M. A.

KAZI INSTITUTE OF CHEMISTRY, UoS, JAMSHORO

Organic Chemistry Practical Model Paper (BS-IV and M.Sc (Pass) Final)
Q.1. What is caffeine?
Answer: Caffeine (C8H10N4O2) is a purine with three functional groups: an amine, amide, and an
alkene. It is an organic molecule that has the properties of an organic amine base
Q.2. Why caffeine is basic?
Answer: The basic property of caffeine comes from the lone pair of electrons found around the
nitrogen(s).
Q.3. What is the structure of caffeine?
Answer:

Q.4. Is caffeine is chiral or achiral?

Answer: It is an achiral molecule and does not have any stereoisomers
Q.5. Is caffeine a polar molecule?
Answer: Caffeine is also a polar molecule; this is evident because of the London dispersion
forces, dipole-dipole interactions, and hydrogen bonding present when it is in water. It also has
a very hydrophobic region
Q.6. Is caffeine water soluble?
Answer: The nitrogen present in caffeine controls solubility. Caffeine is soluble in water at
approximately 2.2 mg/ml at 25C, 180 mg/ml at 80 C, and 670 mg/ml at 100C.
Q.7. How caffeine extracted?
Answer: Caffeine was extracted from tea by the use of solid-liquid and liquid-liquid extractions.
An acid/base liquid-liquid extraction took place in order to force caffeine into the organic layer
Q.8. When extracting caffeine, why the water was kept at a high temperature?
Answer: When extracting caffeine, the water was kept at a high temperature because caffeine is
an organic molecule that has the properties of an organic amine base in order to increase
solubility of caffeine in water to about 670 mg/ml at 100C.
Q.9. Why the solution obtained from extracting caffeine from water was later cooled?
Answer: The solution obtained from extracting caffeine from water was later cooled to a lower
temperature in order to impact the solubility once more and to minimize the attraction to the
aqueous layer % Recovery 59.1 % % Error 40.9%while in the separatory funnel. The solution was
also cooled before the dichloromethane was added because dichloromethane has a boiling
point of 40C. If the cold water was not added to lower the temperature, the dichloromethane
would have evaporated and caffeine would not be properly extracted
Q.10. Why Sodium carbonate is added to the extraction medium during caffeine separation?
Answer: Sodium carbonate is basic. Tannins are acidic compounds with a high molecular weight
that have an OH directly bound to an aromatic ring. Because tannins are acidic and can be
converted to phenolic salts by deprotonation of the OH group when a base is added, it is
possible to separate the tannins from caffeine (Dullo, 2008). Sodium carbonate serves two main
functions: to place caffeine in a more basic environment so that it has a higher affinity for
dichloromethane and to cause the tannins to form phenolic salts in the aqueous solution.
Adding something basic to caffeine will make it more neutral, and the like dissolves like idea
can be applied. In this situation, the sodium carbonate acts as a nucleophile and the tannin is an
electrophile. Nucleophile attacks electrophile. It is basically an acid/base reaction. The aqueous
layer (density of 1 g/ml) contained dissolved tannin salts and chlophyll. Dipole-dipole

Dr. Muhammad Qasim Samejo.. 1

 interactions, london-dispersion forces, hydrogen bonding, and ionic bonding with the salts took
place.
Q.11. When dichloromethane was added to extract caffeine from the aqueous solution, why caffeine
transfer into dichloromethane layer?
Answer: caffeine is usually a polar substance, but it becomes significantly less polar when it is in
a basic solution. Therefore, it is soluble in dichloromethane and suspends in the organic layer.
Q.12. Why dichloromethane layer is lower layer?
Answer: Dichloromethane is an alkyl halide and is denser than water, so it is located at the
bottom of the separatory funnel. It has a density of 1.325 g/m. It had chloro functional groups
that make it susceptible to both substitution and elimination reactions
Q.13. What emulsions?
Answer: Emulsions are small droplets of the organic layer that are suspended in the aqueous
that are a result of vigorous shaking of the separatory funnel
Q.14. Why A drying agent was added to the organic layer?
Answer: A drying agent was added to the organic layer because dichloromethane dissolved not
only the caffeine, but water as well. The drying agent, anhydrous CaCl2 was added to remove
excess water so that a pure sample of caffeine could be obtained after the solvent evaporated at
room temperature. Anhydrous calcium chloride has a high affinity for water, and then reverses
back to the hydrous form after it has absorbed the water. Calcium chloride is a preferred drying
agent because the pellets form clumps when excess water is present that make it simple to
identify how much drying agent is needed. The pellets stopped clumping together when excess
water was removed. It is also very rapid, effective, and ideal for microscale experiments
Q.15. What is Soxhlet extraction?
Answer: A Soxhlet extractor is a piece of laboratory apparatus invented in 1879 by Franz von
Soxhlet. It was originally designed for the extraction of a lipid from a solid material. Typically, a
Soxhlet extraction is used when the desired compound has a limited solubility in a solvent, and
the impurity is insoluble in that solvent. It allows for unmonitored and unmanaged operation
while efficiently recycling a small amount of solvent to dissolve a larger amount of material.
Soxhlet extraction. Definition: The process of transferring the partially soluble components of a
solid to the liquid phase using a Soxhlet extractor. The solid is placed in a filter paper thimble
which is then placed into the main chamber of the Soxhlet extractor.

1: Stirrer bar/anti-bumping granules; 2: Still pot (extraction pot) - still pot should not be overfilled and
the volume of solvent in the still pot should be 3 to 4 times the volume of the soxhlet chamber.;
3: Distillation path; 4: Soxhlet Thimble; 5: Extraction solid (residue solid); 6: Syphon arm inlet; 7: Syphon
arm outlet; 8: Reduction adapter; 9: Condenser; 10: Cooling water in; 11: Cooling water out
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Dr. Muhammad Qasim Samejo..
Q.16. What is eugenol?
Answer: Eugenol, C10H12O2 is a one of the compound of phenylpropanoid family. It is a pale
yellow oily compound that extracted from essential oil especially from cloves and bay leaf.
Q.17. Why is eugenol steam-distilled rather than purified by simple distillation?
Answer: Eugenol has a high boiling point (254 C), and many organic compounds decompose at
such high temperatures. Steam distillation allows eugenol to be distilled at a much lower boiling
point (< 100 C), thus minimizing the potential for decomposition.
Q.18. Steam distillation is one way to isolate an essential oil from a plant or fruit. Describe two other
methods.
Answer: Expression (or cold-pressing) is the process of mechanically squeezing the oils out of
the source, and is usually used for isolating citrus fruit essential oils. Solvent extraction is the
process of treating the source with an organic solvent, such as hexane or supercritical carbon
dioxide. The oils dissolve in the organic solvent, and then are isolated by evaporating the
organic solvent.
Q.19. What is the structure of Eugenol?
Answer:

Q.20. How % recovery of Eugenol can be calculated?

Amount of Eugenol isolated
Answer: % = Amount of cloves used 100
Q.21. How eugenol can be isolated from cloves?
Answer: The boiling point of eugenol, an oil found in cloves, is 248 C, but it can be isolated at a
lower temperature by performing a co-distillation with water, this process is also know as a
steam distillation.
Q.22. Why steam distillation is not an effective method for the isolation of eugenol?
Answer: Steam distillation is not an effective method for the isolation of eugenol due to the
interactions between water and the functional groups of eugenol.
Q.23. What type of compounds isolated by Steam distillation?
Answer: Steam distillation is used to isolate, separate or purify those compounds that have high
boiling point or have low decomposition point. The compound to be distilled must be insoluble
or only slightly soluble in water.
Q.24. Why eugenol distilled below 100C even the boiling point of eugenol is 254C?
Answer: The clove oil and the water will co-distill. Remember that both the water and the clove
oil exert a vapor pressure. For this experiment water has the higher vapor pressure compared to
the clove oil, consequently more water will distill. Most compounds, regardless of their boiling
point, will distill at temperatures below pure that of boiling water.
According to DaltonLaw Ptotal = P1 + P2. Boiling will occur when the total pressure equals 760
torr. The vapor pressure of pure water is 100 C is 760 torr. Since the vapor pressure of the
second compound adds to the total pressure, the mixture will distill less than 100C.
Steam distillation relies on the immiscible nature of water and organic compounds. Water boils
at 100C and eugenol boils at 254C. Boiling occurs when the total vapor pressure exceeds the
applied pressure. The vapor pressure of the water allows for the vaporization of eugenol at a
signinficantly lower temperature.
Ptotal = Pwater + Peugenol
Please recall that boiling occurs when the pot liquids have a vapor pressure equal to the external
pressure. In steam distillation, the pressures of the two components must add up to 760 torr
Q.25. What is the theory behind steam distillation (i.e. how does it work and how can it be used to
purify and impure organic compound)?
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Dr. Muhammad Qasim Samejo..
 Answer: Steam distillation is used for separating volatile organic compounds from nonvolatile
inorganic salts or from leaves and seeds of plants. Steam distillation allows separating
substances at lower temperatures which is useful since many organic compounds tend to
decompose at high sustained temperatures which regular distillation would require. By adding
water or steam to the distillation apparatus, the boiling points of the compounds are depressed,
allowing them to evaporate at lower temperatures.
Q.26. What kind of mixtures may be better separated by steam distillation than by simple distillation?
Why?
Answer: Mixtures with organic compounds that are sensitive to high heat should be extracted
by steam distillation. Steam distillation uses water or steam to depress the boiling points and
thus allow separation at lower temperatures. Simple distillation is generally used in two
situations: (1) when the last step in the purification of a liquid compound involves a simple
distillation to obtain the pure product and determine its boiling point (2) when simple
distillation is used to remove a low-boiling solvent from a dissolved organic compound with a
high boiling point. In this experiment there is a big difference between the boiling point of the
two compounds so simple distillation seems like it could be used by situation 2; however, the
low boiling point of hexane make steam distillation a better approach.
Q.27. Mention the Classification Test of eugenol (clove oil)
Answer: The eugenol isolated will be tested for unsaturation using the potassium permanganate
Test and aromaticity with the ferric chloride test.
Q.28. What is Lactose?
Answer: a disaccharide sugar C12H22O11 that is present in milk and yields glucose and galactose
upon hydrolysis and yields especially lactic acid upon fermentation
OR
A white crystalline disaccharide consisting of a glucose and a galactose molecule,
Q.29. What is the structure of lactose?
Answer:

Q.30. What is Casein?

Answer: Casein, the main protein in milk, is a phosphoprotein, meaning that phosphate groups
are attached to the hydroxyl groups of some of the amino acid side-chains. Casein exists in milk
as the calcium salt, calcium caseinate
Q.31. What is the mechanism of isolation of casein from milk?
Answer: Calcium caseinate has an isoelectric point of pH 4.6. Therefore, it is insoluble in
solutions of pH less than 4.6. The pH of milk is about 6.6; therefore, casein has a negative charge
at this pH and is solubilized as a salt. If acid is added to milk, the negative charges on the outer
surface of the casein micelles are neutralized (by protonation of the phosphate groups) and the
neutral protein precipitates, with the calcium ions remaining in solution:
Ca-caseinate + 2H+ ---------- casein + Ca2+
Q.32. Miscible liquids that have different boiling points can be separated by which technique?
Answer: Distillation
Q.33. Which one of the following methods is used to separate the colours in food dyes?
Answer: Chromatography
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Q.34. At what pH casein insoluble in milk?
Answer: Casein exists in milk as the calcium salt, calcium caseinat. Calcium caseinate has an
isoelectric point of pH 4.6. Therefore, casein is insoluble in solutions of pH less than 4.6.The pH
of milk is about 6.6, casein has charge at this pH and is solubilized as a salt.

Q.35. What is the average composition of milk from several mammals consumed by humans.
Answer:
Cow Human Goat Sheep Horse
Water 87.8 87.4 87.0 82.6 90.6
Protein 3.0 1.4 3.3 5.5 2.0
Lipids 3.9 4.0 4.2 6.5 1.1
Sugars 4.6 7.0 4.8 4.5 5.9
Minerals 0.7 0.2 0.7 0.9 0.4
Q.36. The diagram shows the apparatus for separating soil and water. What are the labelled parts?
Answer: A = residue, B = filtrate
Q.37. Sand and gravel may be separated from each other through using
Answer: Sieve
Q.38. Which separation techniques will BOTH separate sand from a mixture of salt and water
Answer: Distillation and evaporation
Q.39. In a coffee machine, the ground coffee is separated from the coffee solution by using which
technique
Answer: filter paper
Q.40. Name the separation technique shown in the diagram
Answer: evaporation
Q.41. Which techniques would best be used to separate soil and water?
Answer: Filtration
Q.42. Liquids that do not mix may be separated by using: Answer: a separating funnel
Q.43. How Separation Techniques can be classify?
Answer:
Basis of Separation Separation Technique
size Filtration, dialysis, size-exclusion chromatography
mass or density centrifugation
complex formation masking
change in physical state Distillation, sublimation, recrystallization
change in chemical state Precipitation, electrodeposition, volatilization
partitioning between phases Extraction, chromatography
Q.44. What is azeotrope?
Answer: An azeotrope or a constant boiling mixture is a mixture of two or more liquids whose
proportions cannot be altered by simple distillation. This happens because, when an azeotrope
is boiled, the vapour has the same proportions of constituents as the unboiled mixture.
Q.45. What is zeotropic mixture?
Answer: A zeotropic mixture is a chemical mixture that never has the same vapor phase and
liquid phase composition at the vaporliquid equilibrium state. Zeotropic mixtures can be
separated by normal distillation

Dr. Muhammad Qasim Samejo..