Download Lab 6

Faculty of Pharmacy & Biotechnology
Organic Chemistry
Laboratory manual
 3rd semester pharmacy students
 Winter 2015-2016
Lab 6:
Qualitative Analysis of Organic Compounds
1
Identification and Classification of organic compounds based on
functional groups.
Background:
Qualitative Analysis of Organic Compounds
The analysis and identification of unknown organic compounds constitutes a very
important aspect of experimental organic chemistry. There is no definite set procedure
that can be applied overall to organic qualitative analysis.
Some basic experimental tests and physical constants are necessary for identifying an
unknown compound. It is important that you understand just what information can and
cannot be obtained from each of them.
The identification and characterization of an unknown organic compound normally refers
to those processes or test that need to be preformed in order to answer the following
important questions:
1. What kind of elements (carbon, hydrogen, nitrogen, ….. ) are in the compound?
2. What kind of functional groups are in the compound?
3. Where in the molecule are these functional groups located?
Identification of organic compounds consists in a systematic procedure, this procedure
may be carried out in steps are:
1.
Preliminary examination or investigation: The preliminary investigation
consists in the study of physical properties of organic compound. of steps.
The various physical properties include condition (state), color, odor, and
solubility.
2.
Determination of physical properties such as melting point, melting point.
3.
Classification by solubility
4.
Functional-group classifications
5.
Elemental analysis (detection of Carbon, nitrogen, sulfur, halogen
elements using sodium fusion test).
6.
Confirmation through the preparation of derivatives.
7.
Special tests.
Most organic liquids are less dense than water, but alkyl halides, polyhalogenated
compounds, and many aryl halides are denser. If an organic liquid is denser than water, it
probably contains halogen.
2
General Scheme of Analysis
A. Preliminary Test:
Note physical characteristics: solid, liquid, color, and odor. Compounds that are yellow to
red in color are often highly conjugated.
1) Condition:
The simple observation as to whether the material is solid or liquid is an important first
guide for the unknown substance
The solid material should be examined to notice whether it is crystalline, amorphous or
fine powder.
In case of the liquid state, the constancy of the liquid material should be observed
(mobile, oily or viscous). Also, determine if the unknown is true liquid or solution by
adding anhydrous copper sulphate placed in a watch glass. The color will not be changed
with true liquids while with solutions it turns blue color.
2) Color:
The color of the original sample is noted, some compounds show color due to impurities,
while many others show colors due to the presence of chromophoric groups
(Conjugation System) in them Such as diene group. The color observation may help to
expect the unknown compound. Many chemical compounds are coloured because they
absorb visible light
3) Odor:
Some organic compounds have characteristic odors, others have disagreeable odors. Any
advantage from the minimal information obtained in this manner is heavily offset by the
risks involved; therefore strong smelling of the sample must be avoided.
The characteristic odors of some compounds are:
1. Alcoholic odor: methanol and ethanol.
2. Bitter almond odor: benzaldehyde and nitrobenzene
3. Mice like odor: Acetamide.
4. Pleasant fruity or floral smell odor: Esters
5. Vinegar like odor; acetic acid.
6. Fishy odor: Amines.
3
7. Phenolic odor: Many phenols
4) Solubility:
The solubility of the unknown in the following reagents provides very useful information.
In general
The solubility of organic compounds can be divided into two major categories:

Solubility in which a chemical reaction is the driving force
Example:

Solubility in acidic solution (such as carboxylic acids or phenols)
O
O
OH
O Na
OH
H2O

Solubility in basic solution (such as basic organic compounds, Amines)
NH2
NH3 Cl
H
H2O

Solubility in which simple solubility or miscibility due to Dipole-dipole
Interaction, Hydrogen bonding - special case of dipole-dipole when there is a
hydrogen bonded to a N, O, or F. (or Ion-dipole - interaction of an ion with a
polar molecule)
examples: dissolving any ionic compound in water), such as
o miscibility of Methanol (CH3OH) with water (H2O)
o dissolving of oxalic acid in water

The solubility is tested in different media: water, sodium hydroxide, and hydrochloric acid. The
solubility testing is carried out at room temperature.

If the organic compound is insoluble in water, acid and alkali, therefor, these compounds are
hydrocarbons, nitrohydro-carbon, Alkyl or Aryl halides, esters and ethers. higher molecular weight
Alcohols, Aldehydes and ketones.

Because hydrocarbons are insoluble in water, indicates that a non-polar functional group is present.

Salts are extremely polar and are usually water soluble.

Acids and amines are more soluble than non-polar compounds (due to H-bonding).

Solubility of amines decreases as the basicity decreases. (solubility decreases with the increase in the
number of carbon atoms)
4
B. Group Classification Tests:
After analysis of the previous tests (preliminary test), further information can be deduced
by performing carefully selected functional group classification tests.
Qualitative tests for Alkanes and Alkenes
I. Unsaturated compounds:
Two common types of unsaturated compounds are alkenes (Example cyclohexene) and alkynes
characterized by the carbon-carbon double and triple bond, respectively, as the functional group.
The two common qualitative tests for unsaturation are the reactions of the compounds with
1. Bromine in carbon tetrachloride.
2. Potassium permanganate.
(a) Bromine in carbon tetrachloride test:
Dissolve the compound and add the bromine and shake. rapid disappearance of the bromine
color to give a colorless solution is a positive test for unsaturation.
The reagent is potentially dangerous.
Keep it off your skin and clothes; protect
your eyes and nose
Br
Br2
Br
(b) Aqueous potassium permanganate test (Bayer test):
The reaction is based on the ability of potassium permanganate to oxidize double bond to diols.
Dissolve the compound and add the potassium permanganate solution dropwise and observe the
result.
OH
KMnO4
5
OH
Qualitative tests for Alkyl halides (Halogenated hydrocarbons)
n-Butyl bromide
Sec. Butyl bromide
Tertiary Butyl bromide
Qualitative tests for alkyl halides are useful in deciding whether the compound in question is a
primary, secondary, or tertiary halide.
Alcoholic Silver Nitrate The overall reaction is shown in the following equation:
RX + AgNO3
AgX + RONO2
Such a reaction will be of the SN1 type. Tertiary halides are more reactive in an SN1 reaction than
secondary halides, which are in turn more reactive than primary halides. Differing rates of silver
halide precipitation would be expected from halogen in each of these environments, namely,
primary < secondary < tertiary. These differences are best determined by testing with silver
nitrate and observing the results.
Add the alkyl halide to solution of silver nitrate, If no reaction is observed within five minutes at
room temperature, warm the mixture and observe any change.
Qualitative tests for Alcohols (R-OH)
The identifying of alcohol is the hydroxyl functional group, -OH bonded to carbon. Alcohols are
neutral and are classified into:
1. Monohydric alcohols
2. Polyhydric alcohols
They are almost colourless neutral liquids,
alcohols less than six carbon atoms are
miscible with water, but more than six
carbon atoms are sparingly soluble
e.g., methyl alcohol, Ethyl alcohol and
Tertiary butanol
e.g. glycerol. The poly-hydric alcohols
are colourless, neutral, viscous liquids
having sweet taste and are soluble in
water.
3. Aromatic alcohols
e.g. benzyl alcohol, aromatic
alcohols are oily colourless
liquids, insoluble in water and
The monohydric alcohols are divided to…
1. Primary alcohols
2. Secondary alcohols
CH3
H
H
H
HO
OH
CH3
H
OH
H
Primary Alcohol
Tertiary Alcohol
Secondary alcohol
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3. tertiary alcohols
General class reactions:
The tests for the hydroxyl group not only detect the presence of the group, but may also indicate
whether it is primary, secondary or tertiary.
1- Jones Reagent (CrO3-H2SO4 in H2O)
This reagent distinguishes primary and secondary alcohols from tertiary alcohols; the test
is based on the much greater resistance to oxidation of tertiary alcohols compared to the
other two types.
Dissolve one drop of your alcohol in acetone and add one drop of the jones reagent, and
shake the tube to mix the contents. Primary and secondary alcohols react within two
seconds as indicated by the disappearance of the orange color of the jones reagent and the
formation of a green or blue-green precipitate or emulsion. Tertiary alcohols do not react
even after 3 minutes.
(I)
RCH2OH
RCHO
RCOOH
(II)
R2CHOH
R2C=O
(III)
R3COH
no visible reaction.
2- Esterification The esters are flavoring or odor concentrates.
The esters may be formed by the direct reaction of a carboxylic acid with an alcohol.
Such a reaction is called an esterification reaction.
O
O
H+ / Heat
R
+
R1
OH
R1
R
OH
Carboxylic Acid
Alcohol
H2O
+
O
Ester
OH
O
CH3
COOH
H+ / Heat
Methyl alcohol react with Salicylic Acid yield
wintergreen odour of methyl Salicylate
+
H3C
OH
Methanol
OH
O
- H2O
Methyl Salicylate
(wintergreen odor)
Salicylic Acid
O
Ethyl alcohol react with Acetic Acid yield fruity odour
of ethyl Acetate
+
H / Heat
H3C
COOH
Acetic Acid
7
+
C2H5
OH
Ethanol
- H2O
C2H5
H3C
O
Ethyl Acetate (Furity odor)
3- Iodoform test: (Presence of three alpha hydrogens)
This experiment shows how methanol and ethanol behave differently when treated
H
H

CH2OH
H
with iodine solution and sodium hydroxide solution. Ethanol reacts to form a yellow
solid, triiodomethane, often called iodoform.
Dissolve your compound in water; Add NaOH solution and warm, then introduce the potassium
iodide - iodine reagent dropwise with shaking, the test is positive if a yellow precipitate of
iodoform is deposited.
O
H3C
H2
C
OH
I- / OHOxidation
O
I- / OHH3C
C
H
Sustitution
I 3C
C
heat / H2O
H
Hydrolysis
CHI3
+ H COOCH3
The Secondary alcohols with a CH3 on the carbon carrying the OH (eg propan-2-ol) give positive
HO
iodoform test
CH3
Qualitative tests for Phenols (Ar-OH)
Phenols are a class of organic compounds consisting of a hydroxyl group (-OH) bonded directly
to benzene ring.
The identification of phenols by
(1) FeCl3 test:
Phenols react with FeCl3 to form a colored complex with the Fe3+ ion. The color varies
from purple to orange depending on the structure of the phenol tested.
OH
O
FeCl3
Fe3+
O
O
 Phenol + FeCl3
give violet
 Cresol + FeCl3
give blue
 Hydroquinine (quinol) + FeCl3
give blue
 α-naphthol +FeCl3
give green
 β-naphthol + FeCl3
give green
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O
O
O
(2) With Chloroform and Sodium hydroxide reaction (formylation)(ReimannTimann reaction)
When phenol is react with chloroform and sodium hydroxide and heat gently, a formyl group –
CHO is introduced, and colored polymer formation.
OH
OH
OHC
CHCl3 / Conc. NaOH
OH
OH
CHO
Qualitative tests for Carbonyl compounds (Aldehyde and Ketone)
O
O
O
Carbonyl group
Aldehyde structure
Identification of carbonyl functional groups:
R
2,4-Dinitrophenyl hydrazine test (DNP)
H
C
Ketone structure
(as Brady's reagent),
R
NHNH2
O
NHN
C
NO2
R
NO2
H+
+
R
C
R
Aldehyde or ketone
NO2
NO2
2,4 dintrophenylhydrazine
2,4 dintrophenylhydrazone derivative
orange/red precipitate
Transfer two drops of unknown to a small test tube and add 4 or 7 drops of 2,4 DNP reagent and
shake. Formation of a red - yellow precipitate (a positive test) indicates the presence of an
aldehyde or ketone functional group.
Distinguishing between aldehyde and ketone functional group:
Fehling's solution.
Aldehydes reduce Fehling's solution to yellow or red copper (I) oxide, but ketone do not react.
Identification of presence of CH3CO- group in aldehyde and ketone
Iodoform reaction:
9
The iodoform test indicates the presence of an aldehyde or ketone in which one of the groups
directly attached to the carbonyl carbon is a methyl group (presence of three alpha hydrogens).
O
O
-
I2 / OH

R
+
CH3
R
HCI3
O
Sodium nitroprusside reaction
The nitroprusside ion forms a coloured complex with methyl ketones. In presence of alkali
Example, acetone is converted to CH3COCH2- ion which reacts with nitroprusside ion
[Fe(CN)5NO]2- to give highly coloured ion [Fe(CN)5NOCH2COCH3]2-.
Salicylic acid test:
The reaction of salicylic acid with formaldehyde in the presence of catalytic amounts of strong
mineral acid (such as Sulphuric acid) results in the condensation product, and polymer formation.
The final polymer is inevitably highly colored (the crimson red color are produced).
COOH
O
HOOC
OH
2
H
COOH
H
H+
HO
OH
Qualitative tests for carboxylic Acids
General Reactions of Carboxylic Acids:
(1) Na2CO3 test:
They decompose Na2CO3 to CO2 and sodium salt of the corresponding acid (distinction from most
phenols).
R-COOH + Na2CO3 → RCOONa + CO2 + H2O
The warm aqueous Na2CO3 is treated with few crystals (or few drops of acid). Effervescence due
the evolution of CO2 indicates the presence of COOH group.
(2) Ferric Chloride Reaction (fe3+ complex carboxylic acid):
FeCl3 will indicate the presence of aliphatic acids turning the solution a yellow color. Aromatic
acids will test as a beige-tan color.
10
For the success of this reaction it is important that the solution should be-neutral. Excess of acid
usually inhibits the production of color or precipitate, and excess of alkali gives gelatinous
reddish-brown precipitate of ferric hydroxide.
To the cold neutral solution of the acid add a few drops of FeCl 3, solution and observe the colour
or the ppt. formed.
3R
FeCl3
COOH
(R
COO )3 Fe + 3 HCl + H2O
heating
(R
COO )(OH)2Fe
Examples
1- Formic acid, HCOOH
Formic acid is the only one, which possesses both carboxyl and aldehyde groups activities
OH
OH
Aldehyde group
O
O
Carboxyl group
H
H
Formic acid is the only carboxylic acid that reduce Fehling reagent, mercuric chloride and
KMnO4
Mercuric chloride test (HgCl2):
Add mercuric chloride solution to formic acid or a solution of formate and warm. A white ppt. of
mercurous chloride Hg2Cl2, insoluble in dil. HCl, is produced.
HCOOH + 2 HgCl2
Hg2Cl2 + CO2 + 2 HCl
2-Lactic Acid CH3CH(OH)COOH
Iodoform Test:
Lactic acid gives positive iodoform test because it contain the CH3CH(OH) group. This test is
done by adding exess NaOH till alkali and blue litmus to the liquid lactic acid. the add excess
iodine solution and warm gently to give yellow ppt of iodoform.
OH
O
NaOH
NaOH
CH
H3C
C
COOH
I2 / 
H3C
11
COOH
I2 / 
CHI3
Yellow ppt
4-Tartaric acid
Action of CaCl2;
When a neutral solution of a tartarate is treated with CaC12 solution a white ppt. of calcium
tartarate is separated on the cold after scratching and stirring
2- Fenton's Reagent: (Oxidation of tartaric acid in the presence of iron)
To a solution of tartaric acid or a tartarate add 1 drop of freshly prepared ferrous sulphate
solution, 1 drop of hydrogen peroxide solution and excess of NaOH solution. An intense violet
colour is produced due to the ferrous salt of dihydroxyfumaric acid, (HOOC-C(OH)=C(OH)COOH). This test is positive to tartaric and tartarates only.
COOH
Fe(II)
Fe(III)
CHOH
ferrous salt of dihydroxyfumaric acid
CHOH
COOH
OH· + OH
H2O2
Qualitative tests for salts of carboxylic Acids
Carboxylic acid salt is the salt (RCOO-M+) formed when a carboxylic acid reacts with a base.
carboxylic acid salts are ionic compounds and soluble in water
Qualitative tests for salts of carboxylic Acids Ester (R-CO-OR-)
Hydroxamic acid test
R-CO-OR' + H2N-OH
R-CO-NH-OH + R'-OH
Esters react with hydroxylamine in the presence of sodium hydroxide to form the sodium salt of
the corresponding hydroxamic acid. On acidification and addition of ferric chloride the magentacoloured iron (III) complex of the hydroxamic acid is formed.
It is always advisable to ensure that an unknown compound does not give a colour with iron (III)
chloride before carrying out the hydroxamic acid test.
Qualitative tests for salts of Amines
12
Reaction with benzenesulphonyl chloride
Benzenesulphonyl chloride reacts with primary and secondary but not with
tertiary amines to yield substituted sulphonamides.
a)
C6H5SO2Cl + H-NHR + NaOH
C6H5SO2NHR + NaCl + H2O
b)
C6H5SO2Cl + H-NR2 + NaOH
C6H5SO2NR2 + NaCl + H2O
The substituted sulphonamide formed from a primary amine dissolves in the alkali medium whilst
that produced from a secondary amine is insoluble in alkali.
Qualitative tests for salts of Amides (R-CO-NH2)
Example: Urea
Action of nitric acid:
When nitric acid is presented, it ionizes. A hydrogen ion [proton] contributed by the acid is
attracted to the oxygen and forms a covalent bond [electrophile H+]. The electronegative NO3- ion
then is attracted to the positive hydrogen ion. This forms an ionic bond and hence the compound
urea nitrate (white ppt).
OH NO3
O
+
H2N
HNO3
H2N
NH2
13
NH2
Acidity test:
Preparation of the Neutral Solution:
(1) When the Unknown is Liquid
In your test tube place 2 ml of the unknown, and then add ½ spatula of Na 2CO3
powder.
(1) When the unknown is liquid:
In small beaker, 5 ml Water
+ 3 ml of Unknown + Add Ammonia dropwise until neutralization occur, using
the Litmus Paper
(2) When the Unknown is Solid
In your test tube place 2 ml Na2CO3 Solution and heat it in the water bath, and
then add ½ spatula of unknown.
If Red L.P (Acidic) ..............................................................add NH 3
If Blue L.P (Alkali)…………….…………………………..…add unk.
If yellow L.P (neutral) …………………………………….… PH ≈7
(2) When the unknown is Solid (soluble or insoluble in water):
In small beaker, 10 ml water, + ½ spatula of the unknown + add 6 drops of
Ammonia, and then stir well vigorous.
Brady’s test:
(In Dry test tube)
Solubility and Miscibility tests:
1 ml Unk. (or quarter spatula)
+ 3 ml H2O Then shake well….
For Liquid Unk.
if One layer formed………..……………….………....….Miscible with water
if Two layers formed..………… ………………….…..Immiscible with water
When the Unknown is Liquid
2 ml Brady’s reagent
+ 3 or 4 drop Unk.
N-FeCl3 test:
1 ml Unk. (or Unk. Soln.)
+ add 3 – 4 drops of N-FeCl3 drop by
drop
(whit and watching the colour)
If you have Acidic Unknown, Use
its Neutral Soln.
For Solid Unk.
if soluble in water……………………………….……..…..….Soluble in water
if ppt with vigorous shake ……………………………..…..Insoluble in water
Fehling test:
CaCl2 test:
Jones test:
1 ml Unk.
+ 1ml Fehling A
+ 1 ml Fehling B
Then Shake well, and boil in water
bath for 5 min.
1 ml Unk. (or Unk. Soln.)
+ 2 ml CaCl2
4 – 5 drops of Unk.
+ 1 ml of acetone
+ 1 ml of jones reagent
and shake
If you have Acidic Unk., Use the
Neutral Soln.
The Decolourization ≡ the
yellow-orange colour of the
jones turns green
Change of the Blue into Reddish
brown is the +ve test
Hydroxamic Acid test
Confirmatory of ethyl acetate.
Chloroform (CHCl3/NaOH) test:
For resoncinol and quinol..
0.5 ml of Unk.
+ 1 ml of hydroxyl amine HCl
+ 1 ml of 30% NaOH
Then heat in water bath for 5 min
One spatula of Unk. (solid)
+ 2 ml 30% NaOH
+ 2 ml chloroform
Then heat gently with shaking.
1 ml of conc. Solution of the Unk.
+ 2 ml HNO3
The formed white ppt will
dissolve in excess water
Fenton test
Confirmatory of Tartaric acid and
Tartrate salts
1 ml of Unk. soln.
+ 1 – 2 drops of FeSO4
+ 1 drop of H2O2
Then shake well
Then add 2 ml of 10% NaOH
2 ml of unk.
+ 3-4 drops of KMnO4
The Decolourization ≡ the purple
colour of the permanganate
turns brown
Sodium Nitroprusside test:
(for Differentiation between
Formaldehyde and Acetaldehyde)…
Alkaline KMnO4:
Confirmatory of formic Acid
(or Formate salts)
1 ml of Unk.
+ 2 ml of sodium nitroprusside
solution
Then add 10% NaOH in excess
2 ml Unk. (or Unk. Soln.)
+ 1 ml 10% NaOH
Warm in water bath 5 min
Then, add 1 ml KMnO4
Then cool the test tube and 2 ml of
dil. HCl
+ 2 ml of ethanol
+ 2 – 3 drops of 5% FeCl3 Soln.
Conc. HNO3 test:
Confirmatory of urea..
KMnO4 test:
(for Differentiation between
Saturated and Unsaturated
hydrocarbons)…
Salicylic Acid test:
Confirmatory of Formaldehyde….
1 ml Unk.
+ ⅓ spatula salicylic Acid
+ add 4 drops conc. H2SO4 (on
the wall)
14
Iodoform test:
(1) For Acetaldehyde
1 ml Unk.
+ 1 ml H2O
+ 2 ml Na2CO3 solution
Boil in water bath for 3 min, and then add 4 or 5 ml Iodine (I2) soln.
Basic Radical test:
(for Differentiation between Ammonium and Sodium Salts)….
Half spatula Unk (solid)
+ 3 ml 30% NaOH
Then shake well
Observe the odour carefully
If Ammonia odour………………………....... Ammonium Salt. (R-COO- NH4+)
If No Ammonia odour ……………………………....Sodium Salt. (R-COO- Na+)
(2) For Acetone
1 ml Unk.
+ 1 ml H2O
+ 2 ml 10% NaOH solution
Boil in water bath for 5 min, and then add 4 or 5 ml Iodine (I2) soln.
(3) For Lactic Acid
1 ml Unk.
+ 2 ml H2O
+ 4 ml 30% NaOH
Boil in water bath for 5 min, and then add 3 or 4 ml Iodine (I2) soln.
(4) For Differentiation between Methanol and Ethanol
1 ml Unk.
+ 2 ml H2O
+ 2 ml 10% NaOH solution
Boil in water bath for 10 min, and then add 4 or 5 ml Iodine (I2) soln.
Esterification test:
(1) Confirmatory of Alcohols….
4 ml Unk.
+ 1 ml appropriate Acid (or ¼ spatula)
+ 3 drops conc. H2SO4, then boil in water bath for 10 min.
Then, pour the contents of the test tube on beaker containing Na2CO3 soln.
For all Iodoform test:
Leave the test tube (stand) for 5 -10 minutes to see the yellow ppt in
the bottom
15
Lab 6
Identification
Lab Report:
Name:
……………………………………………………………………………………………………..……………….........................................................................................................……….……………………………………………………………………………………
ID:
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T:
…………………....................................………………………………………………
You will exam the following tests:
1. The physical characteristicss of each sample:

The condition: ……solid or liquid……………………..………………….……………………………………………………………..

The colour: …………………………………………………………………………………….………………………………………………………..

The solubility: ………………………………………………………………………………………………………………………………………..

With Litmus paper: …………………………………………………………..…………………………………………………………………...
2. The chemical tests…
The test
1. Solubility test
2. Unsaturated
test
(With KMnO4)
3. Alcoholic
AgNO3 test
4. Jones test
5. Iodoform test
The samples
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

observation
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Soluble sample
Insoluble sample
Miscible sample
Immscible sample
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Cyclohexane
Cyclohexene
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n-Butyl bromide
Tert-butyl bromide
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Methanol
Tert-butanol
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Methanol
Ethanol
Lactic Acid
16
6. N-Fecl3 test
7. Brady’s test
8. Fehling test








Resorcinol
Formic Acid
Lactic Acid
Tartric Acid
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Formaldehyde or Acetone
non-carbonyl sample
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Formaldehyde
Acetone
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 An acidic sample
9. Sodium
 Non-acidic sample
Carbonate test  Sodium formate
10. Basic radical
test
11. Hydroxamic
acid test
12. Hinsberg test





Sodium Salt
Ammonium Salt
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Ethyl Acetae
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n-butyl amine
Tri-butyl amine
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17
Cyclohexane
Cyclohexene
n- Butyl Bromide
H2
C
H3C
Tertiary Butyl
Alcohol
Ethanol
H3C
H3C
C
Methanol
Acetaldehyde
Acetone
H2
C
C
H2
Resorcinol
Br
Formaldehyde
CH3
H2
C
Tertiary Butyl
Bromide
O
O
O
OH
OH
H
CH3
Formic acid
Lactic Acid
Tartaric
Acid
H
H3C
Ethyl Acetate
CH3
H3 C
H
n-Butyl Amine
O
O
O
H2
C
H3C
CH
H
C2H5
OH
H3C
OH
H3C
O
H2
C
C
H2
NH2
OH
Tri-Butyl Amine
Urea
Salts of Acids
H3C
H2C
O
CH2
H2C
CH2
N
H2C
H3C
CH2
H2
C
CH3
R
CH2
O M
Wherw, the M is Cation (Sodium or Ammonium)
CH2
18