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MTY1101 LABORATORY MANUAL

Organic Chemistry Part

JANUARY 1, 2019
FAR EASTERN UNIVERSITY
Department of Medical Technology
Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY

EXPERIMENT 8
Hydrocarbons

Compounds that are comprised of only C and H atoms are called hydrocarbons. Because of the
number and variety of hydrocarbons that can exist, some means of classification is necessary.
One way of classification is based on how the carbon atoms are connected. Chain aliphatic
hydrocarbons are compounds consisting of carbons linked either in a single chain or in a branched
chain. Cyclic hydrocarbons are aliphatic compounds that have carbon atoms linked in a closed
polygon (also referred to as a ring).

They can also be classified based on the type of bonds that exist between its carbon atoms.
Saturated hydrocarbons, or alkanes lack π bonds; the names of these compounds usually end
with the suffix “-ane,”. Hydrocarbons containing at least one carbon-to-carbon double bond are
called alkenes, and those compounds with at least one carbon-to-carbon triple bond are called
alkynes. These are compounds that are referred to as unsaturated molecules. Finally, a class of
cyclic hydrocarbons that contain a closed loop (sextet) of electrons are called aromatic.

In general, hydrocarbons are nonpolar and do not mix with polar solvents such as water or ethyl
alcohol. On the other hand, hydrocarbons mix with relatively nonpolar solvents such as ligroin (a
mixture of alkanes), carbon tetrachloride, or dichloromethane. Their chemical reactivity, however,
varies on the type of bond present in the compound. Alkanes undergo combustion, but will
generally be unreactive to most reagents; they can undergo substitution with halogens in the
presence of ultraviolet light. Meanwhile, alkenes and alkynes can also react via addition of
reagents to the double or triple bonds. Lastly, aromatic hydrocarbons undergo substitution in the
presence of catalysts rather than an addition reaction.

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OBJECTIVES
• Differentiate hydrocarbons in terms of intrinsic physical properties, chemical properties,
structure and behavior
• Characterize hydrocarbons based on flammability, active unsaturation and aromaticity
• Observe the reaction mechanisms involved in different classes of hydrocarbons

MATERIALS AND REAGENTS:


Conc. H2SO4 hexane
2% KMnO4 (aq.) toluene
Conc. HNO3 cyclohexane
10% NaOH (aq.) benzene

Litmus paper test tube holder & rack Pasteur pipettes


Distilled water evaporating dishes thermometer
Test tubes 125-ml Erlenmeyer flask beaker
Watch glass

PROCEDURES

For the following experiments, use the following samples: hexane, cyclohexane, benzene, toluene

Precautions

CONC. H2SO4 IS CORROSIVE.


CONC. HNO3 IS CORROSIVE AND OXIDIZING.

A. Physical State, Color and Odor


1. Observe the appearance of the sample at room temperature.
2. Note the color. With a wafting motion, describe the odor.

B. Solubility in conc. H2SO4


1. Place 1 mL of conc. H2SO4 in the test tube.
2. Add the sample dropwise.
3. Observe the miscibility of the sample.
4. Take note of any darkening, color change and warming effect.

C. Ignition Test
1. Place 3-5 drops of the sample in a small watch glass/ evaporating dish.
2. Place a lighted match.
3. Observe the color of flame produced.

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D. Tests for Active Unsaturation

Baeyer’s Test
1. Place 5 drops of the sample in a dry test tube.
2. Add 2 drops of 2% KMnO4 solution.
3. Shake the test tube vigorously.
4. Observe the rate of color change by noting the time.
5. Observe the shift in color (include all possible colors observed before the final color) during
shaking.
6. Compare with water.

E. Test for Aromaticity: Nitration

Preparation of Nitrating mixture


1. Place 2 mL of conc. HNO3 in an Erlenmeyer flask.
2. Immerse the flask in an evaporating dish containing water.
3. Add 2 mL of conc. H2SO4.
4. Cool down.
Nitration test
1. Place 5 drops of the sample in a test tube.
2. Add 8 drops of the nitrating mixture.
3. Agitate the test tube.
4. Observe for the formation of a yellow oily layer.
5. Dilute with 20 drops of water.
6. Observe.
7. Place the test tube in a water bath (~ 50ºC) for 10 minutes.
8. Dilute with 20 drops water.
9. Observe.

F. Basic Oxidation
1. Place 1 drop of the sample in a test tube.
2. Add 1 drop of 2% KMnO4.
3. Add 3 drops of 10% NaOH.
4. Add 7 drops water.
5. Observe the rate of color change.

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MTY1101 – INORGANIC AND ORGANIC CHEMISTRY

EXPERIMENT 8
Hydrocarbons

Group No. and Members:


______ _____________________________________________________________________
Section: _______________
Date: _____________________

DATA AND RESULTS

Compound used Hexane Cyclohexane Benzene Toluene

Bond-line Structure

A. Physical State at RT
Appearance
Color
Odor
B. Solubility in conc. H2SO4
Inference
C. Ignition Test
Inference

D. Test for Aromaticity:


Nitration

Inference
E. Basic Oxidation
Inference

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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY

EXPERIMENT 8
Hydrocarbons

Group No. and Members:


______ _____________________________________________________________________
Section: _______________
Date: _____________________

POST-LAB GUIDE QUESTIONS


1. Which among the hydrocarbons used in the experiment is/are
A. saturated?

B. actively unsaturated?

C. aromatic?

2. Octane is an unbranched alkane of formula C8H18. Based on your observations in this


experiment, predict the following:
a. Solubility in water:

b. Solubility in CCl4:

c. Combustion characteristics:

d. Density versus water:

3. 1-Hexene is an alkene. Based on your observations in this experiment, what should you expect
to see for this compound in the following tests:
a. Bromine test:

b. KMnO4 test:

c. Combustion:

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4. Hydrocarbons do not mix with water, and they float. Explain these characteristics.

5. Write a chemical equation / reaction mechanism for the following:


a. Combustion of an alkane

b. Unsaturated hydrocarbon + bromine

c. Alkenes + concentrated sulfuric acid

d. Unsaturated hydrocarbon + KMnO4

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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY

EXPERIMENT 9
Benzoic Acid and Phenols Identification

Benzoic Acid is a colorless crystalline solid and a simple aromatic carboxylic acid. The name is
derived from gum benzoin, which was the only known source.
Phenol also known as carbolic acid is an aromatic organic compound with the molecular formula,
C6 H5 OH. The molecule consists of a phenyl group bonded to a hydroxyl group. It is a white
crystalline solid that is volatile
OBJECTIVES
Determine the difference between benzoic acid and phenol in terms of different chemical
reactions
MATERIALS
Test tubes with stand Test tube holder
Pipette Filler
Bunsen Burner Dropper
Metal Spatula Erlenmeyer flask

REAGENTS
Benzoic Acid Phenol
Ferric Chloride Sulfuric Acid
Soda Lime Sodium nitrite
Ammonium hyrdoxide Distilled water

PROCEDURES
A. Benzoic Acid Identification Test
1. Take the benzoic acid into the spatula and heat on Bunsen burner.
2. Observe the smoke.
3. With the use of spatula, get a pinch of benzoic acid into the test tube and add soda lime.
4. Hold it with a test tube holder.
5. Place the test tube over the Bunsen burner.
6. Observe the smoke.
7. Take a clean test tube, get a pinch of a benzoic acid, add a few drops of ammonium
hydroxide solution.
8. Hold it with a test tube holder.
9. Slightly heat the test tube quickly over the Bunsen burner then take away from the flame.
(Do it thrice)
10. Add 1 ml of ferric chloride solution.
11. Observe the precipitate.

B. Phenol Identification Test


1. Take the phenol into the spatula and heat on Bunsen burner.

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2. Observe the smoke.


3. With the use of spatula, get a little amount of phenol in a test tube.
4. Add a few drops of concentrated sulfuric acid.
5. Shake it well, carefully.
6. Observe the color.
7. Add a few drops of sodium nitrite.
8. Shake and observe the color.
9. Then pour the solution in an erlemeyer flask with distilled water.
10. Observe the color.

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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY

EXPERIMENT 9
Benzoic Acid and Phenols Identification

Group No. and Members:


______ _____________________________________________________________________
Section: _______________
Date: _____________________

DATA AND RESULTS

Benzoic acid Identification Test

Observation
Benzoic acid
Benzoic acid + ammonium hydroxide
Benzoic acid + ammonium hydroxide +
ferric chloride solution

Phenol Identification Test

Observation
Phenol + Sulfuric Acid
Phenol + Sulfuric Acid + Sodium Nitrite
Phenol + Sulfuric Acid + Sodium Nitrite
solution in distilled water

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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY

EXPERIMENT 9
Benzoic Acid and Phenols Identification

Group No. and Members:


______ _____________________________________________________________________
Section: _______________
Date: _____________________

POST-LAB GUIDE QUESTIONS


Benzoic Acid Test
1. a. What does the color of smoke emitted by benzoic acid indicate?

2. a. What does the color of smoke emitted when benzoic acid and soda lime were mixed
and subjected to flame indicate?

b. Illustrate the reaction mechanism.

3. a. What does the color of precipitate indicate?

Phenol Test

1. a. What does the color of smoke emitted by benzoic acid indicate?

2. What is Liebermann’s reaction? Illustrate the Liebermann’s nitroso reaction for phenols.

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MTY1101 – INORGANIC AND ORGANIC CHEMISTRY

EXPERIMENT 10
Alcohols and Phenols

The alcohols differ widely from their corresponding hydrocarbons in both physical and
chemical properties. The hydrogen of the hydroxyl group is sufficiently acidic to form hydrogen
bond with the oxygen of another alcohol molecule. This results in molecular association which
makes alcohols exhibit higher boiling points and higher heats of vaporization than the
hydrocarbon counterparts. Intermolecular H-bond occurs between water and alcohols which lead
to solubility up to alcohols with C5 and in some instances, may form constant boiling mixtures
known as azeotropes.

The chemical properties of the alcohols may be summarized as; reactions involving acidic
H; replacement of the hydroxyl group; elimination to produce olefins, or by oxidation.
All the alcohols possess some acidic properties, but the primary alcohols are the most
acidic and the tertiary alcohols the least acidic. The weak acid property of alcohols can be
explained by the reaction of alcohols with Na metal to form alkoxide and hydrogen gas.
The ease of replacement of hydrogen (1°>20°>39°) may be illustrated in the equation:

Alipathic alcohols react with acid to form organic esters (esterification reaction)

The alcohols also undergo replacement of the hydroxyl group with ease of reactivates: 3°>2°>1°.
The presence of more alkyl radical groups attached to the functional carbon or carbinol carbon,
increases electron density of the carbon, and allows Weakening of C-0 bond: - This property of
alcohols may be illustrated by Lucas reagent (HCl-ZnCl2)

.
Tertiary alcohols readily eliminate hydroxyl group to yield alkenes. Primary alcohols are
more resistant to elimination reactions and require stronger reagent's, like sulfuric acid and higher
temperature.

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The three classes of alcohols differ in the ease of attack by oxidizing agents like acidified
K2CrO4 or K2Cr2O7, KMnO or even Cuo. Primary alcohols are readily oxidized to aldehydes and
secondary alcohol to ketones. Tertiary alcohols are most resistant, as oxidation of the alcohol
group would involve cleavage of a carbon to carbon bond to smaller fragments.

Oxidation of methanol to formaldehyde with heated CuO may be illustrated by the


equation:

The aldehyde is treated with resorcinol and H2SO4 which gives pink-red ring at the junction
of the liquids, which is a means of detecting methyl alcohol in alcoholic beverages:

Phenols are more acidic than aliphatic alcohol due to the lone pair in oxygen which
delocalizes towards the sp carbon of the benzene ring. The delocalized lone pair leaves oxygen
partially positive, weakening the O-H bond, which allows H to ionize..

Phenols react with bases like NaOH to produce sodium phenoxide or with alcohols to form
alkyl phenoxide or ether.

Phenols react with electrophilic reagents by substituting H on the 0 - p positions with


electrophiles like B+ or NO2+, with Br2 it reacts to form 2,4,6 trinitrophenol or picric acid.

OBJECTIVES
Determine the physical properties of different alcohols
Differentiate primary, secondary, tertiary alcohol, and phenols
Determine the reaction mechanism of different alcohols

MATERIALS

Methanol Phenol Lucas Reagent


n-butyl alcohol Water Ethanol
sec-butyl alcohol NaOH solution KMnO4
tert-butyl alcohol Oil Dil. Sulfuric acid

Test tubes
Beaker Bunsen burner Iron ring
Wireloop Iron stand Water bath

PROCEDURES

For the following tests, use the following samples:


a. Methanol
b. n-butyl alcohol
c. sec-butyl alcohol
d. tert-butyl alcohol
e. Phenol

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I. Physical Properties
A. Odor.
1. Observe the odor of each of the following alcohols.
B. Solubility in water.
1. Test the solubility of the alcohols given by adding 5 drops of each into 1 mL
H2O contained in 5 separate test tubes.
C. Solubility in NaOH solution
1. Test the solubility of the alcohols given by adding 5 drops of each into 1 mL
H2O contained in 5 separate test tubes.
D. Solubility in alcohol
1. Test the solubility of the alcohols given by adding 5 drops of each into 1 mL
H2O contained in 5 separate test tubes.
E. Solubility in oil
1. Test the solubility of the alcohols given by adding 5 drops of each into 1 mL
H2O contained in 5 separate test tubes.

II. Replacement of the Hydroxyl Group


1. Place 10 drops of the following samples in separate test tubes.
2. Add 1 ml Lucas reagent (ZnCl, in HCI) and shake the tubes.
3. Note the relative time required for the appearance of turbidity indicating a
second liquid layer (formation of insoluble alkyl chloride).
4. Rationalize the relative ease by which each class of alcohol undergoes
substitution reaction.

III. Ease of Oxidation


1. Place 10 drops of the sample alcohols in 3 separate clean test tubes.
2. Add 10 drops each of potassium permanganate solution and a drop of dilute
sulfuric acid.
3. Place the tubes in a beaker of boiling water.
4. Remove the tubes at intervals to shake and observe any color changes.
5. Note carefully the time when each mixture undergoes decolorization.

IV. Esterification for ethanol and methanol only


1. In a test tube, place 1 mL of samples, 1 mL conc. acetic acid and 5 drops of
conc. sulfuric acid in a water bath for 2 minutes.
2. Then pour into about 30 mL of cold water in a beaker.
3. Stir the solution.
4. Describe the odor of the new product formed.
5. Repeat (A) using 0.5 g of salicylic acid, with 2 mL of methanol and 5 drops of
conc. sulfuric acid.
6. Identify the new product formed, note its odor and give the medicinal use of this
compound.

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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY

EXPERIMENT 10
Alcohols and Phenols

Group Number and Members:


____________________________________________________________________
Date started: ________________
Date finished: _______________

DATA and RESULTS

Properties methanol Phenol n-butyl sec-butyl tert-butyl


Odor
Sol. in water
Sol. in NaOH solution
Sol. in ethanol
+ Lucas Reagent

+ KMnO4 + dil. H2SO4

Esterification Observation
Ethanol

Methanol

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MTY1101 – INORGANIC AND ORGANIC CHEMISTRY

Provide the Chemical Reactions for


a. + Lucas Reagent
b. + KMnO4 + dil. H2SO4
c. Esterification

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MTY1101 – INORGANIC AND ORGANIC CHEMISTRY

EXPERIMENT 10
Alcohols and Phenols

Group No. and Members:


______ _____________________________________________________________________
Section: _______________
Date: _____________________

POST-LAB GUIDE QUESTIONS

1. Why is tertiary alcohol more easily oxidized in acid medium than in neutral or
alkaline medium?

2. Which is a better proton acceptor, OH or –OCH2CH3? What are the relative basicities of
NaOH, sodium n-propoxide, sodium isopropoxide?

3. Which of the following will you predict to be more soluble in water? Give the reason for
your answer.

a.) n-hexyl alcohol or n-hęptyl alcohol

b.) n-butyl alcohol or tert-butyl alcohol

4. Will salicyclic acid give positive result with the FeCl, test? Why?

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MTY1101 – INORGANIC AND ORGANIC CHEMISTRY

EXPERIMENT 11
Aldehydes and Ketones

Aldehydes and Ketones are functional isomers. Both substances have the functional carbonyl
(C=O) group. Because of the great differences in the electronegativity between C & O a carbonyl
group has a partial positive C and a partially negative O (due to inductive effect and pi electron
delocalization). The dipolar character of both groups result in similar reactions:

1. Addition of a variety of reagents at the carbonyl group.


2. Reduction of the carbonyl group
3. Condensation and polymerization

Most aldehydes and ketones react by addition (nucleophilic additions AN) at the carbonyl carbon,
with groups like NH3, NaHSO3, HCN and RMgX. The addition reactions are influenced by steric
hindrance. If the group attached to the carbonyl group are large or bulky, some addition reactions
are completely prevented. Thus, the addition of NaHSO2 or HCN occurs with aldehydes and
methyl ketones but not with other alipathic ketones.

The addition of ammonia derivatives is generally followed by loss of water (AN - E) so that the
product isolated contains the carbon - nitrogen double bond.

Other ammonia derivatives which react similarly are hydroxylamine (H2NOH) and semicarbazide
(H2NNHCONH2). These reactions are not very susceptible to steric hindrance.
Reduction of the carbonyl group to the corresponding alcohol is easily accomplished by a variety
of reagents like LiAlH4, lithium aluminum hydride, or by catalytic hydrogenation which may be
illustrated as:

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The carbonyl group activates the hydrogens on adjacent carbon atoms especially alpha hydrogen,
so that in the presence of basic catalyst, aldol condensation takes place.

Aldehydes and ketones differ principally in their resistance to oxidation. Aldehydes undergo
oxidation with mild oxidizing agents whereas ketones are inert. Cupric ion in alkaline solution
oxidizes the aldehydes to the salts of organic acids. Formation of brick red precipitate of cuprous
oxide with Fehling's reagent is a proof of the reaction.

Cu(OH), normally precipitated in basic solution and Cu++ ion forms soluble complex with Rochelle
salt which acts as stabilizing agent. Benedict's reagent is another oxidizing agent which contains
Cu2+ and citrate salt (sodium citrate).
Silver ion in alkaline medium also oxidizes aldehydes. The common test solution is Tollen's
reagent (ammoniacal silver nitrate) where silver ion is reduced to metallic silver in the form of
silver mirror and the aldehyde acting as reducing agent. The reaction is represented as:

Aldehydes and ketones are compounds that upon oxidation may produce acids react with halogen
in the presence of a base by substitution of alpha hydrogen (haloform reaction). The reaction
involves the removal of an alpha hydrogen to form an enolate ion. Addition of halogen to the
enolate ion will initiate faster substitution of alpha hydrogen by nucleophilic halogen. Presence of
electron attracting halogen on the alpha carbon initiates further replacement of remaining alpha
hydrogen by halogen. The resulting alpha haloketone is attacked by a base to initiate a carbon to
carbon bond cleavage.

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The reaction is represented as:

Aldehydes and ketones with - COCH3, (methyl ketone) react similarly with sodium nitroprusside
which produce blood red solution that eventually changes to wine red upon addition of acetic acid.
Absence of methyl ketones changes blood red solution to yellow.

Schiff's reagent (fuchsia dye (magenta color) + SO2) chemical name is bis-N- sulfuric acid of p-
rosaniline hydrochloride, is purple in the presence of aldehydes but is very pale pink in the
presence of ketones. It is considered as general test for aldehydes since even aromatic aldehydes
give positive purple test.

OBJECTIVES
Determine physical and chemical properties of aldehyde and ketones
Differentiate aldehyde and ketone through different chemical reaction
Understand the mechanism involved during the chemical reaction

MATERIALS

Acetaldehyde Methyl ethyl ketone Benedict’s reagent


37% Formaldehyde Sodium nitroprusside Phenylhydrazine
Butyraldehyde 3M NaOH Schiff’s reagent
Benzaldehyde Acetic acid Fehling’s reagent
Acetone Tollen’s reagent Sulfuric acid

Test tubes Bunsen burner Water bath


Beaker Iron stand
Wireloop Iron ring

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PROCEDURES
I. Physical Properties
1. Try the solubility in water and ethyl alcohol using 3 drops of each of samples acetaldehyde,
formaldehyde, butyraldehyde, benzaldehyde, acetone, methylethylketone in separate test
tubes.
2. Describe the odor of each samples.
II. Chemical Properties
A. Test with sodium nitroprusside
1. In separate test tubes, place 10 drops each of the samples.
2. Add 2 mL water to each then 2 drops of very dilute solution of sodium nitroprusside.
3. Shake each test tube and add 2 drops of 3M NaOH.
4. Note the depth of color in each tube.
5. Now, add 2 drops of dilute acetic acid solution to each, shake and let stand for 1
minute.
6. Note the colors of the two solutions.
7. This test may be used to distinguish acetone from other simple ketones.
B. Oxidation by Silver Ion (Tollen's Reagent)
1. To a very clean test tube, place 5 drops of silver nitrate solution and add dropwise
dilute ammonium hydroxide until the precipitate that first formed is almost dissolved.
2. Then add 1-4 drops samples.
3. Shake and warm in water bath.
4. Repeat the above procedure using the other sample solutions.
C. Oxidation by Copper Ion (Fehling's or Benedict's)
1. Mix in a test tube 10 drops each of Fehling's A and B or use 1 mL Benedict's solution.
2. Add 1 mL water.
3. Warm in water bath to about 60°C, then add 5 drops of samples.
4. Boil for 1 minute.
5. Observe if precipitation occurs.
6. Observe color changes and note if there is coating on the test tube.
7. Repeat using the other sample solution.
8. Compare the results
D. Action of a Strong Base
1. Boil 5 drops of samples using water bath with 3 mL water containing 5 drops of 3M
NaOH solution.
2. Note color and odor changes.
3. Repeat with other sample solutions.
E. General Schiff’s test
1. To 10 drops of Schiff's reagent, add 2 drops of samples.
2. Set aside.
3. Repeat with other sample solutions.
4. Observe and compare the results.
F. Bisulfite Addition
1. Place 4 mL 40% sodium bisulfite solution.
2. Add 1 mL of ethanol in test tube.
3. Add 5 drops samples.

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4. Mix the contents thoroughly and cool in an ice bath.


5. Observe.
G. Reaction with Phenylhydrazine
1. In separate test tubes, prepare two solutions each containing 5 drops phenylhydrazine
and 1 mL acetic acid solution in 3 mL water.
2. Add 10 drops of samples in each test tube.
3. Allow the solutions to stand until a precipitate is formed.
4. Cool the mixture in an ice bath.
5. Scratch the walls of each test with a glass stirring rod to induce crystallization.
6. Describe the appearance of the crystals formed.
7. Note that Phenylhydrazine is very poisonous, take care to avoid getting it on skin or
inhaling the vapor.
H. Autooxidation
1. Transfer a few drops of samples to a watch glass.
2. Expose to the atmosphere for 5 to 10 minutes.
3. Observe the formation of precipitate.
I. Oxidation
1. Shake 5 drops of sample with about 5 mL of warm water.
2. Test 5 drops of the solution with 1 mL ammoniacal silver nitrate solution in a test tube.
3. Treat another 5 drops of the sample with 10 drops each of Fehling's A & B solution in
another test tube.
4. Heat both tubes in a water bath.
5. Observe.
6. Try a drop or two of the solution above with 10 drops of Schiff's reagent.
7. Observe what happens.

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EXPERIMENT 11
Aldehyde and Ketone

Group Number and Members:


____________________________________________________________________
Date started: ________________
Date finished: _______________

DATA and RESULTS

I. Physical and chemical properties of aldehydes and ketones


Odor Solubility + nitroprusside + Tollens
Test Reagent
Samples water alcohol
Acetaldehyde

Formaldehyde

Benzaldehyde

Butyraldehyde

Acetone

Methylethylketone

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Tests Bennedict’s Strong Base Schiff’s test + Bisulfite


Samples Reagent
Acetaldehyde

Formaldehyde

Benzaldehyde

Butyraldehyde

Acetone

Methylethylketone

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Tests + Phenylhydrazine Autooxidation Oxidation


Samples
Acetaldehyde

Formaldehyde

Benzaldehyde

Butyraldehyde

Acetone

Methylethylketone

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MTY1101 – INORGANIC AND ORGANIC CHEMISTRY

EXPERIMENT 11
Aldehyde and Ketone

Group No. and Members:


______ _____________________________________________________________________
Section: _______________
Date: _____________________

POST-LAB GUIDE QUESTIONS


1) How does formaldehyde act as disinfectant or as a preservative of biological specimens?

2) What are the uses of urotropine? Give its structure. Explain the action of each.

3) Is the use of HCHO as a food preservative permitted by law? Explain.

4) Give the practical use of the reduction of AgNO3 by means of aldehydes.

5) What is paraldehyde? Give one use of paraldehyde in medicine.

6) Give the commercial use of acetone.

7) What is the presence of acetone in urine and breath an indication of?

8) What is meant by autooxidation?

9) Formaldehyde undergoes addition reactions more readily than all of other aldehyde, Explain
why.

10) Predict the product/s formed when aldehydes and ketones undergo aldol condensation.
Complete the equation below and provide a name to the products formed.

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EXPERIMENT 12
Amines, Amino Acids, and Proteins

Organic compounds which contain nitrogen compounds are commonly categorized as


amines or amides. They are similar to alcohols in such a way that they vary on the number of R-
groups attached to the nitrogen atom. The nitrogen derivatives of carboxylic acids which contain
a carbonyl carbon and an amine group are classified as amides. In amines it is common for R-
groups to be present in behalf of the Hydrogen atom. This is the reason why amines possibly form
hydrogen bonds which makes small amines slightly soluble in distilled water. On the other hand,
amides have the same property with amines to form hydrogen bonds. This instance along with its
existing carbonyl carbon increases the occurrence of dipole-dipole interactions.
Amino acids are the basic structural unit that makes up a protein. These amino acids
contain amine and carboxyl as its functional group. This shows the importance of amines in
different physiological activity. Different neurotransmitters such as epinephrine, norepinephrine,
dopamine, serotonin, and histamine, contains amines. Likewise, different drugs which are
commonly used as antagonist for these neurotransmitters also contain amines, like antihistamine,
ephedrine, and chlorpromazine. Moreover, amides are often used as polymers, such as nylon
because they were able to resist hydrolysis. Biologically, amides consist the secondary structure
of proteins due to hydrogen bonds and its linkage is called a peptide bond.
OBJECTIVES
The students are expected:
1. To observe some chemical and physical properties of amines, amino acid, and protein;
2. To observe some of the characteristic color reactions of amino acids and protein; and
3. To observe protein denaturation.

MATERIALS
Amines Proteins
Diphenylamine Albumin
Aniline Gelatin

Amino acid 2% Ninhydrin


Alanine 10% NaOH
Glutamic acid 2% CuSO4
Phenylalanine HNO3
Arginine

Test tubes water bath iron ring


Litmus papers iron stand Bunsen burner

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MTY1101 – INORGANIC AND ORGANIC CHEMISTRY

PROCEDURES

A. Solubility Behavior in water


Use all the materials for this test. The mixtures yielded will be used for the succeeding
tests.
1. Place a few crystals of solids or 3 drops of liquid sample in test tube.
2. Add 1 ml of distilled water.
3. Shake to mix. Observe.
4. Test the resulting mixture with red or blue litmus paper.

B. Solubility of Amines in Aqueous acid


1. To the aqueous mixtures of amines in Section A, add 10 drops of concentrated HCl.
2. Shake to mix. Observe.

C. Color Reactions of Amino Acids and Proteins


1. Ninhydrin test (Use aniline, alanine, and gelatin)
a. Spot a small drop of aqueous solution on a strip of filter paper.
b. Allow to dry. Place to drops of 2% Ninhydrin in acetone solution on the sample
spot.
c. Evaporate the solvent. Allow color development.
d. Inspect the strip after 30 minutes.

2. Biuret Test (Use distilled water, alanine, gelatin, and albumin)


a. Place 5 drops aqueous sample in a test tube.
b. Add 5 drops 10% NaOH. Shake to mix.
c. Add 2 drops 2% CuSO4.
d. Shake to mix. Examine the resulting mixture.

D. Protein Denaturation
1. By heat
a. Place 10 drops of 1% albumin solution in a test tube.
b. Boil in a water bath for 10 minutes.
c. Examine the resulting mixture.

2. By strong acid
a. Place 10 drops of 1% albumin solution in a test tube.
b. Add 10 drops of concentrated HNO3 by slowly pouring the acid down the side of
the test tube.
c. Examine the resulting mixture.

Page 27 of 30
Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY

EXPERIMENT 12
Amines, Amino Acids, and Proteins

Group No. and Members:


______ _____________________________________________________________________
Section: _______________
Date: _____________________

DATA AND RESULTS


A. Solubility Behavior in water
Sample Observation

B. Solubility of Amines in Aqueous acid


Sample Observation

C. Color Reactions of Amino Acids and Proteins


Sample Observation
Ninhydrin Test

Biuret Test

Page 28 of 30
Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY

D. Protein Denaturation
Effectors Observation
Heat
Strong Acid

Page 29 of 30
Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY

EXPERIMENT 12
Amines, Amino Acids, and Proteins

Group No. and Members:


______ _____________________________________________________________________
Section: _______________
Date: _____________________

POST-LAB GUIDE QUESTIONS


1. Compare the solubility of amino acids and proteins in water.

2. Explain the effect of acid on the solubility of water-insoluble amines.

3. What chemical test can be used to classify primary, secondary, and tertiary amine?
Explain how tests were performed.

4. Explain how heat and strong acid denature protein.

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