8: Organic Chemistry – So me Basic Principles and Techniques

Chemistry Worksheet

Standard: 11th Science Subject: Chemistry

Student Name:

Q1. Which functional group is present in a molecule of CH3​OCH2​CH3​?

1. Ether
2. Carboxyl
3. Ketone
4. Aldehyde
5. Ester
Q2. The atom or the group of atoms by which the characteristic reactions of organic compounds are determined, that atom or group of atoms is called
____________.
1. Hydrocarbon
2. Functional group
3. Atom
4. Compound
Q3. Electrophilic addition reactions proceed in two steps. The first step involves the addition of an electrophile. Name the type of intermediate formed in the
first step of the following addition reaction.
H 3C − HC = CH 2 + H + → ?
1. 2° Carbanion
2. 1° Carbocation
3. 2° Carbocation
4. 1° Carbanion
Q4. Pick out the wrong statement.
1.

2.

3. Hyperconjugation is no bond resonance.

4. Dopole moment of CH 2 = CH − Cl < CH 3Cl
Q5. Which of the following is a homocyclic alicyclic compound?
1.

2.

3.

​
4.

Q6. The fragrance of flowers is due to the presence of some steam volatile organic compounds called essential oils. These are generally insoluble in water at
room temperature but are miscible with water vapour in vapour phase. A suitable method for the extraction of these oils from the flowers is:
1. Distillation.
2. Crystallisation.
3. Distillation under reduced pressure.
4. Steam distillation.
Q7. In presence of HCl(aq.);H2​S gas results the precipitation of group-2 cations but not of group-4 cations during qualitative analysis. It is due to:
1. Lower concentration of S2-
2. Higher concentration of S2-
3. Lower concentration of H+
4. Higher concentration of H+
Q8. Which of the following are members of same homologous series?
1. HCOOCH3​and CH3COOCH3
2. HCOOH and HCOOCH3
3. CH3COCH3​and CH3​CH2​CHO
4. C2H5​OH and CH3OCH3
Q9. Which one of the following is not an alcohol?
1. (CH3​)2​CHCH2​CH2​OH
2. (CH3​)3​C−CH2​OH
3. (CH3)2​−CH−OH
 4. CH3​CH2CH2​CH2COOH
Q10. Which of the statements below best describes a functional group?
1. It is the non-polar section of an organic molecule.
2. It is a highly reactive group of elements with similar outer shell electron configurations.
3. It is an atom or a group of atoms which determines the chemical properties of a compound.
4. It is the part of a chelate ligand attracted to the central ion.
Q11. CH 3​ − CH = CH − C ≡ CH has lUPAC name:
1. pent - 2 - en- 4 - yne
2. pent - 4 - yn - 2 - ene
3. pent - 1 - yn - 3 - ene
4. pent - 3 - en - 1 - yne
Q12. Which of the following is correct about the number of bonds formed by atoms of different elements in acetaldehyde?(Report your answer in the ratio
of H:O:C)
1. 4:2:2
2. 4:1:2
3. 4:1:3
4. 3:3:3
Q13. Which type of bond is formed between carbon atom and nitrogen atom?
1. Covalent bond.
2. Ionic bond.
3. Dative bond.
4. None of these.
Q14. Which one is a nucleophilic substitution reaction among the following?
1. CH 3CHO + HCN → CH 3CH(OH)CN
H+
2. CH 3 − CH = CH 2 + H 2O → CH 3 − CH − CH 3 | OH
3. RCHO+ R ′ MgX → R − CH − R′ | OH
4. CH 3 | CH 3 − CH 2 − CH − CH 2Br + NH 3 → CH 3 | CH 3 − CH 2 − CH − CH 2NH 2
Q15. Which method of estimation is shown in the figure given below?

1. Carius method.
2. Kjeldahl's method.
3. Duma's method.
4. None of these.
Q16. The IUPAC name of iso-octane is:
1. 2, 2-dimethylpentane.
2. 2, 3-dimethylpentane.
3. 2, 3, 3-trimethylpentane.
4. 2, 2, 4-trimethylpentane.
Q17. How many pi bonds are present in phosgene?
1. 1
2. 2
3. 3
4. 4
Q18. Which of the following is a correct representation of condensed formula forHOCH 2CH 2CH 2CH(CH 3)CH(CH 3)CH(CH 3)CH 3?
1. HO(CH 2) 2CHCH 3CH(CH 3) 2
2. HO(CH 2) 2CH(CH 3)CH(CH 3) 2
3. HOCH 2CHCH 3CH(CH 3) 2
4. None of the above
Q19. Given two compounds, one more polar than the other, which one will move up the silica stationery phase higher than the other in TLC?
1. Polar compound
2. Non polar compound
3. Both will move equally
4. None will move
Q20. The molecular formulae for phosgene and tear gas are .......... and ......... respectively.
1. COCl2​and CCl3​NO2​
2. SOCl2​ and CCl3​NO2​
3. COCl2​ and CCI3​NO2​
4. SOCl2​and CCI3​NO2​
Q21. What is the name of tube in which a known mass of an organic compound is heated for the quantitative analysis of sulphur?
1. Borosil tube.
2. Carius tube.
3. Kjeldahl tube.
4. None of these.

Q22. Identify the correct decreasing order of priority of the functional groups from the following:
1. −CONH2​, −C=O, −HC=O, −CN
2. −CONH2​​, −CN, −HC=O, −C=O
3. −CN, −CONH2​​, −C=O, −HC=O
4. −CN, −CONH2​​, −HC=O, −C=O
Q23. The compound of the molecular formula, C6​H14​has two tertiary carbons. Its IUPAC name is:
1. n-hexane
2. 2−methylpentane
3. 2, 3−dimethylbutane
4. 2, 2−dimethylpentane
Q24. In which of the following representations given below spatial arrangement of group/ atom different from that given in structure ‘A’?
 1.

2.

3.

4.

Q25. Which of the following compounds will exhibit geometrical isomerism?

1. 1-phenyl-2-butene.
2. 3-phenyl-1-butene.
3. 2-phenyl-1-butene.
4. 1, 1-diphenyl-1-propane.
Q26. The fruity smell is of a/an:
1. Aldehyde
2. Ketone
3. Alcohol
4. Ester
Q27. Which one of the following has the most nucleophilic nitrogen?
1.

2.

3.
 4.

Q28. The main source of organic compounds is:

1. Coaltar
2. Petroleum
3. Both (a) and (b)
4. None of the above
Q29. Arrange the above in the decreasing order of reactivity towards HBr:

1. a > b > c
2. b > a > c
3. b > c > a
4. a > c > b
Q30. Which of the following compounds will not give Lassaigne's test for nitrogen?
1. NH 2 − NH 2
2. C 6H 5NHNH 2
3. C 6H 5 − N = N − C 6H 5
4. NH 2CONH 2
Q31. identify the rate of reaction of given compounds in E2​reaction:

1. a > b > c > d

2. a > c > b > d
3. b > a > c > d
4. b > d > a > c
Q32. Passing H2​S gas into a mixture of Mn2+,Ni2+,Cu2+,Hg2+ ions in acidified aqueous solution precipitates:
1. CuS and HgS
2. MnS and CuS
3. MnS and NiS
4. NiS and HgS
Q33. The indicator which is used to find the strength of caustic soda solution with the help of oxalic acid is:
1. Methyl orange
2. Phenolphthalein
3. Potassium permanganate
4. None of the above
Q34. The structure of iso-butyl group in an organic compound is:
1.

2. CH 3 − CH 2 − CH 2 − CH 3
3. CH 3 − CH 2 − CH 2 − CH 2 −
4. CH 3 | CH 3 − C − | CH 3
Q35. Which of the following method is used to purify liquids having very high boiling points and those which decompose at or below their boiling points?
1. Simple distillation.
2. Fractional distillation.
3. Distillation under reduced pressure.
4. None of the above.
Q36. Which of the following is not in accordance to IUPAC system?
1. Br− CH 2 − CH = CH 2 1-bromoprop 2-ene
2. CH 3 | CH 3 − CH 2 − C − CH 2 − CHCH 3 | | Br CH 3 4-bromo-2, 4-dimethyle hexane
3.

4. CH 3 − C − CH 3 − CH 2CH 2COOH || O 5-oxohexanoic acid

Q37. Note: In the following questions a statement of Assertion (A) followed by a statement of Reason (R) is given. Choose the correct option out of the choices
given below each question.
Assertion (A): Components of a mixture of red and blue inks can be separated by distributing the components between stationary and mobile phases in
paper chromatography.
Reason (R): The coloured components of inks migrate at different rates because paper selectively retains different components according to the difference
in their partition between the two phases.
1. Both A and R are correct and R is the correct explanation of A.
2. Both A and R are correct but R is not the correct explanation of A.
3. Both A and R are not correct.
4. A is not correct but R is correct.
Q38. Note: In the following questions a statement of Assertion (A) followed by a statement of Reason (R) is given. Choose the correct option out of the choices
given below each question.
Assertion (A): Energy of resonance hybrid is equal to the average of energies of all canonical forms.
Reason (R): Resonance hybrid cannot be presented by a single structure.
1. Both A and R are correct and R is the correct explanation of A.
2. Both A and R are correct but R is not the correct explanation of A.
3. Both A and R are not correct.
4. A is not correct but R is correct.
Q39. In the following Questions, the Assertion and Reason hrve been put forfiird. Read the statements csrefully end choose the correct alternative from the
following:
1. Both Assertion and Reason are true and Reason is the correct explanation of Assertion.
2. Both Assertion rnd Reason are true but Reason is not the correct explenatlon of Assertion.
 3. Assertion is true but Reason is false.
4. Both Assertion and Reason arc false.
Assertion: A Mixture of o-nitrophenol and p-nitrophenol can be separated by steam distillation.
Reason: p-nitrophenol is steam volatile while 0-nitrophenol is not steam volatile.
Q40. Match the terms mentioned in Column I with the terms in Column II.
Column I Column II
(i) Carbocation (a)Cyclohexane and 1- hexene.
Conjugation of electrons of C–H σ bond with empty p-orbital present at adjacent positively cha
(ii) Nucleophile (b)
rged carbon.
(ii Hyperconjugati
(c) sp2 hybridised carbon with empty p-orbital.
i) on
(i
Isomers (d)Ethyne
v)
(v) sp hybridisation(e)Species that can receive a pair of electrons.
(v
Electrophile (f) Species that can supply a pair of electrons.
i)

Q41. Match Column I with Column II.

Column I Column II
Dumas meth
(i) (a)AgNO3
od.
Kjeldahl’s me
(ii) (b)Silica gel.
thod.
(ii Carius metho
(c) Nitrogen gas.
i) d.
(i Chromatogra
(d)Free radicals.
v) phy
Ammonium sul
(v) Homolysis (e)
phate.

Q42. If a liquid compound decomposes at its boiling point, which method (s) can you choose for its purification. It is known that the compound is stable at low
pressure, steam volatile and insoluble in water.
Q43. Suggest a method to purify:
1. Camphor containing traces of common salt.
2. Kerosene oil containing water.
3. A liquid which decomposes at its boiling point.
Q44. Name the electrophile/ nucleophile generated by following species:
1. HNO3 + H2SO4
2. CH3COCl
3. alc. KCN
Q45. Arrange the following:
+ + + +
1. C 6H 5 CHCH 3, C 6H 5 CHCH = CH 2, C 6H 5CH 2CH 2, C 6H 5 C(CH 3) 2 in order of increasing stability.
2. CH 3CH 2+ , C 6H 5CH 2+ , (CH 3) 3C + , CH 2 = CHCH 2+ in order of decreasing stability.
3. HC ≡ C − , CH 2 = CH − , CH 3CH 2− , CH 3− , (CH 3) 2CH − , C 6H 5CH 2− in order of increasing stability.
Q46. Which of the following selected chains is correct to name the given compound according to IUPAC system.

Q47. Identify the type of reactions:

sunlight
1. CH 4 + Cl 2 → CH 3Cl + HCl
conc.H 2SO 4
2. C 6H 6 + (conc.)HNO 36 → C 6H 5NO 2 + H 2O

3. Br | CH 3 − CH = CH 2 + HBr → CH 3 − CH − CH 3

4. O OH ‖ | CH 3 − C − CH 3 + HCN → CH 3 − C − CH 3 |
HBr
5. CH 3 − CH = CH 2 → CH 3CH 2CH 2Br
peroxide

6. CH 3Cl + KOH(aq) → CH 3OH + KCl

Q48. The order of basicity of amines expected on the basis of inductive effect is NH3 < RNH2 < R3N. However, the observed order of basicity is NH3 < RNH2 <
R2NH > R3N. How will you account for the difference?
Q49. Note: Consider structures I to VII and answer the questions:
1. CH 3 − CH 2 − CH 2 − CH 2 − OH
2. CH 3 − CH 2 − CH − CH 3 | OH
3. CH 3 | CH 3 − C − CH 3 | OH
4. CH 3 − CH − CH 2 − OH | CH 3
5. CH 3 − CH 2 − O − CH 2 − CH 3
6. CH 3 − O − CH 2 − CH 2 − CH 3
7. CH 3 − O − CH − CH 3 | CH 3
Identify the pairs of compounds that represents chain isomerism.
Q50. Note: Consider structures I to VII and answer the questions:
1. CH 3 − CH 2 − CH 2 − CH 2 − OH
2. CH 3 − CH 2 − CH − CH 3 | OH
3. CH 3 | CH 3 − C − CH 3 | OH
4. CH 3 − CH − CH 2 − OH | CH 3
5. CH 3 − CH 2 − O − CH 2 − CH 3
6. CH 3 − O − CH 2 − CH 2 − CH 3
7. CH 3 − O − CH − CH 3 | CH 3
 Identify the pairs of compounds that represents position isomerism.
Q51. 0.90g of organic compound on combustion gave 2.64g of CO2, and 0.63g of H2O. Calculate the percentage of C and H in the compound.
Q52. Give the IUPAC names of the following compounds:
1.

2.

3.

4.

5.

6. Cl 2CHCH 2OH
Q53. What is meant by hybridisation? Compound CH2 = C = CH2 contains sp or sp2 hybridised carbon atoms. Will it be a planar molecule?
Q54. Explain, how is the electronegativity of carbon atoms related to their state of hybridisation in an organic compound?
Q55. Which is more stable and why?
⊕ ⊕
1. C 6H 5 − CH 2 or C 6H 11CH 2
. .
2. (C 6H 5)CH or C 6H 5CH 2
. .
3. (C 6H 5)CH 2 or CH 2 = CH − CH 2
Q56. Identify the functional groups in the following compounds.
1.

2.

3.

Q57. Note: Consider structures I to VII and answer the questions:

1. CH 3 − CH 2 − CH 2 − CH 2 − OH
2. CH 3 − CH 2 − CH − CH 3 | OH
3. CH 3 | CH 3 − C − CH 3 | OH
4. CH 3 − CH − CH 2 − OH | CH 3
5. CH 3 − CH 2 − O − CH 2 − CH 3
6. CH 3 − O − CH 2 − CH 2 − CH 3
7. CH 3 − O − CH − CH 3 | CH 3
Identify the pairs of compounds which are functional group isomers.
Q58. “Stability of carbocations depends upon the electron releasing inductive effect of groups adjacent to positively charged carbon atom involvement of
neighbouring groups in hyperconjugation and resonance.”
Write structures of various carbocations that can be obtained from 2-methylbutane. Arrange these carbocations in order of increasing stability.
Q59. 1. What is role of copper oxide in estimation of carbon and hydrogen?
2. How do we test phosphorus in given organic compound?
⊕ ⊕
3. What is shape of CH 3 (methyl carbocation) and CH 3 (methyl carbanion)?
Q60. 1. Draw cis and trans-structures for Hex-2-ene. Which isomer will have higher boiling point and why?
2.

Q61. 1. Write IUPAC name of the following:

2. CH 2CH 2CHO and CH 3C − CH 3 || O

3. Draw the structure of 3-oxopentanal.
Q62. Write down the formulae of the first four members of each homologous series beginning with the following compounds.
 1. CH 2 = CH 2
2. HCOOH
3. CH 3COCH 3
4. CH 3OH
5. HC ≡ CH
Q63. The following techniques are used to quantitatively estimate extra elements in organic compound. Identify the name of the method and the element
estimated by this method.
1. A known mass of an organic compound is heated with fuming HNO3 in presence of AgNO3.
2. Organic compound is heated with dry copper oxide in atmosphere of CO2.
3. Organic compound is heated with conc. H2SO4.
Q64. In DNA and RNA, nitrogen atom is present in the ring system. Can Kjeldahl method be used for the estimation of nitrogen present in these? Give reasons.
Q65. In which of the following compounds the C-Cl bond ionisation shall give most stable carbocation?
1. CH 3 − CH − Cl | CH 3
2. Cl | CH 3 − C − CH 3 | CH 3
3.

1. ​ H | O 2NH 2C − C − Cl | H
Q66. Identify the functional groups present in the following compounds.
1.

2.

3. CH 3 − CH 2 − CO − CH 2 | CH 2 − COCl
4. O ‖CH 2 = CH − CH 2 − C − NH 2
Q67. 1. Write IUPAC name of the following:
CH 3CHCH ≡ CH | CH = CH 2
2. Draw the structure of Pent-4-en-2-ol.
3. What is nucleophile? Give one example.
Q68. Write structural formulae for all the isomeric amines with molecular formula C4H11N.
Q69. 0.25g of an organic compound gave 30cm3 of moist dinitrogen at 288K and 745mm pressure. Calculate the percentage of nitrogen.
(Aq. tension at 288K = 12.7mm).
Q70. 1. Give one example of position isomerism.
2. What are electrophiles? Give one example of electrophilic substitution reaction.
3. Write the chemistry of Lassaigne's test for qualitative analysis of nitrogen.
Q71. “Stability of carbocations depends upon the electron releasing inductive effect of groups adjacent to positively charged carbon atom involvement of
neighbouring groups in hyperconjugation and resonance.”
The structure of triphenylmethyl cation is given below. This is very stable and some of its salts can be stored for months. Explain the cause of high stability
of this cation.

Q72. For testing halogens in an organic compound with AgNO3 solution, sodium extract (Lassaigne’s test) is acidified with dilute HNO3. What will happen if a
student acidifies the extract with dilute H2SO4 in place of dilute HNO3?
Q73. What is the hybridisation of each carbon in H2C = C = CH2.
Q74. Which of the two structures A and B given below is more stabilised by resonance.
⊖
Explain CH 3COOH A and CH 3 COO B
Q75. Benzoic acid is a organic compound. Its crude sample can be purified by crystallisation from hot water. What characteristic differences in the properties of
benzoic acid and the impurity make this process of purification suitable?
Q76. Give IUPAC name of the following compounds:
1.

2.

Q77. 1. Mention the type of hybridisation of each carbon in the compound CH3-CN.
2. Draw the structure of 2-methylpropan-2-ol.
Q78. Classify the following pairs as position, chain, functional isomers or metamers:
1. Diethylamine and Methylpropylamine.
2. Ethanol and Dimethylether.
Q79. How many o and it bonds are present in each of the following molecules?
1. CH 3CH 2C ≡ N
2. CH 3 − CH = CH − CH 2 − C ≡ CH
3. CH 2 = C = CH 2
Q80. 1. Give condensed and bond line structural formulae of the following:
1. Cyclo octa-1,5-diene.
 2. 2(4-iso butyl phenyl) propanoic.
2. Identify electrophilic centre in the following CH3CHO and CH3CN.
Q81. Arrange the following in decreasing order of stability:

Q82. Give the common name of:

1. Methanol olido.
2. Ethanol.
3. Ethoxyethane.
4. Ethanoic acid.
5. 1, 4-dimethyl benzene.
Q83. What is the correct order of priority for following functional groups of organic compound in IUPAC nomenclature?
O ‖ − COOH − , − OH, − CHO, − C −
Q84. Draw structure of all isomeric ethers having molecular formula C5H12O.
Q85. Compounds with same molecular formula but differing in their structures are said to be structural isomers. What type of structural isomerism is shown by
CH3-S-CH2-CH2-CH3 and

Q86. Why is staggered conformation of ethane more stable than eclipsed conformation?
Q87. “Stability of carbocations depends upon the electron releasing inductive effect of groups adjacent to positively charged carbon atom involvement of
neighbouring groups in hyperconjugation and resonance.”
Which of the following ions is more stable? Use resonance to explain your answer.

Q88. Name the compounds whose line formulae are given below.
1.

2.

Q89. An alkane has a molecular mass of 72. Draw all its possible chain isomers and write their IUPAC names.
Q90. M
0.35g of an organic compound was Kjeldahlised. The ammonia evolved on distilling the Kjeldahlised extract with 100ml of 10 H 2SO 4
The residual acid
M
required 154ml of 10 NaOH
for complete neutralization. Calculate the percentage of nitrogen in organic compound.
Q91. What are the possible structures for a carboxylic acid with a molecular formula C4H8O2 and label each C atom as sp, sp2 and sp3?
Q92. Resonance structures of propenal are given below. Which of these resonating structures is more stable? Give reason for your answer.
⊕ ⊖
CH 2 = CH − CH = O ↔ CH 2 − CH = CH − O I II
Q93. Identify the most stable species in the following set of ions giving reasons:
⊖ ⊖ ⊖ ⊖ CH 3, CH 2Cl, CHCl 2, CCl 3
Q94. Write IUPAC names of the following:
1.

2. .

Q95. A liquid with high boiling point decomposes on simple distillation but it can be steam distilled for its purification. Explain how is it possible?
Q96. You have a mixture of three liquids A, B and C. There is a large difference in the boiling points of A and rest of the two liquids i.e., B and C. Boiling point of
liquids B and C are quite close. Liquid A boils at a higher temperature than B and C and boiling point of B is lower than C. How will you separate the
components of the mixture. Draw a diagram showing set up of the apparatus for the process.
Q97. 1. Write two important differences between inductive effect and resonance effect.
2. Give reasons to explain the following observations:
1. Carbon atom number 2 in CH3CH2Cl has more positive charge than that in CH3-CH2-Br.
2. CH3-CH=CH-CH=CH2(I) is more stable than CH3-CH=CH-CH2-CH=CH2(II)
Q98. 1. Out of different gases formed in Duma's method, which gas is not absorbed over an aqueous solution?
2. What is function of K2SO4 and a little of CuSO4 added in Kjeldahl's flask?
M
3. 0.4g of compound was Kjeldahl's and ammonia evolved was absorbed into 50mL of 4
H 2SO 4 The residual acid was diluted with distilled water and
M
made up to 150mL. 20mL of this diluted acid required 31mL of 4
NaOH solution for complete neutralisation. Calculate % of N in compound.
Q99. Read the passage given below and answer the following questions from 1 to 5.
A reagent that brings an electron pair to the reactive site is called a nucleophile (Nu:) i.e., nucleus seeking and the reaction is then called nucleophilic. A
reagent that takes away an electron pair from reactive site is called electrophile (E+) i.e., electron seeking and the reaction is called electrophilic.
Electron Displacement Effects in Covalent Bonds The electron displacement in an organic molecule may take place either in the ground state under the
influence of an atom or a substituent group or in the presence of an appropriate attacking reagent. The electron displacements due to the influence of an
atom or a substituent group present in the molecule cause permanent polarlisation of the bond. Inductive effect and resonance effects are examples of
this type of electron displacements. Temporary electron displacement effects are seen in a molecule when a reagent approaches to attack it. This type of
electron displacement is called electrometric effect or polarisability effect.
Inductive Effect When a covalent bond is formed between atoms of different electronegativity, the electron density is more towards the more
electronegative atom of the bond. Such a shift of electron density results in a polar covalent bond. Bond polarity leads to various electronic effects in
organic compounds. Let us consider cholorethane (CH3 CH2Cl) in which the C–Cl bond is a polar covalent bond. It is polarised in such a way that the carbon-
1 gains some positive charge (δ + ) and the chlorine some negative charge (δ − ) The fractional electronic charges on the two atoms in a polar covalent
bond are denoted by symbol (delta) and the shift of electron density is shown by an arrow that points from(δ + ) to (δ − ) end of the polar bond.

In turn carbon-1, which has developed partial positive charge (δ + )draws some electron density towards it from the adjacent C-C bond. Consequently,
some positive charge(δδ + )develops on carbon-2 also, where (δδ + ) symbolises relatively smaller positive charge as compared to that on carbon – 1. In
other words, the polar C – Cl bond induces polarity in the adjacent bonds. Such polarisation of σ- bond caused by the polarisation of adjacent σ-bond is
referred to as the inductive effect.
Resonance Structure There are many organic molecules whose behaviour cannot be explained by a single Lewis structure. An example is that of benzene.
Its cyclic structure containing alternating C–C single and C=C double bonds shown is inadequate for explaining its characteristic properties.

As per the above representation, benzene should exhibit two different bond lengths, due to C–C single and C=C double bonds. However, as determined
experimentally benzene has a uniform C–C bond distances of 139 pm, a value intermediate between the C–C single(154 pm) and C=C double (134 pm)
bonds. Thus, the structure of benzene cannot be represented adequately by the above structure. Further, benzene can be represented equally well by the
energetically identical structures I and II.

Therefore, according to the resonance theory the actual structure of benzene cannot be adequately represented by any of these structures, rather it is a
hybrid of the two structures (I and II) called resonance structures. The resonance structures (canonical structures or contributing structures) are
hypothetical and individually do not represent any real molecule. They contribute to the actual structure in proportion to their stability.
Resonance Effect The resonance effect is defined as ‘the polarity produced in the molecule by the interaction of two π-bonds or between a π-bond and
lone pair of electrons present on an adjacent atom’. The effect is transmitted through the chain. There are two types of resonance or mesomeric effect
designated as R or M effect. (i) Positive Resonance Effect (+R effect) In this effect, the transfer of electrons is away from an atom or substituent group
attached to the conjugated system. This electron displacement makes certain positions in the molecule of high electron densities. This effect in aniline is
shown as : (ii) Negative Resonance Effect (- R effect) This effect is observed when the transfer of Electrons is towards the atom or substituent Group
attached to the conjugated system. For Example in nitrobenzene this electron Displacement can be depicted as : The atoms or substituent groups, which
represent +R or –R electron displacement effects are as follows: +R effect: – halogen, –OH, –OR, –OCOR, –NH2, –NHR, –NR2, –NHCOR, – R effect: – COOH,
–CHO, > C = O, – CN, – NO2 The presence of alternate single and double bonds in an open chain or cyclic system is termed as a conjugated system. These
systems often show abnormal behaviour. The examples are 1,3- butadiene, aniline and nitrobenzene etc. In such systems, the π-electrons are delocalised
and the system develops polarity.
Electromeric Effect (E effect) It is a temporary effect. The organic compounds having a multiple bond (a double or triple bond) show this effect in the
presence of an attacking reagent only. It is defined as the complete transfer of a shared pair of π-electrons to one of the atoms joined by a multiple bond
on the demand of an attacking reagent. The effect is annulled as soon as the attacking reagent is removed from the domain of the reaction. It is
represented by E and the shifting of the electrons is shown by a curved arrow ( ). There are two distinct types of electromeric effect.
a) Positive Electrometric Effect (+E effect)- In this effect the π−electrons of the multiple bond are transferred to that atom to which the reagent gets
attached. For example

b) Negative Electromeric Effect (–E effect) -In this effect the \pi- electrons of the multiple bond are transferred to that atom to which the attacking reagent
does not get attached. For example: When inductive and electromeric effects operate in opposite directions, the electomeric effect predominates.

1. A reagent that brings an electron pair to the reactive site is called a …

1. nucleophile
2. electrophile
3. amphoteric
 4. amphophillic
2. A reagent that takes away an electron pair from reactive site is called ..
1. nucleophile
2. electrophile
3. amphoteric
4. amphophillic
3. The … effect is defined as the polarity produced in the molecule by the interaction of two π-bonds or between a π-bond and lone pair of electrons
present on an adjacent atom.
1. hindrance
2. inductive
3. resonance
4. hyperconjunction
4. –OH group, represent … electron displacement effect.
1. M+
2. M-
3. R-
4. R+
5. – COOH group, represent … electron displacement effect.
1. M+
2. M-
3. R-
4. R+
Q100. Read the passage given below and answer the following questions from 1 to 5.

Hyperconjugation is a general stabilising interaction. It involves delocalisation of σ electrons of C—H bond of an alkyl group directly attached to an atom of
unsaturated system or to an atom with an unshared p orbital. The σ electrons of C—H bond of the alkyl group enter into partial conjugation with the
attached unsaturated system or with the unshared p orbital. Hyperconjugation is a permanent effect. To understand hyperconjugation effect, let us take an
example of CH 32 + (ethyl cation) in which the positively charged carbon atom has an empty p orbital. One of the C-H bonds of the methyl group can align
in the plane of this empty p orbital and the electrons constituting the C-H bond in plane with this p orbital can then be delocalised into the empty p orbital
as depicted in Figure.
This type of overlap stabilises the carbocation because electron density from the adjacent σ bond helps in dispersing the positive charge.

In general, greater the number of alkyl groups attached to a positively charged carbon atom, the greater is the hyperconjugation interaction and
stabilisation of the cation. Thus, we have the following relative stability of carbocations:

Hyperconjugation is also possible in alkenes and alkylarenes. Delocalisation of electrons by hyperconjugation in the case of alkene can be depicted as in
Figure.
There are various ways of looking at the hyperconjugative effect. One of the way is to regard C—H bond as possessing partial ionic character due to
resonance.
The hyperconjugation may also be regarded as no bond resonance.

The hyperconjugation may also be regarded as no bond resonance.

Methods of purification of organic compounds Once an organic compound is extracted from a natural source or synthesised in the laboratory, it is essential
to purify it. Various methods used for the purification of organic compounds are based on the nature of the compound and the impurity present in it. The
common techniques used for purification are as follows :
i) Sublimation
ii) Crystallisation
iii) Distillation
iv) Differential extraction and
v) Chromatography
Finally, the purity of a compound is ascertained by determining its melting or boiling point. Most of the pure compounds have sharp melting points and
boiling points. New methods of checking the purity of an organic compound are based on different types of chromatographic and spectroscopic
techniques.
Sublimation On heating, some solid substances change from solid to vapour state without passing through liquid state. The purification technique based
on the above principle is known as sublimation and is used to separate sublimable compounds from non- sublimable impurities.
Crystallisation This is one of the most commonly used techniques for the purification of solid organic compounds. It is based on the difference in the
solubilities of the compound and the impurities in a suitable solvent. The impure compound is dissolved in a solvent in which it is sparingly soluble at room
temperature but appreciably soluble at higher temperature. The solution is concentrated to get a nearly saturated solution. On cooling the solution, pure
compound crystallises out and is removed by filtration. The filtrate (mother liquor) contains impurities and small quantity of the compound. If the
compound is highly soluble in one solvent and very little soluble in another solvent, crystallisation can be satisfactorily carried out in a mixture of these
solvents. Impurities, which impart colour to the solution are removed by adsorbing over activated charcoal. Repeated crystallisation becomes necessary for
the purification of compounds containing impurities of comparable solubilities.

Distillation This important method is used to separate

i) volatile liquids from nonvolatile impurities and
ii) the liquids having sufficient difference in their boiling points.

Liquids having different boiling points vaporise at different temperatures. The vapours are cooled and the liquids so formed are collected separately.
Chloroform (b.p 334 K) and aniline (b.p. 457 K) are easily separated by the technique of distillation (Fig 12.5). The liquid mixture is taken in a round bottom
flask and heated carefully. On boiling, the vapours of lower boiling component are formed first. The vapours are condensed by using a condenser and the
liquid is collected in a receiver. The vapours of higher boiling component form later and the liquid can be collected separately.
Partition Chromatography: Partition chromatography is based on continuous differential partitioning of components of a mixture between stationary and
mobile phases. Paper chromatography is a type of partition chromatography. In paper chromatography, a special quality paper known as chromatography
paper is used. Chromatography paper contains water trapped in it, which acts as the stationary phase. A strip of chromatography paper spotted at the base
with the solution of the mixture is suspended in a suitable solvent or a mixture of solvents (Fig. 12.13). This solvent acts as the mobile phase. The solvent
rises up the paper by capillary action and flows over the spot. The paper selectively retains different components according to their differing partition in
the two phases. The paper strip so developed is known as a chromatogram. The spots of the separated coloured compounds are visible at different heights
from the position of initial spot on the chromatogram. The spots of the separated colourless compounds may be observed either under ultraviolet light or
by the use of an appropriate spray reagent as discussed under thin layer chromatography.

1. Hyperconjunction involves delocalisation of … electrons of C—H bond of an alkyl group directly attached to an atom of unsaturated system or to an
atom with an unshared p orbital.
1. \sigma
2. \pi
3. \delta
4. \eta
2. Which of the is an example of technique used for purification.
1. Distillation
2. Differential extraction
3. Chromatography
4. All the above
3. On heating, some solid substances change from solid to vapour state without passing through liquid state is known as …
1. Melting
2. Boiling
3. Sublimation
4. Condensation
4. The hyperconjugation may also be regarded as ….
1. bonding resonance
2. no bond resonance
3. no bond induction
4. bonding induction
5. Chromatography paper contains water trapped in it, which acts as the … phase.
1. mobile
2. stationery
3. Secondary
4. quaternary
 8: Organic Chemistry – So me Basic Principles and Techniques
Chemistry Worksheet

Standard: 11th Science Subject: Chemistry

Student Name:

Q1. Which functional group is present in a molecule of CH3​OCH2​CH3​?

1. Ether
2. Carboxyl
3. Ketone
4. Aldehyde
5. Ester
Ans: 1. Ether
Explanation:
The functional group present in CH3​−O−CH2​CH3​is an ether group −O−.
Note: In general, ethers can be represented as R−O−R′.
Q2. The atom or the group of atoms by which the characteristic reactions of organic compounds are determined, that atom or group of atoms is called ____________.
1. Hydrocarbon
2. Functional group
3. Atom
4. Compound
Ans: 2. Functional group
Explanation:
Functional groups are specific substituents or moieties within molecules that are responsible for the characteristic chemical reactions of those molecules.
Examples: −OH, −COOH, −COOR etc.
Hence, the atom or the group of atoms by which the characteristic reactions of organic compounds are determined, that atom or group of atoms is called functional group.
Q3. Electrophilic addition reactions proceed in two steps. The first step involves the addition of an electrophile. Name the type of intermediate formed in the first step of the
following addition reaction.
H 3C − HC = CH 2 + H + → ?
1. 2° Carbanion
2. 1° Carbocation
3. 2° Carbocation
4. 1° Carbanion
Ans: 3. 2° Carbocation
Explanation:
When the electrophile attacks CH3 – CH = CH2, delocalisation of electrons can take place in two possible ways

As 2° carbocation is more stable than 1° carbocation, the first addition is more feasible.
Q4. Pick out the wrong statement.
1.

2.

3. Hyperconjugation is no bond resonance.

4. Dopole moment of CH 2 = CH − Cl < CH 3Cl
Ans: 1.

Explanation:
It is aromatic ∵ it has (4n + 2)π, i.e., 6π electrons which are delocalised.
Q5. Which of the following is a homocyclic alicyclic compound?
1.

2.

3.

​
4.
Ans: 2.

ExPlanation:
Alicyclic (aliphatic cyclic) compounds contain carbon atoms joined in the form of a ring. Homocyclic means it contains only C-atoms in the ring, e.g.

Q6. The fragrance of flowers is due to the presence of some steam volatile organic compounds called essential oils. These are generally insoluble in water at room temperature but
are miscible with water vapour in vapour phase. A suitable method for the extraction of these oils from the flowers is:
1. Distillation.
2. Crystallisation.
3. Distillation under reduced pressure.
4. Steam distillation.
Ans: 4. Steam distillation.
Explanation:
Essential oils are insoluble in water, soluble in steam and have high vapour pressure. Therefore, they can be separated by steam distillation.
Q7. In presence of HCl(aq.);H2​S gas results the precipitation of group-2 cations but not of group-4 cations during qualitative analysis. It is due to:
1. Lower concentration of S2-
2. Higher concentration of S2-
3. Lower concentration of H+
4. Higher concentration of H+
Ans: 2. Higher concentration of S2-
Explanation:
Due to common ion effect, the ionisation of H2​S is suppressed and at low concentration of S2- ions, the second group sulphides are precipitated.
Q8. Which of the following are members of same homologous series?
1. HCOOCH3​and CH3COOCH3
2. HCOOH and HCOOCH3
3. CH3COCH3​and CH3​CH2​CHO
4. C2H5​OH and CH3OCH3
Ans: 1. HCOOCH3​and CH3COOCH3
Explanation:
A homologous series is a family of hydrocarbons with similar chemical properties that share the same general formula.
Both given compound HCOOCH3​ and CH3​COOCH3​are homologous series of a simple ester group RCOOH, where a successive methyl group −CH3​added to previous one.
Q9. Which one of the following is not an alcohol?
1. (CH3​)2​CHCH2​CH2​OH
2. (CH3​)3​C−CH2​OH
3. (CH3)2​−CH−OH
4. CH3​CH2CH2​CH2COOH
Ans: 4. CH3​CH2CH2​CH2COOH
Explanation:
(d) is the correct answer as the group associated with it is carboxylic acid group.
Q10. Which of the statements below best describes a functional group?
1. It is the non-polar section of an organic molecule.
2. It is a highly reactive group of elements with similar outer shell electron configurations.
3. It is an atom or a group of atoms which determines the chemical properties of a compound.
4. It is the part of a chelate ligand attracted to the central ion.
Ans: 3. It is an atom or a group of atoms which determines the chemical properties of a compound.
Explanation:
Functional groups are specific groups or recognizable group of atoms or bonds within molecules that are responsible for the characteristic chemical reactions of those
molecules.
These functional group give characteristic properties to the carbon chain to which it is attached, e.g., aldehydic group or carboxylic group.
Q11. CH 3​ − CH = CH − C ≡ CH has lUPAC name:
1. pent - 2 - en- 4 - yne
2. pent - 4 - yn - 2 - ene
3. pent - 1 - yn - 3 - ene
4. pent - 3 - en - 1 - yne
Ans: 4. pent - 3 - en - 1 - yne
Q12. Which of the following is correct about the number of bonds formed by atoms of different elements in acetaldehyde?(Report your answer in the ratio of H:O:C)
1. 4:2:2
2. 4:1:2
3. 4:1:3
4. 3:3:3
Ans: 2. 4:1:2
Explanation:
CH3​CHO − Acetaldehyde
No of atoms of H:O:C = 4:1:2
Q13. Which type of bond is formed between carbon atom and nitrogen atom?
1. Covalent bond.
2. Ionic bond.
3. Dative bond.
4. None of these.
Ans: 1. Covalent bond.
Explanation:
A covalent bond is formed between carbon and nitrogen atom. If duplet (2) or octet (8) is completed by sharing of electrons between two electronegative elements, the bond
formed is called covalent bond.
Q14. Which one is a nucleophilic substitution reaction among the following?
1. CH 3CHO + HCN → CH 3CH(OH)CN
H+
2. CH 3 − CH = CH 2 + H 2O → CH 3 − CH − CH 3 | OH
3. RCHO+ R ′ MgX → R − CH − R′ | OH
4. CH 3 | CH 3 − CH 2 − CH − CH 2Br + NH 3 → CH 3 | CH 3 − CH 2 − CH − CH 2NH 2
Ans: 4. CH 3 | CH 3 − CH 2 − CH − CH 2Br + NH 3 → CH 3 | CH 3 − CH 2 − CH − CH 2NH 2
Q15. Which method of estimation is shown in the figure given below?

1. Carius method.
2. Kjeldahl's method.
3. Duma's method.
4. None of these.
Ans: 1. Carius method.
Q16. The IUPAC name of iso-octane is:
1. 2, 2-dimethylpentane.
2. 2, 3-dimethylpentane.
3. 2, 3, 3-trimethylpentane.
4. 2, 2, 4-trimethylpentane.
Ans: 4. 2, 2, 4-trimethylpentane.
Q17. How many pi bonds are present in phosgene?
1. 1
2. 2
3. 3
4. 4
Ans: 1. 1
Explanation:
From the image we can see that there is only 1 pi-bond present in phosgene (cabonyl chrolide).
Q18. Which of the following is a correct representation of condensed formula forHOCH 2CH 2CH 2CH(CH 3)CH(CH 3)CH(CH 3)CH 3?
1. HO(CH 2) 2CHCH 3CH(CH 3) 2
2. HO(CH 2) 2CH(CH 3)CH(CH 3) 2
3. HOCH 2CHCH 3CH(CH 3) 2
4. None of the above
Ans: 2. HO(CH 2) 2CH(CH 3)CH(CH 3) 2
Explanation:
The correct condensed formula forHOCH 2CH 2CH 2CH(CH 3)CH(CH 3)CH(CH 3)CH 3
is HO(CH 2) 3CHCH 3CH(CH 3) 2
Q19. Given two compounds, one more polar than the other, which one will move up the silica stationery phase higher than the other in TLC?
1. Polar compound
2. Non polar compound
3. Both will move equally
4. None will move
Ans: 2. Non polar compound
Explanation:
Polar compounds will have more interaction with silica gel and hence polar compounds won't move much in the stationery phase.
Non polar compounds will have lesser interaction with the silica or the stationery phase and will move higher than the polar compound.
Q20. The molecular formulae for phosgene and tear gas are .......... and ......... respectively.
1. COCl2​and CCl3​NO2​
2. SOCl2​ and CCl3​NO2​
3. COCl2​ and CCI3​NO2​
4. SOCl2​and CCI3​NO2​
Ans: 1. COCl2​and CCl3​NO2​
Q21. What is the name of tube in which a known mass of an organic compound is heated for the quantitative analysis of sulphur?
1. Borosil tube.
2. Carius tube.
3. Kjeldahl tube.
4. None of these.

Ans: 2. Carius tube.

Explanation:
Tube in which a known mass of an organic compound is heated for the quantitative analysis of S is known as Carius tube.
Q22. Identify the correct decreasing order of priority of the functional groups from the following:
1. −CONH2​, −C=O, −HC=O, −CN
2. −CONH2​​, −CN, −HC=O, −C=O
3. −CN, −CONH2​​, −C=O, −HC=O
4. −CN, −CONH2​​, −HC=O, −C=O
Ans: 2. −CONH2​, −CN, −HC=O, −C=O
Explanation:
Amides > Nitriles > Aldehydes > ketones
Q23. The compound of the molecular formula, C6​H14​has two tertiary carbons. Its IUPAC name is:
1. n-hexane
2. 2−methylpentane
3. 2, 3−dimethylbutane
4. 2, 2−dimethylpentane
Ans: 3. 2, 3−dimethylbutane
Explanation:
Molecular formula of the compound is C6​H14​. The compound has 2 tertiary carbon.
Then the probable structure of the compound will be CH3​−CH(Me)−CH(Me)−CH3​.
Name of this compound is 2, 3-dimethylbutane.
Q24. In which of the following representations given below spatial arrangement of group/ atom different from that given in structure ‘A’?

1.

2.
 3.

4.

Ans:

Explanation:
The spatial arrangement of groups or atoms can be checked by doing two interchange and bringing H below the plane of the paper. Find out the sequence of the remaining
groups in a particular order whether clockwise or anticlockwise starting from atom with highest atomic number to atom with lower atomic numbers. Hence, option (ii) has
same spatial arrangement as (A) while in rest three is different.
Q25. Which of the following compounds will exhibit geometrical isomerism?
1. 1-phenyl-2-butene.
2. 3-phenyl-1-butene.
3. 2-phenyl-1-butene.
4. 1, 1-diphenyl-1-propane.
Ans: 1. 1-phenyl-2-butene.
Q26. The fruity smell is of a/an:
1. Aldehyde
2. Ketone
3. Alcohol
4. Ester
Ans: 4. Ester
Explanation:
Esters have a fruity smell due to their volatile nature caused by their chemical composition and conformations.
Q27. Which one of the following has the most nucleophilic nitrogen?
1.

2.

3.
 4.

Ans: 1.

Explanation:
∵ Lone pair of electrons are easily available. In (b) lone pair is delocalised, in (c) -COCH3 is electron withdrawing, in (d) C6H5- is electron withdrawing.
Q28. The main source of organic compounds is:
1. Coaltar
2. Petroleum
3. Both (a) and (b)
4. None of the above
Ans: 3. Both (a) and (b)
Explanation:
Petroleum and coaltar are the main sources of organic compounds.
Q29. Arrange the above in the decreasing order of reactivity towards HBr:

1. a > b > c
2. b > a > c
3. b > c > a
4. a > c > b
Ans: 2. b > a > c
Explanation:
Among a, b and c electron donating ability order is −OCH3​> −CH3 ​> −CH2​OCH3​more the electron donating ability of substituent more is the stability of carbocation.
Q30. Which of the following compounds will not give Lassaigne's test for nitrogen?
1. NH 2 − NH 2
2. C 6H 5NHNH 2
3. C 6H 5 − N = N − C 6H 5
4. NH 2CONH 2
Ans: 1. NH 2 − NH 2
Explanation:
Because it does not have carbon.
Q31. identify the rate of reaction of given compounds in E2​reaction:

1. a > b > c > d

2. a > c > b > d
3. b > a > c > d
4. b > d > a > c
Ans: 1. a > b > c > d
Explanation:
The rate of reaction depends on the leaving ability of halide ions.
Leaving Ability: I− > Br− > Cl− > F− (Acidic nature).
Strong acids act as a strong leaving groups.
Q32. Passing H2​S gas into a mixture of Mn2+,Ni2+,Cu2+,Hg2+ ions in acidified aqueous solution precipitates:
1. CuS and HgS
2. MnS and CuS
3. MnS and NiS
4. NiS and HgS
Ans: 1. CuS and HgS
Explanation:
Cu2+ and Hg2+ lie in IInd group of qualitative analysis H2​S in acid medium is reagent for it.
HCl → H+ + Cl−
H2​S ⇋ 2H+ + S2−
Q33. The indicator which is used to find the strength of caustic soda solution with the help of oxalic acid is:
1. Methyl orange
2. Phenolphthalein
3. Potassium permanganate
4. None of the above
Ans: 2. Phenolphthalein
Explanation:
An indicator is a chemical substance that undergoes a colour change at the endpoint. The endpoint of an acid-base titration can be determined using acid-base indicators.
Acid Base indicators are either weak organic acids or weak organic bases. The colour change of an indicator depends on the pH of the medium.
The un-ionized form of an indicator has one colour, but its ionized form has a different colour.
Phenolphthalein is used to find the strength of caustic soda solution with the help of oxalic acid.
Q34. The structure of iso-butyl group in an organic compound is:
1.
 2. CH 3 − CH 2 − CH 2 − CH 3
3. CH 3 − CH 2 − CH 2 − CH 2 −
4. CH 3 | CH 3 − C − | CH 3
Ans: 1.

Explanation:
'Iso' means one Me group is present in side chain. Hence, the structure of iso-butyl group is
CH 3 | CH 3 − C − CH 2 | C
Q35. Which of the following method is used to purify liquids having very high boiling points and those which decompose at or below their boiling points?
1. Simple distillation.
2. Fractional distillation.
3. Distillation under reduced pressure.
4. None of the above.
Ans: 3. Distillation under reduced pressure.
Explanation:
Distillation under reduced pressure method is used to purify liquids having very high boiling points and those, which decompose at or below their boiling points. Such liquids
are made to boil at a temperature lower than their normal boiling points by reducing the pressure on their surface. A liquid boils at a temperature at which its vapour pressure
is equal to the external pressure. The pressure is reduced with the help of a water pump or vacuum pump.
Q36. Which of the following is not in accordance to IUPAC system?
1. Br− CH 2 − CH = CH 2 1-bromoprop 2-ene
2. CH 3 | CH 3 − CH 2 − C − CH 2 − CHCH 3 | | Br CH 3 4-bromo-2, 4-dimethyle hexane
3.

4. CH 3 − C − CH 3 − CH 2CH 2COOH || O 5-oxohexanoic acid

Ans: 1. Br− CH 2 − CH = CH 2 1-bromoprop 2-ene
Q37. Note: In the following questions a statement of Assertion (A) followed by a statement of Reason (R) is given. Choose the correct option out of the choices given below each
question.
Assertion (A): Components of a mixture of red and blue inks can be separated by distributing the components between stationary and mobile phases in paper chromatography.
Reason (R): The coloured components of inks migrate at different rates because paper selectively retains different components according to the difference in their partition
between the two phases.
1. Both A and R are correct and R is the correct explanation of A.
2. Both A and R are correct but R is not the correct explanation of A.
3. Both A and R are not correct.
4. A is not correct but R is correct.
Ans: 1. Both A and R are correct and R is the correct explanation of A.
Explanation:
In paper chromatography, a special quality paper known as chromatography paper, is used. Chromatography paper contains water trapped in it, which acts as the stationary
phase. A strip of chromatography paper spotted at the base with the solution of the mixture is suspended in a suitable solvent or a mixture of solvents. This solvent acts as the
mobile phase. The solvent rises up the paper by capillary action and flows over the spot. The paper selectively retains different components according to their differing
partition in the two phases. The paper strip so developed is known as a chromatogram. The spots of the separated coloured compounds are visible at different heights from
the position of initial spot on the chromatogram.
Q38. Note: In the following questions a statement of Assertion (A) followed by a statement of Reason (R) is given. Choose the correct option out of the choices given below each
question.
Assertion (A): Energy of resonance hybrid is equal to the average of energies of all canonical forms.
Reason (R): Resonance hybrid cannot be presented by a single structure.
1. Both A and R are correct and R is the correct explanation of A.
2. Both A and R are correct but R is not the correct explanation of A.
3. Both A and R are not correct.
4. A is not correct but R is correct.
Ans: 4. A is not correct but R is correct.
Explanation: Canonical structures always have more energy than resonance hybrid. Resonance hybrids are always more stable than any of the canonical structures. The
delocalization of electrons lowers the orbitals energy and gives stability.

Q39. In the following Questions, the Assertion and Reason hrve been put forfiird. Read the statements csrefully end choose the correct alternative from the following:
1. Both Assertion and Reason are true and Reason is the correct explanation of Assertion.
2. Both Assertion rnd Reason are true but Reason is not the correct explenatlon of Assertion.
3. Assertion is true but Reason is false.
4. Both Assertion and Reason arc false.
Assertion: A Mixture of o-nitrophenol and p-nitrophenol can be separated by steam distillation.
Reason: p-nitrophenol is steam volatile while 0-nitrophenol is not steam volatile.
Ans: 3. Assertion is true but Reason is false.
Q40. Match the terms mentioned in Column I with the terms in Column II.
Column I Column II
(i) Carbocation (a) Cyclohexane and 1- hexene.
Conjugation of electrons of C–H σ bond with empty p-orbital present at adjacent positively ch
(ii) Nucleophile (b)
arged carbon.
(ii Hyperconjugati
(c) sp2 hybridised carbon with empty p-orbital.
i) on
(i
Isomers (d)Ethyne
v)
sp hybridisatio
(v) (e)Species that can receive a pair of electrons.
n
 (v
Electrophile (f) Species that can supply a pair of electrons.
i)
Ans: Column I Column II
(i) Carbocation (c) sp2 hybridised carbon with empty p-orbital.
(ii) Nucleophile (f) Species that can supply a pair of electrons.
(iii) Hyperconjugation (b) Conjugation of electrons of C–H σ bond with empty p-orbital present at adjacent positively charged carbon.
(iv) Isomers (a) Cyclohexane and 1- hexene.
(v) sp hybridisation (d) Ethyne
(vi) Electrophile (e) Species that can receive a pair of electrons.

Q41. Match Column I with Column II.

Column I Column II
Dumas meth
(i) (a) AgNO3
od.
Kjeldahl’s m
(ii) (b)Silica gel.
ethod.
(ii Carius meth
(c) Nitrogen gas.
i) od.
(i Chromatogr
(d)Free radicals.
v) aphy
Ammonium su
(v) Homolysis (e)
lphate.

Ans: Column I Column II

(i) Dumas method. (c) Nitrogen gas.
(ii) Kjeldahl’s method. (e) Ammonium sulphate.
(iii) Carius method. (a) AgNO3
(iv) Chromatography (b) Silica gel.
(v) Homolysis (d) Free radicals.

Q42. If a liquid compound decomposes at its boiling point, which method (s) can you choose for its purification. It is known that the compound is stable at low pressure, steam volatile
and insoluble in water.
Ans: Steam distillation can be used for its purification. This method is applied to separate substances which are steam volatile and immiscible with water.
Q43. Suggest a method to purify:
1. Camphor containing traces of common salt.
2. Kerosene oil containing water.
3. A liquid which decomposes at its boiling point.
Ans: 1. Sublimation camphor sublimes while common salt remains as residue in the China dish.
2. Since the two liquids are immiscible, the technique of solvent extraction with a separating funnel is used. The mixture is throughly shaken and the separating funnel is
allowed to stand. Kerosene being lighter than water forms the upper layer while water forms the lower layer.
The lower water layer is run off using the stop cock of the funnel and kerosene oil is obtained. It is dried over anhydrous CaCl2 or MgSO4 and then distilled to give pure
kerosene oil.
3. Distillation under reduced pressure.
Q44. Name the electrophile/ nucleophile generated by following species:
1. HNO3 + H2SO4
2. CH3COCl
3. alc. KCN
Ans: 1.

1. O ‖CH − C ⊕ is electrophile O O ‖ ‖CH 3 − C − Cl − → CH 3 − C ⊕ + Cl −

2. CN − is nucleophile

KCN → K + + CN −
Q45. Arrange the following:
+ + + +
1. C 6H 5 CHCH 3, C 6H 5 CHCH = CH 2, C 6H 5CH 2CH 2, C 6H 5 C(CH 3) 2 in order of increasing stability.
2. CH 3CH 2+ , C 6H 5CH 2+ , (CH 3) 3C + , CH 2 = CHCH 2+ in order of decreasing stability.
3. HC ≡ C − , CH 2 = CH − , CH 3CH 2− , CH 3− , (CH 3) 2CH − , C 6H 5CH 2− in order of increasing stability.
Ans: + + + +
1. C 6H 5CH 2CH 2 < C 6H 5 CHCH 3 < C 6H 5 C(CH 3) 2 < C 6H 5 CHCH = CH 2
+ + +
2. (CH 3) 3C + > C 6H 5CH 2 > CH 2 = CHCH 2 > CH 3CH 2
3. (CH 3) 2CH − < , CH 3CH 2− < CH 3− < CH 2 = CH − < C 6H 5CH 2− < HC ≡ C −
Q46. Which of the following selected chains is correct to name the given compound according to IUPAC system.

Ans: According to IUPAC nomenclature, the selected longest carbon chain must have maximum functional groups present in the compound. Therefore, only in one selected chain of
4 carbon atoms including both the functional group is corrected one.

In other three, carbon atoms are in selected chain but both the functional groups are not included.
Q47. Identify the type of reactions:
sunlight
1. CH 4 + Cl 2 → CH 3Cl + HCl
conc.H 2SO 4
2. C 6H 6 + (conc.)HNO 36 → C 6H 5NO 2 + H 2O

3. Br | CH 3 − CH = CH 2 + HBr → CH 3 − CH − CH 3

4. O OH ‖ | CH 3 − C − CH 3 + HCN → CH 3 − C − CH 3 |
 HBr
5. CH 3 − CH = CH 2 → CH 3CH 2CH 2Br
peroxide

6. CH 3Cl + KOH(aq) → CH 3OH + KCl

Ans: 1. Free radical substitution.
2. Electrophilic substitution reaction.
3. Electrophilic addition reaction.
4. Nucleophilic addition reaction.
5. Free radical addition.
6. Nucleophilic substitution reactions.
Q48. The order of basicity of amines expected on the basis of inductive effect is NH3 < RNH2 < R3N. However, the observed order of basicity is NH3 < RNH2 < R2NH > R3N. How will you
account for the difference?
Ans: This order of basicity is observed in case of solvent phase as the energy of hydration also becomes important here. The following important factors can be considered.
1. Effect of electrion releasing groups: More the number of electron-releasing groups present in a molecule, more is the increase in its electron density and more is the basic
character. So, according to this effect, the order should be NH3 > RNH2 <R2NH <R3N.
2. Hydration enthalpy: The more hydrogen bonds a molecule (ammonium ion) can form with water, the more will be its basic character. So, the order should be NH3 > RNH2 <
R2NH < R3N.

3. Inductive effect: The more is the crowding of groups in a molecule, the lesser will be its basicity. So, the order should be NH3 > RNH2> R2NH > R3N.
Combining all the factors, we get the order of basicity as NH3 > RNH2 > R2N.​​
Q49. Note: Consider structures I to VII and answer the questions:
1. CH 3 − CH 2 − CH 2 − CH 2 − OH
2. CH 3 − CH 2 − CH − CH 3 | OH
3. CH 3 | CH 3 − C − CH 3 | OH
4. CH 3 − CH − CH 2 − OH | CH 3
5. CH 3 − CH 2 − O − CH 2 − CH 3
6. CH 3 − O − CH 2 − CH 2 − CH 3
7. CH 3 − O − CH − CH 3 | CH 3
Identify the pairs of compounds that represents chain isomerism.
Ans: When two are more compounds have similar molecular formula but differnt carbon skeletone, these are referred to as chain as isomers and the phenomenon is termed as
chain isomerism.
1. CH 3 − CH 2 − CH 2 − CH 2 − OH
2. CH 3 − CH 2 − CH − CH 3 | OH are position isomers.
3. CH 3 | CH 3 − C − CH 3 | OH
4. CH 3 − CH − CH 2 − OH | CH 3 are position isomers.
Q50. Note: Consider structures I to VII and answer the questions:
1. CH 3 − CH 2 − CH 2 − CH 2 − OH
2. CH 3 − CH 2 − CH − CH 3 | OH
3. CH 3 | CH 3 − C − CH 3 | OH
4. CH 3 − CH − CH 2 − OH | CH 3
5. CH 3 − CH 2 − O − CH 2 − CH 3
6. CH 3 − O − CH 2 − CH 2 − CH 3
7. CH 3 − O − CH − CH 3 | CH 3
Identify the pairs of compounds that represents position isomerism.
Ans: In position isomerism, two or more compounds differ in the position of substituent, functional group or multiple bonds but molecular formula is same. In the given structures,
I and II, III and IV, and VI and VII are position isomers.

1. CH 3 − CH 2 − CH 2 − CH 2 − OH
2. CH 3 − CH 2 − CH − CH 3 | OH are position isomers.
3. CH 3 | CH 3 − C − CH 3 | OH
4. CH 3 − CH − CH 2 − OH | CH 3 are position isomers.
6. CH 3 − O − CH 2 − CH 2 − CH 3 and
7. CH 3 − O − CH − CH 3 | CH 3 are position isomers.
Q51. 0.90g of organic compound on combustion gave 2.64g of CO2, and 0.63g of H2O. Calculate the percentage of C and H in the compound.
Ans: 12 Weight of CO 2 formed
% of C = 44 × Weight of organic compound × 100
12 2.64 3168
= 44
× 0.90
× 100 = 39.6
= 80%
2 Weight of H 2O formed
% of H = 18
× Weight of organic compound
× 100
12 0.63 126
= 18
× 0.90
× 100 = 16.2
= 7.77%
Q52. Give the IUPAC names of the following compounds:
1.

2.

3.

4.
 5.

6. Cl 2CHCH 2OH
Ans: 1. Propylbenzene.
2. 3-methylpentanitrile.
3. 2, 5-dimethylheptane.
4. 3-bromo-3-chloroheptane.
5. 3-chloropropanal.
6. 2, 2-dichloroethanol.
Q53. What is meant by hybridisation? Compound CH2 = C = CH2 contains sp or sp2 hybridised carbon atoms. Will it be a planar molecule?
Ans: Hybridization is defined as an intermixing of a set of atomic orbitals of slightly different energies, thereby forming a new set of orbitals having equivalent energies and shapes.
For example, one 2s-orbital hybridizes with two 2p-orbitals of carbon to form three new sp2 hybrid orbitals. These hybrid orbitals have minimum repulsion between their
electron pairs and thus, are more stable. Hybridization helps indicate the geometry of the molecule.
In CH2 = C = CH2 (allene)
Carbon atom land Sp2 hybridized as each one has 3σ bonds while carbon atom 2 has 2σ bonds and it is sp hybridized. allene molecule as a whole is non-planar.
Q54. Explain, how is the electronegativity of carbon atoms related to their state of hybridisation in an organic compound?
Ans: Electronegativity increases with increasing s-character. This is because s-electrons are more strongly attracted by the nucleus than p-electrons.
sp3 – 25% s-character, 75% P-character
sp2 – 33% s-character, 67% P-character
sp – 50% s-character, 50% P-character
Hence, the order of electronegativity is sp3 < sp2 < sp
Q55. Which is more stable and why?
⊕ ⊕
1. C 6H 5 − CH 2 or C 6H 11CH 2
. .
2. (C 6H 5)CH or C 6H 5CH 2
. .
3. (C 6H 5)CH 2 or CH 2 = CH − CH 2
Ans: ⊕
1. C 6H 5CH 2 is more stable due to resonance (5 resonating structures).
2. (C6H5)CH is more stable due to more resonating structures.
3. C6H5CH2 is more stable due to 5 resonating structures whereas CH2=CH-CH2 has two resonating structures.
Q56. Identify the functional groups in the following compounds.
1.

2.

3.

Ans: 1.

2.
3.

Q57. Note: Consider structures I to VII and answer the questions:

1. CH 3 − CH 2 − CH 2 − CH 2 − OH
2. CH 3 − CH 2 − CH − CH 3 | OH
3. CH 3 | CH 3 − C − CH 3 | OH
4. CH 3 − CH − CH 2 − OH | CH 3
5. CH 3 − CH 2 − O − CH 2 − CH 3
6. CH 3 − O − CH 2 − CH 2 − CH 3
7. CH 3 − O − CH − CH 3 | CH 3
Identify the pairs of compounds which are functional group isomers.
Ans: Compounds I to IV, i.e., alcohols, and V to VII, i.e., ethers, are functional group isomers with molecular formula C4H10O and different functional groups (-OH in I to IV and -O -
in V to VII).
Hence, I and V, I and VI, I and VII; II and V, II and VI, II and VII; HI and V, IH and VI; IH and VII; IV and V, IV and VI, IV and VH are functional group isomers.
Q58. “Stability of carbocations depends upon the electron releasing inductive effect of groups adjacent to positively charged carbon atom involvement of neighbouring groups in
hyperconjugation and resonance.”
Write structures of various carbocations that can be obtained from 2-methylbutane. Arrange these carbocations in order of increasing stability.
Ans: 2-Methylbutane has four possible carbocations
+ + CH 3 − CH − CH 2 − CH 2 CH 3 − CH − CH − CH 3 | | CH 3 CH 3 I(1 ∘ ) II
∘ ∘
+ + CH 3 − C − CH 2 − CH 3 CH 2 − CH 2CH − CH 2 − CH 3 | | CH 3 CH 3 III(3 ) IV(1 )
I < IV < II < III
Stability of carbocation increases in the order 1° < 2° < 3°. Out of I and IV, IV is more stable than I because in IV, CH3 group is at a-carbon and in I, it is at β-carbon and +I-effect
decreases with distance
Q59. 1. What is role of copper oxide in estimation of carbon and hydrogen?
2. How do we test phosphorus in given organic compound?
⊕ ⊕
3. What is shape of CH 3 (methyl carbocation) and CH 3 (methyl carbanion)?
Ans: 1. It acts as oxidising agent. It oxidises C to CO2 and H2 to H2O.
2.
Fuse the given organic compound with Na2O2
The solution is boiled with conc. HNO3 and then added ammonium molybdate. Canary yellow precipatate confirms the presence of phosphorus.

Q60. 1. Draw cis and trans-structures for Hex-2-ene. Which isomer will have higher boiling point and why?
2.

Ans: 1.

cis-Hex-2-ene has higher dipole moment and therefore, it has higher boiling point.
2.

is not aromatic, Due to the presence of sp3

carbon (carbon 3), the system is not planar, Futher, it contains only four n electsons. Hence, it is not aromatic because it does not contain planar delocalised cloud with
(4n+ 2)π electrons.
Q61. 1. Write IUPAC name of the following:

2. CH 2CH 2CHO and CH 3C − CH 3 || O

3. Draw the structure of 3-oxopentanal.
Ans: 1.

2. Functional isomerism.
3. O ‖CH 3 − CH 2 − C − CH 2 − C − H ‖ O is structive of 3-oxo pentanal.
Q62. Write down the formulae of the first four members of each homologous series beginning with the following compounds.
1. CH 2 = CH 2
 2. HCOOH
3. CH 3COCH 3
4. CH 3OH
5. HC ≡ CH
Ans: 1. CH 2 = CH 2, CH 3CH = CH 2,
CH 3CH 2CH = CH 2, CH 3CH 2CH 2CH = CH 2
2. HCOOH, CH 3COOH, CH 3CH 2COOH,
CH 3CH 2CH 2COOH
3. CH 3COCH 3, CH 3CH 2COCH 3, CH 3CH 2CH 2COCH 3,
CH 3CH 2CH 2CH 2COCH 3
4. CH 3OH, CH 3CH 2OH, CH 3CH 2CH 2OH, CH 3CH 2CH 2CH 2OH
5. HC ≡ CH, CH 3C ≡ CH, CH 3CH 2C ≡ CHCH 3CH 2CH 2C ≡ CH
Q63. The following techniques are used to quantitatively estimate extra elements in organic compound. Identify the name of the method and the element estimated by this method.
1. A known mass of an organic compound is heated with fuming HNO3 in presence of AgNO3.
2. Organic compound is heated with dry copper oxide in atmosphere of CO2.
3. Organic compound is heated with conc. H2SO4.
Ans: 1. Estimation of halogen by Carius method.
2. Estimation of nitrogen by Dumas method.
3. Estimation of nitrogen by Kjeldahl's method.
Q64. In DNA and RNA, nitrogen atom is present in the ring system. Can Kjeldahl method be used for the estimation of nitrogen present in these? Give reasons.
Ans: DNA and RNA have nitrogen in the heterocyclic rings. Nitrogen present in rings, azo groups and nitro groups cannot be removed as ammonia. So, Kjeldahl’s method cannot be
used for the estimation of nitrogen present in these.
Q65. In which of the following compounds the C-Cl bond ionisation shall give most stable carbocation?
1. CH 3 − CH − Cl | CH 3
2. Cl | CH 3 − C − CH 3 | CH 3
3.

1. ​ H | O 2NH 2C − C − Cl | H
Ans:

Q66. Identify the functional groups present in the following compounds.

1.

2.

3. CH 3 − CH 2 − CO − CH 2 | CH 2 − COCl
4. O ‖CH 2 = CH − CH 2 − C − NH 2
Ans: 1. Functional groups are -NH2(amino), -OMe(methoxy) and -CHO(aldehydic)
2. Carbon-carbon double bond, -NO2(nitro)and -COOH(carboxylic)
3. -CO-(keto), -COCl(acylchloride)
4. | | − C = C − (carbon-carbon double bond), O ‖ − C − NH 2 (acitamide).
Q67. 1. Write IUPAC name of the following:
CH 3CHCH ≡ CH | CH = CH 2
2. Draw the structure of Pent-4-en-2-ol.
3. What is nucleophile? Give one example.
Ans: 3 4 5
1. CH, − CH − CH ≡ CH | CH = CH 2 2 1 3-methyl pent-1-en-4yne

1 2 3 4 5
2. CH 3 − CH − CH − CH = CH 2 | OH
3. Nucleophile is a species which is either negatively charged or has lone pair of electron.
Q68. Write structural formulae for all the isomeric amines with molecular formula C4H11N.
Ans: 1. CH 3 − CH 2 − CH 2 − CH 2 − NH 2
2. CH 3 − CH 2 − CH − CH 3 | NH 2
3. CH 3 − CH − CH 2 − NH 2 | CH 3
4. CH 3 | CH 3 − C − NH 2 | CH 3
5. CH 3 − CH 2 − CH 2 − NH − CH 3
6. CH 3 − CH − NH − CH 3 | CH 3
7. CH 3 − CH 2 − NH − CH 2 − CH 3
8. CH 3 − CH 2 − N − CH 3 | CH 3
Q69. 0.25g of an organic compound gave 30cm3 of moist dinitrogen at 288K and 745mm pressure. Calculate the percentage of nitrogen.
(Aq. tension at 288K = 12.7mm).
Ans: Pressure of moist dinitrogen obtained = 745mm
Aq. tension at same temperature = 12.7mm
∴ Pressure due to nitrogen = 745 - 12.7 = 732.3mm
To calculate the volume of N2 at S.T.P.
P 1V 1 P 2V 2
=
T1 T2
P 1V 1
⇒ V2 = T1
732.3 × 30 × 273
= 288 × 760
= 27.4cm 3
28 × 27.4 × 100
∴ % of Nitrogen = 22400 × 0.25
= 13.7%
Q70. 1. Give one example of position isomerism.
2. What are electrophiles? Give one example of electrophilic substitution reaction.
3. Write the chemistry of Lassaigne's test for qualitative analysis of nitrogen.
Ans: 1.
Cl | CH 3CH 2CH 2Cl and CH 3 − CH − CH 31 − Cholropropane 2 − Cholropropane
2. Those species which are positively charged or electron deficient are called electrophiles. e.g. H+, AlCl3, Cl+

2. Fuse the organic compound with sodium metal. Sodium reacts with 'C' and 'N' present in organic compound to form NaCN.

Na+ C + N → NaCN
Add FeSO4 to L.E. (Lassaigne's extract)

6NaCl + FeSO 4 → Na 4[Fe(CN) 6] + NaSO 4

Dilute H2SO4 is added to convert Fe2+ to Fe3+ and blue colour is formed due to formation of ferric ferrocyanide.

4Fe 3 + + 3Na 4[Fe(CN) 6] → Fe 4[Fe(CN) 6] 3 + 12Na + Blue colouration

Q71. “Stability of carbocations depends upon the electron releasing inductive effect of groups adjacent to positively charged carbon atom involvement of neighbouring groups in
hyperconjugation and resonance.”
The structure of triphenylmethyl cation is given below. This is very stable and some of its salts can be stored for months. Explain the cause of high stability of this cation.

Ans: Triphenylmethyl cation is very stable because +ve charge of methyl carbon is delocalized in three phenyl rings. In each phenyl ring, +ve charge is developed on 2 ortho position
and para position, i.e. three resonating structures. Total resonating structures given by triphenylmethyl cation are nine. Hence, it is very stable. These structures can be shown
as.

Q72. For testing halogens in an organic compound with AgNO3 solution, sodium extract (Lassaigne’s test) is acidified with dilute HNO3. What will happen if a student acidifies the
extract with dilute H2SO4 in place of dilute HNO3?
Ans: On adding dilute H2SO4 for testing halogens in an organic compound with AgNO3, white precipitate of Ag2SO4 is formed. This will interfere with the test of chlorine and this
Ag2SO4 may be mistaken for white precipitate of chlorine as AgCl. Hence, dilute HNO3 should be used instead of dilute H2SO4.
Q73. What is the hybridisation of each carbon in H2C = C = CH2.
Ans: In (1) (2) (3)H 2C = C = CH 2, carbon (1) and (3) are sp2 hybridised and carbon (2) is sp hybridized.
Q74. Which of the two structures A and B given below is more stabilised by resonance.
⊖
Explain CH 3COOH A and CH 3 COO B
Ans: Resonating structures of A and B are as follows:

Structure (II) is less stable than structure (I) because later carries separation of positive and negative charges. Therefore, contribution of structure (II) is less than that of (1)
towards the resonance hybrid of compound (A), i.e. CH3COOH. On contrary, structure (III) and (IV) are of equal energy and hence contribute equally towards the resonance
⊖
hybrid of compound (B). Therefore, structure (B) is more stable than structure (A) i.e. CH 3 COO .
Q75. Benzoic acid is a organic compound. Its crude sample can be purified by crystallisation from hot water. What characteristic differences in the properties of benzoic acid and the
impurity make this process of purification suitable?
Ans: Benzoic acid is sparingly soluble in water at room temperature but appreciably soluble at higher temperature. The solution is concentrated to get a nearly saturated solution.
On cooling the solution, pure compound crystallises out.
Q76. Give IUPAC name of the following compounds:
1.

2.

Ans: 1.

2.
Q77. 1. Mention the type of hybridisation of each carbon in the compound CH3-CN.
2. Draw the structure of 2-methylpropan-2-ol.
Ans: 1. 1st carbon is ‘sp' and 2nd carbon is sp3 hybridised.
2
| CH 3 − C ≡ N
2. CH 3 | CH 3 − C − CH 3 | OH2 − Methylpropan-2-ol
Q78. Classify the following pairs as position, chain, functional isomers or metamers:
1. Diethylamine and Methylpropylamine.
2. Ethanol and Dimethylether.
Ans: 1. They are metamers.
2. They are functional isomers.
Q79. How many o and it bonds are present in each of the following molecules?
1. CH 3CH 2C ≡ N
2. CH 3 − CH = CH − CH 2 − C ≡ CH
3. CH 2 = C = CH 2
Ans: 1. σ C − C = 2,
σ C − H = 5,
σ C − N = 1,
πC − N = 2
2. CH 3CH = CHCH 2C ≡ CH
σ C − C = 5,
σ C − H = 8,
πC − C = 3
3. CH 2 = CH = CH 2
σ C − C = 2,
σ C − C = 4,
π C − H = 2,

Q80. 1. Give condensed and bond line structural formulae of the following:
1. Cyclo octa-1,5-diene.
2. 2(4-iso butyl phenyl) propanoic.
2. Identify electrophilic centre in the following CH3CHO and CH3CN.
Ans: 1.

2.

In both these molecules, carbon acquiring +ve charge is the electrophilic centre.
Q81. Arrange the following in decreasing order of stability:

Ans: II > IV > I > III.

∵ OCH3 group has +R effect, CH3 is electron releasing will destabilize carbocation where -NO2 group is electron withdrawing, will destabilize carbocation.
Q82. Give the common name of:
1. Methanol olido.
2. Ethanol.
3. Ethoxyethane.
4. Ethanoic acid.
5. 1, 4-dimethyl benzene.
Ans: 1. Methyl alcohol.
2. Ethyl alcohol.
3. Diethyl ether.
4. Acetic acid.
5. P-xylene.
Q83. What is the correct order of priority for following functional groups of organic compound in IUPAC nomenclature?
O ‖ − COOH − , − OH, − CHO, − C −
Ans: O O O ‖ ‖ ‖ − OH < − C − < − C − H < − C − OH is order of preference.
Q84. Draw structure of all isomeric ethers having molecular formula C5H12O.
Ans: Six different structural isomers of ethers can be drawn from molecular formula C5H12O.
1. CH 3 − CH 2 − CH 2 − CH 2 − O − CH 3
2. CH 3 − CH 2 − CH − CH 3 | OCH 3
3. CH 3 − CH 2 − CH 2 − OCH 3 | CH 3
4. CH 3 | CH 3 − C − CH 3 | OCH 3
5. CH 3 − CH 2 − CH 2 − O − C 2H 5
6. CH 3 − CH − CH 3 | OC 2H 5
Q85. Compounds with same molecular formula but differing in their structures are said to be structural isomers. What type of structural isomerism is shown by CH3-S-CH2-CH2-CH3
and

Ans: The two isomers which differ in the position of the functional group on the carbon skeleton are called position isomers and the phenomenon is known as position isomerism.
Thus, A and B may be regarded as position isomers but they are not considered as metamers since metamers are those isomers which have different number of carbon atoms
on either side of the functional group. But here, the number of carbon atoms on either side of sulphur atom (functional group) is the same, i.e. 1 and 3.

Q86. Why is staggered conformation of ethane more stable than eclipsed conformation?
Ans: It is because staggered conformation has no torsional strain. It has less repulsion between C-H bonds as these are far away,
∴ more stable.
Q87. “Stability of carbocations depends upon the electron releasing inductive effect of groups adjacent to positively charged carbon atom involvement of neighbouring groups in
hyperconjugation and resonance.”
Which of the following ions is more stable? Use resonance to explain your answer.

Ans:

Structure A is more stable than B. Carbocation A is more Planar and electrons from the ring shift to side group CH 2+ and stabilized by resonance. Structure (B) is non-planar
and does not undergo resonance. Double bond is more stable with in the ring as compared to side chain.
Q88. Name the compounds whose line formulae are given below.
1.

2.

Ans: 1.

3-ethyl-4-methylhept-5-en-2-one (C-atoms of the longest possible chain are numbered in such a way that the functional group, > C = 0, gets the lowest possible locant)
2.

3-nitrocyclohex-1-ene (C-atoms of the ring are numbered in such a manner that double bond gets the lowest possible locant followed by the -NO2 group)
Q89. An alkane has a molecular mass of 72. Draw all its possible chain isomers and write their IUPAC names.
Ans: First of all, we will derive the molecular formula.
Molecular formula of alkane is CnH2n+2.
∵ Molecular mass = 72
∴ 12n + 2n + 2 = 72
n=5
The alkane is C5H12. The possible chain isomers are,
1. CH 3 − CH 2 − CH 2 − CH 2 − CH 3 Pentane
2. CH 3 − CH − CH 2 − CH 3 | CH 3 2 − methylbutane
3. CH 3 | CH 3 − C − CH 3 | CH 3 2 , 2 − dimethyl propane
Q90. 0.35g of an organic compound was Kjeldahlised. The ammonia evolved on distilling the Kjeldahlised extract with 100ml of M M
10 H 2SO 4
The residual acid required 154ml of 10 NaOH
for complete neutralization. Calculate the percentage of nitrogen in organic compound.
Ans: 2M 1V 1 = M 2V 2(H 2SO 4) (NaOH)
[ ∵ H2SO4 is dibasic acid]
1 1
2× 10
× V1 = 10
× 154
V 1 = 77ml
Volume of neutralised with NH3
= 100 − 77 = 23ml
2.8 × M × V 1
% of N = W
2.8 1
= 0.35
× 10
× 23 = 18.4%
Q91. What are the possible structures for a carboxylic acid with a molecular formula C4H8O2 and label each C atom as sp, sp2 and sp3?
Ans: The possible structures for a carboxylic acid with molecular formula C4H8O2 are
1.

2.

Q92. Resonance structures of propenal are given below. Which of these resonating structures is more stable? Give reason for your answer.
⊕ ⊖
CH 2 = CH − CH = O ↔ CH 2 − CH = CH − O I II
Ans: The structure having more covalent bonds in a resonating structure, has more stability. Further, there is charge separation in structure (II) and the terminal carbon has only a
sextet of electrons in (II). These two factors makes structure (II) less stable.
⊕ ⊖
CH 2 = CH − CH = O ↔ CH 2 − CH = CH − O I II
Hence, I > II in terms of stability.
Q93. Identify the most stable species in the following set of ions giving reasons:
⊖ ⊖ ⊖ ⊖ CH 3, CH 2Cl, CHCl 2, CCl 3
Ans: − CCl 3 is the most stable because Cl is more elecrtonegative then hydrogen. on replacing hydrogen by chlorine, negative on C is reduced and the species becomes stable.
Q94. Write IUPAC names of the following:
1.

2. .

Ans: 1. 2, 3-dimethyl-4-oxo pent-2-en-oic acid.

2. 1, 3, 3-trimethyl cyclohex-1-ene.
Q95. A liquid with high boiling point decomposes on simple distillation but it can be steam distilled for its purification. Explain how is it possible?
Ans: Steam distillation: This type of distillation is essentially a co-distillation with water and is carried out when a solid or liquid, practically insoluble in water, is volatile with steam,
possess a vapour pressure of about 10-15 mm of mercury but the impurities are non-volatile. The principle of steam distillation is based on Dalton’s law of partial pressures.
Let p1 and p2 be the vapour pressures of water vapour and the organic liquid at the distillation temperature. The liquid boils when total pressure is equal to the atmospheric
pressure p, i.e.,
p = p1 + p2 or p2 = p − p1

This process is used in the purification of compounds such as chlorotoluenes, aniline and nitrobenzene. It is also employed in the isolation of essential oils from flowers.
Q96. You have a mixture of three liquids A, B and C. There is a large difference in the boiling points of A and rest of the two liquids i.e., B and C. Boiling point of liquids B and C are quite
close. Liquid A boils at a higher temperature than B and C and boiling point of B is lower than C. How will you separate the components of the mixture. Draw a diagram showing
set up of the apparatus for the process.
Ans: Liquids having different boiling points vaporize at different temperatures. The vapours are cooled and then liquids so formed are collected separately. Liquid A can be
separated from B and C because of large difference in boiling point. Liquid B and C have boiling points very close to each other and cannot be separated by simple distillation
hence separated by fractional distillation. Liquid B distilled first because the order of boiling points of A, B and Care as follows: B<C<A,
Q97. 1. Write two important differences between inductive effect and resonance effect.
2. Give reasons to explain the following observations:
1. Carbon atom number 2 in CH3CH2Cl has more positive charge than that in CH3-CH2-Br.
2. CH3-CH=CH-CH=CH2(I) is more stable than CH3-CH=CH-CH2-CH=CH2(II)
Ans: 1.
S. No Inductive effect Resonance effect
1. It involves o electrons. It involves π − electrons or lone pair of electrons.
2. It decreases with distance and vanishes after 4th carbon atom. It is all along the length if system is conjugated (alternate double bonds).
3. It is shown by even non-planar compounds. It is shown by only planar compounds.

2.
1. Polarisation of CH3CH2Cl and CH3CH2 Br can be shown as follows.
δδ + δ+ δ− δδ + δ+ δ−
CH 3 − CH 2 − Cl CH 3 − CH 2 − Br
Chlorine is more electronegative than Bromine. C-Cl bond is more polar than C-Br bond. Hence, inductive effect of 'Cl' is greater on the second carbon than Br.
2. Resonating structures of (I)

It is more stable due to resonance effect due to conjugation i.e., alternate double bonds than II in which there is no resonance due to absence of conjugation.
Q98. 1. Out of different gases formed in Duma's method, which gas is not absorbed over an aqueous solution?
2. What is function of K2SO4 and a little of CuSO4 added in Kjeldahl's flask?
M
3. 0.4g of compound was Kjeldahl's and ammonia evolved was absorbed into 50mL of 4
H 2SO 4 The residual acid was diluted with distilled water and made up to 150mL.
M
20mL of this diluted acid required 31mL of 4
NaOH solution for complete neutralisation. Calculate % of N in compound.
Ans: 1. N2 gas is not absorbed by KOH.
2. K2SO4 increases boiling point of H2SO4 and CuSO4 acts as catalyst.
3. 2M 1V 1 = M 2V 2(H 2SO 4) (NaOH)
1
⇒ 2 × M 1 × 20 = 31 × 20
31
⇒ M1 = 800
M 1V 1 = M 2V 2
31 1
800
× 150 = 4
× V2
M
⇒ V2 = 23.25mL is residual acid. Volume of 4
H 2SO 4 neutralised with NH3
= 50 − 23.25 = 26.75mL
1.4 × M × 2 × V 1
%of N = m
1
1.4 × 4 × 2 × 26.75
= 0.4
74.9
= 1.6
= 46.8%
Q99. Read the passage given below and answer the following questions from 1 to 5.
A reagent that brings an electron pair to the reactive site is called a nucleophile (Nu:) i.e., nucleus seeking and the reaction is then called nucleophilic. A reagent that takes away
an electron pair from reactive site is called electrophile (E+) i.e., electron seeking and the reaction is called electrophilic.
Electron Displacement Effects in Covalent Bonds The electron displacement in an organic molecule may take place either in the ground state under the influence of an atom or a
substituent group or in the presence of an appropriate attacking reagent. The electron displacements due to the influence of an atom or a substituent group present in the
molecule cause permanent polarlisation of the bond. Inductive effect and resonance effects are examples of this type of electron displacements. Temporary electron
displacement effects are seen in a molecule when a reagent approaches to attack it. This type of electron displacement is called electrometric effect or polarisability effect.
Inductive Effect When a covalent bond is formed between atoms of different electronegativity, the electron density is more towards the more electronegative atom of the bond.
Such a shift of electron density results in a polar covalent bond. Bond polarity leads to various electronic effects in organic compounds. Let us consider cholorethane (CH3 CH2Cl)
in which the C–Cl bond is a polar covalent bond. It is polarised in such a way that the carbon-1 gains some positive charge (δ + ) and the chlorine some negative charge (δ − ) The
fractional electronic charges on the two atoms in a polar covalent bond are denoted by symbol (delta) and the shift of electron density is shown by an arrow that points from
(δ + ) to (δ − ) end of the polar bond.

In turn carbon-1, which has developed partial positive charge (δ + )draws some electron density towards it from the adjacent C-C bond. Consequently, some positive charge
(δδ + )develops on carbon-2 also, where (δδ + ) symbolises relatively smaller positive charge as compared to that on carbon – 1. In other words, the polar C – Cl bond induces
polarity in the adjacent bonds. Such polarisation of σ- bond caused by the polarisation of adjacent σ-bond is referred to as the inductive effect.
Resonance Structure There are many organic molecules whose behaviour cannot be explained by a single Lewis structure. An example is that of benzene. Its cyclic structure
containing alternating C–C single and C=C double bonds shown is inadequate for explaining its characteristic properties.
 As per the above representation, benzene should exhibit two different bond lengths, due to C–C single and C=C double bonds. However, as determined experimentally benzene
has a uniform C–C bond distances of 139 pm, a value intermediate between the C–C single(154 pm) and C=C double (134 pm) bonds. Thus, the structure of benzene cannot be
represented adequately by the above structure. Further, benzene can be represented equally well by the energetically identical structures I and II.

Therefore, according to the resonance theory the actual structure of benzene cannot be adequately represented by any of these structures, rather it is a hybrid of the two
structures (I and II) called resonance structures. The resonance structures (canonical structures or contributing structures) are hypothetical and individually do not represent any
real molecule. They contribute to the actual structure in proportion to their stability.
Resonance Effect The resonance effect is defined as ‘the polarity produced in the molecule by the interaction of two π-bonds or between a π-bond and lone pair of electrons
present on an adjacent atom’. The effect is transmitted through the chain. There are two types of resonance or mesomeric effect designated as R or M effect. (i) Positive
Resonance Effect (+R effect) In this effect, the transfer of electrons is away from an atom or substituent group attached to the conjugated system. This electron displacement
makes certain positions in the molecule of high electron densities. This effect in aniline is shown as : (ii) Negative Resonance Effect (- R effect) This effect is observed when the
transfer of Electrons is towards the atom or substituent Group attached to the conjugated system. For Example in nitrobenzene this electron Displacement can be depicted as :
The atoms or substituent groups, which represent +R or –R electron displacement effects are as follows: +R effect: – halogen, –OH, –OR, –OCOR, –NH2, –NHR, –NR2, –NHCOR, – R
effect: – COOH, –CHO, > C = O, – CN, – NO2 The presence of alternate single and double bonds in an open chain or cyclic system is termed as a conjugated system. These systems
often show abnormal behaviour. The examples are 1,3- butadiene, aniline and nitrobenzene etc. In such systems, the π-electrons are delocalised and the system develops
polarity.
Electromeric Effect (E effect) It is a temporary effect. The organic compounds having a multiple bond (a double or triple bond) show this effect in the presence of an attacking
reagent only. It is defined as the complete transfer of a shared pair of π-electrons to one of the atoms joined by a multiple bond on the demand of an attacking reagent. The effect
is annulled as soon as the attacking reagent is removed from the domain of the reaction. It is represented by E and the shifting of the electrons is shown by a curved arrow ( ).
There are two distinct types of electromeric effect.
a) Positive Electrometric Effect (+E effect)- In this effect the π−electrons of the multiple bond are transferred to that atom to which the reagent gets attached. For example

b) Negative Electromeric Effect (–E effect) -In this effect the \pi- electrons of the multiple bond are transferred to that atom to which the attacking reagent does not get attached.
For example: When inductive and electromeric effects operate in opposite directions, the electomeric effect predominates.

1. A reagent that brings an electron pair to the reactive site is called a …

1. nucleophile
2. electrophile
3. amphoteric
4. amphophillic
2. A reagent that takes away an electron pair from reactive site is called ..
1. nucleophile
2. electrophile
3. amphoteric
4. amphophillic
3. The … effect is defined as the polarity produced in the molecule by the interaction of two π-bonds or between a π-bond and lone pair of electrons present on an adjacent
atom.
1. hindrance
2. inductive
3. resonance
4. hyperconjunction
4. –OH group, represent … electron displacement effect.
1. M+
2. M-
3. R-
4. R+
5. – COOH group, represent … electron displacement effect.
1. M+
2. M-
3. R-
4. R+
Ans: 1. (a) nucleophile
2. (b) electrophile
3. (c) resonance
4. (d) R+
5. (c) R-
Q100. Read the passage given below and answer the following questions from 1 to 5.

Hyperconjugation is a general stabilising interaction. It involves delocalisation of σ electrons of C—H bond of an alkyl group directly attached to an atom of unsaturated system or
to an atom with an unshared p orbital. The σ electrons of C—H bond of the alkyl group enter into partial conjugation with the attached unsaturated system or with the unshared
p orbital. Hyperconjugation is a permanent effect. To understand hyperconjugation effect, let us take an example of CH 32 + (ethyl cation) in which the positively charged carbon
atom has an empty p orbital. One of the C-H bonds of the methyl group can align in the plane of this empty p orbital and the electrons constituting the C-H bond in plane with
this p orbital can then be delocalised into the empty p orbital as depicted in Figure.
This type of overlap stabilises the carbocation because electron density from the adjacent σ bond helps in dispersing the positive charge.

In general, greater the number of alkyl groups attached to a positively charged carbon atom, the greater is the hyperconjugation interaction and stabilisation of the cation. Thus,
we have the following relative stability of carbocations:

Hyperconjugation is also possible in alkenes and alkylarenes. Delocalisation of electrons by hyperconjugation in the case of alkene can be depicted as in Figure.
There are various ways of looking at the hyperconjugative effect. One of the way is to regard C—H bond as possessing partial ionic character due to resonance.
The hyperconjugation may also be regarded as no bond resonance.

The hyperconjugation may also be regarded as no bond resonance.

Methods of purification of organic compounds Once an organic compound is extracted from a natural source or synthesised in the laboratory, it is essential to purify it. Various
methods used for the purification of organic compounds are based on the nature of the compound and the impurity present in it. The common techniques used for purification
are as follows :
i) Sublimation
ii) Crystallisation
iii) Distillation
iv) Differential extraction and
v) Chromatography
Finally, the purity of a compound is ascertained by determining its melting or boiling point. Most of the pure compounds have sharp melting points and boiling points. New
methods of checking the purity of an organic compound are based on different types of chromatographic and spectroscopic techniques.
Sublimation On heating, some solid substances change from solid to vapour state without passing through liquid state. The purification technique based on the above principle is
known as sublimation and is used to separate sublimable compounds from non- sublimable impurities.
Crystallisation This is one of the most commonly used techniques for the purification of solid organic compounds. It is based on the difference in the solubilities of the compound
and the impurities in a suitable solvent. The impure compound is dissolved in a solvent in which it is sparingly soluble at room temperature but appreciably soluble at higher
temperature. The solution is concentrated to get a nearly saturated solution. On cooling the solution, pure compound crystallises out and is removed by filtration. The filtrate
(mother liquor) contains impurities and small quantity of the compound. If the compound is highly soluble in one solvent and very little soluble in another solvent, crystallisation
can be satisfactorily carried out in a mixture of these solvents. Impurities, which impart colour to the solution are removed by adsorbing over activated charcoal. Repeated
crystallisation becomes necessary for the purification of compounds containing impurities of comparable solubilities.

Distillation This important method is used to separate

i) volatile liquids from nonvolatile impurities and
ii) the liquids having sufficient difference in their boiling points.
 Liquids having different boiling points vaporise at different temperatures. The vapours are cooled and the liquids so formed are collected separately. Chloroform (b.p 334 K) and
aniline (b.p. 457 K) are easily separated by the technique of distillation (Fig 12.5). The liquid mixture is taken in a round bottom flask and heated carefully. On boiling, the vapours
of lower boiling component are formed first. The vapours are condensed by using a condenser and the liquid is collected in a receiver. The vapours of higher boiling component
form later and the liquid can be collected separately.
Partition Chromatography: Partition chromatography is based on continuous differential partitioning of components of a mixture between stationary and mobile phases. Paper
chromatography is a type of partition chromatography. In paper chromatography, a special quality paper known as chromatography paper is used. Chromatography paper
contains water trapped in it, which acts as the stationary phase. A strip of chromatography paper spotted at the base with the solution of the mixture is suspended in a suitable
solvent or a mixture of solvents (Fig. 12.13). This solvent acts as the mobile phase. The solvent rises up the paper by capillary action and flows over the spot. The paper selectively
retains different components according to their differing partition in the two phases. The paper strip so developed is known as a chromatogram. The spots of the separated
coloured compounds are visible at different heights from the position of initial spot on the chromatogram. The spots of the separated colourless compounds may be observed
either under ultraviolet light or by the use of an appropriate spray reagent as discussed under thin layer chromatography.

1. Hyperconjunction involves delocalisation of … electrons of C—H bond of an alkyl group directly attached to an atom of unsaturated system or to an atom with an unshared
p orbital.
1. \sigma
2. \pi
3. \delta
4. \eta
2. Which of the is an example of technique used for purification.
1. Distillation
2. Differential extraction
3. Chromatography
4. All the above
3. On heating, some solid substances change from solid to vapour state without passing through liquid state is known as …
1. Melting
2. Boiling
3. Sublimation
4. Condensation
4. The hyperconjugation may also be regarded as ….
1. bonding resonance
2. no bond resonance
3. no bond induction
4. bonding induction
5. Chromatography paper contains water trapped in it, which acts as the … phase.
1. mobile
2. stationery
3. Secondary
4. quaternary
Ans: 1. (a) \sigma
2. (d) All the above
3. (c) Sublimation
4. b) no bond resonance
5. b) stationery