Question 1.

What are hybridisation states of each carbon atom in the following

compounds? CH2=C=O, CH3CH=CH2, (CH3)2CO, CH2=CHCN, C6H6.
Answer:

Question 2. Indicate the a- and n-bonds in the following molecules:

C6H6 , C6H12, CH2Cl2, CH=C=CH2, CH3NO2, HCONHCH3
Answer:

Question 3. Write bond-line formulas for: Isopropyl alcohol, 2,3-Dimethylbutanal, Heptan-4-one.

Answer:

Question 4. Give the TUPAC names of the following compounds:

Answer: (a) Propylbenzene (b) 3-Methylpentanenitrite (c) 2, 5-Dimethylheptane

(d) 3-Bromo- 3-chloroheptane (e) 3-Chloropropanal (f) 2, 2-Dichloroethanol

Question 5.Which of the following represents the correct TUPAC name for the compounds
concerned?
(a) 2, 2-Dimethylpentane or 2-Dimethylpentane (b) 2, 4, 7-Trimethyloctane or 2, 5, 7-
Trimethyloctane (c) 2-Chloro-4-methylpentane or 4-Chloro-2-methylpentane (d) But-3-yn- l-ol or But-
4-ol-yne.
Answer: (a) 2, 2-Demethylpentane (b)2, 4, 7-Trimethyloctane. For two alkyl groups on the same carbon its
locant is repeated twice, 2, 4, 7-locant set is lower than 2, 5, 7.
(c) 2- Chloro-4-methylpentane. Alphabetical order of substituents, (d) But-3-yn-l-ol. Lower locant for the
principal functional group, i.e., alcohol.

Question 6. Draw formulas for the first five members of each homologous series beginning with the
following compounds,
(a) H—COOH (b) CH3COCH3 (c) H—CH=CH2
Answer: (a) CH3—COOH
CH3CH2—COOH CH3CH2CH2—COOH
CH3CH2CH2CH2—COOH
(b) CH3COCH3
CH3COCH2CH3
CH3COCH2CH2CH3
CH3COCH2CH2CH2CH3
CH3CO(CH3)4CH3
(c) H—CH=CH2
CH3CH=CH2
CH3CH2CH=CH2
CH3CH2CH2CH=CH2
CH3CH2CH2CH2CH=CH2

Question 7. Give condensed and bond line structural formulas and identify the functional group(s)
present, if any, for: (a) 2, 2, 4-Trimethylpentane (b) 2-Hydroxy-l, 2, 3-propanetricarboxylic acid (c)
Hexanedial.
Answer:

Question 8. Identify the functional groups in the following compounds:

Answer:

Question 9. Which of the two: O2NCH2CH2O– or CH3CH2O– is expected to be more stable and why?
Answer: O2N——<——- CH2——<——- CH2 —<——- O– is more stable than CH3——<——-CH2——<
——-O- because NO2 group has -I-effect and hence it tends to disperse the -ve charge on the O-atom. In
contrast, CH3CH2 has +I-effect. It, therefore, tends to intensify the -ve charge and hence destabilizes it.

Question 10. Explain why alkyl groups act as electron donors when attached to a π-system.
Answer: Due to hyperconjugation, alkyl groups act as electron donors when attached to a π- system as
shown below:

Question 11. Draw the resonance structures for the following compounds. Show the electron shift
using curved-arrow notation. (a) C6H5OH (b) C6H5N02 (c) CH3CH=CHCHO (d) C6H5—CHO (e) C6H5—
CH2 (f) Ch3Ch=ChCh2
Answer:
Question 12. What are electrophiles and nucleophiles? Explain with examples:
Answer: Electrophiles: The name electrophiles means electron loving. Electrophiles are electron deficient.
They may be positive ions or neutral molecules.

Ex: H , Cl , Br , NO , R C , RN , AlCl , BF
+ + +
2
+
3
+
2
+
3 3

Nucleophiles: The name nucleophiles means ‘nucleus loving’ and indicates that it attacks the region of low
electron density (positive centres) in a substrate molecule. They are electron rich they may be negative ions
or neutral molecules.
Ex: Cl Br , CN , OH , RCR , NH , RNH , H O, ROH etc.
– – – –
2
–
3 2 2

Question 13. Identify the reagents shown in bold in the following equations as nucleophiles or
electrophiles
(a) CH3COOH + HO– ———–> CH3COO– + H2O
(b) CH3COCH3 + CN ———–> (CH3)2 C(CN)(OH)
(c) C6H5 + CH3CO ———–> C6H5COCH3
Answer: Nucleophiles: (a) and (b) and Electrophile : (c)

Question 14. Classify the following reactions in one of the reaction type studied in this unit.
(a) CH3CH2Br + HS– ———–> CH3CH2SH + Br–
(b) (CH3)2C=CH2 + HCl ———–> (CH3)2CCl—CH3
(c) CH3CH2Br + HO– ———–> CH2=CH2 + H2O + Br–
(d) (CH3)3C—CH2OH + HBr ———–> (CH3)2 C Br CH2CH2CH3 + H2O
Answer: (a) Nucleophilic substitution (b) Electrophilic addition
(c)Bimolecular elimination (d) Nucleophilic substitution with rearrangement.

Question 15. What is the relationship between the members of following pairs of structures? Are
they structural or geometrical isomers or resonance contributors?

Answer: (a) Structural isomers (actually position isomers as well as metamers)

(b) geometrical isomers
(c) resonance contributors because they differ in the position of electrons but not atoms

Question 16. For the following bond cleavages, use curved-arrows to show the electron flow and
classify each as homolysis or heterolysis. Identify reactive intermediate produced as free radical,
carbocation and carbanion.

Answer:

Question 17. Explain the terms inductive and electromeric effects. Which electron displacement
effect explain the following correct orders of acidity of the carboxylic acids?
(a) Cl3CCOOH > Cl2CHCOOH > ClCH2 COOH
(b) CH3CH2COOH > (CH3)2 CHCOOH > (CH3)3CCOOH
Answer: Inductive Effect: The inductive effect refers to the polarity produced in a molecule as a result of
higher electronegativity of one atom compared to another.Atoms or groups which lose electron towards a
carbon atom are said to have +1 Effect.
Those atoms or groups which draw electron away from a carbon atom are said to have -I Effect.
Commomexamples of -I effect are:
NO2, F, Cl, Br, I, OH etc.
Examples of +1 effect are (Electron releasing)
(CH3)2C— , (CH3)2CH—, CH3CH2— CH3— etc.
Electromeric effect: The electromeric effect refers to the polarity produced in a multiple bonded compound
as it is approached by a reagent.

The atom A has lost its share in the electron pair and B has gained this share.
As a result A acquires a positive charge and B a negative charge. It is a temporary effect and takes place
only in the presence of a reagent.
(a) -I-effect as shown below:
As the number of halogen atoms decreases, the overall -I- effect decreases and the acid strength
decreases accordingly.

(b) +I-effect as shown below:

As the number of alkyl groups increases, the +I-effect increases and the acid strength
decreases accordingly.

Question 18. Give a brief description of the principles of the following techniques taking an example
in each case: (a) Crystallisation (b) Distillation (c) Chromatography
Answer: (a) Crystallisation: In this process the impure solid is dissolved in the minimum volume of a
suitable solvent. The soluble impurities pass into the solution while the insoluble ones left behind. The hot
solution is then filtered and allowed to cool undisturbed till crystallisation is complete. The crystals are then
separated from the mother liquor by filtraration and dried.
Example: crystallisation of sugar.
(b) Distillation: The operation of distillation is employed for the purification of liquids from non-volatile
impurities. The impure liquid is boiled in a flask and the vapours so formed are collected and condensed to
give back pure liquid in another vessel. Simple organic liquids such as benzene toluene, xylene etc. can be
purified.
(c) Chromatography: Chromatography is based on the principle of selective distribution of the
components of a mixture between two phases, a stationary phase and a moving phase. The stationary
phase can be a solid or liquid, while the moving phase is a liquid or a gas. When the stationary phase is
solid the basis is adsorption and when it is a liquid the basis is partition. Chromatography is generally used
for the Reparation of coloured substances such as plant pigments or dyestuffs.

Question 19. Describe the method, which can be used to separate two compounds with different
solubilities in a solvent S.
Answer: Fractional crystallisation is used for this purpose. A hot saturated solution of these two
compounds is allowed to cool, the less soluble compound crystallises out while the more soluble remains in
the solution. The crystals are separated from the mother liquor and the mother liquor is again concentrated
and the hot solution again allowed to cool when the crystals of the second compound are obtained. These
are again filtered and dried.

Question 20. What is the difference between distillation, distillation under reduced pressure and
steam distillation?
Answer: Distillation is used in case of volatile liquid mixed with non-volatile impurities.
Distillation under reduced pressure: This method is used to purify such liquids which have very high boiling
points and which decompose at or below their boiling points.
Steam distillation is used to purify steam volatile liquids associated with water immiscible impuritites.
Question 21. Discuss the chemistry of Lassaigne’s test.
Answer: Lassaigne’s test: Nitrogen, sulphur, halogens and phosphorous present in an organic
compound are detected by Lassaigne’s test.
First of all compounds are converted to ionic form by fusing the compound with sodium metal.

Cyanide, sulphide or halide of sodium are extracted from the fused mass by boiling it with distilled water.
This extract is known as sodium fusion extract.

Question 22. Differentiate between the principle of estimation of nitrogen in an organic compound
by (i) Dumas method (ii) Kjeldahl’s method.
Answer: (i) Dumas method: The organic compound is heated strongly with excess of CuO ‘ (Cupric
Oxide) in an atmosphere of CO2 when free nitrogen, CO2 and H2O are obtained.
(ii)Kjeldahl’s method: A known mass of the organic compound is heated strongly with cone. H2SO4, a little
potassium sulphate and a little mercury (a catalyst). As a result of reaction the nitrogen present in the
organic compound is converted to ammonium sulphate.

Question 23. Discuss the principle of estimation of halogens, sulphur and phosphorus present in an
organic compound.
Answer: Estimation of halogens: It involves oxidising the organic substance with fuming nitric acid in the
presence of silver nitrate. The halogen of the substance is thus converted to silver halide which is
separated and weighed:
1Weight of organic compound = W gm
weight of silver halide = x g.

Estimation of sulphur: The organic substance is heated with fuming nitric acid but no silver nitrate is
added. The sulphur of the substance is oxidised to sulphuric acid which is then precipitated as barium
sulphate by adding excess of barium chloride solution. From the weight of BaSO4 so obtained the
percentage of sulphur can be calculated.

Estimation of phosphorous: The organic substance is heated with fuming nitric acid whereupon
phosphorous is oxidised to phosphoric acid. The phosphoric acid is precipitated as ammonium
phosphomolybdate, (NH4)3 PO4 .12MOO3, by the addition of ammonia and ammonium molybdate solution
which is then separated, dried and weighed.

Question 24. Explain the principle of paper chromatography.

Answer: This is the simplest form of chromatography. Here a strip of paper acts as an adsorbent. It is
based on the principle which is partly adsorption. The paper is made of cellulose fibres with molecules of
water adsorbed on them. This acts as stationary phase. The mobile phase is the mixture of the components
to be identified prepared in a suitable solvent.
Question 25. Why is nitric acid added to sodium extract before adding silver nitrate for testing
halogens ?
Answer: Nitric acid is added to sodium extract so as to decompose
NaCN + HNO3 ——-> NaNO3 + HCN
Na2S + 2HNO3 ——> 2NaNO3 + H2S

Question 26. Explain the reason for the fusion of an organic compound with metallic sodium for
testing nitrogen, sulphur and halogens.
Answer: Organic compound is fused with sodium metal so as to convert organic compounds into
NaCN, Na2S, NaX and Na3PO4. Since these are ionic compounds and become more reactive and thus can
be easily tested by suitable reagents.

Question 27. Name a suitable technique of separation of the components from a mixture of calcium
sulphate and camphor.
Answer: Sublimation.Because camphor can sublime whereas CaSO4 does not.

Question 28. Explain, why an organic liquid vaporises at a temperature below its boiling point in its
steam distillation ?
Answer: It is because in steam distillation the sum of vapour pressure of organic compound and steam
should be equal to atmospheric pressure.

Question 29.Will CCl4 give white precipitate of AgCl on heating it with silver nitrate? Give reason for
your answer.
Answer: No. CCl4 is a completely non-polar covalent compound whereas AgNO3 is ionic in nature.
Therefore they are not expected to react and thus a white ppt. of silver chloride will not be formed.

Question 30. Why is a solution of potassium hydroxide used to absorb carbon dioxide evolved
during the estimation of carbon present in an organic compound?
Answer: CO2 is acidic in nature and therefore, it reacts with the strong base KOH to form K2CO3.
2KOH + CO2 ——–> K2CO3+ H2O.

Question 31. Why is it necessary to use acetic acid and not sulphric acid for acidification of sodium
extract for testing sulphur by lead acetate test?
Answer: For testing sulphur sodium extract is acidified with acetic acid because lead acetate is soluble and
does not interfere with the test.

Question 32. An organic compound contains 69% carbon and 4.8% hydrogen, the remainder being
oxygen. Calculate the masses of carbon dioxide and water produced when 0.20 g of this compound
is subjected to complete combustion.
Answer:

Question 33. 0.50 g of an organic compound was Kjeldahlished. The ammonia evolved was passed
in 50 cm3 of IN H2SO4. The residual acid required 60 cm3 of N/2 NaOH solution. Calculate the
percentage of nitrogen in the compound.
Answer:

Question 34. 0.3780 g of an organic compound gave 0.5740 g of silver chloride in Carius estimation.
Calculate the percentage of chlorine in the compound.
Answer: Mass of the compound = 0.3780 g
Mass of silver chloride = 0.5740 g

Question 35. In an estimation of sulphur by Carius method, 0.468 of an organic sulphur compound
gave 0.668 g of barium sulphate. Find the percentage of sulphur in the compound.
Answer: Mass of the compound = 0.468 g
Mass of barium sulphate= 0.668 g

Question 36.
Answer:

Question 37. In Lassaigne’s test for ntrogen in an organic compound, the Prussian blue colour is
obtaine d due to the formation of:
(a) Na4[Fe(CN)6] (b)Fe4[Fe(CN)6]3
(c) Fe2[Fe(CN)6] (d)Fe3[Fe(CN)6]4 .
Answer: (b) is the correct answer.

Question 38. Which of the following carbocation is most stable?

Answer: (b) is the most stable since it is a tertiary carbocation.

Question 39. The best and latest technique for isolation, purification and separation of organic
compounds is: (a) Crystallisation (b) Distillation
(c) Sublimation (d) Chromatography.
Answer: (d) is the correct answer.

Question 40. The following reaction is classified as:

CH3CH2I + KOH (aq) ———-> CH3CH2OH + KI
(a) electrophilic substitution (b) nucleophilic substitution
(c) elimination (d) addition
Answer: (b) It is a nucleophilic substitution reaction. KOH (aq) provides OH- ion for the nucleophile attack.

MORE QUESTIONS SOLVED

I. Very Short Answer Type Questions

Question 1. How will you separate a mixture of two organic compounds which have different
solubilities in the same solvent?
Answer: By fractional crystallisation.

Question 2. An organic liquid decomposes below its boiling point. How will you purify it?
Answer: By distillation under reduced pressure.

Question 3. Suggest a suitable technique for separating naphthalene from kerosene oil present in a
mixture.
Answer: Simple distillation.

Question 4. Arrange the following in increasing order of C—C bond length: C2H & C2H4, C2H2.
Answer: C2H2 (120 pm) < C2H4 (134 pm) < C2H6 (154 pm)

Question 5. Name the process used to separate sugar and salt.

Answer: Fractional crystallisation using ethanol as a solvent.

Question 6. Which gas is liberated in Kjeldhal’s method?

Answer: Ammonia gas (NH3)
Question 7. What is Lassaigne’s extract?
Answer: When organic compound is fused with sodium metal and then extracted by water, it is called
Lassaigne’s extract.

Question 8. What type of solids are separated by fractional crystallisation?

Answer: Those solids which are soluble in the same splvent but to a different extent i.e., differ in their
solubility.

Question 9. Name a suitable adsorbent used in the process of column chromatography.

Answer: Al2O3 (alumina)

Question 10. Name three types of chromatography.

Answer: Column chromatography, paper chromatography and thin layer chromatography.

Question 11. Which method is used to extract a compound in aqueous solution?

Answer: Differential extraction.

Question 12. In Carius method, sulphur is estimated by precipitating it as which compound?

Answer: BaSO4.

Question 13. Which elements are estimated by Liebig’s Method?

Answer: Carbon and hydrogen.

Question 14. Which type of compounds are purified by steam distillation?

Answer: Stea