Carbohydrate reaction

HERMIN HARDYANTI UTAMI (111 304 0202)

CHEMISTRY DEPARTMENT

MATHEMATIC AND SCIENCE FACULTY

STATE UNIVERSITY OF MAKASSAR

2012

ORGANIC CHEMISTRY 2

COMPLETE REPORT

RATIFICATION PAGE

The complete report of Organic Chemistry II with the title of

“Carbohydrate reaction” which made by :

Name : Hermin Hardyanti Utami

ID : 111 304 0202

Group : VII

Class : ICP B

Have been checked by assistant and assistant coordinator. So, this report is

accepted.

Makkassar, December 2012

Assistant Coordinator

Fandi Ahmad, S.Pd.

Assistant

Nurhajawarsi, S.Pd

Known By,

Responsibility Lecturer

Dra. Hj. Ramdani, M.Si.

A. Tittle of Experiment

Carbohydrate reaction

B. Purposes

At the last experiment, student can be understand about :

1. Differenciate between reducing sugar with nonreducing sugar.

2. Differenciate between disaccharide that has the aldehyde group

(hemiacetal) or ketone (hemiketal) free and non free.

C. Background

In theleaf of a plant, the simple compounds carbondioxyde and water are

combined to rofm sugar (+) glucose. This process known as photosynthesis

requires catalyst be green coloring matter chlorophyll and requires energy in the

form light. Thousand of (+) glucose molecules can then be combined to form the

much larger molecules of cellulose which constitute to supporting frame work of

the plant (+). Glucose molecules can also be combined which is then stored in the

seeds to serve as food for a new grawing plant.

Positive glucose, cellulose, starch and glycogen all belong to the class of

organic compounds known as carbohydrates. Carbohydrate containing in grain or

feed of it to animals to be converted into meat and fat which we then eat. We

build houses and furniture from cellulose in the form of wood. Rhus

carbohydrates quite literally provide us with the necessary of life food, clothing

and shelter (Morison and Boyd,2001:1070)

According to McMurry (2008:687) classification of carbohydrate is :

1. Simple vs complex:

a. Simple carbohydrates can’t be hydrolyzed to smaller units.

b. Complex carbohydrates are made up of two or more simple sugar linked to

sugar.

A disaccharide is composed of two monosaccharides.

A polysaccharide is composed of three or more monosaccharides.

2. Aldose vs ketose:

a. A monosaccharide with an aldehyde carbonyl group is an aldose.

b. A monosaccharide with a ketone carbonyl group is a ketose.

3. Tri-,tetr-,pent-,etc-. indicate the number of carbons in the monosaccharide.

According to Carrey (2000:998-999) characteristic properties of an aldehyde

function is its sensitivity to oxidation. A solution of copper (II) sulphic as its

citrate complex (benedict’s reagent) is comaple of oxidation aliphatic aldehydes to

the corresponding carbocxylic acid:

O O

R C H + 2Cu2+ R C O

- + Cu2O + 3H2O

The formation of a red precipitate of copper (II) oxide by reduction of Cu(II) is

taken as positive copper test with benedict’s reagent are termed reducing sugar.

Aldose are reducing sugar since they process an aldehyde function on their open

chain form. Its also to ketones are reducing sugar. Under the conditions of the test

ketones equilibrate with aldoses by way of enediol intermediates and the aldose

are oxidated by the reagent.

According to Myamus (2006) many student have been investigating

carbohydrate supplementation in relation to time of investigation frequency of

investigation and concentration of the glucose solution. Although carbohydrate

(glucose) is extremely important to fatty acid oxidation. Glucose then plays an

important role for muscle performance especially during relatively long and

intense activities. Knowing that carbohydrate is the oxidizable fuel during high

intensive exercise those athletes who train intensely or complete for consecutive

days without consuming adequate amounts of carbohydrates are not able

mavimante glycolen storage and consequently are unable to perform at their best.

According to Wissmann (2006:29) carbohydrate metabolism. Prior the

examining gender related differences in carbohydrate in carbohydrates loading.

Gender of different between carbohydrate metabolism must be eamined. There

appears to be no difference between genders in basal level of muscle glycogen

skeletal muscle in hexosinase. In addition, there have yet to be any studies

conducted assessing different in glycogen synthase activity or brancing enzyme.

Knowledge of change of these enzyme could assist in the understanding of

gender.

The general testing of carbohydrate that simple is molisch test. This reaction

occur tof the color change as the influence of mixture of one furan derivative that

form fugar reaction with acid and α-naphtol. Disaccharide has the aldehyde group

(hemiacetal) or ketone (hemiketal) free, like the lactose occure in the

homogeneous reaction. The melting point of crystal and formation osazone time is

specific, means can be used as identification or derivative of sugar kind

(Tim Dosen,2012:10-11).

D. Chemical and Equipment

1. Chemical

a. Aquadest (H2O)

b. Ethanol (C2H5OH) solution

c. Sucrose (C12H22O11)solution

d. Fructose (C6H12O6) solution

e. Lactose (C12H22O11) solution

f. Glucose (C6H12O6) solution

g. Sample sugar solution

h. α-naphtol solution

i. concentrated sulphuric acid (H2SO4)

j. Silver nitric (AgNO3) solution

k. Ammonium hydroxide (NH4OH) solution

l. Benedict solution

m. Phenilhydrazin (NH2NHPh) solution

n. Matches

o. Hydrochloric acid (HCl) 10% solution

p. Sodium hydroxide (NaOH) 10% solution

q. Litmus paper

r. Universal indicator

s. Cotton

t. Ice / cool water

2. Equipment

a. Big test tube (10 pieces)

b. Small test tube (10 pieces)

c. Test tube rack (2 pieces )

d. Stir bar (3 pieces )

e. Dropping pipette (14 pieces)

f. Beaker glass 500 ml (2 pieces )

g. Graduated cylinder 10 ml (3 pieces )

h. Bunsen burner (2 pieces )

i. Triangle (2 pieces )

j. Asbestoz Gauze (2 pieces )

k. Spray flask (1 piece )

l. Soft cloth and rough cloth (2 pieces)

E. Work Procedure

1. Molisch test

a. 2 ml of sugar solution (sucrose, glucose, fructose, lactose, sample) was

filled into the small test tube.

b. Each was added by 3 drops of α-naphtol.

c. Each was added by 3 drops of concentrated H2SO4.

d. Each was observed the occur change.

2. Tollens test

a. Tolens reactant test was made by mix of:

1 ml of AgNO3 5%

10 drops of NH4OH 2%

b. It was react to sugar solution (sucrose, fructose, glucose, lactose,

sample) with 5 drops of each solution into small test tube.

c. Each was observed the occur change.

3. Benedict test

a. 5 ml of benedict solution was filled into big test tube.

b. Each was added with sugar solution (sucrose, fructose, glucose,

lactose, sample).

c. Each was heated some minutes until change occur.

d. Each was let stand until occur the precipitate.

4. Osazone test

a. 10 ml of sugar solution (sucrose, fructose, glucose, lactose, sample)

was filled into big test tube.

b. Each was added by 5 ml of phenilhydrazin until form two layers.

c. Each was shaked and and closed it with cotton.

d. Each was heated until 30th

minutes.

e. Each was let stand the first in room temperature and the second at cold

water.

f. Each was observed the occur change.

5. Sucrose hydrolysis by acid

a. 10 ml of sucrose solution was filled into big test tube.

b. It was added by 10 ml of HCl 10%.

c. It was heated until 50th

minutes.

d. It was checked with blue litmus paper.

e. If the litmus paper is change to red, it was added by NaOH 10% until

the pH is neutral.

f. It was compared with benedict and took 10 drops.

g. It was added by 5 ml of benedict.

h. It was observed the occur change.

F. Observation Result

No. Observation Result

1.

2.

3.

4.

1.

2.

3.

4.

5.

Molisch test :

Sample, sucrose, lactose, fructose,

glucose was filled into test tube.

It was added by α-naphtol.

It was took 3 drops of sugar

solution.

It was added by concentrated

H2SO4

Tollens test :

Sample solution was added by

tollens reactant

Sucrose solution was added by

tollens reactant

Fructose solution was added by

tollens reactant

Glucose solution was added by

tollens reactant

Lactose solution was added by

tollens reactant

- 2 ml of sugar solution.

- 3 drops of α-naphtol,

- Not dissolve mixture

- Separate :

Colorless solution

Purple ring

Black solution

- 5 drops of sample, produce

brownish grey solution.

- 5 drops of sucrose, produce


- 5 drops of fructose, produce

silver mirror precipitate.


silver mirror precipitate.



1.

2.

3.

4.

5.

Benedict test :

Benedict solution (5 ml) was

added by sample solution (10

drops) and let stand it.


added by fructose solution (10



added by glucose solution (10



added by lactose solution (10



added by sucrose solution (10


- Blue solution

- Blue solution

- Orange solution

- Red precipitate

- Dark red solution

- Red precipitate

- Dark red solution

- Red precipitate

- Blue solution

- Blue solution

1.

Osazone test :

Sample solution

- 10 ml of sample solution was

added by 5 ml of

phenilhydrazin.

- It was shaked

- It was heated 30th

minutes

- It was let stand in room

temperature and cold down in

- Separate :

Transparent solution

Yellow solution

- Turbidity yellow solution

- Separate :

Yellow oily solution

Yellow solution

- Separate :


2.

3.

4.

cold water

Fructose solution

- 10 ml of fructose solution was

added by 5 ml of

phenilhydrazin.

- It was shaked


minutes



cold water

Glucose solution

- 10 ml of glucose solution was

added by 5 ml of

phenilhydrazin.

- It was shaked


minutes



cold water

Lactose solution

- 10 ml of lactose solution was

added by 5 ml of

phenilhydrazin.

- It was shaked


minutes

Yellow solution

- Separate :


Yellow solution


- Separate :


Yellow solution

- Separate :


Orange solution

- Separate :


Yellow solution


- Separate :


Yellow solution

- Separate :


Yellow solution

- Separate :


Yellow solution


- Separate :


5.



cold water

Sucrose solution

- 10 ml of sucrose solution was

added by 5 ml of

phenilhydrazin.

- It was shaked


minutes



cold water

Yellow solution

- Separate :

White solution

Yellow solution

- Separate :


Yellow solution


- Separate :


Yellow solution

- Separate :

Yellow solution

Brownish red solution

1.

2.

3.

4.

Sucrose hydrolysis by acid :

10 ml of sucrose was added by 10

ml HCl 10% and heated 50th

minutes.

It was checked by blue litmus

It was neutralized by some drops

of NaOH 10%

It was compared with benedict,

took, added by 5 ml of benedict

- Orange solution

- Acid pH

- Neutral pH

- Same color with benedict

namely blue solution.

G. Discussion

1. Molisch Test

This test has function to know about carbohydrate sample. Molisch

reagent reacted to dissolving α-naphtol into alcohol. The positive test showed by

purple ring forming. This test there are sample, sucrose, glucose, lactose, and

fructose that was added by α-naphtol, then added by concentrated H2SO4 with

careful to forming the purple ring. This occur because carbohydrate was

hydrolyzed by H2SO4 to monosaccharide and occurring hydrated to fulfular or

hydroxy methyl fulfular and will be condensation to forming complex that purple

color.

As function of H2SO4 is as dehydrator or catalyst and α-naphtol as reagent

to condensation react. The fifth sample showing the positive that contain

carbohydrate. The difference color intensity that occur because sugar source from

monosaccharide and disaccharide. As for the reaction is :

CHO

H C OH

HO C H H2SO4 C CH

H C OH 3H2O C C + 2

H C OH HOCH O COOH

CH2OH

Glucose α-naphtol

O

C CH

C C

HOCH O CH2 O+

O

HO3S OH SO3H

Purple ring

CHO

H C O

HO C H H2SO4 C CH

H C OH 3H2O C C + 2

H C OH HOCH O COOH

CH2OH

Fructose α-naphtol

OH

C CH

C C

HOCH O CH2 O+

O

HO3S OH SO3H

Purple ring

CH2OH CH2OH

H O O

OH

HO OH

H

OH H H

H OH O O O H OH

Lactose

+ 2 H2SO4

3H2O

OH

HC CH O C C

C C C C C CH2 O+

HOH2C O OH HOH2C O

SO3H OH HO3S

CH2OH

H O O

CH2OH

HO OH

H

OH H

H OH O O O H OH

Sucrose

+ 2 H2SO4

3H2O

OH

HC CH O C C

C C C C C CH2 O+

HOH2C O OH HOH2C O

SO3H OH HO3S

Sample solution + 2 H2SO4

-H2O

HC CH O

C C C complex compound purple

HOH2C O OH

2. Tollens Test

Tollens test has function to identificating the aldehyde or hemiacetal group

that will be oxidated by tollens reagent. It positive test showing the silver nitric

form as mark that there is carbohydrate recducing. In this experiment, the solution

that produce positive is glucose and fructose, but lactose, sucrose and sample is

negative result. This is not same with theory, because lactose is reducing sugar but

sucrose was same with the theory is not reducing sugar because bonding of it

chain between two sugar unit that included heamiacetal carbon atom and

hemiketal carbon atom from two unit of sugar so is not easy to decompose and it

structure chaining with it hemiacetal structure, so it result is negative. As for the

structure is :

2AgNO2(aq) + 2NaOH(aq) Ag2O(s) + 2NaNO3(aq) + H2O(l)

Ag2O(s) + 2NaNO3(aq) + H2O(l) + 4NH3 2Ag(NH3)2NO3 + 2NaOH

2AgNO3 + 4NH3 2[Ag(NH3)2]+ + NO3

2-

Tollens reagent

AgNH32+

ion will be oxidating the sugar compound that contain aldehyde

group. So, AgNO3 and NH4OH has function to make tollens reagent

2[Ag(NH3)2]+

that function as oxidator. As for the reaction is :

C6H12O6 + 3OH + Ag(NH3)2+ C6H12O7

- + 2Ag

+ + 4NH3 + H2O

Silver mirror

CH2OH CH2OH

H O H2O

OH Ag(NH3)2

HO OH

H OH

OH O

H OH H OH

glucose

CH2OH

H O

HO OH

CO2- +

2Ag

H OH silver mirror

CH2OH

H O O

CH2OH

HO OH

H

OH H + 2Ag(NH3)2+

+ OH-

H OH O O O H OH

Sucrose

Sample solution + 2Ag(NH3)2+

+ OH-

3. Benedict test

This test has function to differenciating reducing sugar and non reducing

sugar based on it concentrated.it positive result forming the red brick precipitate.

In this experiment, sugar solution (fructose, lactose, glucose, sucrose, and sample)

was reacted by benedict and heated until forming red brick precipitate. Only

sample and sucrose in this experiment that has no precipitate.

Glucose can be reacted with Cu2+ because is aldose group that has free

aldehyde group. Lactose consist of 2 monosaccharides but borh of chain is not

using it hemiacetal carbon atom and easy to oxidated. Fructose because there is

tautomeric namely ketose change to ketoenol and become to aldose group.

Fructose is very fast to showing the positive result because there is reducing

accelerating and has the high molarity because there is aldehyde and free ketose in

carbohydrate molecule and ketone group direct dehydrated become to fulfural,

while aldehyde occurring transformation to ketose then become to fulfural.

Sucrose cannot be oxidated because it has aldehyde group and free ketone group,

it same with sample solution that showing the negative result so that it is include

the nonreducing sugar. As for the reaction :

CH2OH

H O H

HO OH

H

OH + Cu

2+ + 5OH

-

H OH

glucose

CH2OH

H O O

HO OH

H C

OH + Cu2O + 3H2O

H OH

red-brick

CHOH O CH2OH

HO OH

H

+ Cu2+

+ 5OH-

H OH

Fructose

COOH

H OH

HO OH

H CH2OH

+ Cu2O + 3H2O

H OH

red-brick

CH2OH

H O

O CH2OH

HO H OH H OH + Cu2+

+ 5OH-

OH H O O O OH H

Sucrose

CH2OH CH2OH

H O O

OH

HO OH

H

OH H H + Cu2+

+ 5OH-

H OH O O O H OH

Lactose

COOH

H OH

2 HO OH

H CH2OH

+ Cu2O + 3H2O

H OH

red-brick

sample solution + Cu2+

+ 5OH-

4. Osazone test

In this test, sugar solution that used is sucrose, lactose, glucose, fructose.

The fourth of it solution was added by phenilhydrazin. According to the theory,

monosaccharide react with more phenilhydrazin will be producing hablur that

yellow color. Disaccharide that has aldehyde group (hemiacetal) or free ketone

(hemiketal) like lactose occurring the homogen reaction. But at the last

experiment there are no solution form the hablur. This case occur because the

oxidating process is not perfectly. As for the reaction :

CHO

H C OH

HO C H

H C OH + H2N NH

H C OH

CH2OH

Glucose

CHO

H C H2N NH

HO C H

H C OH

H C OH

CH2OH

Glucosazone

CHO

H C O

HO C H

H C OH + H2N NH

H C OH

CH2OH

Fructose

CHO

H C H2N NH

HO C H

H C OH

H C OH

CH2OH

Fructosazone

H O

O CH2OH

HO H OH H OH + H2N NH

OH H O O O OH H

Sucrose

CH2OH CH2OH

H O O

OH

HO OH

H

OH H H + H2N NH

H OH O O O H OH

Lactose

CH2OH CH2OH

H O OH

HO OH

H

OH H H2N NH

H OH O O O H OH

Lactose

5. sucrose hydrolysis by acid

In this experiment, sugar that will be hydrolyzed is sucrose with way of

addition HCl that has function to hydrolyzing to glucose and fructose. This

mixture was heated to accelerate the reaction process. After that solution then was

cold down and neutralized with NaOH addition. Proving of neturalization

suolution was checked by litmus paper. This mixture was added by benedict then

forming red brick precipitate that marking that sucrose was hydrolyzed to glucose

and fructose that has aldehyde group and ketone. As for the reaction is :

CH2OH

H O

O CH2OH

HO H OH H OH

OH H O O O OH H

Sucrose CH2OH

H O

H

H

O

CH2OH 4Cu

HO H OH OH OH H OH H

OH H OH H

CH2OH CH2OH

H OH

O

H

OH

HO H OH C OH + OH OH H CH2OH 2Cu2O

OH H H OH red-brick

6.Unknown Sugar

In molisch experiment, sample that was tested is positive namely has

furfural group. Tollens test at addition obtained negative namely there is no silver

mirror precipitate. This testing also producing negative result namely the sample

is non reducing sugar. Osazone sample producing negative result namely the

sample is non monosaccharide.

H. Closing

1. Conclusion

Based on the experiment that hade been done, so it may be conclude that :

a. Reducing sugar is a carbohydrate that has free hemiacetal group on

cyclic and aldehyde group on its opened chain or has ketone as

hemiketal.

b. Sucrose is named on non reducing sugar because of its bond between

C1 on the glucose and C2 on fructose causes fructose does not has free

hemiacetal anymore.

2. Suggestion

a. Student can be more careful in doing the experiment.

b. Student can me more compact with friends group.

BIBLIOGRAPHY

Furniss, B.Ss. dkk.1989. Vogel’s Textbook of Practical Organic Chemistry, Fifth

Edition. England : Longman Group UK Limited.

Mcmurry, Susan.2008. Study Guide and Solution Manual For McMurry,

Fundamental of Organic Chemistry, Sevent Edition. USA : Thomson,

Brooks / Cole.

Rasyid, Muhaidah. 2009. Kimia Organik I. Makasar : Badan Penerbit UNM.

Tim Dosen. 2012. Penuntun Praktikum Kimia Organik II. Makassar :Jurusan

Kimia FMIPA UNM.

Valderrama, Alonso Aguierre. Conformational Analysis of Thiosugar: Theoretical

NMR Chemical Shifts And JH.H Coupling Constant Of 5-Thiopiranose

Monosaccharides. Spain : Journal Of Carbohydrate Chemistry.

Voss, Patricia, G.dkk. Inhibition of Free Cel Splicing by Saccharides that Bind

Galectins and SR Proteins. USA : Journal Of Carbohydrate Chemistry.

Wahjudi, dkk. Common Textbook, Edisi Revisi, Kimia Organic II. Malang : JICA.

Question Answer

1. The reaction of tollens test :

CH2OH CH2OH

H O H2O

OH Ag(NH3)2

HO OH H OH

OH O

H OH H OH

glucose

CH2OH

H O

HO

OH

CO2- + 2Ag

H OH silver mirror

CH2OH

H O O CH2OH

HO OH H

OH H + 2Ag(NH3)2+

+ OH-

H OH O O O H OH

Sucrose

2. Molecule structure of sucrose :

CH2OH

H O O CH2OH

HO OH H

OH H

H OH O O O H OH

Sucrose

Sucrose gives negative result for tollens and benedict test because it has not

free hemiacetal or aldehyde in open chain because it is anomeric atomic carbon

bond in glycoside.

3. Glucose and fructose have osazone crystal because its monosaccharide they

have hemicetal and free aldehyde group.

4. Hydrolysis sucrose with acid react with phenilhydrazin produce compound

because influence of enzyme interface that make of change of rotation

polarizasm to left and right namely muersion sugar.

5. Five ethyl groups can filled to glucose and fructose, it means that they have

hydrogen atoms that can replaced with acetyl group.

CH2OH

H O CH2OH O CH2OH

HO OH H CHOH

OH H

H OH H OH

Glucose fructose

6. Five ethyl groups can filled to glucose and fructose, it means that they have

hydrogen atoms that can replaced with acetyl group.

CH2OH

H O O CH2OH

HO OH H

OH H

H OH O O O H OH

Sucrose

7. Sugar that contain sucrose after hydrolyze is glucose and fructose and sugar

that reduction with benedict test is glucose.

Carbohydrate reaction

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