prepare

and submit the laboratory

1. Which among the test sample are soluble in water? Explain why it is
soluble in water.
2. Which among the test sample are soluble in strong base? Explain why
it is soluble in an acid.
3. Explain why there are some organic compounds that are soluble in
strong acid?

This guide questions will serve as your quiz and to be submitted along
with your lab report. The laboratory report sheets provided will be
submitted by the student after every exercise through email or courier.
See abridged for the schedule of submission.

Additional Resources

Use References style here

References

A. M. Acabal, A. D. Acabal, G. Albarico, K. Bandibas, Y. Bandibas, C. Calibo, J. G. Jansalin, Ma.

T. Loreto, E. Quevedo, A. Ramal, M. A. Villar and R.A. Villaber, Chem 120.1 Organic
Chemisty (Laboratory)[Laboratoty Manual]

https://www.researchgate.net/figure/The-solubility-test-Flowchart_fig1_320613936 [Date
Accessed August 16, 2020]

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 Exercise No. 8:
Hydrocarbons
Introduction

Hydrocarbons are compounds containing only hydrogen and carbon; they

may be divided according to the functional group(s) present in their
molecules into four general classes.
1. Alkanes (paraffins) and their cyclic analogues do not have any functional
group. Only two types of bonds are present in the molecule: carbon-carbon
(sp3 - sp3 -) sigma bonds, and carbon hydrogen (sp3 -s) sigma bonds. Both
are nonpolar, and no ionic reaction is possible. Light-catalyzed halogenation
is a free-radical reaction involving latter bond type, and can be made to occur
wherever this bond is present.
2. Alkenes (olefins) and their cyclic analogues possess the carbon-carbon
double bonds as their functional group. The pi component (p-p) of the double
bond consists of an electron cloud above and below the sigma (sp2 - sp2 )
bond. Thus the double bond is an electron-rich site and may react with
electrophillic reagents or oxidizing agents: mechanism of the reaction may be
ionic or free-radical, depending upon the reagent and the experimental
conditions.
3. Alkynes (acetylene) are compounds having the carbon-carbon triple bond
as a functional group. The two pi components in the triple bond are subject to
similar reactions as that in the double bond of alkenes. Special reactions of
alkynes with the triple bond at the end of the carbon chain involve cleavage of
the end C-H (sp-s) bond.
4. Aromatic hydrocarbons have the aromatic pi system as the functional
group. Aromatic pi bonds are less reactive than those of alkenes and alkynes,
and many of the reactions undergone by the latter cannot be made to occur
with aromatic hydrocarbons lacking pi bonds outside the ring. The aromatic
pi systems is responsible for a unique set of ionic reactions (electrophillic
aromatic substitution) but these will not be taken up.

Learning Outcomes

1. To differentiate the types of hydrocarbons.

2. To identify the characteristic chemical tests for each of hydrocarbons.
 32 CHEM 120.1: Organic Chemistry Laboratory

Figure 13 Preparation of Acetylene

Materials

 Crucible cover cyclohexane Benzene

 Crucible tong cyclohexene Toluene
 Medicine dropper acetylene Separatory funnel
 Tirrill burner 0.1M Br2 in CCl4 Filter flask
 Test tube Carbon paper Rubber tubing
 Test tube rack Dilute KMnO4 Blue litmus paper
 Wash bottle Calcium carbide 5 mL pipet
 Ammoniacal AgNO3

Procedure

Examine the liquid hydrocarbon samples and subject each compound

to the tests described below.
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A. Ignition Test
Place 3 drops of the hydrocarbons in a porcelain crucible cover and
bring to the edge of a burner flame with the aid of crucible tongs.
Record all observations as to the flammability of the sample and the
nature of the flame (color and sootiness).

B. Reaction with Bromine

Place 1 mL of 0.1M Br2 in CCl4 solution into each of 2 test tubes, one
tube wrapped in carbon paper to protect contents from light. Add 3
drops of the sample to each tube, stopper, and shake gently to mix.
Observed the unwrapped tube for fading of Br2 (about 10 minutes),
then compare with the contents of the two test tubes. Where fading
has occurred, test for presence of HBr by adding 10 drops of distilled
water to the final reaction mixture and testing the water layer with
litmus paper. Record the results.

C. Reaction with Cold Dilute Permanganate

Place 1 mL of dilute KMn04 solution in a test tube, add 5 drops of the
sample and shake to mix. After 5 minutes of intermittent shaking,
examine the tube contents.

D. Reaction with Ammoniacal Silver Nitrate Solution

Place 10 drops of the silver reagent in a clean, small test tube, and
add 2 drops of the hydrocarbon. Mix the contents of the tube
thoroughly, and observe. Transfer any precipitate obtained into a
vessel provided by the laboratory instructor.

Preparation and Testing of Acetylene Gas

Introduce about 5 gm calcium carbide limps into a dry 250-mL
distilling flask, and assembled the rest of the set-up for the
generation of acetylene. Add about 100 mL water to the dropping
funnel, then allow a few drops to fall on the solid and wait a couple of
minutes for the air to be displaced from the apparatus. Adding more
water when necessary, use the gas evolved for test B, C, and D
described above. Bubble the gas through the contents of the test tube
for a full minute, wherever the procedure says to add the
hydrocarbons.

Caution:
1. Bromine can produce painful burns, if any is spilled on the skin,
wash it off immediately.
2. Shaking is necessary if the hydrocarbon is not soluble in the
reagent.

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 34 CHEM 120.1: Organic Chemistry Laboratory

3. Partial reduction of KMn04 can be due to impurities; even dust

can have this effect. Therefore the test is to be considered as
negative if the purple color is not completely destroyed.
4. Safety precautions must be observed in disposing of any solid
precipitate formed in this test, as they may be explosive when dry.
Treatment with warm 6N HN03 converts them to harmless
products.
5. Pure acetylene is colorless and odorless. The odor of the gas
generated from calcium carbide is due to impurities (phosphorus
and arsine).

Guide questions and instructions on how to prepare

and submit the laboratory

1. Balance the following reactions:

CCl4
a. cyclohexane + O2 g) acetylene + Br2
uv
b. cyclohexene + Br2 h) acetylene + KMnO4
c. cyclohexene + Br2
d. cyclohexene + KMnO4
e. CaC2 + H2O
f. acetylene + AgNO3

2. Which among hydrocarbons gives negative results in reaction with

bromine? Why?
3. In reaction with cold dilute permanganate, which among test samples
give positive results? Show the chemical reaction.
4. Differentiate the hydrocarbons under study in terms of: a)
hybridization of carbon b) geometry c) bond angle and d) reactivity

This guide questions will serve as your quiz and to be submitted along
with your lab report. The laboratory report sheets provided will be
submitted by the student after every exercise through email or courier.
See abridged for the schedule of submission.

Additional Resources
References

A. M. Acabal, A. D. Acabal, G. Albarico, K. Bandibas, Y. Bandibas, C. Calibo, J. G. Jansalin, Ma.

T. Loreto, E. Quevedo, A. Ramal, M. A. Villar and R.A. Villaber, Chem 120.1 Organic
Chemisty (Laboratory)[Laboratoty Manual]

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 st
For instructional purposes only • 1 Semester SY 2020-2021 35

https://www.sarthaks.com/143637/how-is-acetylene-prepared-in-the-laboratory-a-draw-a-
diagram?fbclid=IwAR0JxetgtSgZuLuK8DonwmSZzXfwcSRh4NJbx_tJsC28Y89VudTJ9QmiBJE
[Date Accessed: August 24, 2020]

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 Exercise No. 9a:
Classification Test for
Functional Groups
a. Aromatic Hydrocarbons
Introduction

Preliminary investigation of the structure of an organic compound involves

the functional groups that could be present in a compound. The presence of
functional group is identified by reacting the compound to a reagent which
gives a characteristic visible result.
It is necessary to try out an unfamiliar classification test on one or two
reference compounds of known structure before using the test on your
unknown compound. For example, if you suspect that your compound may be
an alkene, you will want to test whether it can decolorize bromine. You should
try this test first on known compounds such as cyclohexene and cyclohexane,
so that you can observe directly both positive and negative results for this
test. The inexperienced student may be frustrated easily by ambiguous
results. This frustration can be minimized by doing control tests on reference
compounds.

Learning Outcomes

1. To know the different chemical test of aromatic hydrocarbons.

2. To Show the chemical equations involved in classifying tests.
 st
For instructional purposes only • 1 Semester SY 2020-2021 37

Figure 14 Friedel-Crafts alkylation reaction of Benzene

Materials

 Crucible cover Conc. HNO3 Ice water bath

 Crucible tong Conc. H2SO4 Tirrill burner
 Medicine dropper Le Rosen reagent Aniline
 Test tube holder 50 mL beaker Phenol
 Test tube Hexane Toluene
 Test tube rack benzene Chlorobenzene
 Wash bottle chloroform Anhydrous AlCl3

Procedure

A. Test for Aromaticity

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 38 CHEM 120.1: Organic Chemistry Laboratory

1. Nitration
a. Cautiously mix 10 drops concentrated HNO3 and 10 drops
concentrated H4SO4 in a test tube placed in a beaker containing
cold water.
b. Add 10 drops of benzene dropwise to the acid mixture.
c. Shake the mixture occasionally.
d. Pour the mixture drop by drop into a beaker containing 5 mL, of
ice cold water. Observe the color and odor of the product formed.

2. Le Rosen Test
a. In a 5 mL test tube, place 5 drops of Le Rosen reagent (10%
solution of formaldehyde in conc. H2SO4)
b. Incline the test tube and carefully add 5 drops of benzene.
Observe the color.

B. Ignition Test

Safety Information: Carry out this test in an efficient hood.

Place a small amount of the unknown (a few drops or a few

milligrams) in a porcelain crucible cover. While holding the cover with
tongs, bring it very near a Bunsen burner flame and allow the
substance to ignite. Many alkanes and their substituted derivatives
burn with a clean yellow or bluish flame, whereas most aromatic
compounds burn with a smoky flame. Some halogen compounds also
burn with a smoky flame, but elemental analysis easily distinguishes
the two. Polyhalogenated compounds can be very difficult to ignite.
Inorganic and organic salts always leave a residue upon burning or
may not burn at all. The higher the oxygen content of a compound, the
greater the propensity for the compound to burn with a colorless or
blue flame.

C. Reaction with Aluminum Chloride/Chloroform

Safety Information: Carry out this test in an efficient hood.

Chloroform is volatile and toxic. Wear gloves and dispense the

chloroform in a hood. Place 1 mL of dry chloroform in a dry test tube;
add 0.1 mL of a liquid, or 75 mg of a solid, unknown, or reference
compound; mix thoroughly; and tilt the test tube to moisten the wall of
the tube. Then add 0.25 g of anhydrous aluminum chloride so that
some of the powder strikes the wetted side of the test tube. Note the
color change of the powder and the solution. Try the test with toluene,
chlorobenzene, and hexane as reference compounds.

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Cleanup: Place the entire reaction mixture in the halogenated-waste

container.
Aromatic compounds and their derivatives usually give characteristic
colors when they come into contact with a mixture of aluminum
chloride and chloroform. Generally, nonaromatic compounds do not
produce a color on the AlCl3. These color effects may be summarized
as follows:

Compound Class Color

Benzene derivatives Orange to red
Naphthalene Blue
Biphenyl or phenanthrene Purple
Anthracene Green

The colors in this classification test result from Friedel-Crafts

reactions between chloroform and the aromatic compounds. Stable,
highly colored carbocation salts form on the aluminum chloride
surface through alkylation and hydride-transfer reactions see Fig 8a.1.

Guide questions and instructions on how to prepare

and submit the laboratory

1. Explain the result of benzene obtained in ignition test.

2. What is the compound responsible for the visible result in nitration?
Show the reaction involved.
3. What is the difference in the reaction with aluminium
chloride/chloroform between aromatic and aliphatic hydrocarbons?
4. Give other test to classify aromatic hydrocarbons. Show reaction.
5. What is the role of concentrated sulfuric acid in the nitration of
benzene?

This guide questions will serve as your quiz and to be submitted along
with your lab report. The laboratory report sheets provided will be
submitted by the student after every exercise through email or courier.
See abridged for the schedule of submission.

Additional Resources

Use References style here

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 40 CHEM 120.1: Organic Chemistry Laboratory

References

A. M. Acabal, A. D. Acabal, G. Albarico, K. Bandibas, Y. Bandibas, C. Calibo, J. G. Jansalin, Ma.

T. Loreto, E. Quevedo, A. Ramal, M. A. Villar and R.A. Villaber, Chem 120.1 Organic
Chemisty (Laboratory)[Laboratoty Manual]

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 Exercise No. 9b:
Classification Test for
Functional Groups
b. Alcohols and Phenols
Introduction

The alcohols may be represented by the general formula R-OH. If R is a

saturated alkyl group, the reactions of alcohols will be mainly those of the
relatively reactive hydroxyl group rather than those of the comparatively inert
alkyl group. The phenols unlike the alcohols have the hydroxyl group bound to
a carbon atom that forms part of the aromatic ring. This feature greatly alters
the properties of the phenolic hydroxyl and helps to distinguished it from the
hydroxyl group of the alcohols.

Learning Outcomes

1. To be able to differentiate the three types of alcohols.

2. To distinguish the reactions of alcohols and phenols.

Figure 15 Types of Alcohols

n-butyl alcohol benzyl alcohol

sec-butyl alcohol phenol

 42 CHEM 120.1: Organic Chemistry Laboratory

Materials

 Spatula n-butyl alcohol 6N NaOH

 wash bottle Sec-butyl alcohol I2 in KI sol’n
 Medicine dropper Tert-butyl alcohol 95% alcohol
 Test tube holder 3% FeCl3 sol’n. α-naphthol
 Test tube Lucas reagent Cathechol
 Test tube rack phenol Resorcinol
 Methyl alcohol 5% K2Cr2O7 Na metal
 Ethyl alcohol acetone Funnel
 Isopropyl alcohol n-propyl alcohol Clay triangle
 Tripod Filter paper 50 mL beaker

Procedure

I. Test for Alcohols and Phenols

1. Reaction of Alcohols
Water reacts with metallic sodium to form hydrogen and sodium
hydroxide. In a similar manner alcohols react to form hydrogen and
sodium alkoxides.

2R-0H + 2Na 2R0- Na+ + H2

Phenols react with metallic sodium to yield hydrogen and sodium

phenoxide,

2 Na + 2 2 + H2

Phenol Sodium phenoxide

A. Reaction with sodium metal

In a 5mL – test tube, place 20 drops of n-butyl alcohol. Carefully add a
tiny piece of Na metal and observe the appearance of bubbles. Repeat
the procedures using the other test samples, secbutylalcohol, and tert-
butylalcohol.. Compare the rate of evolution of gas of these 3 test
samples.

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B. Lucas Test
The Lucas test for distinguishing between primary, secondary, and
tertiary alcohols (the class of an alcohol is the same as of its alkyl
group) is based on the relative rates of reaction of the different
classes with hydrogen chloride. The Lucas reagent is a solution of
zinc chloride in concentrated hydrochloric acid. A tertiary alcohol
reacts rapidly with the reagent to give an insoluble alkyl chloride which
appears as a cloudy dispersion or as a separate layer in the solution. A
secondary alcohol gives a clear solution at first as the alcohol
dissolves which becomes cloudy within five minutes. A primary
alcohol dissolves to produce a solution that remains clear for several
hours.

ZnCl2
R-OH + HCl R-Cl + H2O

In a 5 mL – test tube, place 20 drops of Lucas reagent and 10 drops of

n-butyl alcohol. Shake the tube vigorously and stopper. Observe the
formation of a layer. Record the time the insoluble layer appears.
Repeat the procedure using the other test samples, sec-butyl alcohol
and tert-butyl alcohol Compare the rate of formation of a layer in these
three test samples.

C. Reaction with Potassium Dichromate

When the saturated, aliphatic alcohols are oxidized under relatively
mild conditions, the product of the reaction depends upon the class of
the alcohol being oxidized. Thus, primary alcohols give first aldehydes
and finally carboxylic acids as oxidation products.

[O] O [O] O
R-CH2-OH R-C R-C
H OH

Primary alcohol Aldehyde Carboxylic acid

By proper choice of the oxidizing agent it is often possible to stop the

reaction at either the aldehyde or carboxylic acid stage. Secondary
alcohols give ketones as oxidation products.

0H O
R-CH-R ' R-C - R'
Secondary alcohol Ketone

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 44 CHEM 120.1: Organic Chemistry Laboratory

Tertiary alcohols are inert toward most mild oxidizing agents.

R
[O]
OH
C No reaction
R” R’

Tertiary alcohol
OH

Alcohols which have the structure CH3- CH-R ( R = H, alkyl, or aryl) and

O
aldehyde or ketones which have the structure CH3-C - R ( R = H, alkyl,
or aryl) react with an alkaline solution of the halogens (hypohalite
solutions) to yield the corresponding haloforms. Indeed, the “haloform
reactions” often is performed as a diagnostic test on an unknown
compound suspected of having the above structure arrangements.
The preparation of iodoform may be illustrated by the following
reaction sequence:

2 Na0H + I2 NaI + Na0I

OH O
R – CH – CH3 + Na0I R –C – CH3 + NaI + H20
O O
R – C – CH3 + 3 Na0I R –C – CI3 + 3 Na0H
O O
R – C – Cl3 + Na0H R – C – 0 - Na+ + CHI3
Iodoform

Chloroform and bromoform may be prepared in a similar manner, but

in as much as they are liquids, they are less useful for diagnostic
purposes. Iodoform, on the other hand, is a yellow solid (mp: 119-
120°) with a sharp, easily recognizable odor.

To 10 drops of acetone in a test tube add drops of water and 10 drops

of dilute (6N) sodium hydroxide. To the alkaline solution of acetone
add, dropwise, an iodine-potassium iodide solution. Continue to add
iodine until the brown color no longer is discharged and only a light
yellow color remains. If less than 20 drops of the iodine-potassium
iodide solution is used, heat the test tube in the water bath at 60° and
add any additional iodine-potassium iodine needed. Collect the
precipitate that forms on the Hirsch funnel, wash it on the filter with

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drops of (5%) dilute sodium hydroxide, and dry on a piece of clay plate,
or on a large piece of filter paper placed on a watch glass. Repeat the
iodoform test using (a) ethyl alcohol, (b) methyl alcohol, (c) isopropyl
alcohol, and (d) n-propyl alcohol (Note 1).
Note 1. For alcohols having very low water solubility it may be
necessary to dissolve the sample (10 drops or 0.1g ) in 5 mL of
dioxane. In such instances it is advisable to run a blank on the
dioxane, for some samples of dioxane have given positive iodoform
tests.
2. Reaction of Phenols
A. Ferric Chloride Test
Phenols and enols often react with ferric chloride to produce
characteristic colors. Not all phenols and enols give colors, therefore,
a negative test is not necessarily significant.

In a 5 mL test tube, place 20 drops of 95% ethanol and 2 drops of

liquid phenol. Add 5 drops of 3% FeCl3 solutions and mix. What do
you observe? Repeat the procedures using the other test samples, -
naphthol, catechol, and resorcinol.

B. Bromine Water test Bromine reacts very readily with phenols to

introduce one or more bromine.

In a 5 mL test tube, place 20 drops of 95% ethanol and 5 drops of

phenol. Add bromine water dropwise with shaking until the bromine
color is no longer discharged. Record your observation. Repeat the
procedures the other test samples, -naphthol, catechol, and
resorcinol.

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 46 CHEM 120.1: Organic Chemistry Laboratory

Guide questions and instructions on how to prepare

and submit the laboratory

1. Compare the rate of evolution of gas of 3 alcohols in reaction with Na

metal. Explain the reaction involved.
2. Are phenols considered as alcohols? Explain why or why not?
3. Draw and name 8 isomeric alcohols with the formula C6H12O. Which of
these alcohols would react with aqueous acidic CrO3? Show the
products you would expect from each reaction.
4. Show Grignard Addition reactions creating alcohols from carbonyls.
5. Explain why phenols are more acidic than alcohols. Show some
reaction if necessary.

This guide questions will serve as your quiz and to be submitted along
with your lab report. The laboratory report sheets provided will be
submitted by the student after every exercise through email or courier.
See abridged for the schedule of submission.

Additional Resources

https://chemistry.stackexchange.com/questions/90414/halogenation-of-phenol [Date
Accessed: August 24, 2020]

References

A. M. Acabal, A. D. Acabal, G. Albarico, K. Bandibas, Y. Bandibas, C. Calibo, J. G. Jansalin, Ma.

T. Loreto, E. Quevedo, A. Ramal, M. A. Villar and R.A. Villaber, Chem 120.1 Organic
Chemisty (Laboratory)[Laboratoty Manual]

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 Exercise No. 9c:
Classification Test for
Functional Groups
c. Carbonyl Compounds
Introduction

Carbonyl compounds are everywhere in nature. Most biologically important

molecules contain carbonyl (C=O) groups, as do many pharmaceutical agents
and many of the synthetic chemicals that touch our everyday lives.

formaldehyde acetone acetic acid acetoaminophen

(an aldehyde) (a ketose) (a carboxylic acid) (an amide)

It is useful to classify carbonyl compound into 2 categories: a) aldehydes and

O
ketoses b) caboxylic acid and their derivative. The acyl (R-C-) groups of
aldehydes and ketones are bonded to substituents (-H and –R,) respectively,
that can’t stabilize a negative charge and therefore can’t act as leaving
groups. Aldehydes and ketones behave similarly and undergo many of the
same reactions. The acyl groups in carboxylic acid and their derivatives are
bonded to substituents (oxygen, nitrogen, halogen) that can stabilize a
negative charge and can serve as leaving group in substitution reaction. The
chemistry of these compounds is therefore similar.
 48 CHEM 120.1: Organic Chemistry Laboratory

Learning Outcomes

1. To observe characteristic reactions of aldehydes, ketones, carboxylic

acids and carboxylic acid derivatives.

Materials

 Stirring rod Acetaldehyde Hot water bath

 wash bottle Acetone Hot plate
 Medicine dropper Cyclohexanone Conc. H2SO4
 Test tube holder Benzaldehyde 10% NaOH
 Test tube Formaldehyde Acetic anhydride
 Test tube rack Tollen’s reagent Ethyl benzoate
 Red litmus paper Acetanilide Acetyl chloride
 Blue litmus paper Salicylic acid
 2,4-Dinitrophenlyhydrazine

Procedure

1. Test for Aldehydes and Ketones

a. 2,4-Dinitrophenylhydrazine test In a 5-mL test tube, place 5 drops
of 2,4-DNPH solution and 3 drops of formaldehyde. Heat in a
water bath for 5 minutes. Record your observation. Repeat
procedure using the other test sample: acetaldehyde, acetone and
cyclohexanone, benzaldehyde.

b. Tollens test Place 10 drops of Tollen’s reagent (ammoniacal

AgNO3) in a clean test tube and add 4 drops of formaldehyde and
shake. Heat gently in water bath for one minute and observe.
Repeat procedure using acetone, acetaldehyde, cyclohexanone
and benzaldehyde.

2. Test for Carboxylic Acid and its Derivatives

a. Formation of esters In a 10 mL test tube mix a pinch of salicylic
acid and 20 drops of methanol. Add 5 drops of concentrated
H2SO4 & shake the mixture well. Heat the mixture in a water bath
for about 5 minutes. Record your observation.
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 st
For instructional purposes only • 1 Semester SY 2020-2021 49

b. Hydrolysis of acid derivatives In a 5-mL test tube place a pinch of

acetanilide and add 20 drops of 10% NaOH. With a stirring rod
hold a piece of moist red litmus paper over the mouth of the test
tube while heating the mixture to boiling in a water bath. Note any
changes in the color of the litmus paper and the change in odor of
the mixture.

c. Comparative ease of hydrolysis To a small amount (5 drops of

liquid or a pinch of solid) of sample (acetyl chloride, acetic
anhydride, ethyl benzoate, acetanilide) in a dry test tube,
cautiously add 20 drops water and observe closely for any sign of
reaction (e.g. evaluation of heat). If none is detected, heat the
tube for 2 minutes in a hot water bath. Where reaction appears to
be complete, test the cold mixture for free acid using blue litmus
paper.

CAUTION:
ACETYL CHLORIDE AND ACETIC ANHYDRIDE MUST BE HANDLED
IN THE FUNE HOOD. THESE COMPOUNDS ARE LACHRYMATORY
AND CAUSE PAINFUL BURNS ON THE SKIN.

Guide questions and instructions on how to prepare

and submit the laboratory

1. How esters form? Show the reaction.

2. Show the reaction of acetyl chloride hydrolysis.
3. Arrange the following in the order of decreasing acidity: carboxylic
acids, alcohols, phenols and water.
4. Give one pharmaceutical product that contain carbonyl compound.
Give the formula.
5. What is the compound responsible for the visible result of
formaldehyde in tollen’s test? Show the reaction involves.

This guide questions will serve as your quiz and to be submitted along
with your lab report. The laboratory report sheets provided will be
submitted by the student after every exercise through email or courier.
See abridged for the schedule of submission.

Additional Resources

Use References style here

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Vision: A globally competitive university for science, technology, and environmental conservation.
TP-IMD-04
Mission: Development of a highly competitive human resource, cutting-edge scientific knowledge V0 07-15-2020
and innovative technologies for sustainable communities and environment. No. DOPAC-IM-
SC003.1
 50 CHEM 120.1: Organic Chemistry Laboratory

References

A. M. Acabal, A. D. Acabal, G. Albarico, K. Bandibas, Y. Bandibas, C. Calibo, J. G. Jansalin, Ma.

T. Loreto, E. Quevedo, A. Ramal, M. A. Villar and R.A. Villaber, Chem 120.1 Organic
Chemisty (Laboratory)[Laboratoty Manual]

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Vision: A globally competitive university for science, technology, and environmental conservation.
TP-IMD-04
Mission: Development of a highly competitive human resource, cutting-edge scientific knowledge V0 07-15-2020
and innovative technologies for sustainable communities and environment. No. DOPAC-IM-
SC003.1