DEPARTMENT OF CHEMISTRY

FACULTY OF SCIENCE

ORGANIC CHEMISTRY
I CHM3201

LABORATORY REPORTS

for

LABORATORY MODULE

SEMESTER 2
2019/2020

1
MODULE 2: Purification of organic mixtures

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 solvent
Hot Cold Hot Cold Hot Cold
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)
 °
Melting point of pure benzoic acid = C

Pure benzoic acid was obtained as:

i) (shape)

ii) (color)

Discussion

Conclusions
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 dissolve 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.
MODULE 3: Extraction of organic mixtures

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)

Discussion
Conclusions

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?
MODULE 4: Thin layer chromatography

Name : Matric :

Demo : Lab : Date :

1. Explain from your understanding the meaning ‘like attracts like’ related to polarity.

2. Answer the following question in relation to the experiment.

a) Draw the TLC profiles acquired by the three solvent systems used.

b) Calculate the Rf of the main spots in each solvent system.

3. How are the spots on the TLC plates observed? Why the spots should not be observed or
detected only by one method?

4. When using the mobile phase system of hexane:ethyl acetate (9:1), lawsone spot can be
detected near the bottom of the TLC plate. What can you do to make the lawsone spot be
observed above Rf = 0.5?

5. Identify chemical constituents in the three plant samples.

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.

Results

Procedure 1 and 2:

Draw the 3-dimensional structure and the Newman projection of ethane and propane
conformers.

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.

Procedure 5:

Draw boat and half-boat confirmation of cyclohexane and their Newman projection.

Procedure 6:

Draw cyclohexane with proper axial and equatorial bonds.

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).
MODULE 6: Stereochemistry - chirality

Name : Matric :

Demo : Lab : Date :

Objectives

Concepts/Theory

1. Stereochemistry

2. Absolute configuration

Results

Procedure

1:

Draw the models:

Are the models superimposable?

Do these models represent the same compound?

Do these models represent enantiomers?

Procedure 1b:

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 .

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:
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.

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:

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

chiral carbon(s) chiral carbon(s)

HOH
c) d)
NH2 OH
Cl H

chiral carbon(s) chiral carbon(s)

2. Determine the relationship between the following pairs of molecules

H
a) OH OH
; H CH CH Relationship :
H3C 2 3
CH2CH3
CH3

Br H
Br
H3C H ; H3C Relationship :
b) CH CH
Br CH2CH3 2 3

H Br
H

CH3
H O
HO H H
H OH
c) ; Relationship :
H3CH2C OH
CH3
CH2CH3
H
 Br
CH2CH3

d) H3C OH ; HO Br Relationship :
Br CH2CH3

CH3 H3C Br
CH3

3. i) Convert the following Newman projections to Fischer projections.

ii) Determine the R and S configuration of each chiral carbon.

CH3 CH CH
H 2 3
a) HO CH3
b)
CH3
HO H Cl H Cl
H
MODULE 7: Substitution reaction of alkyl halides

Name : Matric :

Demo : Lab : Date :

Data/Results

1. Write chemical equations for:

PART A

SN1 Reaction (only for 1 alkyl bromide)

SN2 Reaction (only for 1 alkyl chloride)

2. Observations

PART A

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

1 1-bromobutane

2 2-bromobutane

3 1-chlorobutane

4 2-chlorobutane

5 2-chloro-2-methylpropane
 Reactivity order:

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:

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
b) SN2

Discussion

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.

PART B

1. Which solvent mixture causes the fastest reaction? Why?

MODULE 8: Oxidation of alcohol (Preparation of benzoic acid)

Name : Matric :

Demo : Lab : Date :

Objectives

Data/Results

Weight of benzyl alcohol = g

Weight of purified benzoic acid = g

Benzoic acid theoretical = g

weight (Show the calculation)

Yield of benzoic acid = %

Benzoic acid was obtained as .

Melting point for benzoic acid is °C.

Discussion

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

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)
MODULE 9: Hydration of alkenes

Name : Matric :

Demo : Lab : Date :

Objectives

Data and Results

1. Observation

Physical appearance of product :

Odour :

Colour :

Weight :

2. Calculation of the product

i) Theoretical yield (in gram)

ii) Experimental yield (in gram and percentage)

Mechanism

Discussion

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.
MODULE 10: Nucleophilic addition of a carbonyl group

Name : Matric :

Demo : Lab : Date :

Objectives

1. Write down your observation here.

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:

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

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

5. What is the final appearance and the melting point of your product?
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.
MODULE 11: Fischer esterification

Name : Matric :

Demo : Lab : Date :

Objectives

Data and Results

1. Observations.

SET Ester Name Appearance bp Odour Weight

2. Calculation for the product.

a) Theoretical Yield (in gram)

b) Experimental Yield (in gram and percentage)

Mechanism

Discussion

Conclusions
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?
MODULE 12: Carbohydrates chemistry

Name : Matric :

Demo : Lab : Date :

Objectives

Data and Results

A. REDUCING SUGAR TEST

Observation
Sugar Conclusion
Tollens test Benedicts test
Glucose

Sucrose

Fructose

Lactose

B. PHENYLHYDRAZINE TEST

Sugar/ Melting point of

Observation
compound precipitate
Acetaldehyde

Glucose

Sucrose

Fructose

Lactose
C. HYDROLYSIS OF DISACCHARIDE AND POLYSACCHARIDE

Hydrolysis Observation

Sucrose with acid

Starch with acid

Sucrose with enzyme

Reactions / Mechanism

1. Write the equation for Tollen’s test on glucose and sucrose

2. Write the mechanism for hydrolysis of sucrose catalysed by an acid.

Discussion
Conclusion

QUESTIONS

1. Identify which are reducing and non-reducing sugars among the four samples tested.

2. Explain sucrose character on Tollen’s and Benedict reagents.

3. Explain why osazone obtained from D-glucose and D-fructose have the same melting
points.

4. Draw lactosazone structure.

MODULE 13: Qualitative organic functional group tests

Name : Matric :

Demo : Lab : Date :

Objectives

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

Test Observation Inference

2. Observations.

Compound Test 1 Test 2 Test 3 Test 4 Test 5

3. Classification of compounds.

Compound Class

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.

O
H HO
OH

H H
O

2. Give suitable mechanisms for both Tollen’s and Iodoform tests.