Experiment 8

EXPERIMENT 8
By Kite Alberto, Melinda Gatchalian, Eula Ildefonso
Ensure that a compound is pure by chromatography, distillation, extraction techniques
Once purity is established, physical properties (mp, bp, odor) are determined
For ultimate identification of our unknown compound, we must know the different elements present other than C-H. (Elemental Analysis)
We also conducted solubility tests using solvents like water, dilute acids etc and the results provide info regarding various functional groups that may or may not be present.
But this is not enough thats why the next and perhaps the most important step for the determination of the unknown compound is the determination of the functional groups present through many qualitative chemical tests. Every visible reaction is an indication of the presence of a particular type of functional group/s.
INTRODUCTION
A.TESTS FOR UNSATURATION B. TESTS FOR AROMATICITY C. TESTS FOR ACIDITY AND BASICITY D.TESTS FOR ALKYLHALIDES E. TESTS FOR ALCOHOLS AND PHENOLS F. TESTS FOR ALDEHYDES AND KETONES
A. TEST FOR UNSATURATION
1. REACTION WITH BROMINE IN METHYLENE CHLORIDE 2. BAEYER TEST FOR UNSATURATION
3. IGNITION TEST
ACETYLENE GAS
3DROPS 2% Br2
evol'n of gas, formation of dark orange layer(bottom) and light orange layer(top)
BENZENE
3DROPS 2% Br2
no change(orange sol'n)
STYRENE
3drops 2% Br2
evol'n of gas, no change in color
HEXANE
3drops 2% Br2
red orange sol'n
1. REACTION WITH BROMINE IN METHYLENE CHLORIDE
METHODOLOGY & RESULTS
ACETYLENE
INTERPRETATION CPD RESPONSIBLE FOR THE RESULT
BENZENE
STYRENE
HEXANE
H-C C-H
1. REACTION WITH BROMINE IN METHYLENE CHLORIDE
What test/s could be used to differentiate saturated and unsaturated hydrocarbons? Explain how the test could differentiate them. The decoloration of Bromine solution test and Baeyer test differentiate saturated from unsaturated hydrocarbons. In decoloration of bromine solution test, if the test compound is unsaturated, the orange-brown color of the aqueous bromine solution rapidly disappears. Bromine adds to each of carbon of the bond then the pi bond converts into a sigma bond and thus become saturated. In the permanganate test, an unsaturated compound reduces the purple permanganate ion (MnO4-), forming a precipitate of brown manganese (IV) oxide (manganese oxide, MnO2). As a result of this reaction, an OH group is added to each carbon at each end of a multiple bond. When this happens, the multiple bond becomes saturated.
TESTS FOR UNSATURATION
ANSWERS TO QUESTIONS
Illlustrate with equation the reaction of Br2 in methylene chloride with acetylene
Figure 1: Bromine Test Alkene
Figure 2: Bromine Test Alkyne
ACETYLENE GAS
3DROPS 1% AQ SOLN KMnO4
dark brown precipitate
3DROPS BENZENE 1% AQ SOLN KMnO4
formation of red violet layer (bottom) and red layer (top)
3DROPS STYRENE 1% AQ SOLN KMnO4
reddish brown precipitate
3DROPS
HEXANE
1% AQ SOLN KMnO4
formation of purple layer(bottom) and colorless layer(top)
2. BAEYER TEST FOR UNSATURATION
ACETYLENE INTERPRETATION CMPD RESPONSIBLE FOR THE RESULT
BENZENE
STYRENE
HEXANE
MnO2
MnO2
2. BAEYER TEST FOR UNSATURATION
Do alkynes give all tests which alkenes exhibit? What tests could be used to differentiate them? No. The silver acetylide test could be used to differentiate between an alkyne and an alkene. It only produces a positive test (formation of a silver precipitate) on alkynes.
ACETYLENE GAS
blue flame with yellow soot
XYLENE
sooty
STYRENE
sooty
HEXANE
no soot
3. IGNITION TEST
ACETYLENE INTERPRETATION
XYLENE
STYRENE
HEXANE
CMPD RESPONSIBLE FOR THE RESULT
C(s) and CO2 (g)

3. IGNITION TEST
Does toluene behave in the same way like the other unsaturated hydrocarbons? Why? In our case, we used xylene as a substitute for toluene. Xylene does not behave in the same way like other unsaturated hydrocarbons because of the presence of a benzene ring. This stable structure due to resonance is less reactive than the other saturated hydrocarbons. The shared electrons in the saturated bonds of the aromatic compound ring prevent aqueous bromine solution from reacting with them.
TEST FOR AROMATICITY
What is the role of concentrated sulfuric acid in the nitration of toluene? (We used xylene as a sample) Concentrated sulfuric acid acts as an electrophilic generator. It displaces weaker acids from their salts with nitric acid itself, sulfuric acid acts as both an acid and a dehydrating agent, forming nitronium ion, NO2+.
B. TEST FOR AROMATICITY
1. NITRATION 2. LE ROSEN TEST
VISIBLE RESULT: light yellow sol'n and smells like rugby HEAT at 50C. Shake ocassionally Place in an ice bath + 10 drps of toluene MIX 10 drps HNO3 + 10 drps conc. H2SO4
Pour into a an ice cold water
1. NITRATION
Show the mechanism
A. Nitration
OR.....
Incline tt + Toluene
5 drps Le Rosen reagent
cherry red sol'n
2. LE ROSEN TEST
C. TESTS FOR ACIDITY AND BASICITY
1. Ph OF AQUEOUS SOLUTION 2. NaHCO3 TEST 3. AgNO3 TEST 4. SILVER ACETYLIDE TEST
2 drps Acetic acid
Dissolve in 20 drps H2o
2.5
---COO- + H3O+
2 drps Phenol
---O- + H3O
2 drps Aniline
---NH3+ + H3O
2 drps Benzoic acid (20mg+20 drps 95%ethanol)
---COO- + H3O
1. pH OF AQUEOUS SOLUTION
2 drps acetic acid
20 drps 5% NaHCO3
evol'n of gas, clear sol'n
2 drps Phenol
20 drps 5% NaHCO3
2 drps Aniline
20 drps 5% NaHCO3
2 drps Benzoic acid
20 drps 5% NaHCO3
2. NaHCO3TEST
ACETIC ACID
INTERPRETATION CMPD RESPONSIBLE FOR THE RESULT
PHENOL
ANILINE BENZOIC ACID
CO2
CO2
2. NaHCO3TEST
What test could be used to differentiate carboxylic acids from phenols? Explain how the test could differentiate them. The NaHCO3 test could be used. Carboxylic acids are soluble in sodium bicarbonate solution while phenols are not. A visible evolution of bubbles happens during the reaction of a carboxylic acid. Phenols do not. Ethanolic silver nitrate test could also be used. Carboxylic acids initiate the production of precipitate (silver carboxylate salt). Phenols do not.
TEST FOR ACIDITY AND BASICITY
2 drps acetic acid
20 drps 95% ethanol + 20 drps 2% ethanolic AgNO3
If precipitate frorm: add 5% HNO3
cloud formation, white ppt
2 drp phenol
If precipitate frorm: = 5% HNO3
formation of orange layer(bottom), no ppt
2 drp Aniline
formation of orange to red layer(bottom), no ppt
2 drp Benzoic acid
cloudy white sol'n, white ppt
3. AgNO3 TEST
ACETIC ACID
INTERPRETATION CMPD RESPONSIBLE FOR THE RESULT
PHENOL
ANILINE
BENZOIC ACID
SILVER ACETATE
SILVER BENZOATE
3. AgNO3 TEST
Give the equation involved in the reaction of ammoniacal silver nitrate. C2H2 + Ag(NH3)OH C2Ag2 + NH4+ + NH3
acetylene with
Only acids will react to form the precipitate due to the departure of H from the molecule and replacing it with a silver ion.
The ammoniacal silver ion reacts with acetylene to form C2Ag2 (Silver acetylide), which is the solid precipitate.
1M NH3 dropwise
20 drps 2% AgNO3
white ppt with black soot
pour
AgC-CAg
Tt with acetylene gas(stopper and shake)
4. SILVER ACETYLIDE TEST
Tollen's reagent for the silver acetylide test should always be freshly prepared. Why? It is because Tollen's reagent when left standing decomposes and forms a highly explosive precipitate-silver fulminate, which is dangerous in laboratory experiment.
Explain why the terminal hydrogen in acetylene is acidic when in fact the electronegativity values of hydrogen and carbon are almost the same. Terminal alkynes are unusual hydrocarbons for they can be deprotonized using an appropriate base to generate carbanion. This is an acidic situation since terminal alkynes have an sp-hybridized orbital with 50% s character, meaning it is a highly electronegative orbital, the electron pair shared with H(terminal and directly attached to the unsaturation) is tightly held by the nucleus of C making it electrostatically stabilized. So, The H+ now, to relieve the tension can leave off the chain. Since this is a positive H, then terminal alkynes are acidic.
D. TESTS FOR ALKYL HALIDES
1. BEILSEN TEST 2. ALCOHOL AgNO3 TEST
SAMPLES
VISIBLE REACTION
INTERPRETATION
STRUCTURES RESPONSIBLE FOR REACTION
Ethylbromide Tert-butylchloride Sec-butylchloride Benzylchloride
Blue-Green Green Green smoky Yellow-Green (small amt) smoky Yellow-Green (extreme small amt)
+ + + + +
CuBr CuCl2 CuCl2
CuCl2
Chorobenzene
CuCl2
1. BEILSEN TEST
In the Beilstein test, the appearance of green flame indicates the presence of what compound?
The green flame is caused by the copper halide which is formed from the combustion reaction of copper (II) oxide (from heated copper wire) and the alkyl halide.
TEST FOR ALKYL HALIDES
20 drps 2% alcoholic AgNO3
2 drps ethylchloride
Shake tt in H2O bath for 1 min
Ethylbromide
milky green solution
+ +
AgBr AgCl
Tert-butylchloride chalk formation (t-butyl solidifies)
Sec-butylchloride no change (white)

Chorobenzene clear solution
+
-
AgCl
2. ALCOHOLIC AgNO3 TEST
Why is the order of reactivity of the alkyl halides toward alcoholic silver nitrate 3o>2o >1o? Tertiary carbocations formed by the heterolysis of alkyl halide is more stable due to C-H hyperconjugation. The positive charge is distributed to a greater number of surrounding hydrogen atoms compared to the secondary and primary alkylhalides. The primary carbonium ion is the least stable since its positive charge is concentrated only to the carbon atom.
In the silver nitrate test for halides, explain why alcohol is used as the solvent for silver nitrate and not water.
Water is not used as the solvent because it is highly polar, considering that the reaction proceeds with a hydrocarbon. Ethanol, having both hydrophobic and hydrophilic portion, can considerably dissolve the polar nitrate and the nonpolar alkyl chain. Alkylhalides AgBr and AgCl form precipitates insoluble in ethanol and provides indicator for the alkylhalide test.
E. TEST FOR ALCOHOLS AND PHENOLS

1. REACTIONS OF ALCOHOLS REACTION WITH Na METAL LUCAS TEST REACTIONS WITH K2Cr2O7
2. ALCOHOL AgNO3 TEST FeCl3 TEST BROMINE WATER TEST MILLONS TEST
20 DRPS NBUTYLALCOHOL (SEC-BUTYL, TERT-BUTYL ALCOHOLS)
Na METAL
Test Sample
Visible Results
Structure or formula of compound responsible for the visible results H2 H2 H2
n- butyl alcohol Sec- butyl alcohol tert- butyl alcohol
Rapid evolution of gas Moderate evolution of gas Slight to no evolution of gas
1. REACTIONS OF ALCOHOLS 1.1 REACTIONS WITH Na METAL
20 DRPS NBUTYLALCOHOL (SEC-BUTYL, TERT-BUTYL ALCOHOLS)
Na METAL Na METAL
Test Sample n- butyl alcohol sec- butyl alcohol tert- butyl alcohol
Visible Results No layer formation Moderate layer formation Fast layer formation
1. REACTIONS OF ALCOHOLS 1.2 LUCAS TEST
20 DROPS NBUTYLACLCOHOL
ACIDIFY WITH 2M H2SO4
5DROPS 3% K2Cr2O7
Test Sample
Visible Results
n- butyl alcohol Sec- butyl alcohol tert- butyl alcohol
Blue- green solution Blue- green solution Blue green
1. REACTIONS OF ALCOHOLS 1.3 REACTIONS WITH K2Cr2O7
Test Sample
Visible Results
Phenol - napthol Cathechol Resorcinol
Reddish-brown
Gray Blue green
2. REACTIONS OF PHENOLS 2.1 FeCl3 TEST
20 DROPS 95% ETHANOL
20 DROPS PHENOL
BROMINE WATER
Test Sample
Visible Results
Phenol napthol Cathechol Resorcinol
Turns to brown Turns to brown Dark brown Dark brown
2. REACTIONS OF PHENOLS 2.2 BROMINE WATER TEST
5 DROPS MILLONS REAGENT

SHAKE HEAT IN WATER BATH (2MINS)
Test Sample
Visible Results
Phenol Catechol Resorcinol
Forms layer Forms layer Forms layer Has white layer at the bottom Has white layer at the bottom
5 DROPS OF SAMPLE
Tyrosine Albumin
2. REACTIONS OF PHENOLS 2.3 MILLONSTEST
F. TEST OF ALDEHYDES AND KETONES 1. 2,4-DNPH TEST 6. FEHLINGS TEST
2. BISULFITE TEST
7. MOLISCH TEST 3. SCHIFFS TEST 8. BENEDICTS TEST 4. TOLLENS TEST 5. IODOFORM TEST 9. BARFOEDS TEST
10. SELIWANOFFSTEST
5 DROPS 2,4DPNH HEAT IN WATER 3 DROPS SAMPLE

BATH(5 MINS)
Ad
Ac
1. 2,4-DPNH TEST
Test samples
Visible result
Structure or formula of compound responsible for the visible results

NO2 NO2
Formaldehyde
Solid yellow precipitate

NO2
Acetaldehyde
Clear yellow solution with orange precipitate

NO2
Acetone Benzaldehyde
Yellow orange solution with orange precipitate

NO2
NO2
Orange precipitate 1. 2,4-DPNH TEST
NO2
20 DROPS SODIUM BISULFIDE

Test samples Visible result
5 DROPS SAMPLE
Structure or formula of compound responsible for the visible results
Formaldehyde Acetaldehyde
no reaction clear solution clear solution white precipitate at the bottom (C5H6)CH(OH)SO3 Na+
MIX. COOL IN AN ICE BATH
2. BISULFIDE TEST
ADD
20 DROPS SCHIFFS REAGENT
5 DROPS SAMPLE
Visible result
Test samples
Structure or formula of compound responsible for the visible results Schiffs reagent complex with methanol Schiffs reagent complex with ethanol Unconjugated Schiffs reagent complex Schiffs reagent complex with methylphenol
Formaldehyde Acetaldehyde
dark violet solution with metallic appearance violet solution
Acetone
light pink
Benzaldehyde
royal blue solution
3. SCHIFFS TEST
Ad
Ac
3. SCHIFFS TEST
20 DROPS TOLLENS REAGENT

5 DROPS SAMPLE
HEAT IN WATER BATH AND OBSERVE CHANGES

Test samples Visible result Black solution with silver substance (silver mirror) With silver substance clear solution [no reaction] brown precipitate at the top
Structure or formula of compound responsible for the visible results Silver metal
Formaldehyde
Acetaldehyde
Silver metal
Silver metal
4. TOLLENS TEST
Before heating
After heating
4. TOLLENS TEST
20 DROPS 10% NaOH + 5 DROPS SAMPLE ADD 10% NaOH (DROPWISE)
ADD I2/KI W/ MIXING UNTIL BROWN COLOR PERSIST MIX UNTIL BROWN COLOR DISAPPEARS -> YELLOW SHAKE VIGOROUSLY AND STAND (15 MINS)
HEAT IN A WATER BATH @ 6O C (2 MINS)
ADD 5 DROPS DISTILLED WATER
5. IODOFORM TEST
Test samples
Visible result
Structure or formula of compound responsible for the visible results NaOH [-] CHI3 CHI3 NaOH [-]
Formaldehyde Acetaldehyde Acetone Benzaldehyde
no reaction (clear solution) yellow precipitate with strong odor blurry precipitate brown precipitate
5. IODOFORM TEST
Test Samples Formaldehyde Acetaldehyde Acetone
Visible Result negative blue to blue green color, layer formation Fehlings reagents color, electric blue
Benzaldehyde
blue color, oil layer

6. FEHLINGS TEST
6. FEHLINGS TEST
Test samples Glucose Maltose Sucrose Boiled Starch
Visible result blue blue blue blue violet violet violet violet ring ring ring ring
Structure or formula of compound responsible for the visible results -naphthol -naphthol -naphthol -naphthol
7. MOLISCH TEST
7. MOLISCH TEST
20 DROPS Benedicts reagent Heat in water bath 5 drops sample

Test samples Visible result
Structure or formula of compound responsible for the visible results cuprous oxide cuprous oxide copper complex with water [-] copper complex with water [-]
Glucose Maltose Sucrose Boiled Starch
red precipitate over yellow solution

green blue solution Blurry precipitate over blue solution darker blue solution
8. BENEDICTS TEST
8. BENEDICTS TEST
20 DROPS Barfoeds reagent
Heat in water bath

5 drops sample
Test samples Visible result Structure or formula of compound responsible for the visible results cuprous oxide cuprous oxide Cuprous oxide Cuprous oxide
2 layers: blue over red clear blue solution clear top over blue solution Aqua blue in color
9. BARFOEDS TEST
20 DROPS Seliwanoffs reagent
Heat in water bath

5 drops sample
Test samples Visible result Structure or formula of compound responsible for the visible results Colored complex of furfural with resorcinol Colore complex of furfural with recorcinol colored complex of furfural with resorcinol colored complex of furfural with resorcinol
very, very light orange clear, light brown orange pink orange pink orange
10. SELIWANOFFSTEST
G. TEST FOR AMINES
1. HINSBERG TEST 2. NITROUS ACID TEST
20 DROPS 10% NaOH
+
10% NaOH DROPWISE
5 DROPS sample
+ +
5 DROPS benzenesulfonyl chloride
cover tube with cork & shake for about 5mins. if not basic
if precipitate forms
40 DROPS water
then shake
3M HCl DROPWISE
1. HINSBERG TEST
Test samples
Visible result
Structure or formula of compound responsible for the visible results C6H5SO2NRNa+ C6H5SO2NRH
Methylamine
Clear light orange with brown precipitate
Dimethylamine
Trimethylamine Aniline N-methylaniline
No change
Clear light yellow; gel Precipitate formed; release of heat Evolution of white smoke
C6H5SO2NR2
NR3 3RNH + ClC6H5SO2NRNa+ C6H5SO2NRH
1. HINSBERG TEST
3 DROPS sample
+
40 DROPS 2M HCl
cool in ice bath
5 DROPS cold 20% NaNO2
if no evolution of colorless gas nor formation of yellow to orange color is obtained, warm half of the soln at room temp. + ice cold soln (dropwise) of about 50mg of -naphthol in 2ml of 2M NaOH
2. NITROUS ACID TEST
Test samples
Visible result
Structure or formula of compound responsible for the visible results N2 (CH3)2NN=O
Methylamine Dimethylamine
Trimethylamine
Aniline N-methylaniline
evolution of colorless gas bubbles light orange, clear solution yellow; clear gas evolution of gas; yellow, brown solution; release of heat light brown orange solution with gas
(CH3)3N+
N2 C6H5CH3NN=O
2. NITROUS ACID TEST
H. TEST FOR CARBOXYLIC ACID AND ITS DERIVATIVES 1. FORMATION OF ESTERS

2. HYDROLYSIS OF ACID DERIVATIVES
3. HYDROXAMIC ACID TEST FOR ACID DERIVATIVES
pinch salicylic acid
+
20 DROPS methanol Test Sample
+
Visible Result
5 DROPS conc. H2SO4 shake well
5 mins
Structure responsible
Salicylic acid
white-yellow
solid precipitate
1. FORMATION OF ESTERS 1.1 REACTION OF CARBOXYLIC ACID AND ALCOHOL
20 DROPS water
cover tube with cork & gently shake the mixture
20 DROPS 25% NaOH
+
10 DROPS ethanol
mix
Test Sample
Visible Result
+
5DROPS benzoylchloride
Benzoylchloride
solid white precipitate (bottom) smells like alcohol
1. FORMATION OF ESTERS 1.2 SCHOTTEN-BAUMANN REACTION
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 H2O bath TEST SAMPLES Benzamide VISIBLE RESULTS red litmus to blue, burnt odor
2. HYDROLYSIS OF ACID DERIVATIVES 2.1 HYDROYSIS OF BENZAMIDE
20 DRPS Ethyl acetate
5 drps 25% NaOH

HCl (dropwise)
loosely cover the test tube with a cork and heat in water bath for 15 minutes
TEST SAMPLES Ethylacetate
VISIBLE RESULTS strong sour odor
2. HYDROLYSIS OF ACID DERIVATIVES 2.2 HYDROLYSIS OF AN ESTER
20 DRPS water
Red and blue litmus paper
20 drps Acetic Anhydride
gently shake and feel the tube
TEST SAMPLES
VISIBLE RESULTS
STRUCTURE/FORMULA OF COMPOUND RESPONSIBLE FOR RESULT (CH3CO)2O + H2O 2CH3COOH
Acetic anhydride
blue litmus to red
2. HYDROLYSIS OF ACID DERIVATIVES 2.3 HYDROLYSIS OF ANHYDRIDE
Reaction mechanism 1o Amine
2o Amine
3o Amine
Test Samples Ethylacetate Benzamide Acetic anhydride Benzoylchloride
Visible Result
Structure/ Formula of Compound Responsible for Result HX NH4 RCO2H ROH
blue litmus; odorless pink litmus; odorless red litmus; acetic acid odor blue litmus; alcohol odor
What property of alcohol is demonstrated in the reaction with Na metal? What is the formula of the gas liberated? The acidity of alcohol is demonstrated in the reaction w/ Na metal. The gas liberated is H2.
Dry test tube should be used in the reaction between the alcohols and the Na metal. Why? Because Na metal reacts with water that may cause ignition.
Why is the Lucas test not used for alcohols containing more than eight carbon atoms? The Lucas test applies only to alcohols soluble in the Lucas reagent (monofunctional alcohols with less than 6 carbons and some polyfunctional alcohols). The long chains of C-bond atoms act as non-polar makes the hydroxyl group less functional. This results in the insolubility of the alcohol in the reagent and would make the test ineffective. Explain why the order of reactivity of the alcohols toward Lucas reagent is 3>2>1. The reaction rate is much faster when the carbocation intermediate is more stabilized by a greater number of electron donating alkyl group bonded to the positive carbon atom.This means that the greater the alkyl groups present in a compound, the faster its reaction would be with the Lucas solution.
What functional group is responsible for the observed result in Millons test?
Hydroxyphenyl group or the phenolic OH Why is the Schiffs test considered a general test for aldehydes? This is because any aldehyde readily reacts with Schiffs reagent to form positive results.Schiffs reagent involves a bisulfite ion stuck in the original molecular structure. Aldehydes change this arrangement and thus there is a consequent change as the reaction progresses.
Why is it advantageous to use a strong acid catalyst in the reaction of aldehyde or ketone with 2,4-DNPH? It is because a strong acid when used as a catalyst reverses the sequence of reactions. In the presence of a relatively weaker acid, the strong nucleophile attacks the substrate then the electrophile follows suit.
Whereas in the presence of a strong acid, the strong hydronium ion is more ready for protonation to the oxygen of the carbonyl group. The weaker nucleophile (which thrives in basic medium) then attacks the carbon to stabilize the forming hemiacetal. Water abstracts the H+ and a hemiacetal is formed. Hemiacetals are relatively less stable products that will form acetals and will not show the visible changes that are expected of the test.
Show the mechanism for the reaction of acetaldehyde with the following reagents:
a. 2,4-DNPH
b. NaHSO3
What structural feature in a compound is required for a positive iodoform test? Will ethanol give a positive iodoform test? Why or why not?
Show the mechanisms for the iodoform reaction using acetaldehyde as the test sample.
What test will you use to differentiate each of the following pairs? Give also the visible result. a. acetaldehyde and acetone Schiffs test reaction with acetaldehyde will result to a purple solution. Acetone on the other hand will not react. Tollens test acetaldehyde will form a silver mirror. Acetone on the other hand will not have any reaction.
b. acetaldehyde and benzaldehyde BIsulfites test will differentiate an aliphatic aldehyde from an aromatic aldehyde. Aldehyde will react faster than benzaldehyde. Both will form a re precipitate due to cuprous oxide.

Experiment 8

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EXPERIMENT 8

By Kite Alberto, Melinda Gatchalian, Eula Ildefonso

Ensure that a compound is pure by chromatography, distillation, extraction techniques

A. TEST FOR UNSATURATION

1. REACTION WITH BROMINE IN METHYLENE CHLORIDE 2. BAEYER TEST FOR UNSATURATION

evol'n of gas, no change in color

red orange sol'n

1. REACTION WITH BROMINE IN METHYLENE CHLORIDE

METHODOLOGY & RESULTS

1. REACTION WITH BROMINE IN METHYLENE CHLORIDE

METHODOLOGY & RESULTS

Figure 2: Bromine Test Alkyne

TESTS FOR UNSATURATION

3DROPS 1% AQ SOLN KMnO4

dark brown precipitate

3DROPS BENZENE 1% AQ SOLN KMnO4

formation of red violet layer (bottom) and red layer (top)

3DROPS STYRENE 1% AQ SOLN KMnO4

reddish brown precipitate

formation of purple layer(bottom) and colorless layer(top)

2. BAEYER TEST FOR UNSATURATION

METHODOLOGY & RESULTS

ACETYLENE INTERPRETATION CMPD RESPONSIBLE FOR THE RESULT

2. BAEYER TEST FOR UNSATURATION

METHODOLOGY & RESULTS

TESTS FOR UNSATURATION

blue flame with yellow soot

METHODOLOGY & RESULTS

CMPD RESPONSIBLE FOR THE RESULT

C(s) and CO2 (g)

METHODOLOGY & RESULTS

TEST FOR AROMATICITY

TEST FOR AROMATICITY

B. TEST FOR AROMATICITY

1. NITRATION 2. LE ROSEN TEST

Pour into a an ice cold water

METHODOLOGY & RESULTS

Show the mechanism

TEST FOR AROMATICITY

TEST FOR AROMATICITY

5 drps Le Rosen reagent

cherry red sol'n

METHODOLOGY & RESULTS

C. TESTS FOR ACIDITY AND BASICITY

1. Ph OF AQUEOUS SOLUTION 2. NaHCO3 TEST 3. AgNO3 TEST 4. SILVER ACETYLIDE TEST

2 drps Acetic acid

Dissolve in 20 drps H2o

Dissolve in 20 drps H2o

Dissolve in 20 drps H2o

2 drps Benzoic acid (20mg+20 drps 95%ethanol)

Dissolve in 20 drps H2o

METHODOLOGY & RESULTS

2 drps acetic acid

evol'n of gas, clear sol'n

evol'n of gas, clear sol'n

evol'n of gas, clear sol'n

2 drps Benzoic acid

evol'n of gas, clear sol'n

METHODOLOGY & RESULTS

ANILINE BENZOIC ACID

METHODOLOGY & RESULTS

TEST FOR ACIDITY AND BASICITY