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APPROVAL SHEET

Complete report of Organic Chemistry II entitled Carbohydrates Reaction


has been written by
Class

: ICP A of Chemistry

Group

: I (One)

It has been checked by assistant and assistant coordinator. So this report is accepted.

Makassar, January
Assistant Coordinator,

Assistant,

Zulqifli Alqadri

Surianti
Known by,
Responsibility Lecture

Muhammad Syahrir, S.Pd., M.Si


ID. 19740907 200501 1 004

2015

A. EXPERIMENT
Carbohydrates Reaction
B. OBJECTIVES
Before doing the experiment, student must understand about the glucose,
fructose, sucrose, and lactose structures. After doing this experiment with use the
reagent, student be able to understand about:
1. Difference between reducing sugar with non reducing sugar
2. Difference between disaccharide that have free and unfree of aldehyde
(hemyacetal) or ketone (hemycetal) group.
C. LITERATURE REVIEW
Organic chemistry is the study of the chemistry of carbon. We classify almost
all of the compounds containing carbon of organic compounds. We consider only a
few, such as carbonates, cyanides, etc, as inorganic. Scientist once believed that only
living organisms could produce organic compounds. However, in 1828, the German
chemist Friedrich Wohler showed this to be incorrect when he produced the first
organic compound from inorganic starting materials. Carbon is capable of strongly
bonding to itself and other elements. There appears to be no limit to how many
carbon atoms can bond together. These factors allow carbon to form long, complex
chain and rings (Moore, 2007: 306).
Sugar/ carbohydrate is widely present in all the living substances hence it is
called the staff of life. It is present as a storage form in all the fruits, vegetables in its
various forms and quantities. Sugar is generalized name for a class of sweet-flavored
substances used as food. They are carbohydrates and are composed of carbon,
hydrogen, and oxygen. There are various types of sugar derived from different
sources. Simple sugars are called monosaccharides and include glucose, fructose, and
galactose. Glucose, fructose and galactose are all simple sugars, monosaccharides,
with the general formula C6H12O6. Disaccharides : sucrose, maltose, and lactose are
all compound sugars, disaccharides, with the general formula C 12H22O11.
Polysaccharides are long carbohydrates molucules of repeated monomer units joined

together by glycosidic bonds. Polysaccharides have a general formula of C x(H2O)y


(Pandya, 2013: 1-2).
The monosaccharides have a couple of characteristics that prove to be
important in terms if their structure and function. They all have at least one carbon
that is bonded to four different groups ( a chiral carbon), and most form five and sixmembered rings easily. The presence of chiral carbons allows these compounds to
exist as two different optical isomers that are nonsuperimposable mirror images of
each other (Moore, 2007: 314).
D.
1.
a.
b.
c.
d.
e.
f.
g.
h.
i.
j.
k.
l.
m.
n.
o.
p.
q.
r.
2.

APPARATUS AND CHEMICALS


Apparatus
Small test tube
(14 pieces)
Big test tube
(6 pieces)
Beaker 800 ml
(1 piece)
Beaker 250 ml
(1 piece)
Graduated cylinder 10 ml
(1 piece)
Graduated cylinder 25 ml
(1 piece)
Tweezers
(1 piece)
Stopwatch
(1 piece)
Pipette
(10 pieces)
Tripod and asbestos gauze
(@ 1 piece)
Bunsen burner
(1 piece)
Small test tube rack
(1 piece)
Big test tube rack
(1 piece)
Spraying bottle
(1 piece)
Stirring rod
(1 piece)
Matches
(1 piece)
Smooth rag
(1 piece)
Rough rag
(1 piece)
Chemicals
-napthol solution
a.
(C10H8O)
b.
c.
d.
e.
f.
g.

Concentrated of sulphuric acid


Glucose
Fructose
Sucrose
Lactose
Sample X

(H2SO4)
(C6H12O6)
(C6H12O6)
(C12H22O11)
(C12H22O11)

h.
i.
j.
k.
l.
m.
n.
o.
p.
q.
r.
E.
1.
a.

Silver nitrate 1%
(AgNO3)
Sodium hydroxide 10%
(NaOH)
Hydrochloric acid 10%
(HCl)
Benedict reagent
(Cu2+ + OH-)
Phenylhydrazine
(NH2NHC6H5)
Ammonium hydroxide 5%
(NH4OH)
Aquadest
(H2O)
Cotton
Litmus paper
Ice cube
Tissue
PROCEDURES
Molisch Test
Glucose, fructose, sucrose, lactose, and sample x were entered into the different

test tubes as much as 2 ml.


b. The -napthol as much as 5 drops were dropped into each test tubes.
c. Concentrated of sulphuric acid as much as 2 ml were added throughout the wall
d.
2.
a.
b.
c.

of test tube carefully.


The changes were observed.
Tollens Test
Silver nitrate as much as 2 ml were entered into a test tube.
Ammonium hydroxide 5% was dropped to dissolved the precipitation.
The previous solution (Tollens reagent) as much as 2 ml were moved into 3

different test tubes.


d. Glucose, sucrose, and sample x were added into each test tube as much as 5
e.
3.
a.
b.

drops.
The silver mirror formation was observed.
Benedicts Test
Benedict reagent as much as 5 ml was entered into 5 test tubes.
Glucose, fructose, sucrose, lactose, and sample x were added into each test tube as

c.
d.
4.
a.

much as 10 drops.
All of the test tubes were heated.
The change was observed.
Osazones Test
Glucose, fructose, sucrose, lactose, and sample x were entered into the different

test tubes as much as 4 ml.


b. Phenylhydrazine was added into each test tube as much as 2 ml.
c. All of the tubes were heated.
5. Hydrolysis of sucrose by an acid

a.
b.
c.
d.
e.

Sucrose and sample x were entered into different test tubes as much as 10 ml.
HCl 10% was added into each test tube as much as 10 ml.
All of the test tubes were heated about 50 minutes, then cooled.
Some drops of NaOH 10% were dropped into the test tubes.
All of the solution in each test tube were tested by litmus paper, then tested with

Benedicts reagent.
f. All of the test tubes were heated again.
F. OBSERVATION RESULT
TREATMENTS
1. Molisch Test
a. Glucose
2 ml of glucose (colorless) + 5drops of

RESULTS

Formed purple ring

-napthol (brownish) + 2 ml of
H2SO4 (colorless)
b. Fructose
2 ml of fructose (colorless) + 5drops of Formed purple ring
-napthol (brownish) + 2 ml of

H2SO4 (colorless)
c. Sucrose
2 ml of sucrose (colorless) + 5drops of Formed purple ring
-napthol (brownish) + 2 ml of
H2SO4 (colorless)
d. Lactose
2 ml of lactose (colorless) + 5drops of Formed purple ring
-napthol (brownish) + 2 ml of

H2SO4 (colorless)
e. Sample X
2 ml of sample x (colorless) + 5drops of Formed purple ring
-napthol (brownish) + 2 ml of

H2SO4 (colorless)
2. Tollens Test
a. Glucose
2 ml of Tollens reagent + 5drops of

Formed silver mirror

glucose
b. Sucrose
2 ml of Tollens reagent + 5drops of Not formed silver mirror
sucrose
c. Sample X
2 ml of Tollens reagent + 5drops of Formed silver mirror
sample x
3. Benedicts Test
a. Glucose
5 ml of Benedict (blue) + 10drops of
glucose

Bottom: red brick precipitation; Top:


blue greenish solution; the fourth faster
formed

b. Fructose
5 ml of Benedict (blue) + 10drops of Formed red brick precipitation and the
fructose
c. Sucrose

first that formed

5 ml of Benedict (blue) + 10drops of Two layers: 1. Red brick precipitation;


sucrose
d. Lactose

2. Blue solution; the last formed

5 ml of Benedict (blue) + 10drops of Formed red brick precipitation and the


lactose
e. Sample X

third that formed

5 ml of Benedict (blue) + 10drops of Formed red brick precipitation and the


sample x
4. Osazones Test
a. Glucose
4 ml of glucose (colorless) + 2 ml of

second that formed

Formed yellow hablur

heated
until

phenylhydrazine (colorless)
b. Fructose

4 ml of fructose (colorless) + 2 ml of Formed yellow hablur; there are many


hablur that formed

heated
until

phenylhydrazine (colorless)
c. Sucrose

4 ml of sucrose (colorless) + 2 ml of Formed yellow hablur


heated
until

phenylhydrazine (colorless)
d. Lactose

4 ml of lactose (colorless) + 2 ml of Formed yellow hablur


heated
until

phenylhydrazine (colorless)
e. Sample X

4 ml of sample x (colorless) + 2 ml of Formed yellow hablur


heated
until

phenylhydrazine (colorless)

5. Hydrolysis of sucrose by an acid


a. Sucrose
10 ml of sucrose (colorless) + 10 ml of

HCl 10% (colorless)

heated
50 minutes

test with litmus paper

solution (after added NaOH 10%)


Red

cooled + NaOH 10% (colorless)

Colorless (after heated) light yellow

brick

solution

Benedicts reagent)
test

(after

added

with Benedicts resgent

heated
until change

b. Sample X
10 ml of sample x (colorless) + 10 ml of Colorless (after heated) light yellow

HCl 10% (colorless)

heated
50 minutes

solution (after added NaOH 10%)


Red

cooled + NaOH 10% (colorless)

test with litmus paper

with Benedicts resgent

brick

solution

(after

added

Benedicts reagent)
test

heated
until change

G. DISCUSSION
Carbohydrate is a composition that consist of carbon, hydrogen, and oxygen
elements that contain in plants such as hulled rice, corn, wheat, tubers, and formed
through the assimilation prcess of a plant. The objective of this experiment are can
diferentiate between reducing sugar and non reducng sugar and diferentiate the
disaccharide that have free and unfree of aldehyde or keton group. In this experiment
is doing several testing such as:
1. Molisch Test
The objective of this test is to prove that the solution that used is a
carbohydrate or not. The samples that used are glucose, fructose, sucrose, lactose, and
sample x. The existance of carbohydrate is showed by the formation of purple ring at
the surface between acid layer and sugar layer. All of the sugars are formed purple

ring after reacted with

-napthol solution that used as Molischs reagent for

condensation reaction. the samples was added with concentrated of H 2SO4 that used
to hydrolysis the bond at saccharide to form furfural. This furfural will react with
-napthol to form a purple ring. The reaction that occur at each sugars:

a. Glucose
OH

HC

CH

H2SO4/H3O

CH2OH
OH
H
OH
H
HO
OH
H
OH
H

-3H2O

HOOC

COOH
a-napthol

hydroxy methyl furfural

HC

CH

C
O

HOOC

OH

purple
compound

CH

b. Fructose

O
HO

H2SO4/H3O
CH 2OH

OH

CH

HC

CH 2OH

-3H2O

HOOC

OH

COOH
a-napthol

hydroxy methyl furfural

c. Sucrose

CH

=
HOOC

HC

C
O

OH

CH

purple
compound

CH 2OH
H

O
HO

CH 2OH

OH

OH

H2SO4/H3O

HC

CH

HO

CH2OH
OH
H
OH H

-3H2O

HOOC

OH

COOH
a-napthol

hydroxy methyl furfural

CH

OH

HC

C
O

HOOC

purple
compound

CH

d. Lactose

OH

H
O

CH2OH
OH
H
OH H
OH
H
OH

H2SO4/H3O

HC

CH

HO

CH2OH
OH
H
OH H

-3H2O

HOOC

OH

COOH
a-napthol

hydroxy methyl furfural

CH

HOOC

HC

C
O

OH

CH

purple
compound

2. Tollens Test
The objective of this test is to know which sugar that can classified as
reducing sugar that showed by the existance of silver mirror that formed at a sample
(sugar). In this experiment, sample that used are glucose, sucrose, and sample x, then
reacted with Tollens reagent. Glucose that react with Tollens reagent formed silver
mirror that means glucose is a reducing sugar because can reducing the Tollens
reagent. Sucrose that react with Tollens reagent cant form silver mirror that means
sucrose is a non reducing sugar because the bond between two unit of its sugar are
already engaging carbon atom of hemyacetal and hemycetal, so is not easy to
separated that cause sucrose cant to reduce the Tollens reagent. Sample x that resct

with Tollens reagent produce silver mirror precipitation that means sample x is a
reducing sugar. The reactions that occur:
a. Preparation of Tollens reagent
2Ag+ + NO3- + 2NH4OH Ag2O + 2NH4NO3 +H2O
(white)
2Ag(NH ) + + OH3 2

Ag2O + 4NH3 +H2O

(Tollens reagent)
b. Tollens Test
1) Glucose
CH 2OH

CH 2 OH
O H

H
OH

H
H

HO

OH
OH

OH

=O
H

HO
H

+ 2Ag(NH3)2 + OH-

OH

CH 2 OH

H
H
OH

OH

HO

COO-

+ 2Ag 4NH3 + H2O


(silver mirror)

2) Sucrose
CH2OH
OH
H
H
OH H
HO
H
OH

CH 2OH

+ 2Ag(NH3)2 + OH-

HO
CH 2OH

OH

3. Benedicts Test
The objective of this test is to diferentiate between reducing sugar and non
reducing sugar, where its positive test from a reducing sugar is produce red brick
precipitation. This test used five sample that are glucose, fructose, sucrose, lactose,
and sample x. In this test, the sugar solutions are react with Benedicts reagent then
heated, where the function of heated is to accelerating the reaction and after heated,

the red brick precipitation will formed at all of the samples. Glucose that react with
Benedicts reagent produce a red brick precipitation that means glucose is a reducing
sugar. Fructose react with Benedicts reagent also produce a red brick precipitation
that means fructose is also a reducing sugar. Sucrose react with Benedicts reagent
produce a red brick precipitation, but actually sucrose cant react because sucrose
didnt have a free aldehyde or ketone group so cant to reduce the Benedict reagent
(Cu) become a red brick precipitation. Lactose react with Benedicts reagent produce
red brick precipitation that means lactose have a free hemyacetal group that can make
a rotation become an open chain, so can reduce Cu2+ become Cu+. Sample x react
with Benedicts reagent produce a red brick precipitation that means sample x is a
reducing sugar. The reactions that occur:
a. Glucose
CH 2 OH

CH 2 OH
O H

H
H
OH

OH

2+

+ 2Cu

HO

+ 5 OH

OH

COO-

OH

OH

+ Cu2O + 3H2O
(red brick)

HO

b. Fructose
CH 2 OH
CH 2 OH
H

2+

+ 2Cu

HO

+ 5 OH

OH

CH 2 OH
OH

H
H

OH

c. Sucrose
CH2OH
OH
H
H
OH H
HO
H
OH

d. Lactose

CH 2OH

O
HO

CH2OH
OH

+ Cu2O + 3H2O
(red brick)

HO

CH2OH

+ 2Cu2+ + 5 OH-

H
HO

CH 2 OH
OH
H
OH H
H

H
O

OH

CH 2 OH
OH
H
OH H
OH
H
OH

CH2OH

CH2OH
O H

H
H
OH
HO

OH
H

OH

OH
H

OH

CH2OH

CH2OH

H
OH

HO

OH

+ 2Cu2+ + 5 OH-

O H

COO- +

OH

OH

HO

HO
H

OH

COO -

+ Cu2O + 6H2O
(red brick)

4. Osazones Test
The objective of this test is to diferentiate between disaccharide that have a
free and unfree of aldehyde (hemyacetal) or ketone (hemycetal) group. The sugar
solution that used in this test are glucose, fructose, sucrose, lactose, and sample x. All
of the sugars are added with phenylhydrazine. Monosaccharide such as glucose and
fructose react with phenylhydrazine and form yellow hablur because have a free
aldehyde or ketone group. Sucrose in this test show positive test but actually sucrose
cant react because sucrose have aldehyde and ketone group that bonded at its
monomer (unfree). Lactose is also react to form yellow hablur that caused because
lactose have a free aldehyde or ketone group so can react phenylhydrazine and form
hydrazone or osazone. Sample x also show positive test because sample x contain a
free aldehyde or ketone group. The reaction that occur:
a. Glucose

O
H

H
C = N - NH -

OH

HO

C=O

H
+ H2N-NH-

HO

OH

OH

OH

CH 2OH

OH
CH 2OH

H
C = N - NH C= N - NH + H2N-NH-

HO

OH

OH
CH 2OH
(glucosazone)

b. Fructose
CH 2OH
O
HO

C = N - NH -

C = N - NH -

H - C - OH

+ H2N-NH-

C=O

OH

OH

OH

CH 2OH

OH

HO

CH 2OH
H
C = N - NH C= N - NH HO
H

H
OH
CH 2OH
(fructosazone)

c. Sucrose

HO

H
OH
OH
CH 2OH

CH2OH
OH
H
H
OH H
HO
H
OH

CH2OH

+ H2N-NH-

HO
CH 2OH

OH

d. Lactose
H
C = N - NH -

CH2OH
OH
H
H
OH H
HO
H
OH

CH2OH
OH
H
H
OH H
OH
H
OH

C= N - NH + H2N-NH-

HO

OH

OH
CH 2OH
(glucosazone)

5. Hydrolysis of sucrose by an acid


In this test, sucrose is added with HCl 10% to give an acid state and to
hydrolizing sucrose become glucose and fructose. Sample x is also used in this test
will hydrolized become its composer molecules. The addition of NaOH is to
neutralizing and to detecting the sugar is already hydrolized or not, so added
Benedicts reagent as the test reagent. Before the addition of NaOH and Benedict
solution, the sugar solution are heated firstly to complete the reaction and to
accelerate the hydrolysis process. The result of this test is gained positive test from
sucrose and sample x that is a formation of red brick precipitation. The result show
that sucrose and sample x are already hydrolized by HCl become its
monosaccharides. The reaction that occur:

CH2OH
OH
H
H
OH H
HO
H
OH

CH 2 OH
CH2OH

2OH-

H
OH

COO-

OH
H

H
H
OH

OH

OH

+ Cl-

HO

CH 2OH
OH

OH

CH2OH + Cu2O + H2O

(red brick)

HO

HO
H

HO

CH2OH

O
H

CH 2 OH

O H

H
OH

CH2OH
OH

CH2 OH

2Cu2+

heated

+ HCl

HO

6. Sugar Identification
Based on the tests to sample x that reacted with Molischs reagent form purple
ring that means the sample x contain carbohydrate. React with Tollens reagent form
silver mirror precipitation that means sample x is a reducing sugar. React with
Benedicts reagent is also show positive test that is form red brick precipitation that
means sample x is a reducing sugar. React with phenylhydrazine form yellow hablur
or hydrazone. And hydrolized with HCl, then react with Benedicts reagent form red
brick precipitation. Based on the tests, sample x have a free aldehyde or ketone group.
The type of sample x is from monosaccharide that is fructose.
H. CONCLUSION AND SUGGESTION
1. Conclusions
a. The reducing sugars are glucose, fructose, and lactose whereas the non reducing
sugar is sucrose.
b. Saccharide that have free aldehyde and ketone group and easy to oxidized is
reducing sugars such as glucose, fructose, and lactose whereas the saccharide that
not have free aldehyde and ketone group is non reducing sugar like sucrose.
2. Suggestions
a. For the next apprentice should prepared the solution well so there is no mistake in
the experiment.
b. For the next apprentice should use nice reagent so can get a good result.

BIBLIOGRAPHY
Bruice, P.Y. 2003. Organic Chemistry Fourth Edition. London: Blackwell Science
aaaaaaaLtd
Kelly, M. 2013. Test For Reducing Sugar. http://www.ehow.com/about_55297_testaaaaaaareducing-sugars.html
Moore, J.T & Richard, H.L. 2007. Chemistry For The Utterly Confused. USA:
aaaaaaaMcGraw Hill Company
Morrison, R.T & Robert, N.B. 2002. Organic Chemistry Sixth Edition. New Delhi:
aaaaaaaPrentice-Hall of India Private Limited
Neuman, R.C. 2000. Organic Chemistry. California: University of California
Okatch, H & Nelson, T. 2003. Profiling Of Carbohydrate Polymers In Biotechnology
aaaaaaaUsing Microdyalysis Sampling, High Performance Anion Exchange
aaaaaaaChromatography With Integrated Pulsed Electrochemical Detection/ Mass
aaaaaaaSpectrometry. African Journal Of Biotechnology. Vol 2 (12).
Pandya, A.V, et al. 2013. Estimation Of The Type And Quantity Of Sugar In Milk.
aaaaaaaJournal Of Chemical, Biological, And Physical Sciences. Vol 3 (4).
Sunarya, Y. 2012. Kimia Dasar 2. Bandung: Yrama Widya
Tim Dosen. 2014. Penuntun Praktikum Kimia Organik II. Makassar: Laboratorium
aaaaaaaKimia UNM

ANSWER OF QUESTIONS
1. The reaction of glucose with Tollens reagent
2. The reaction of lactose with Benedict reagent
3. The molecular formula of sucrose is C12H22O11. Sucrose cant react with Tollens
and Benedict reagents because sucrose is consist of glucose and fructose that each
of them have aldehyde and ketone group. Due to the different groups, the
aldehyde and ketone group form strong bond that cause sucrose does not have a
free carbonyl group.
4. Glucose and fructose form same osazone because glucose and fructose are
monosaccharide group. If viewed from the binding of phenylhydrazine on the
glucose and fructose structure, phemylhydrazine attached to the C 1 and C2 atoms
in both these sugar solution.
5. Hydrolysis of sucrose with acid then reacted with excess phenylhydrazine will
produce a compound only because of the influence of the enzyme invertase which
leads to changes in direction of polarization rotation plane to the right and left are
called inverse which produces one compound, i.e sugar inverse.
6. The meaning of five acetyl group can be incorporated into the molocule of
glucose and fructose is that glucose and fructose can bind acetyl group by 5
which is enclosed double bond are bonded to one another.
7. The meaning of only 8 acetyl group which may be included in the sucrose
molecule, instead of 10 is that 8 OH groups owned by sucrose where its H atoms
can be replaced with an acetyl group.
8. Hydrolysis of sucrose sugar are glucose and fructose. Glucose and fructose are
able to reduce Benedict reagent because have free hemiacetal and hemicetal
groups.

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