Experiment # 8A - QUALITATIVE ANALYSIS (A-E)

Avila, Kimberly & Pascual, Ian

Group 7, Chem 31.1, AB1, Ms. Sarah Sibug
May 15, 2014

ACETYLENE GAS
CaC2 + 2H2O ---> C2H2 + Ca(OH)2

ALKYL HALIDES - alcoholic AgNO 3 test

silver nitrate in ethanol was used to separate the
RX bond and create AgX
Although pure water is polar and a protic solvent,
it cannot initially dissolve the alkyl halides.
Therefore ethanol is used because the final
product AgCl is insoluble in polar solvents
SN1 since ethanol and -NO3 are both weak
nucleophiles
AgCl = white precipitate
AgBr = pale yellow precipitate
AgI = yellow precipitate
stability of the carbocation created by the leaving
group dictates reactivity. Stability: tertiary (3 0) >
secondary (20) > primary (10).
chlorobenzene should not react since the
removal of Cl would make the ring positively
charged. Benzyl chloride can because the charge
is on the methyl group

AROMATICITY - nitration
Aromatic rings have less reactive bonds and
undergoes electrophilic aromatic substitution
H2SO4 as a catalyst would protonate HNO 3 and
make NO2+ and H2O. -NO2 would substitute an H
from the ring in the ortho or para position,
especially since xylene has two methyl groups,
giving 2,6-dimethylnitrobenzene (C8H9NO2)

However, since benzoic acid has a deactivating

COOH attached to it, the -NO2 would attach in
the meta position

+ = weak almond smell and oily yellow solution

indicates the acidity of the H bonded to the

carbons in triple bonds
AgNO3 / NH4OH

HCCH ----> AgCCAg + 2HNO3

http://www.orgsyn.org/demo.aspx?prep=cv1p0372

ACIDITY/BASICITY
- AgNO3 test
carboxylic acid would react with AgNO 3/ethanol
to form a carboxylate salt with Ag
+ = white precipitate
HNO3 would lead to the H atom attaching to the
carboxylate ion, forming the carboxylic acid again
and dissolving the precipitate which would not
happen if AgX was created instead.
Acetic acid = CH3COO-Ag+

Benzoic acid = AgC7H5O2

AgNO3

HNO3

RCOOH ------>RCOO- Ag+ ----->RCOOH

ethanol

- Silver acetylide test

Tollen's reagent (ammoniacal solution of silver
nitrate) can be used to replace the hydrogen
bonded to the sp carbons
releases silver acetylide (AgCCAg) and HNO 3
useful in differentiating acetylene/ethyne (HCCH)
with ethylene/ethene (H2CCH2)
UNSATURATION

- Br2/I2 in CH2Cl2/CHCl3
methylene chloride or chloroform are inert
solvents; do not affect
electrophilic addition; no react with aromatic
+ = removal of color of Br2/I2
RHC=CHR --------> R(Br)HCCH(Br)R
- Baeyer test (KMnO4)
for presence of alkenes and alkynes
Baeyer's reagent is an alkaline solution of cold
KMnO4
+ = brown precipitate from MnO2
E+ addition, react only with styrene and ethyne

Jones' reagent (K2Cr2O7) oxidizes H attached to

carbon where OH is attached. 30 alcohols
therefore do not react.
+ = green color (Cr3+)
excess of primary alcohol with lack of oxidizing
agent creates aldehydes

excess of oxidizing agent creates carboxylic acid

20 alcohols create ketones

H2O

H2C=CH2 -------> (OH)H2CCH2(OH) + MnO2

H2O

HCCH -----------> (OH)2HCCH(OH)2 + MNO2

- Ignition test
burning of aromatic ring or unsaturated is
incomplete combustion
+ = yellow flame and soot
soot is the deposited carbon. The more sooty the
result, the higher the degree of unsaturation
increase in blue flame indicates increase in O2
assuming complete reaction:
C6H6 + 7.5O2 ----> 6CO2 + 3H2O
C6H14 + 9O2 ----> 6CO2 + 6H2O
C6H6 + O2 ----> CO2 + H2O + C(s)
ALCOHOLS
- Na metal
acidity of alcohol determines rate of bubbling
because hydrogen released is the acidic H.
Therefore, 10 > 20 > 30

PHENOLS
- FeCl3 test
+ = colored complex (ferric phenoxide)
colored complex may also be due to the solvent
used, as some phenols will color in chloroform,
alcohol, or aqueous.
pyridine

3ArOH + FeCl3 ------>Fe(OAr)3

- Br water test
+ = discoloration
OH attached to benzene is very receptive to E +.
Therefore bromination occurs

ROH + Na -------> RO-Na+ + H2

- Lucas test
Lucas reagent (ZnCl2 + HCl) converts OH to alkyl
chloride.
+ = formation of layer
alcohol solubility in reagent is limited to 6 carbons
stability of carbocation created determines rate of
layer formation. 30 > 20 > 10
10 - RCH2OH + HCl ----> non
20 - R2CHOH + HCl ----> R2CHCl + H2O
30 - R3COH + HCl ----> R3CCl + H2O

- Jones test

- Millon's test
+ = colored complex (red?)
Millon's reagent ((Hg(NO3))2 in H2O) creates
mercuric salts
test for 4-hydroxyphenylalanine
Mercurous and mercuric ions in nitrous and nitric
acid