IPUC CHEMISTRY

DEPARTMENT OF CHEMISTRY
KS PRE-UNIVERSITY COLLEGE, BENGALURU-109
KS PUC CLASS:I PUC SUBJECT:CHEMISTRY

ORGANIC CHEMISTRY - SOME BASIC PRINCIPLES AND TECHNIQUES

ONE MARK QUESTION

1. What is catenation?
2. Write the functional group of aldehydes.
3. Identify the functional group present in CH,CH;COCH3.
4. What is IUPAC name of diethyl ethers.
5. Name the reaction intermediate formed, during homolytic fission of a covalent bond.
6. Among primary, secondary and tertiary carbocation which is most stable?
7. Arrange the following carbocations in the increasing order of their stability.
CH: CH3 CH,

CH, CH-CH, CH-C-CH3

8. Among primary, secondary and tertiary carbanion which is least stable?

9. Arrange the following carbanions inthe increasing order of their stability.
CH3 CH3 CH3

CH2 CH-CH CHsCHs

10. Define mesomeric (or) resonance effect.
11. What is electromeric effect?
12. Which one of the following shows maximum hyperconjugation effect?
CH,CH=CH2, (CH3)2C=CH2, CH,=CH2
13, Which effect involves the displacement of electron pair under the influence of an attacking
reagent.
14. Name the method used to separate the liquids with smaller difference in boiling points.
15. Mention one use of chromatography.
16. Suggest asuitable method toseparate sugar and salt from an aqueous solution
containing them.
17. Which is the suitable absorbent in the process of Column Chromatography?
18. What is steam distillation?
19. Mention the elements detected by Lassaigne's extract.
20. What is the formula of Ferric ferrocyanide?
21. Why is fusion of organic compound with sodium required?
22. Which gas is liberated in Duma's process?
23. Which gas is liberated in Kjeldahl's method?
24. Name the compound which is formed during Carius method for the estimation of
phosphorous.

TWO MARKS QUESTIONS

1. What are Alicylic compounds? Give example.
2. What are aromatic compounds? Give example.
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3. What are Heterocyclic compounds? Give example.

4. What is functional group? Give the functional group of alcohols.
5. Explain homologous series with an example.
6. Explain functional isomerism with an example.
7. Explain position isomerism with example.
8. Explain chain isomerism with an example.
9. What is heterolytic fission? Give example.
10. What is homolytic fission? Give example.
11. What is free radical? Give example.
12. What is carbocation? Give example.
13. What is carbanion? Give example.
14. Mention the hybridization state of carbon in CHy* and mention itsshape.
15. Mention the hybridization state of carbon in CHg and mention its shape.
16. Explain inductive effect with a suitable example.
17. Define -I effect. Give example.
18. Define +I effect. Give example.
19. Explain -R effect. Give example.
20. Explain +R effect. Give example.
21. What is resonance energy? Write the resonance structure of benzene.
22. What is -E effect. Give example.
23. What is +E effect. Give example.
24. Identify the type of electron displacement effect in the following
i)
CH,-CH,cI
64
i) \

25. Write any two differences between inductive and electromeric effect.
26. Write any two differences between inductive and resonance effect (mesomeric effect).
27. Define chromatography. Mention its type which depends on selective adsorption and
desorption.
28. How is C and H detected by copper oxide method?
29. What is the action of CO, gas on lime water? Write the chemical equation.
30. How do youdetect Sulphur using Lassaigne's test/sodium fusion extract?
31. Using SFE how would you detect halogen in organic compound?
32. 0.1g of an organic compound gave 0.08g of silver bromide. Calculate the percentage of
bromine in the organic compound. (atomic mass of Ag = 108g, Br = 80g)
33. What are electrophiles? Give example.
34. What are nucleophiles? Give example.

THREE MARKS QUESTIONS

1. How is Lassaigne's extract prepared? How do youdetect nitrogen by Lassaigne's test?
2. How is Sulphur estimated by Carius method?
3. How to estimate halogens from Carius method?
4. What are the characteristics of homologous series?
5. Give a note on thin layer chromatography.
6. Write a note on column chromatography.
7. Write the principle involved in the estimation of carbon and hydrogen by Liebig's method.
Give diagram and calculations.
8. Howis nitrogen estimated by Kjeldahl's method?
9. How is nitrogen estimated by Duma's method?
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ANSWERS
ONE MARK QUESTIONS
themselves resulting in
1. Catenation is the property of atoms to form covalent bond among
the formation of long chain molecules.
2. -CHO (or)
3. -CO- ’ Ketone
4. -R-0-R- ’ Alkoxy
5. Free radical
6. Tertiary carbocation
7. CH3 CH3 CH3

CH, CH-CH3 CH3-CCH3

(Methyl carbocation < primary carbocation < secondary carbocation < tertiary carbocation)
8. Tertiary carbanion
9. CH3 CH3 CH3

CH3-C
(Tertiary carbanion < secondary carbanion < primary carbanion <Methyl carbanion)
10. Polarity is induced in a molecule by interaction of two pi bonds or between a pi bod and
lone pair of electrons in a conjugated system. This effect is known as resonance (or)
mesomeric effect.
11. The transfer of shared pair of pi electrons to one of the atoms joined by a multiple bond
on attack of a reagent is called electromeric effect.
12. (CH,),C=-CH,
13. Electromeric effect
14. Fractional distillation
15.- Used to separate components
- Used to purify compounds
- Used to isolate compounds
- Used for identification of components
16. Crystallization
17. Al,0, (alumina) or silica gel
18. Steam distillation is the method used to separate organic compounds from non-volatile
impurities by distillation with steam.
19. Nitrogen, Sulphur, halogen, phosphorous
20. Fe, [Fe(CN)6]3.XH,0
21. It is done so as to convert organic compound into inorganic compound.
22. Nitrogen gas
23. Ammonia gas
24. Mg(NH,)PO, which on heating gives Mg2P,0, (Magnesium pyrophosphate)

TWO MARKS QUESTIONS

1. Saturated hydrocarbons joined by covalent bond to form ring structure are called alicyclic
compounds.
Example -

Cyclopropane cyclobutane

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aromatic compounds.
2. Compounds containing atleast one benzene ring are called
Example - Benzene, naphthalene etc.
as N, S, O etc. in the ring are
3. Cycliccompounds having one or more heteroatoms such
called heterocyclic compounds.
Example - Furan, Tetrahydrofuran, Pyridine etc.
determine the characteristic chemical
4. Functional group is an atom or group of atoms which
properties of the organic compound.
Functional group of alcohols : -OH
5. Aseries of same class of organic compounds which can be represented by a general
formula and in which successive members differ by -CH,- group is called a homologous
series.
Example - Alkanes CH3-CH3 CH-CH-CH3
Ethane Propane
groups are called
6. Two compounds having same molecular formula but different functional
functional isomers and this phenomenon is called functional isomerism.
Example - Aldehydes and ketones
CH,CH,CHO CH,COCH3
Propanal Propanone
7. Two compounds having same molecular formula but differ in the poaition of the same
functional group or substituent on the carbon chain are called position isomers and this
phenomenon is called position isomerism.
Example - Chloropropane (C,H,CI) has two position isomers
CH,CH,CH,CI CH,CH(CI)CH3
1-chloropropane 2-chloropropane
8. Two or more compounds having same molecular formula but differ in the carbon chain
structure are called chain isomers and this phenomenon is called chain isomerism.
Example - CH,CH,CH,CH3 CH3-CH-CH,
n-butane
CH3
isobutane
9. An unsymmetrical breaking of a covalent bond, where the shared pair of electrons remain
with one of the fragments resulting in the formation of positive and negatively charged
particles.
CH3-Br ’ CH,* + Br -
10. Symmetrical breaking of a covalent bond, where each of the fragments contain one
electron resulting in formation of free radical.
CI - CI’ Ci' + Ci
11. Aneutral species containing an oddelectron formed due to homolytic fission of a covalent
bond is called a free radical.
Example - CHg-Cl ’ CH;° + CI'
12. Apositively charged carbon species formed due to heterolytic fission of covalent bond.
Example - CH3-Br ’ CH,* + Br
13. A negatively charged carbon species formed due to heterolytic fission of covalent bond.
Example - CH3-MgI ’ CH, + Mg*I
14. Hybridization - sp
Shape - Planar
15. Hybridization - sp
Shape - Tetrahedral

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16. Polarity is developed in a molecule due to displacement of bonded pair of sigma electrons
towards the more electronegative atom. This effect is known as inductive effect.
Example -66
CH,CH,-CI
Due to inductive effect Cl acquires partial negative charge and Cacquires partial positive
charge developing polarity in the molecule.
17. Partial displacement of bonded pair of sigma electrons towards the substituent is called -I
effect.
Example: -NO2, - CN, -F, -COOH, -CI, -Br, -I, -0CH3 etc.
(They are considered as electron withdrawing groups)
18. Partial displacement of bonded pair of sigma electrons away from the substituent is called
-I effect.
Example: Alkyl groupslike methyl (-CH3) &ethyl (-CH2 - CH3)
(They are considered as electron donating groups)
19. Resonance effect in which the displacement of electrons takes place towards the
substituent group attached to conjugated system is called-R effect.
N N

Groups such as -NO2, -CN, -CHO, - COOH, - COOR etc. shows -R effect.
20. Resonance effect in which the displacement of electrons takes place away from the
substituent group attached to conjugated system is called +Reffect.
:NH, NI, NH, ANH, NH,

Groups such as -CI, -Br, -I, -NH2, -NHR, -OH, -OR, -SH, -0CH3 etc. shows +R effect.
21. The difference in energy between the energy of resonance structure and the lowest
energy (or) most stable canonical structure is called resonance energy.

22. It is an electromeric effect in which pi electrons of multiple bond are transferred to the
atom to which attacking reagent does not attack.

>c<+ CN ’>Ç-<
CN
23. It is an electromeric effect in which pielectrons of multiple bond are transferred to the
atom to which reagent attacks.
c <+H -c<
H
24. i) -I effect (negative inductive effect) i) +E effect (positive electromeric effect)

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25.
ELECTROMERIC EFFECT
INDUCTIVE EFFECT
It is a permanent effect It is atemporary effect
It is a weak effect It is astrong effect
This involves shifting of sigma bonds This involves shifting of pi bonds
Presence of attacking reagent is not Presence of attacking reagent is required
required
Develops partial charge in molecule Develops complete charge in molecule
This occurs in saturated system This occurs in unsaturated system

26.
INDUCTIVE EFFECT RESONANCE EFFECT
Does not involve delocalization of It involves delocalization of electrons
electrons
It is a weak effect It is astrong effect
This involves displacement of pi
This involves displacement of sigma electrons
electrons
This effect decreases with increase of This effect remains same throughout the
distance from substituent group conjugated system

Develops partial charge in molecule Develops complete charge in molecule

This occurs in saturated system This occurs in conjugated system

components, to purify, to isolate and for

27. Chromatography is a technique used to separate
identification of components.
layer chromatography)
Adsorption chromatography (Column chromatography and thin heated with copper oxide.
hydrogen is
28. The given organic compound containing carbon and
oxidized to carbon dioxide and water
Carbon and hydrogen present in the compound are
respectively.
C+ 2Cu0 ’ 2Cu + CO,
2H + CUO Cu + H,0
confirming the presence of
The carbon dioxide turns lime water milky forming turbidity,
carbon.
CO, + Ca(OH)) CaCO, + H,0
blue coloured hydrated copper
Water when treated with white copper sulphate turns into
sulphate, confirming the presence of hydrogen.
5 H,0 + CusO, ’ CuSO4.5H,0
White Blue
turbidity, confirming the presence of
29. The carbon dioxide turns lime water milky forming
carbon.
CO; + Ca(OH), ’ CaCO, + H,0
Lime water milky
acetate is added. Black
30. i) Sodium fusion extract is acidified with acetic acid. Lead
precipitate of lead sulphide is obtained confirming the presence of Sulphur.
2Na + S ’ NaS
Na,S + (CH;CO0),Pb ’ PbS + 2CH,COONa
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ii) Sodium fusion extract is treated with sodium nitroprusside. The appearance of violet
colour indicates the presence of Sulphur.
Na,S + Na[Fe(CN),NO]’ Na.[Fe(CN),NOS]
Violet colour
31. Sodium fusion extract is acidified with nitric acid, then treated with silver nitrate solution
"White precipitate obtained soluble in excess of NHaOH - Chlorine is present
"Pale yellow precipitate obtained sparingly soluble in NH,OH - Bromine is present
"Yellow precipitate obtained insoluble in NH,OH - Iodine is present
Na + X’ NaX
NaX + AgNO ’NaNO, + AgX (X = Cl, Br, I)
Silver nitrate Silver halide
32. Given: Mass of organic compound = m = 0.1g
Mass of silver bromide (AgBr) = mj = 0.08g

Atomic mass of Brx m1 x 100 80 x 0.03 x 100

= 34.04%
Percentage of Br = 188 x 0.1
Molecular mass of AgBr x m
33. The electron deficient species or positively charged ions which are capable of accepting
electrons are called electrophiles.
Example -Positively charged electrophiles: H*, Ci, Br*, NO, etc.
Neutral electrophiles: SO3, BF3, AlCl3 etc.
34. The electron rich species or negatively charged ions which are capable of donating
electrons.
Example - Negatively charged nucleophiles: Cl, Br, OH, etc.
Neutral nucleophiles: NH3, R,NH, RNH2, ROH, etc.

THREE MARKS QUESTIONs

1. In Lassaigne's test, small piece of sodium is taken in a fusion tube, heated and melted.
Little amount of organic compound is added to the tube. The tube is heated till it turns red
hot and dropped in distilled water in a china dish. The contents are heated and filtered. The
fltrate obtained is sodium fusion extract (SFE) or Lassaigne's reagent.
Na + C+ NNaCN
2Na + S Na,S
Na + X NaX (X=Cl, Br, I)

Nitrogen is detected by boiling Sodium fusion extract with ferrous sulphate and acidified
with concentrated Sulphuric acid which produces prussian blue colour confirming the
presence of nitrogen.
"Sodium cyanide reacts with ferrous sulphate to form sodium hexacyanidoferrate (II)
Na + C+ N ’NaCN
FeSO, + 2NaCN Fe(CN)2 + Na,SO4
Fe(CN)2 + 4NaCN ’ Na, [Fe(CN)6]
sodium hexacyanidoferrate (II)

"On heating with conc. Sulphuric acid, Fe* is oxidized to Fe which reacts with sodium
hexacyanidoferrste (II)to produce iron (III) hexacyanidoferrate (ferric ferrocyanide)
which is Prussian blue in colour.
3 Na, [Fe(CN)6] + 4Fe* ’ Fe, (Fe(CN )6]3.xH,0
Prussian blue

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acid. Sulphur present in the

2. Organic compound is heated in carius tube with fuming nitric
precipitate of
compound is oxidized to sulphuric acid. On adding BaCl, solution, white
washed, dried and weighed.
barium sulphate (BaSO4) is formed. This precipitate is filtered,
Calculation: Let mass of organic compound be mg
Let mass of barium sulphate (BaS04) be m1 g
233g of BaSO4 gives 32g of sulphur
32 x m1 x 100
Percentage of Sulphur = 233 X m
presence of silver nitrate in a hard
3. Organic compound is heated with fuming nitric acid in H,0. Halogen
glass tube, i.e., carius tube. Carbon and hydrogen are oxidized to CO, and
present forms silver halide (AgX). It is filtered, dried and weighed.
Calculation: Let mass of organic compound be mg sealed capllary
Let mass of AgX formed be mi g
Atomic mass of Xx m1x 100
Percentage of X = (X = CI, Br, I)
Molecular mass of AgX x m

35.5 x m1 x 100
Percentage of CIl = 143.5 x m
2 cm

80 x m1 x 100
Percentage of Br = fuming HNo,
188 x m
AgNO,
organic
127 x m1 x 100 compound
Percentage of I= 235 X m

4. - All the members can be represented by a general formula.

- Every successive members of the series differ by -CH2 group.
- All the members can be prepared by similar methods.
- All the members will have similar chemical properties.
mixture
5. Thin layer chromatography is a technique involving separation of componentsof a
over athin layer of adsorbent (Alumina, Silica gel) coated on aglass plate. This plate is
known as thin layer chromatography plate (TLC plate) or chromoplate.
end of
The mixture to be purified is applied as asmall dot about 2cm above the bottom
plate. The TLC plate (stationary phase) is placed in a little amount of eluant (mobile phase)
distances
in aclosed jar. As eluant rises up the plate, components move up to different
depending on different degrees of adsorption. When the solvent moves upto 3/4th of the
plate, it is removed and solvent front is marked. Components moved on plate as spots are
marked.
of its
The relative adsorption of each component of the mixture is expressed in terms
retention factor (Ri)
Distance moved by component from base line Solvent
Re= Front
Distance moved by solvent from base line
-Spot

+ Base
Line

components of a mixture
6. Column chromatography is a technique involving separation of
over a column of adsorbent (Alumina, Silica gel).

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In this technique, column of adsorbent - stationary phase is packed in a glass tube with
astopcock at lower end with a glass wool placed at bottom. Compound to be purified is
placed on top of the adsorbent column. An appropriate eluant (solvent usedto remove
adsorbed substance) - mobile phase is allowed to flow down the column slowly.
Dependingon the degree of adsorption, components separate in the column, i.e, most
adsorbed component remains on top and least adsorbed component flows down. Different
components are collected in separate conical flasks. Further, eluant is distilled or
evaporated to obtain pure component. Lmobile
phase
losded
sarnole
sample
LTseoaralion stronger
interacions

stationay
phese -resolved
eaker
bands
interactions

oeluted.
molecules

7. A known mass of organic compound is burnt in presence of oxygen and copper oxide.
Carbon and hydrogen present in the compound are oxidized to CO, and H,0 respectively.
This mixture is allowedto pass through U-tubes containing anhydrous CaCl, and KOH
solution. CO, is adsorbed in KOH solution and H,0 is absorbed in anhydrous CaClz.
Percentage of carbon can be estimated by determining the increase in mass of KOH
solution and percentage of hydrogen can be estimated by determining the increase in mass
of anhydrous CaCzhple in Platinum boat CuO pallets
Combustion
tube

Excess
Oxygen

Pure dry
Oxygen

Anhydrous Calcium chloride KOH Solution

Calculation: Let mass of organic compound be 'm'g

Let mass of CO, = M1 9
44g of CO, gives 12g of C
12 x m1 x 100
Percentage of carbon = 44 X m

Let mass of H,O = m2 9

18g of H,0 gives 2g of H
2 x m2 x 100
Percentage of hydrogen = 18 x m
8. Organic compound containing nitrogen is heated with conc. HSO4. Nitrogen is converted to
ammonium sulphate. This mixture is heated with NaOH. Ammonia gas is liberated. This
liberated ammonia gas is passed into standard solution of acid (H,SO4). Amount of
ammonia produced is determined by estimating the amount of acid consumed.
Amount of acid consumed is estimated by back titration, wherein, acid is titrated with an
alkali solution (NaOH). NaOH will neutralize the unreacted acid left in the solution and the
volume of unreacted acid is determined. By taking a difference of initial volume of acid and
amount of acid unreacted, amount of acid consumed by ammonia is determined.
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Yeldah'e

Contents of
Kjeldahl's Mask
Kjeldahl's after digestion
EiRsk /+NaOH

Known

standard
ncid

Calculation: Let mass of organic compound be mg

NaOH),
Volume of acid unreacted (vol. titrated with
ai (MV)acid = az (MV) NaOH
1x MV (NaOH) V
VH2SO4 = 2 x M(acid)
Initial volume - volume of acid
Volume of acid consumed by NHa (V) = unreacted (Vi)
V= initial volume - Vi
14 x 2x M (acid)x Vx 100
Percentage of nitrogen 1000 x m

heated with copper oxide in presence of CO2,

9. Nitrogen containing organic compound is nitrogen oxide is formed, it is reduced to
yielding nitrogengas with CO, and H,0. If collected
heated copper gauze. Nitrogen gas is
nitrogen by passing the gas mixture over a
whereas CO, and H,0 are collected in aqueous
in the upper part of graduated nitrometer
KOH solution.
nitrogen

co, E M
furnace

mercury seat
nitrometer

'm'g
Calculation: Let mass of organic compound be
PXVix273 V
Volume of nitrogen at STP = 760 xT
pressure - aqueous tension
Where p is pressure of nitrogen,p= atmospheric
V, is volume of nitrogen
K)
T is temperature at K (°c + 273 =
22400 ml nitrogen at STP weighs 28g
28 x V x 100
Percentage of nitrogen = 22400 x m

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