Organic Derivatives of Water Flashcards
can be classified based on
the number of alkyl groups attached
to the carbon that contains the
hydroxyl group
alcohol
react with various oxidizing agents
primary and secondary alcohol
alcohols that are
unreactive, but most reactive to
nucleophilic substitution in Lucas
reagent
tertiary alcohol
quite reactive
to nucleophilic substitution
secondary alcohol
unreactive to
nucleophilic substitution
primary alcohol
only oxidized only by the
strongest oxidative agents
phenol
useful chemical
test for determining phenols from
alcohols
ferric chloride test
generally unreactive as it
has a very stable bond
ethers
organic derivatives of water include
hydroxyl
carbonyl
carboxyl
amine
ester
ether
thiol
materials and reagent needed for test of organic derivatives of water
1-butanol
2-butanol
2-methyl-2-propanol
cyclohexanol
ethylene glycol
Phenol
2-napthtol
Bayer’s reagent
KmnO4
Sodium dichromate
Na2Cr2O7
sulfuric acid
H2SO4
reagents needed
lucas reagent
Bayer’s reagent
1.00M Sodium dichromate
Sulfuric acid
Ferric Chloride
Distilled Water
1.00M NaOH
Iodine solution
sodium metal
equipment needed
Test tube
Pasteur pipettes
corrosive substances used
phenol
conc. sulfuric acid
sodium dichromate
NaOH
what to do
with corrosive substances
avoid skin contact
its vapor is toxic, so
avoid inhalation
diethyl ether
how many drops of the following are placed on separate dry test tube:
➢ 1-butanol
➢ 2-butanol
➢ 2-methyl-2-propanol
➢ Cyclohexanol
➢ Ethylene glycol
➢ Phenol
➢ 2-napthtol
procedures of solubility in water
2 mL of distilled water
shake and observe
procedures of acidic properties of alcohols (using sodium metal)
add a small piece of dry sodium metal
add 2 mL of each sample,
observe the rate of evolution of
hydrogen gas
test for solubility in NaOh
5 drops of NaOH
shake and observe solubility
Bayer’s oxidation
5 drops of Bayer’s reagent,
shake and observe
chromic acid oxidation
add 5 mL of Na2Cr2O7
2 drops of conc. H2SO4,
and add 2 drops of sample, observe.
lucas test
add 2mL of Lucas reagent,
add sample,
seal the test tube
shake and observe reaction
ferric chloride test
add small amount of sample
add 1 mL of deionized water
and add several drops of 2.5 M aqueous ferric chloride solution
shake and observe reaction.
compounds tested that are soluble in water
1-butanol
2-methyl-2propanol
ethylene glycol
what bonds do 1- butanol, 2-methyl-2-propanol and
ethylene glycol have with water
molecules
hydrogen bonds
where the water has a
slightly positive charge on this
hydrogen
where the water has a
slightly negative charge on these
oxygen
contains hydroxyl (-OH)
group, which is the functional group
responsible for its solubility in water,
the oxygen atom in the hydroxyl
group can form hydrogen bonds with
water molecules, allowing 1-butanol
to dissolve in water
1-butanol
contains a
hydroxyl group, enabling it to form
hydrogen bonds with water
molecules. The presence of a
branched alkyl group does not
significantly affect its solubility since
the hydroxyl group is the main
determining factor
2-methyl-2-propanol
- is a diol, meaning it
contains two hydroxyl groups. These
hydroxyl groups can also form
hydrogen bonds with water
molecules, facilitating its solubility.
Additionally, ethylene glycol has a
small molecular size, further
enhancing its solubility in water
ethylene glycol
not soluble in water
compared to other alcohols due to it
having a bulky cyclohexyl group attached to the hydroxyl (-OH)
functional group.
cyclohexanol
introduces a
significant nonpolar component to
the molecule, making it less
compatible with the polar nature of
water
cyclohexyl group
The nonpolar nature
of the cyclohexyl group makes this
more hydrophobic, or waterrepellent.
cyclohexanol
qualities that can influence solubility and insolubility in water
presence of polar functional groups
size and shape
hydrophobicity
results of acidic properties of alcohol using sodium metal
1-butanol - positive
2-butanol - positive
2-methyl-2-propanol - positive
is an organic compound
with a hydroxyl group bound to an
aliphatic carbon atom
alcohol
this character of alcohol is
revealed through its reactions with
active metals.
acidic
reason of acidity of
alcohol which decreases as the
electron density on the oxygen atom
increases
polarity of OH
primary alcohol that is
more acidic than secondary and
tertiary alcoho
1-butanol
exhibit a faster
reaction when combined with the
sodium metal and the evident release
of hydrogen gas
primary alcohol
in this, there is a
decrease in acidity strength due to
the addition of alkyl group on carbon
tertiary alcohol
result of chromic acid oxidation
1-butanol - positive
2-butanol - positive
2-methyl-2-propanol - negative
- To test the oxidation of alcohol, the
following are mixed together for the chromic oxidation test:
sodium dichromate (NaCr2O7)
sulfuric acid (H2SO4)
products on oxidation depend on the
type of alcohol:
primary
secondary
tertiary
tested positive in the chromic acid oxidation
due to the disappearance of the redorange color of chromic acid and the formation of a blue-green color of the Cr (III) ion
1-butanol, 2-butanol,
formed if a sample is positive in the chromic acid
oxidation
chromium (III) ion
as this oxidizes the C2O7 ions in the solution are reduced to chromium (III)
alcohol
showed resistance to oxidation by
to the oxidizing agent
2-methyl-2-propanol
- demonstrated by
the retention of the solution’s original
color in chromic acid oxidation
negative reaction
process where the
hydrogen atom in the -OH and the αhydrogen atom on the carbon atom to
which the -OH is attached are
removed to form a C=O bond
oxidation
does not contain an
α-hydrogen, the C=O cannot be
formed.
tertiary
- formed via the oxidation of
secondary alcohols
ketones
formed via the oxidation of primary alcohols
aldehyde
result of lucas test
1-butanol - negative
2-butanol - positive
2-methyl-2-propanol - positive
its reactivity determines
whether they are classified as
primary, secondary, or tertiary. This
is due to the substitution of a
hydroxyl group produced from the
provided alcohol in place of the
chloride (Cl-) in the zinc-chloride
bond.
Lucas test
after mixing the Lucas reagent with
this, a change of color from colorless
to slightly clear and white,
respectively, was seen.
2-butanol and 2-methyl-2-propanol
remains colorless (no
reaction) in Lucas test
1-butanol
the change of color of
the solution from clear to cloudy
suggests that this has been formed
and therefore indicates a positive
reaction for the Lucas test.
chloroalkane
- are the most
reactive to nucleophilic substitution
in the Lucas reagent
tertiary alcohol
are moderately
reactive in Lucas reagent
secondary alcohol
are unreactive in
Lucas reagent
primary alcohol
its
mechanism starts when the OH
group of alcohol is protonated by
hydrochloric acid
nucleophilic substitution
is a stronger
nucleophile than water (H₂O),
chlorine
formed in the
nucleophilic substitution in the Lucas
test
carbocation
immediately attacks
the carbocation in the lucas test
chloride anion
formed after the
chloride anion attacking the
carbocation
alkyl chloride
is insoluble, making the
solution murky
alkyl chloride
result of iodoform test
1-butanol - negative
2-butanol - positive
2-methyl-2-propanol - negative
is used to
differentiate the ability of primary,
secondary, and tertiary alcohols to
undergo oxidation and form a yellow
precipitate called iodoform (CHI3)
iodoform test
yellow precipitate that was
formed in the iodoform test
iodoform (CHI3)
sample that has visible
yellow precipitate
2-butanol
has no visible precipitate in the test
1-butanol and 2-methyl-2-propanol
did not show iodoform because of them lacking a
methyl ketone group next to the carbonyl
group
1-butanol
when iodine
(I2) was allowed to react with these
two compounds, it only produced a
colorless solution without any
precipitate.
1-butanol
the solution
turning into a yellow color without
any visible precipitate in it and thus
inferring that tertiary alcohols does
not give the iodoform reaction
2-methyl-2-propanol
- has shown a positive
result indicated by the cloudy yellow
precipitate seen in the test tube.
Unlike 1-butanol, this has a methyl
ketone group, which is essential for
the iodoform to occur.
2-butanol
result of ferric chloride test
phenol - positive
2-napthol - negative
are organic
substances that have an aromatic
ring and a hydroxyl group directly
connected
phenol
due to the phenol having
this, phenol reacts with ferric
chloride to produce colored
compounds
enol group
what the phenol group
interacts with to generate a colored
complex, which is violet in color
ferric ion
is created in the
ferric chloride test, , which results in
various colored water soluble
complex compounds, phenols react with ferric chloride solution to yield
blue, violet, or green coloring.
ferric phenoxide
this hue in ferric
chloride test suggest that it is
produced by ortho, meta, or paracresol with resorcinol
violet or blue
gives green color
beta-naphthol
- gives pink color.
alpha-naphthol
forms a
deep red colo
acetic acid and formic acid
demonstrated a
negative reaction, as seen by its clear
yellowish hue, ferric chlorideoriginal color.
2-naphthol