Laboratory Report

MODULE 2: LIQUID-LIQUID PHASE EXTRACTION

Name : Matric :
Demo : Lab : Date :
________________________________________________________________________
Objectives

Data and Results

Results Benzoic acid Triphenyl carbinol

Weight of compound in mixture (g)

Weight of compound recovered (g)

Percentage of recovery (%)

Melting point (º C)
Laboratory Report

Discussion

Conclusions
Laboratory Report

QUESTIONS

1. Why do you use NaHCO3 in Section B?

2. What is the purpose of HCl in Section C?

3. During the distillation, why do you use water bath for heating?
Laboratory Report

MODULE 3: RECRYSTALLIZATION
Name : Matric :

Demo : Lab : Date :

________________________________________________________________________

Objectives

Data and Results

A. To select suitable solvent (write D if dissolve; ND if does not dissolve)

Solvent/ Water Ethanol Acetone Suitable

samples Hot Cold Hot Cold Hot Cold solvent
Naphthalene

Cinnamic acid

Acetamide

Benzamide

Benzoic acid

B. Recrystallization of benzoic acid

Weight of impure benzoic acid = ____________ g

Weight of pure benzoic acid = ____________ g

Percentage of pure benzoic acid = ____________ g

(Obtained after recrystallization)
Laboratory Report

Melting point of pure benzoic acid = __________ °C

Pure benzoic acid was obtained as:

i) (shape) _________________

ii) (color) __________________

Discussion

Conclusions
Laboratory Report

QUESTIONS

1. Draw a flow chart to show how recrystallisation can be carried out on compound containing
impurities that: a) Do not dissolve in the solvent used (hot or cold), b) Dissolved in solvent the
used (hot or cold).

2. Compound X dissolved in both hot and cold acetone but do not dissove in either hot or cold
water. What is the most suitable solvent for recrystallisation of X? Draw a flow chart to show
how X can be purified.
Laboratory Report

MODULE 4: IDENTIFICATION OF FUNCTIONAL GROUPS USING IR

SPECTROSCOPY AND QUALITATIVE TESTS

Name : Matric :

Demo : Lab : Date :

________________________________________________________________________

Objectives of the Experiments:

Task 1
Table 1

Homologous Series Functional Group/ Wavenumber/ cm-1 Intensity

Bond
Alcohol O-H 3200 -3600 (broad) Strong
Aldehyde C=O

C-H (aldehyde)

Ketone

Carboxylic acid

Ester

Amine
Laboratory Report

Task 2
Table 2

Unknown Wavenumber/ cm-1 Functional Group/ Inference/ Conclusion

Bond
A Compound A is an/ a …..

Task 3

1. Functional group classification tests (in tabular form).

Test Observation Inference

Laboratory Report

2. Observations.

Compound Test 1 Test 2 Test 3 Test 4 Test 5

A
Laboratory Report

3. Classification of compounds.

Compound Class
▪
A ▪

▪
B ▪

▪
C ▪

▪
D ▪

▪
E ▪

QUESTIONS

1. Below is the structure of pepperonione, a molecule found in pizza that helps the human brain
recognize patterns and therefore makes organic chemistry much easier to learn. Circle and label
all the functional groups in the compound.
Laboratory Report

2. Compound X showed negative observation when tested with Tollen’s and Lucas reagent.
Yellow precipitate was not observed when iodoform test was conducted. Infrared spectrum of
compound X is given below. Which of the following is likely to be X. Give your reasons.
(Pentanal, Pentanol, 3-Pentanone or 2-Pentanone)

IR Spectrum of X
Laboratory Report

MODULE 5: CONFORMATIONAL ANALYSIS OF ALKANES AND CYCLOHEXANES

Name : Matric :
Demo : Lab : Date :
________________________________________________________________________

Objectives

Concepts/Theory

1. Conformational analysis

2. Relative potential energy of staggered conformation against eclipse conformation.

Laboratory Report

Results
Procedure 1 and 2:
Draw the 3-dimensional structure and the Newman projection of ethane and propane conformers.
Laboratory Report

Determine the relative stability of the conformers

Procedure 3:
Make models of butane and sight down the central C-C bond. Determine their relative stability.

Procedure 4:
Draw the chair conformation of cyclohexane and its Newman projection.
Laboratory Report

Procedure 5:
Draw boat and half-boat confirmation of cyclohexane and their Newman projection

Procedure 6:
Draw cyclohexane with proper axial and equatorial bonds.
Laboratory Report

Procedure 7:
Draw models of methylcyclohexane in chair confirmation and their Newman projection. Make a
model of these two conformations.

Discussion
(Discuss on the relative stability of the conformations above and the reasons why the differences
in stability).
Laboratory Report

MODULE 6: STEREOCHEMISTRY
Name : Matric :
Demo : Lab : Date :
________________________________________________________________________

Objectives

Concepts/Theory

1. Stereochemistry

2. Absolute configuration
Laboratory Report

Results
Procedure 1:
Draw the models:

Are the models superimposable? _________________________

Do these models represent the same compound? ______________________

Do these models represent enantiomers? _________________________

Procedure 1b:
Laboratory Report

Procedure 2:
Maximum possible number of stereoisomers for two stars ____________ .
Draw the model of mirror image.

Sketch the sawhorse projection for the mirror image next to the original structure.

Is your second model superimposable on the original model? ______________.

Nonsuperimposable mirror images are called _____________________.
Laboratory Report

Interchange the Br and H atoms bonded at C-2. Sketch the sawhorse projection. Then sketch its
mirror image.

Are these two structures superimposable? _________________.

Nonsuperimposable mirror images are called _______________________.
What term describes how is the first pair related to the second pair? __________________.
They are stereoisomers that are not enantiomers. Stereoisomers that are not enantiomers are called
_____________________________.

Procedure 3:
Laboratory Report

Procedure 4:
Build a model of its mirror image and sketch it to the right of the above structure.

Are the mirror images superimposable? ___________________ .

Nonsuperimposable mirror images are called __________________________.

Exchange the Cl and H atoms at C-2 and sketch the structure in the space below. Build a model of
the new structure’s mirror image and sketch it to the right below.
Laboratory Report

Are these structures superimposable? _______________________.

When two structures are superimposable, they are identical. Identical mirror images of compounds
that contain two or more stereocenters are called ________ forms.

Procedure 5:

Procedure 6:
Laboratory Report

Procedure 7:

QUESTIONS

1. How many chiral carbons are presence in the following molecules and indicate them by
asterisk (*).

a. (CH3)2CHCH2CH2OH b. CH3CH2CH(OH)CH3

H OH

c. d.
NH2
OH
Cl H

H
Cl
e. f. Br
H NH2
Cl OH
Laboratory Report

2. Determine the relationship between the following pairs of molecules

Br
OH H
OH Br
H
H3C H H3C
a.
CH2CH3 ; H CH2CH3 b.
H3C CH2CH3
Br CH2CH3
;
CH3 H Br
H

CH3
H OH Br

H OH HO H CH2
c. H3C OH HO CH3 Br
; d
H3CH2C OH CH3 ;
Br CH2CH3 H3C Br
CH2CH3
H CH3
CH3
Laboratory Report

MODULE 7: NUCLEOPHILIC ADDITION OF CARBONYL GROUP

Name : Matric :
Demo : Lab : Date :
________________________________________________________________________

Objectives

1. Write down your observation here.

Laboratory Report

2. Write down a balance chemical equation for the reaction.

3. Calculate the no of moles of the reactants. (You need to know the MW of your reactants.)

Vanillin: Sodium borohydride:

4. Calculate the maximum amount of vanillyl alcohol that can be generated.

Laboratory Report

5. What is the weight of vanillyl alcohol obtained? Calculate the percentage of yield.

6. What is the final appearance and the melting point of your product?
Laboratory Report

Questions
1. Write down the mechanism of the reaction.

2. Give the correct IUPAC name of the alcohol produced.

3. Draw the structure the product of the reaction of vanillin with hydrogen cyanide.
Laboratory Report

MODULE 8: NUCLEOPHILIC ACYL SUBSTITUTION OF CARBOXYLIC ACIDS

Name : Matric :
Demo : Lab : Date :
________________________________________________________________________

Objectives

Data and Results

1. Observations.

SET Ester Name Appearance bp Odour Weight

Laboratory Report

2. Calculation for the product.

a) Theoretical Yield (in gram)

b) Experimental Yield (in gram and percentage)

Mechanism
Laboratory Report

Discussion

Conclusions
Laboratory Report

QUESTIONS

1. Why did you wash your product with water?

2. Write the equation when the organic phase was washed with sodium carbonate?

3. Explain the function of the acid catalyst in the reaction.

4. What will be the reactants required to produce benzyl acetate via Fischer esterification reaction?
Laboratory Report

MODULE 9: SUBSTITUTION REACTIONS OF ALKYL HALIDES

Name : Matric :
Demo : Lab : Date :
________________________________________________________________________
Objectives

Data/Results
1. Write chemical equations for:

PART A

SN1 Reaction (only for 1 alkyl bromide)

SN2 Reaction (only for 1 alkyl chloride)

Laboratory Report

2. Observations

PART A
SN1 Reaction:
Time
No
No. Name of RX Without With Observation Reaction
Heating Heating

1 1-bromobutane

2 2-bromobutane

3 1-chlorobutane

4 2-chlorobutane

5 2-chloro-2-methylpropane

Reactivity order:
Laboratory Report

SN2 Reaction:
Time
No
No Name of RX Without With Observation Reaction
. Heating Heating

1 1-bromobutane

2 2-bromobutane

3 1-chlorobutane

4 2-chlorobutane

5 2-chloro-2-methylpropane

Reactivity order:
Laboratory Report

PART B

Label Solvent Mixture Polarity Order of Time for Pink

Solvent Mixture Colour Disappeared

X 55:45 acetone:water

Y 60:40 acetone:water

Z 65:35 acetone:water

Reactivity order:

Mechanism

a) SN1
Laboratory Report

b) SN2

Discussion
Laboratory Report

Conclusion

QUESTIONS
PART A

1. Comparing the primary halides 1 and 3, was there a difference in reactivity in the SN2 reaction?
If so, why?

2. Explain the difference in reactivity of alkyl chlorides 3, 4, and 5 in the SN1 reaction.
Laboratory Report

PART B
1. Which solvent mixture causes the fastest reaction? Why?
Laboratory Report

MODULE 10: ELIMINATION REACTION OF ALCOHOL

Name: Matric:
Demo: Lab: Date :
________________________________________________________________________

Objectives:

Observation:

Results:
i. Mass of product after distillation (M1):
ii. Mass of product after base wash (M2):
iii. Calculate the yield of the reaction:
Laboratory Report

Characterization:
Wavenumber/ cm-1 Functional Group/ Bond

Conclusion:

QUESTIONS

1. As alternative to IR spectroscopy, a chemical test can also be done to confirm presence of

a functional group Describe a chemical test that can be done to confirm conversion of
alcohol to alkene.

2. Draw the mechanism for the acid-catalysed elimination reaction of cyclohexanol.

Laboratory Report

3. For acid-catalysed elimination reaction of 2-methylcyclohexanol, draw all possible

products and predict which one will be the major product.

4. In the experiment conducted above, the product was not purified further. Explain how the
purity of the product can be determined using IR spectroscopy. Suggest a purification
technique that can be used to purify the alkene product.
Laboratory Report

MODULE 11: HYDRATION OF ALKENES

Name : Matric :
Demo : Lab : Date :
________________________________________________________________________

Objectives

Data and Results

1. Observation

Physical appearance of product :

Odour :

Colour :

Weight :
Laboratory Report

2. Calculation of the product

i) Theoretical yield (in gram)

ii) Experimental yield (in gram and percentage)

Mechanism

Discussion
Laboratory Report

Conclusion

Questions

1. What is Markovnikov’s Rule?

2. Explain why hexan-2-ol is formed as the major product when 1-hexene undergoes acid
catalyzed hydration.

3. Suggest the reasons that hexan-2-ol has much higher boiling point than hex-1-ene.
Laboratory Report

MODULE 12: OXIDATION OF ALCOHOL

Name : Matric :
Demo : Lab : Date :
________________________________________________________________________

Objectives

Data/Results

Weight of benzyl alcohol = ____________ g

Weight of purified benzoic acid = ____________ g

Benzoic acid theoretical weight = ____________ g

(Show the calculation)
Laboratory Report

Yield of benzoic acid = ____________ %

Benzoic acid was obtained as ______________________.

Melting point for benzoic acid is ______ °C.

Discussion
Laboratory Report

Conclusion

QUESTIONS

1. This experiment can be done in a neutral condition, for example using active MnO2. Suggest
the experimental steps.

2. What products would you expect from oxidation of the following compounds with
Laboratory Report

a) CrO3 in aqueous acid and b) pyridinium chlorochromate?

i) 1-Hexanol ii) 2-Hexanol iii) Hexanal

3. Why the boiling points of alcohol is higher than ether with comparable molecular weight.

4. What alcohols would give the following products on oxidation?

O
O

CH3

a). CH3CHCHO b). c).