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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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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY
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
PROCEDURES
For the following experiments, use the following samples: hexane, cyclohexane, benzene, toluene
Precautions
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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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY
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.
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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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY
EXPERIMENT 8
Hydrocarbons
Bond-line Structure
A. Physical State at RT
Appearance
Color
Odor
B. Solubility in conc. H2SO4
Inference
C. Ignition Test
Inference
Inference
E. Basic Oxidation
Inference
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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY
EXPERIMENT 8
Hydrocarbons
B. actively unsaturated?
C. aromatic?
b. Solubility in CCl4:
c. Combustion characteristics:
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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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY
4. Hydrocarbons do not mix with water, and they float. Explain these characteristics.
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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.
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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY
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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY
EXPERIMENT 9
Benzoic Acid and Phenols Identification
Observation
Benzoic acid
Benzoic acid + ammonium hydroxide
Benzoic acid + ammonium hydroxide +
ferric chloride solution
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
2. a. What does the color of smoke emitted when benzoic acid and soda lime were mixed
and subjected to flame indicate?
Phenol Test
2. What is Liebermann’s reaction? Illustrate the Liebermann’s nitroso reaction for phenols.
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Far Eastern University
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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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY
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.
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.
OBJECTIVES
Determine the physical properties of different alcohols
Differentiate primary, secondary, tertiary alcohol, and phenols
Determine the reaction mechanism of different alcohols
MATERIALS
Test tubes
Beaker Bunsen burner Iron ring
Wireloop Iron stand Water bath
PROCEDURES
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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY
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.
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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY
EXPERIMENT 10
Alcohols and Phenols
Esterification Observation
Ethanol
Methanol
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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY
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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY
EXPERIMENT 10
Alcohols and Phenols
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.
4. Will salicyclic acid give positive result with the FeCl, test? Why?
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Far Eastern University
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:
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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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY
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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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY
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
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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY
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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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY
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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY
EXPERIMENT 11
Aldehyde and Ketone
Formaldehyde
Benzaldehyde
Butyraldehyde
Acetone
Methylethylketone
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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY
Formaldehyde
Benzaldehyde
Butyraldehyde
Acetone
Methylethylketone
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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY
Formaldehyde
Benzaldehyde
Butyraldehyde
Acetone
Methylethylketone
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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY
EXPERIMENT 11
Aldehyde and Ketone
2) What are the uses of urotropine? Give its structure. Explain the action of each.
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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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY
EXPERIMENT 12
Amines, Amino Acids, and Proteins
MATERIALS
Amines Proteins
Diphenylamine Albumin
Aniline Gelatin
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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY
PROCEDURES
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.
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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY
EXPERIMENT 12
Amines, Amino Acids, and Proteins
Biuret Test
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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY
D. Protein Denaturation
Effectors Observation
Heat
Strong Acid
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Far Eastern University
MTY1101 – INORGANIC AND ORGANIC CHEMISTRY
EXPERIMENT 12
Amines, Amino Acids, and Proteins
3. What chemical test can be used to classify primary, secondary, and tertiary amine?
Explain how tests were performed.
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