I.

Solubility Test
5 drops of solvent in test tube
1- 2 drops/pinch test compound
Shake and check solubility

II. S1
Few H bonds (most on one side)
Less than 5C
III. S2
Many H bonds (OH 1:1 with H)
CARBS Reagent Test (+) Result (-)Result Implication Probable Cp
Molisch
sample + 2 drops rgt: -naphthol + 10 drops conc.
H2SO4 5 drops
red violet/purple
ring at interphase
aldopentose,
aldohexose free or combined forms
Benedict's
1mL rgt: CuSO4, Sodium Citrate, NaHCO3. Heat in
boiling water abth. 5 drops
brick red ppt,
Cu2O
free carbs, mono and di
(exc. sucrose) free vs combined C
Bial's
Sample + 10 drops rgt: orcinol, H2SO4 + Heat over
Bunsen until soln boils. 5 drops
blue green
solution
yellow to
brown solution pentose pentose vs hexose
Seliwanoff's
Sample+ rgt: resorcinol, H2SO4. Heat in water
bath. 5 drops
bright red solution
within 20-30secs ketohexose
ketohexose vs
aldohexose
Barfoed's
1mL rgt: Cu(OAc)2 in acetic acid. Heat in water
bath.
5 drops with (+)
result in Benedicts
mono vs di reducing
sugars
water
Soluble:
Ether
Soluble: S1
Insoluble:
S2
Insoluble:
5% NaOH
Soluble: 5%
NaHCO
3
Soluble: A1
Insoluble:
A2
Insoluble:
5% HCl
Soluble: B Insoluble
w/ N or S:
M
w/o N or S:
conc. H
2
SO
4
Soluble: N
Insoluble: I
UNKNOWN ANALYSIS
TIPS/STEPS:
1. Do Solubility Test
2. Do the tests found under the assigned solubility
class/es.
3. Once identified, do general tests for those found in
other solubility classes. (See note)
4. Check presence of carboxylic acid, alcohol or
phenol, carboxylic acid derivative, amide, amines,
hydrocarbons, etc.
(usually first row of each table is the general test)
5. If negative result, proceed with the general tests for
other tables.
6. If it gives positive result, proceed with rows below to
get the specific functional group attached.
NOTE: Compound assigned may belong to different
solubility classes. This is due to the presence of different
functional groups in the compound given. Sometimes,
other functional groups may be present even if a negative
result is obtained while checking the solubility class.
Doing two tests for confirmation purposes would do no
harm :P
Osazone formation
Sample + 10 drops C6H5NHNH2 + 1 drops conc
HCl. Heat in boiling water bath. Record odor. Cool
in ice bath. 5 drops same osazone epimers
Hydrolysis of
Polysaccharides HCl, (see bottom) polysaccharide
polysaccharide vs
disaccharide
Benedict's CuSO4, Sodium Citrate, NaHCO3
brick red ppt,
Cu2O
hydrolyzed
polysaccharide
hydrolyzed vs
unhydrolyzed
polysaccharide
Iodoform I2 in KI yellow solution
blue violet
complex
hydrolyzed
polysaccharide
hydrolyzed vs
unhydrolyzed
polysaccharide


IV. A1 - Strong acids
CARBOXYLIC ACIDS Reagent Test Positive Result Implication
Solubility 1 drop 5% or 0.5M NaHCO3 Pinch or drop bubbles/effervescence, soluble Carboxylic Acid
Formation of esters Sample + 5 or 10 drops alcohol + (if A1: 1 drop conc H2SO4.) 2 drops plastic balloon scent Carboxylic Acid
Solubility Litmus: 2 drops 2% NaOH + sample + 2-3 drops 0.1M FeCl3 dropwise tomato red solution, Fe(OH)2 Aliphatic carboxylic acid
Solubility
3 drops water + sample + (Heat until solid dissolves Cool.) Litmus: 0.3M
NH4OH. Boil excess ammonia. + 1 drop 0.1M FeCl3 Pinch or drop flesh colored ppt, Fe(Ar-COO
-
) Aromatic carboxylic Acid



HYDROLYSIS: micro test
tube: 10drops 10%
sucrose soln +10drops
distilled water.
+boiling stone, +2drops
conc HCl. Boil over flame
for 3mins.
Cool and neutralize
with 10% NaOH. Stir
after each addition of
base.
mortar: Grind 0.5g
starch w/ ditilled water.
Filter paste and wash w/
min. distilled water.
spot plate: drop of
filtrate + drop of I
2
in KI.
Record color.
Rest of filtrate, +5drops
conc HCl. Heat water
bath at 80C
Immediately, spotplate:
drop of heated starch
soln + drop of I
2
in KI.
Record color.
Perform at 1-min
intervals 3x until same
color.
Cool and neutralize with
10% NaOH. Stir at each
base addition.
V. A2 - Weak acids
Phenolic and alcoholic compounds
ALCOHOLS,
PHENOLS,
ETHERS Reagent
Test Sample/
Compound Positive Result Negative Result Implication Probable Compound
Lucas 2mL Lucas rgt: ZnCl2 in HCl 3-4 drops alcohol formation of layers Alcohol
Baeyer's 1 drop KMnO4 5 drops white ppt 1 or 2 Alcohol 1, 2, or 3 Alcohol
Oxidation of Phenols 1 drop KMnO4 5 drops brown ppt Phenol
Reaction (EArS) Br2 in H2O while shaking 3 drops
white ppt (2,4,6-
tribromophenol) Phenol
Complexation 1 drop FeCl3 3 drops decolorization Phenol

VI. B - Base
N containing
Ammonia derivatives: RNH2, RNHR, R-NR2, -N=
AMINES Reagent Test Positive Result (-)Result Implication Probable Cpd
Hinsberg's

2 drops benzenesulfonyl chloride + 1mL 10% NaOH
dpwise. If it heats, cool. If not alkaline, + more NaOH.

2 drops

with visible reaction NVR amine group present
separation of layers 2 or 3 amine 1, 2, or 3 amine
No separation

1 amine
Solubility 5% HCl formation of ppt 1 amine
Solubility Water + residue of 2 or 3 amine dissolved undissolved 2 or 3 amine
Solubility 5% HCl + residue of 2 or 3 amine dissolved undissolved 3 amine 2 or 3 amine

VII. M - Miscellaneous
Contain N but not basic
With S but not acidic
Amides, nitro compounds, 2HN-C=O
CARBOXYLIC ACIDS &
Derivatives Reagent Test Sample/ Compound Positive Result
Negative
Result Implication
Hydrolysis of C. Acid
Derivatives
Sample + 5 drops 2% NaOH.
Heat. Small pinch ammonium scent after heating Amides

VIII. N - Neutral
With double bonds (unsaturation)
Unsaturated compounds: Alkene or alkynes, compounds with O, ketones, ethers, most carboxylic acid derivatives


ACYL COMPOUNDS Reagent Test Positive Result Negative Result Implication Probable Compounds
5 drops 95% CH3CH2OH + 1mL 2,4-DNPH 2 drops yellow ppt/crystals
yellow orange
solution aldehydes, ketones carbonyl compounds
Tollens 5 drops Tollens rgt: Ag(NH3)
+
1 drop
silver mirror (may
need heat)
aromatic or aliphatic
aldehydes aldehydes vs ketones
Schiff's 4 drops Schiffs rgt: leucofuschin (pink) 1 drop purple solution aldehydes
Benedict's
5 drops Benedicts rgt: CuSO4, Sodium
Citrate, NaHCO3 1 drop brick red ppt, Cu2O aliphatic aldehydes
aliphatic vs aromatic
aldehydes
Iodoform
5 drops 10% NaOH + sample + I2 in KI
dpwise. Add until pale yellow. Warm bath. If
colorless, add more I2. Repeat 2 drops yellow ppt, CHI3
methyl ketones or
reduced form of
ketone (alcohol) methyl vs aromatic ketones

CARBOXYLIC ACIDS
Derivatives Reagent Test Positive Result
Negative
Result Implication
Formation of esters
Sample + 5 or 10 drops alcohol + (if A1: 1 drop conc
H2SO4.) 2 drops almond scent Acyl Halide
Hydroxamic Acid
Sample + 1 drop ether + 1 drop alcoholic NH2OH-HCl + 1
drop KOH. Heat to almost boil. Cool Acidify with alc. HCl
+ 1 drop 0.1M FeCl3 1 drop magenta colored Esters
Hydrolysis of C. Acid
Derivatives
Round bottom 10mL: sample + 5mL 25% NaOH. Reflux.
Disappearance of smell. + 6.0M HCl 2mL Sour smell Esters
5 drops water + sample + moisten blue litmus. 3 drops 2 carboxylic acids produced Acetic Anhydrides

IX. I - Inert
With double or triple bonds
Saturated & aromatic hydrocarbons, alkanes
Hydrocarbons Reagent Test Sample/ Compound Positive Result Negative Result Implication
1 drop 0.05M Br2 in light 2 drops
decolorization: orange
solution alkane, alkene
1 drop 0.05M Br2 in dark 2 drops no decolorization alkane, alkene
Oxidation Drops of 0.005m KMnO4 2 drops
(partial) purple decolorization
or (complete) brown ppt no decolorization alkene
Combustion Ignite under hood 5 drops on evap dish blue flame, clear smoke alkane


yellow flame, sooty smoke alkene, aromatic
Alkylation
2 drops t-butyl Cl (mix) +
anhydrous AlCl3 (while inclined
test tube) 1 drop decolorization aromatic


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IMPERIAL, Ria Edeliza S. CHEM 31.1 Organic Chemistry.