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Exercises 6,7,8 Handout
Exercises 6,7,8 Handout
HYDROCARBONS
HYDROCARBONS
OBJECTIVES:
At the end of the exercise, the student should be able to:
Functional Group
is a group of atoms that has
characteristic chemical
behavior in every molecuIe
where it occurs.
(reactive sites)
The chemistry of
every organic molecule,
regardless of size and
complexity, is determined
by the functional groups
it contains.
Functional groups
Hydrocarbons
- they contain only carbon and hydrogen
Hydrocarbons
Aliphatic
Aromatic
Hydrocarbons
Aliphatic
Alkanes
Aromatic
Alkenes
Alkynes
Cyclic aliphatic
Hydrocarbons
Aliphatic
Alkanes
Hydrocarbons
Aliphatic
Alkanes
Hydrocarbons
Aliphatic
H
C
Alkenes
Hydrocarbons
Aliphatic
HC
CH
Alkynes
Hydrocarbons
Aliphatic
Cyclic aliphatic
Hydrocarbons
The most common aromatic
hydrocarbons are those that
contain a benzene ring.
H
H
Aromatic
HYDROCARBONS
Samples:
Cyclohexane
Benzene
Cyclohexene
Toluene
Acetylene
Solubility Tests
Sample
CH2Cl2
H2O
NaOH
H2SO4
cyclohexane
cyclohexene
benzene
toluene
Legend:
(+) miscible
(-) immiscible
Solubility Tests
Sample
CH2Cl2
H2O
NaOH
H2SO4
cyclohexane
cyclohexene
benzene
toluene
Legend:
(+) miscible
(-) immiscible
Solubility Tests
Sample
CH2Cl2
H2O
NaOH
H2SO4
cyclohexane
cyclohexene
benzene
toluene
Legend:
(+) miscible
(-) immiscible
Solubility Tests
Sample
CH2Cl2
H2O
NaOH
H2SO4
cyclohexane
cyclohexene
benzene
toluene
Legend:
(+) miscible
(-) immiscible
Solubility Tests
Explanation:
When alkenes are treated with cold concentrated
sulfuric acid, they dissolve because they react by
electrophilic addition to form alkyl hydrogen sulfates
(ROSO3H)
Halogenation/Bromination
Reagent: Br2/CH2Cl2
Positive Result: loss of red-orange color of Br2
(-)
(+)
Halogenation/Bromination
Reagent: Br2/CH2Cl2
Positive Result: loss of red-orange color of Br2
Sample
Light Reaction
Dark Reaction
cyclohexane
cyclohexene
acetylene
benzene
toluene
Halogenation/Bromination
Explanation:
Halogenation/Bromination
Halogenation/Bromination
Halogenation/Bromination
Halogenation/Bromination
Steps:
Halogenation/Bromination
Halogenation/Bromination
Halogenation/Bromination
Halogenation/Bromination
Halogenation/Bromination
R+H
Halogenation/Bromination
Halogenation/Bromination
Halogenation/Bromination
Reaction: cyclohexane
Halogenation/Bromination
Reaction: toluene
Halogenation/Bromination
Reaction:
toluene undergoes bromination at a faster rate despite
that it is brominated at a 1 carbon
explained by the resonance stabilization of benzyllic
free radical
Halogenation/Bromination
Reaction:
stability of free-radical:
benzyllic > 3o > 2o > 1o > CH3
ease
of formation of free-radical:
Halogenation/Bromination
Halogenation/Bromination
Halogenation/Bromination
Halogenation/Bromination
Halogenation/Bromination
Halogenation/Bromination
Stability of carbocation:
benzyllic > 3o > 2o > 1o
Halogenation/Bromination
Reaction: cyclohexene
Halogenation/Bromination
Reaction: acetylene
Results
Explanation
cyclohexane
absence of unsaturation
cyclohexene
presence of unsaturation
acetylene
presence of unsaturation
benzene
toluene
(-)
(+)
(Heat and the addition of acid are avoided which can promote further
oxidation of the glycol, with cleavage of the carbon-carbon double
bond)
Results
Explanation
Results
Explanation
cyclohexane
cyclohexene
acetylene
terminal alkyne
Exercise 7
OBJECTIVES:
At the end of the exercise, the student should be able to:
Alcohol
Phenol
Ether
Alcohol
Alcohol
Phenol
Ether
organic compounds in which two
saturated carbon atoms are bound
through a single oxygen atom
Samples:
1-Butanol
2-Butanol
tert-Butanol
Phenol
Diisopropyl ether
Solubility Tests
Sample
H2O
NaOH
H2SO4
1-butanol
2-butanol
+/-
tert-butanol
phenol
diisopropyl ether
Solubility Tests
Sample
H2O
NaOH
H2SO4
1-butanol
2-butanol
+/-
tert-butanol
phenol
diisopropyl ether
Solubility Tests
Sample
H2O
NaOH
H2SO4
1-butanol
2-butanol
+/-
tert-butanol
phenol
diisopropyl ether
Solubility Tests
Sample
H2O
NaOH
1-butanol
2-butanol
+/-
tert-butanol
phenol
diisopropyl ether
H2SO4
Solubility Tests
Sample
H2O
NaOH
1-butanol
2-butanol
+/-
tert-butanol
phenol
diisopropyl ether
H2SO4
Solubility Tests
Explanation:
Comparative acidities of alcohols and phenols:
Solubility Tests
Explanation:
Comparative acidities of alcohols and phenols:
The differences in acidities can be explained by the
relative stabilities of the conjugate bases.
Solubility Tests
Explanation:
Comparative acidities of alcohols and phenols:
conjugate base of alcohol: alkoxide
e.g. butanol 1-butoxide
The negative charge on the
O atom of the butoxide is
intensified by the electron
releasing alkyl group
(CH3CH2CH2CH2-) and is
therefore destabilized.
Solubility Tests
Explanation:
Comparative acidities of alcohols and phenols:
conjugate base of alcohol: alkoxide
e.g. 1-butanol 1-butoxide
Solubility Tests
Explanation:
Comparative acidities of alcohols and phenols:
For phenol, it forms upon losing a proton the
resonance-stabilized phenoxide ion.
Solubility Tests
Explanation:
Comparative acidities of alcohols and phenols:
Because of the resonance forms of the phenoxide,
phenol has a greater tendency to lose a proton to form
the more stable phenoxide ion.
phenol is thus a stronger acid than butanol
Solubility Tests
Sample
H2O
NaOH
H2SO4
1-butanol
2-butanol
+/-
tert-butanol
phenol
diisopropyl ether
Solubility in H2SO4
Most organic derivatives of water are soluble in H2SO4.
This solubility test is often used to indicate the presence of
oxygen atoms in a molecule.
Solubility Tests
Explanation:
2o alcohols are oxidized to ketones
Solubility Tests
Explanation:
3o alcohols dont normally react with most oxidizing
agents (no H on the C-OH to oxidize)
Solubility Tests
Explanation:
reaction of a phenol with strong oxidizing agents
yields a quinone
Lucas Test
Reagent: HCl-ZnCl2
Positive Result: appearance of cloudiness due to (alkyl chloride
formed)
Sample
1-butanol
2-butanol
tert-butanol
Result
Lucas Test
Reagent: HCl-ZnCl2
Positive Result: appearance of cloudiness due to (alkyl chloride
formed)
Sample
Result
1-butanol
2-butanol
tert-butanol
Lucas Test
Left to right: 1, 2 & 3 alcohol
immediately after addition of Lucas reagent
Lucas Test
Left to right: 1, 2 & 3 alcohol
2 minutes after addition of Lucas reagent
Lucas Test
Left to right: 1, 2 & 3 alcohol
5 minutes after addition of Lucas reagent
Lucas Test
Left to right: 1, 2 & 3 alcohol
5 minutes after addition of Lucas reagent
Note:
1 alcohols do not turn cloudy
2 alcohols turn cloudy after
2-5 minutes
3 alcohols turn cloudy
instantly with addition of Lucas
reagent
Lucas Test
Left to right: 1, 2 & 3 alcohol
5 minutes after addition of Lucas reagent
Lucas Test
Reactions:
Alcohol
KMnO4
Lucas
1 ROH
2 ROH
3 ROH
Sample
Result
1-butanol
phenol
(-)
(+)
Note:
formation of red color indicates
positive results and therefore the
presence of an aromatic
compound
Tollens Test
Reagent: Ag(NH3)2+
Positive Result: formation of silver mirror
Sample
Result
1-butanol
2-butanol
phenol
Tollens Test
Reagent: Ag(NH3)2+
Positive Result: formation of silver mirror
(+)
(-)
Tollens Test
Reactions:
Iodoform Test
Reagent: I2/KI
Positive Result: formation of yellow precipitate
Sample
Result
1-butanol
2-butanol
Iodoform Test
Left to right: methyl ketone, 2-butanol and alkane
Iodoform Test
Left to right: methyl ketone, 2-butanol and alkane
Iodoform Test
Left to right: methyl ketone, 2-butanol and alkane
Note:
Formation of pale yellow precipitate
indicates positive test for the
presence of methyl ketones.
2-Butanol is oxidized to 2butanone which is a methyl ketone.
it will also produce a pale yellow
precipitate
Iodoform Test
Left to right: methyl ketone, 2-butanol and alkane
Iodoform Test
Generalization:
Sample
Hot Acidic
KMnO4
Lucas Test
FeCl3
Tollens Test
1 ROH
2 ROH
3 ROH
Ar-OH
NA
R-O-R
NA
Exercise 8
OBJECTIVES:
At the end of this laboratory exercise, the student should
be able to:
identify the chemical properties of carbonyl compounds
and carbohydrates
to recognize the similarities and differences in the
chemical reactivity of aldehydes and ketones; and
to apply chemical tests that distinguish among the
different types of carbohydrates.
CARBONYL COMPOUNDS
Result
benzaldehyde
acetone
glucose
starch
Glucose
Acetone
Starch
Result
acetaldehyde
acetone
Note:
precipitate indicates (+)
test for aldehydes and
ketones
Tollens Test
Reagent: Ag(NH3)2+
Positive Result: formation of silver mirror
Sample
Result
acetaldehyde
acetone
Tollens Test
Explanation:
Tollens test is used to differentiate aldehydes from ketones
based on their ability to be oxidized
Iodoform Test
Reagent: I2/KI
Positive Result: formation of yellow precipitate
Sample
Result
cyclohexanone
acetone
Iodoform Test
Left to right: methyl ketone, 2-butanol and alkane
Iodoform Test
Left to right: methyl ketone, 2-butanol and alkane
Iodoform Test
Reaction:
CARBOHYDRATES
often have the formula C x(H2O)y - hydrates of carbon
simple carbohydrates are also known as sugars or
saccharides (Latin saccharum, Greek sakcharon, sugar) and the
ending of the names of most sugars is ose
usually defined as polyhydroxy aldehydes and ketones
substances that hydrolyze to yield polyhydroxy
aldehydes and ketones
they exist primarily in their hemiacetal or acetal forms
CARBOHYDRATES
Classification based on whether the carbohydrate can be
broken down into smaller units:
monosaccharides - simplest CHO, those that cannot be
hydrolyzed into simpler carbohydrates
disaccharides - CHO that undergo hydrolysis to produce
only 2 molecules of monosaccharide
oligosaccharides CHO that hydrolyze to yield 210
molecules of monosaccharide
polysaccharides - CHO that yield a large number of
molecules of monosaccharides (>10)
CARBOHYDRATES
Monosaccharides
further classified as either aldoses or ketoses
CARBOHYDRATES
Monosaccharides
further classified as either aldoses or ketoses
CARBOHYDRATES
Monosaccharides
D (dextrorotatory) and L (levorotatory) designations of
CARBOHYDRATES
Monosaccharides
Addition of an alcohol to an aldehyde:
CARBOHYDRATES
Monosaccharides
Ketones undergo analogous addition reactions with alcohols.
CARBOHYDRATES
Monosaccharides
undergo cyclization
to form hemiacetals
and hemiketals
nucleophilic
addition of the OH
group on C-5
CARBOHYDRATES
Monosaccharides
undergo cyclization
to form hemiacetals
and hemiketals
CARBOHYDRATES
Monosaccharide addition reactions
alcohol
aldehyde
-glucose
CARBOHYDRATES
Monosaccharide addition reactions
Hemiacetal:
one H
one OH
one OR
one -R
CARBOHYDRATES
Monosaccharides
2 possible
configurations on the
hemiacetal and hemiketal:
a). -anomer - -OH
group on anomeric C is
oriented downward
b). -anomer - -OH
group is oriented upward
CARBOHYDRATES
Disaccharides
two monosaccharides joined by glycosidic bond
example:
Lactose composed of D-galactose and D-glucose
Only the anomeric carbon of D-galactose is involved in the formation
of glucosidic bond between D-galactose and D-glucose. That of Dglucose if left free.
CARBOHYDRATES
Disaccharides
two monosaccharides joined by glycosidic bond
example:
Sucrose composed of D-glucose and D-fructose
Both the anomeric carbon of D-glucose and D-fructose are used in the
formation of glycosodic bond.
CARBOHYDRATES
Polysaccharides
composed of several monosaccharide units
examples:
CARBOHYDRATES
Polysaccharides
composed of several monosaccharide units
examples:
Cellulose made up of D-glucose units, but glycosidic bonds
formed are - at the anomeric carbon
Hydrolysis
Reaction
sucrose
sucrose:
D-glucose + D-fructose
starch
cellulose
Hydrolysis
Reaction
sucrose
sucrose:
D-glucose + D-fructose
starch
sucrose:
D-glucose + D-fructose
cellulose
Starch is hydrolyzed because the glycosidic bond is hydrolysable (less
stable than the -glycosidic bond).
Hydrolysis
Reaction
sucrose
sucrose:
D-glucose + D-fructose
starch
sucrose:
D-glucose + D-fructose
cellulose
Molisch Test
Reagent: 10% naphthol in ethanol
Positive Result: purple color at the interface
(-)
(+)
Molisch Test
Reagent: 10% naphthol in ethanol
Positive Result: purple color at the interface
Sample
Result
cyclohexanone
glucose
sucrose
starch
Molisch Test
Explanation:
reaction involves hydrolysis of
glycosidic bond followed by
formation of furfural and
hydroxymethyl furfural
Benedicts Test
Reagent: Cu2+ in Na citrate solution
Positive Result: formation of brick red precipitate
(+)
(+)
(-)
Benedicts Test
Explanation:
Benedicts test is used to differentiate between reducing and
non-reducing sugars
CHOs that contain only acetal groups do not give (+) tests
with Benedicts solutions, and they are called non-reducing
sugars
CARBOHYDRATES
Monosaccharide addition reactions
Hemiacetal:
one H
one OH
one OR
one -R
CARBOHYDRATES
Monosaccharide addition reactions
CARBOHYDRATES
Monosaccharide addition reactions
Benedicts Test
Explanation:
Benedicts Test
Explanation:
Benedicts Test
Explanation:
Sample
Result
glucose
fructose
sucrose
lactose
sucrose hydrolysate
starch hydrolysate
cellulose hydrolysate
Benedicts Test
Explanation:
Sample
Result
glucose
fructose
sucrose
lactose
sucrose hydrolysate
starch hydrolysate
cellulose hydrolysate
Benedicts Test
Explanation:
Sample
Result
glucose
fructose
sucrose
lactose
sucrose hydrolysate
starch hydrolysate
cellulose hydrolysate
Benedicts Test
Explanation:
Sample
Result
glucose
fructose
sucrose
lactose
sucrose hydrolysate
starch hydrolysate
cellulose hydrolysate
Benedicts Test
Explanation:
Sample
Result
glucose
fructose
sucrose
lactose
sucrose hydrolysate
starch hydrolysate
cellulose hydrolysate
Benedicts Test
Explanation:
Sample
Result
glucose
fructose
sucrose
lactose
sucrose hydrolysate
starch hydrolysate
cellulose hydrolysate
In cellulose, no hydrolysis
takes place.
Osazone Test
Reagent: phenyl hydrazine HCl
Positive Result: formation of yellow orange precipitate/crystals
Sample
Reaction time*
fructose
2 min
glucose
5 min
sucrose
30 min
lactose
Osazone Test
Reagent: phenyl hydrazine HCl
Positive Result: formation of yellow orange precipitate/crystals
Osazone Test
Explanation:
Phenylhydrazine reacts with carbonyl compounds to
produce phenyhydrazones (osazones)
Osazone Test
Explanation:
Osazone Test
Explanation:
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