Project learning in chemistry
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Project Learning in Chemistry. Project. Mr YC Chan United Christian College. Project learning in TAS. Purpose Project schedule Grouping Topics Working schedule Project proposal/Teacher’s approval. Project. Assessment of Project learning.

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Project Learning in Chemistry

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Project learning in chemistry

Project Learning in Chemistry

Project

Mr YC Chan

United Christian College


Project learning in chemistry

Project learning in TAS

  • Purpose

  • Project schedule

  • Grouping

  • Topics

  • Working schedule

  • Project proposal/Teacher’s approval

Project


Project learning in chemistry

Assessment of Project learning

  • Students can be assessed once for ability area A and once for area B.

  • A report may be submitted for the whole group of students.

  • Area B for individual students is assessed by their presentation.


Assessment of project learning

Assessment of Project learning

For TAS project work, teacher assessment can include:

  • Plan

  • Progress

  • Product

  • Presentation

Area A

Area B


Project learning in chemistry

S.6A

Ho Yin Ming (7)

Wong Lai Ping (24)

Wong Yan Ting (26)

Yeung Kwai Fong (28)

CHEMISTRY PROJECT

PRESENTATION


Project learning in chemistry

Our objective is to extract the essential oil (limonene) from orange peels and analyze it by polarimetry.

Oh! Our topic is

Isolation of

(R)-(+)-Limonene

from orangepeels.


Project learning in chemistry

Optical isomerism is characterised by compounds having

the same structure but different configurations,

and

because of their molecular asymmetry these compounds

rotate the plane of polarization of plane-polarised light.

Optical isomers have similar physical and chemical properties; the most marked difference between them is their action on plane-polarised light.

For example,

-1

Theory


Project learning in chemistry

The four atoms or groups of atoms attached to the

asymmetric carbon atom are first arranged in order

of priority.

while the

order three groups appear in ascending or descending

order of priority

If the other three groups appear in a clockwise order

of decreasing priority, the configuration is designated by

the letter R (right).

If such movement is anticlockwise, the letter S (left)

is used.

The molecule is then orientated so that the group of

lowest priority is directed away from us,

R and S system


Project learning in chemistry

Rotation of the plane of polarization to the right or in a

clockwise direction is given a + sign.

A substance having this property is called dextrorotatory and has the prefix (+)- to its name.

Rotation of the plane of polarization to the left or in a

anti-clockwise direction is given a – sign.

A substance which rotates the plane of polarization to the

left is calledlavorotator and has the prefix (-)-to its name.

Direction Of Rotation (+/-)


Project learning in chemistry

Limonene

Limonene is an asymmetric object, which cannot be

divided by a plane into two identical halves.Therefore,

limonene is optically active.

Orange peels provide limonene that is virtually 100%

(R)-(+)-limonene,whereas pine needles provide essentially

100% (S)-(-)-limonene.

Limonene is one of the compounds that give lemons their

tangy odor.


Project learning in chemistry

A polarimeter measures the optical activity of compounds,

that is, the effect a chiral compound has on plane-polarized

light.

Structure of polarimeter:

Polarimeter


Project learning in chemistry

analyzer

Polarimeter

tube

polarizer

Sodium lamp

Power supply

A Real Polarimeter


Project learning in chemistry

Calculation of specific rotation :

[α]λ = ――

α

T

l c

α= the observed angle of rotation

l = the length of the light path through the sample (decimeters)

c = the concentration of the sample (g.mL-1 of solution)

˙

Factors affecting magnitude of α :

1.Concentration

˙The greater the concentration of molecules in the path

of the beam, the greater the rotation.

2.Length of sample tube

˙The rotation of the beam is proportional to the length of

the path.

3.Wavelength of light

˙Generally, the magnitude of rotation is larger at shorter

wavelengths.

4.Solvent & Temperature


Project learning in chemistry

Procedures:

1. The white pulp was removed from the peels of two oranges.

  • 2. The peels were ground in a blender to make a slurry. Then

  • the slurry was poured into a 500 ml round-bottomed flask.

  • 4 drops of an antifoaming agent was added to the flask.

3. The 35 ml water level was marked on the outside of the

round-bottomed flask.


Project learning in chemistry

water out

water in

Heat

  • 4. The steam distillation apparatus were set up without the

  • separatory funnel. The 50 ml round-bottomed flask was

  • used as receiver.

  • 5. The orange peel mixture was boiled at a moderately rapid

  • rate by a heater. The 35 ml distillate was collected.


Project learning in chemistry

  • 6. The distillate was poured into a 125-ml separatory funnel

  • and 2 g of sodium chloride was added in it.

  • 7. The separatory funnel was stoppered, shaken and vented

  • for four or five times.

  • 8. 15 ml chloroform was used to rinse the apparatus and

  • let the chloroform drain into the separatory funnel.


Project learning in chemistry

  • 9. The limonene was extracted from the aqueous layer by

  • inverting the separatory funnel and shaking it back and

  • forth gently.

  • 10. The layers were allowed to separate before draining the

  • bottom organic layer into a dry 50 ml Erlenmeyer flask.


Project learning in chemistry

  • 11. The extraction of aqueous layer was repeated by using

  • another 10 ml of chloroform. Two chloroform extracts

  • were combined and dried with anhydrous calcium

  • sulfate for at least 10 min.

  • 12. A dry watch glass was weighted. The chloroform was

  • filtered through filter paper into the watch glass.


Project learning in chemistry

  • 13. The chloroform was evaporated in a steam bath.

  • 14. The watch glass was cooled and was wiped the outside dry

  • before weighting it .

  • 15. The watch glass was heated several additional minutes, and

  • then it was weighted again. The final mass of limonene was

  • obtained.

  • 16. 5 ml of 95% ethanol was obtained to dissolve the obtained

  • limonene.


Project learning in chemistry

  • 17. After filtration,the limonene and 5-mL ethanol was poured

  • directly into the polarimeter tube.


Project learning in chemistry

Some substances that give an odor of limonene was

extracted.

α

T

l c

˙

As the limonene extracted out is in very small amount,

the angle of rotation (α) cannot be observed.

By using the theoretical value of the specific rotation of limonene and the data used in the experiment, the observed angle of rotation (α) can be calculate as following:

[α]λ = ――

α

= _______________________

(18÷10)[(43.871-43.858)÷5]

α = 0.543。

Since the minimum angle shows by the polarimeter is 1℃,

thus, we could not get the value ofαin our experiment.

Results & Calculation


Project learning in chemistry

Discussion:

Only few amount of limonene can be extracted in our experiment.Do you’ve some improvement?

limonene


Project learning in chemistry

This error can be improved by repeating the extraction process of limonene for more times.This

is to ensure that all limonene in the separatory

funnel is separated out

Rotate


Project learning in chemistry

After our discussion, we also think that chloroform could be added to the orange slurry before the process of steam distillation.So more limonene can be extracted.But,at the same time,many unknown substances will formed besides limonene.


Project learning in chemistry

This problem can be improved by using a rotary

evaporator.It can remove all the unknown

substance rapidly in a vacuum,except limonene.

Rotary Evaporator


Project learning in chemistry

There are still some errors caused

in a polarimeter.

Hmmm… is only

this error in your experiment?

The zero readings of polarimeter

don’t meet their position.

The length of the polarimeter

tube is measured by the ruler.

The measuring error is caused.

This experiment can be improved by using polarimeter with digital readout of the observed rotation.This can avoid any human errors.

 The calculated specific

rotation is affected.


Project learning in chemistry

Questions:

(1)Why do we need to add 2g of sodium chloride into the

distillate?

Ans: The sodium chloride helps to minimize emulsions during

the extractions by making the organic layer less soluble

in the aqueous layer.

(2)Why do we dissolve the limonene in the ethanol at the end

of the experiment?

Ans: It is because ethanol have no optical activity. It does

not have specific rotation.


Project learning in chemistry

(3)Why we must peel the oranges just before grinding the

peels?

Ans: In order to prevent loss of the volatile limonene.


Project learning in chemistry

THE

END


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