NCERT General Organic Chemistry Guide
NCERT General Organic Chemistry Guide
UNIT
1. Which property of carbon is responsible for number of carbon compounds? NCERT Page-326/N-256
(a) Catenation
(c) Tetravalency
(b) Isomerism
(d) All of these
(c) 𝑠𝑝, 𝑠𝑝2 , 𝑠𝑝3 and 𝑠𝑝2 (d) 𝑠𝑝, 𝑠𝑝3 , 𝑠𝑝2 and 𝑠𝑝3
x
5. The compound in which C uses its 𝑠𝑝3 -hybrid orbitals for bond formation is
𝑋 𝑋 𝑋 𝑋
(a) HCOOH (b) (H2 N)2 CO (c) (CH3 )3 COH (d) CH3 CHO
9.3 STRUCTURE OF ORGANIC COMPOUNDS
6. 2-Pentene contains NCERT Page-328 / N-258
(a) 15𝜎-and one 𝜋 - bond
(b) 14𝜎-and one 𝜋-bond
(c) 15𝜎 - and two 𝜋 - bonds
(d) 14𝜎 - and two 𝜋 - bonds
(a) 2-cyclohexylbutane
(b) 2 - phenylbutane
(c) 3-cyclohexylbutane
(d) 3 -phenylbutane
11. What is the IUPAC name of the following compound ? NCERT Page-335 / N-266
(c) (d)
13. Identify the correct IUPAC name of the compound given below NCERT Page-333 / N-269
+
(c) (d) None of these
CH3 CHCH2 CH3
35. Which of the following carbocations is most stable: NCERT Page- N − 271
(a) (b)
(c) (d)
36. The organic reactions which proceed through heterolytic bond cleavage called NCERT Page-341 / N-271
(a) ionic
(b) polar
(c) non-polar
(d) Both (a) and (b)
37. The shape of methyl carbanion is similar to that of-
(a) BF3
(b) NH3
(c) methyl free radical
(d) methyl carbocation
38. Homolytic fission of C − C bond in ethane gives an intermediate in which carbon is
(a) 𝑠𝑝3 -hybridised NCERT Page-342 / N-272
(b) 𝑠𝑝2-hybridised
(c) 𝑠𝑝-hybridised
(d) 𝑠𝑝2 𝑑-hybridised
39. Which of the following statements is not correct ? NCERT Page-341 / N-271
(a) Carbocation posses sextet of electrons.
+ +
(b) The order of carbocation stability is: CH3 > (CH3 )2 CH > (CH3 )3 + C
(c) Carbocations have trigonal planar shape
(d) Carbocations are formed by heterolytic cleavage
40. The order of stability of the following carbocations : NCERT Page-341 / N-271
(a) III > II > I (b) II > III > I (c) I > II > III (d) III > I > II
41. Select the most stable carbocation amongst the following NCERT PAGE-N-271
(a) (b)
(c) (d)
42. Arrange the carbanions, (CH3 )3 C̅, C̅Cl3 , (CH3 )2 C̅H, C6 H5 C̅H2 in order of their decreasing stability:
(a) (CH3 )2 C ̅ H > C̅Cl3 > C6 H5 C̅H2 > (CH3 )3 C̅ NCERT Page-342 / N-272
̅ ̅ ̅
(b) CCl3 > C6 H5 CH2 > (CH3 )2 CH > (CH3 )3 C ̅
(c) (CH3 )3 C̅ > (CH3 )2 C̅H > C6 H5 C̅H2 > C̅Cl3
̅̅̅̅2 > C̅Cl3 > (CH3 )3 C̅ > (CH3 )2 C̅H
(d) C6 H5 CH
43. The increasing order of stability of the following free radicals is NCERT Page-342 / N-273
(a) (C6 H5 )2 ĊH < (C6 H5 )3 Ċ < (CH3 )3 Ċ < (CH3 )2 ĊH
(b) (CH3 )2 ĊH < (CH3 )3 Ċ < (C6 H5 )2 ĊH < (C6 H5 )3 Ċ
(c) (CH3 )3 Ċ < (CH3 )2 ĊH < (C6 H5 )2 ĊH < (C6 H5 )3 Ċ
(d) (C6 H5 )3 Ċ < (C6 H5 )2 ĊH < (CH3 )3 Ċ < (CH3 )2 ĊH
44. Which of the following is strongest nucleophile NCERT Page-342 / N-273
−
(a) Br
(b) : OH −
(c) : CN −
(d) C2 H5 O̅:
45. The correct order of nucleophilicity is NCERT Page-N-273
− − − − −
(a) F > OH (b) H2 Ö > OH (c) RÖH > RO (d) NH2 > NH3
..
46. Which of the following species does not act as a nucleophile? NCERT Page- N-273
(a) ROH (b) ROR (c) PCl3 (d) BF3
47. Which of the following pairs represent electrophiles? NCERT Page- N-273
(a) AlCl3 , H2 O
(b) SO3 , NO+2
(c) BF3 , H2 O
(d) NH3 , SO3
48. Which out of A, B, C and D is/are not correctly categorised. NCERT Page-342 / N-273
Nucleophile Electrophile
A. HS − Cl+
B. BF3 (CH3 )3 N
+
C. H2 N − −C = O
D. R3C − X C2 H5 O−
(X = Halogen )
(a) B, C and D (b) C and D (c) C only (d) B and D
49. Polarization of electrons in acrolein may be written as NCERT Page N-274
𝛿− 𝛿+ 𝛿− 𝛿+
(a) C H2 = CH − CH = O (b) C H2 = CH − CH = O
𝛿− 𝛿− 𝛿+ 𝛿−
(c) C H2 = C H − CH = O (d) CH2 = CH − CH = O
50. Point out the incorrect statement about resonance? NCERT Page-346 / N-275
(a) Resonance structures should have equal energy
(b) In resonating structures, the constituent atoms must be in the same position
(c) In resonating structures, there should not be same number of electron pairs
(d) Resonating structures should differ only in the location of electrons around the constituent atoms
51. In which of the following, resonance will be possible? NCERT Page- N-275
(a) CH3 − CH2 − CH2 − CHO (b) CH2 = CH − CH = O
(c) CH3 COCH3 (d) CH2 = CH − CH2 − CH = CH2
52. Which of the following is not correctly matched ? Group showing +𝑅 effect Group showing −𝑅 effect
|
(a) −NHCOR, −COOH (b) −C = O, −OH
(c) −OR, - CHO (d) – OCOR, −NO2
53. The kind of delocalization involving sigma bond orbitals is called NCERT Page-347 / N-277
(a) inductive effect
(c) electromeric effect
(b) hyperconjugation effect
(d) mesomeric effect
54. Choose correct order of stability of carbocation using concept of hyperconjugation. NCERT-347 / N-277
I II III IV
(a) I < II < III < IV (b) IV < III < II < I
(c) III < IV < II < I (d) None of these
55. Hyperconjugation is most useful for stabilizing which of the following carbocations? NCERT Page- N-277
(a) neo-Pentyl (b) tert-Butyl
(c) iso-Propyl (d) Ethyl
56. Which of the following is/are correct for inductive effect ? NCERT Page-344 / N-274
(a) In inductive effect polarisation of sigma bond is caused by the adjacent 𝜎 bond.
(b) Halogens, −NO2 , −CN, and −CH3 are electron withdrawing groups.
(c) −CH2 CH3 and −OC6 H5 are electron donating groups.
(d) +I effect is caused by electron withdrawing effect.
57. Which of the following statements regarding the resonance energy of benzene is correct? NCERT Page-
345 / N-275
(a) Resonance energy is the energy required to break the C − H bond in benzene
(b) Resonance energy is the energy required to break the C − C bond in benzene
(c) Resonance energy is a measure of stability of benzene
(d) Resonance energy is the energy required to convert
58. The polarity is 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 above statement is true for which of the
following? NCERT Page-344 / N-275
(a) Inductive effect
(b) Electromeric effect
(c) Resonance effect
(d) Hyperconjugation
59. Which of the following represents the correct order of stability of the given carbocations?
+ + +
(a) F3 C > F3 C − C + CCH3 NCERT Page-341 / N-271
+ ⇀ ++ +
(b) H3 C > F3 C − C > FF3C
C+
+ + +
(c) F3 C − + > C > F3 C
C+
+ + + F3
I+
(d) F3 C − > H3 C > C
60. The most stable carbanion among the following is NCERT Page-342 / N-272
(a) (b)
(c) (d)
61. For (i) I− , (ii) Cl− , (iii) Br − , the increasing order of nucleophilicity would be NCERT Page-342 / N-272
(a) Cl− < Br − < I−
(b) I − < Cl− < Br −
(c) Br − < Cl− < I −
(d) I − < Br − < Cl−
62. Which of the following does not represent formation of reactive intermediate correctly? NCERT Page-
342 / N-272
(i) (ii)
(iii) (iv)
(iv)
(a) (iv) > (iii) > (ii) > (i) (b) (iv) > (ii) > (iii) > (i)
(c) (iii) > (iv) > (ii) > (i) (d) None of these
68. (CH3 )4 N+ is neither an electrophile, nor a nucleophile because it NCERT Page-342 / N-273
(a) does not have electron pair for donation as well as cannot attract electron pair
(b) neither has electron pair available for donation nor can accommodate electron since all shells of
nitrogen are fully occupied
(c) can act as Lewis acid and base
(d) None of these
69. Which of the following is true?
(a) tert-Butoxide is a stronger base as well as stronger nucleophile than ethoxide.
(b) tert-Butoxide is a weaker base but stronger nucleophile than ethoxide.
(c) tert-Butoxide is a stronger base, but weaker nucleophile than ethoxide.
(d) tert-Butoxide and ethoxide are equally strong bases as well as strong nucleophiles.
70. Arrange the following carbocations in decreasing order of stability. NCERT Page-342 / N-271
(c) (d)
13. 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.
H3 C − HC = CH2 + H + ⟶ ?
(a) 2∘ carbanion
(b) 1∘ carbocation
(c) 2∘ carbocation
(d) 1∘ carbanion
14. Covalent bond can undergo fission in two different ways. The correct representation involving a
heterolytic fission of CH3 − Br is NCERT Page-341 / N-271
(a)
(b)
(c)
(d)
15. Addition of HCl to an alkene proceeds in two steps. The first step is the attack of H + ion to > C = C <
portion which can be shown as NCERT Page-342 / N-272
(a)
(b)
(c)
(b)
(c)
(d)
20. The compound which shows metamerism is : NCERT Page-341 / N-271 / NEET 2021, C
(a) C4 H10 O (b) C5 H12 (c) C3 H8 O (d) C3 H6 O
21. Paper chromatography is an example of NCERT Page-353 / N-284 | NEET 2020, C
(a) Partition chromatography (b) Thin layer chromatography
(c) Column chromatography (d) Adsorption chromatography
22. A tertiary butyl carbocation is more stable than a secondary butyl carbocation because of which of the
following? NCERT Page-341 / N-277 / NEET 2020, C
(a) +R effect of −CH3 groups (b) −R effect of −CH3 groups
(c) Hyperconjugation (d) −I effect of −CH3 groups
23. Which of the following is correct with respect to −I effect of the substituents? (R = alkyl)
(a) −NH2 < −OR < −F NCERT Page-344 / N-274 | NEET 2018, C
(b) −NR 2 < −OR < −F
(c) −NR 2 > −OR > −F
(d) −NH2 > −OR > −F
24. Which of the following carbocations is expected to be most stable? NCERT 2018, A
(a) (b)
(c) (d)
25. The IUPAC name of the compound is : NCERT Page-336 / N-266 | INEET 2017, S
2 (a) 13 (d) 24 (c) 35 (d) 46 (d) 57 (c) 68 (b) 79 (a) 90 (a) 101 (b)
3 (b) 14 (d) 25 (a) 36 (d) 47 (b) 58 (c) 69 (c) 80 (d) 91 (d) 102 (b)
4 (d) 15 (a) 26 (b) 37 (b) 48 (d) 59 (b) 70 (c) 81 (a) 92 (b) 103 (b)
⊕ ⊕
⏟ > CH2 = CH − C H2 > CH3 − CH2 − C H2
Allyl Propyl
Benzyl
41. (b) Structure (𝑏) is a 3 carbocation, and more stable due to resonance with 2Ph-ring while (𝑎) is 2∘ (𝑐)
∘
63. (b) Higher the number of 𝛼 − H, more the hyperconjugating structures, and hence more will be the
stability of the compound.
64. (c) The electronegataive atom in the carbon chain produces −𝐼 effect.
65. (a) Both carbocation and carbanion, get resonance stabilization by phenyl ring present in conjugation.
66. (c) The molecule in which all the atoms have complete octet is more stable. Also, more the number of
resonating structures, more will be the stability.
(a) and (b)
(b) have complete octet but in
(c) and
(d) all atoms do not have complete octet. Hence (c) and (d) are unstable.
67. (b) Electron releasing groups stabilize carbocations whereas electron withdrawing groups (−CF3 )
destabilize carbocation.
68. (b) (CH3 )4 N+ has no electron pair available for donation to act as nucleophile. Valence shell of nitrogen
is completely filled and has no scope for acceptance of extra electrons to act as electrophile.
69. (c) + I effect of three methyl groups weakens the acidity of 𝑡-butyl alcohol. Hence, its conjugate base is
strong.
70. (c) Cyclopropylmethyl carbocation is especially stable because of conjugation between the bent orbitals
of the cyclopropyl ring and the vacant 𝑝-orbitals of the cationic carbon.
71. (d) Filled or empty p-orbitals in conjugation overlaps with each other.
72. (c) (a) −COR, −COOR ⇒ −𝑀; −O𝑅 ⇒ +𝑀
(b) −Cl, −NH2 ⇒ +𝑀; −CHO ⇒ −𝑀
(c) −NO2 , −CN, −SO3 H ⇒ −𝑀
(d) −OH, −NR, −SR ⇒ +𝑀
73. (b) Among the given compounds naphthelene is volatile but benzoic acid is non-volatile (it forms a
dimer). So, the best method for their separation is sublimation, which is applicable to compounds which
can be converted directly into the vapour phase from its solid state on heating and back to the solid
state on cooling. Hence it is the most appropriate method.
74. (c) The atmospheric pressure (𝑝) = the volatile organic compound vap. pressure (p1 ) + the water vap.
pressure (p2 ).
75. (b) If there is a small difference ( 10 or less) in the boiling points of liquids fractional distillation is used,
e.g. acetone b.p. 329 K and methanol b.p. 338 K.
76. (a) Fractional distillation is used for the distillation of petroleum. This method is used for separating a
mixture of two or more miscible, volatile liquids having close (less than 40 degrees) boiling points. (For
example, a mixture of acetone, b.p., 56∘ C and methanol, b.p. 65∘ C )
77. (c) Glycerol decomposes at its boiling point, hence it should be purified by distillation under reduced
pressure.
78. (c) This method allows the purification of compounds not readily distilled at ambient pressure.
79. (a) The latest technique for the purification of organic compounds is chromatography. These are of
various types like column, paper and gas-chromatography.
80. (d) Both silica gel and alumina are used as adsorbents in adsorption chromatography.
81. (a) Chromatography paper contains water trapped in it, which acts as the stationary phase.
82. (c) The mixture of sugars is a homogenous one. Homogeneous mixtures of a solvent and one or more
solutes (dissolved substances) are often separated by chromatography. Chromatography works to
separate a mixture because the components of a mixture distribute themselves differently when they
are in contact with a "two phase system". One phase is stationary and the other is moving or mobile.
The stationary phase may be a solid packed in a tube or a piece of paper. The mobile phase may be
liquid of gaseous.
83. (b) The R𝑓 (retardation factor) value is the ratio of the Solute's distance travelled to the Solvent's
distance travelled.
Polar molecules will attract more toward adsorbent and cover smaller distance from the baseline.
A has maximum R𝑓 so it will less adsorbed on the adsorbent surface and travel faster and will be eluded first.
C has minimum R𝑓 value. So it is more strongly adsobred and less soluble in mobile phase.
84. (b) A special quality paper is used in this chromatography. Chromatographic paper contains water
trapped in it, which acts as the stationary phase.
85. (d) Separating funnel is used when the two liquids are immiscible.
86. (b) Fractional distillation method is used if the difference in boiling points of two liquids is not much.
87. (d) 𝑝-nitrophenol have intermolecular H-bonding whereas picric acid have intramolecular H-bonding.
Picric acid slowly sublimes at room temperature and have explosive property. So TLC is the best method
to separate 100mg of 𝑝-nitrophenol and picric acid. TLC separation is based on polarity of compounds
involved.
88. (b) Na + C + N → NaCN (Compound + sodium fusion extract)
89. (b) Hydrazine (NH2 NH2 ) does not contain carbon and hence on fusion with Na metal, it cannot form
NaCN; consequently hydrazine does not show Lassaigne's test for nitrogen.
90. (a) Prussian blue Fe4 [Fe(CN)6 ]3 is formed in Lassaigne test for nitrogen.
6NaCN + Fe2+ ⟶ Na4 [Fe(CN)6 ] + 2Na+
𝑥H2 O
3Na4 [Fe(CN)6 ] + 4Fe3+ → Fe4 [Fe(CN)6 ]3 ⋅ 𝑥H2 O + 12Na+
Prussian blue
91. (d) To convert covalent compounds into ionic compounds such as NaCN, Na2 S, NaX, etc.
92. (b) Na2 S and NaCN, formed during fusion with metallic sodium, must be removed before adding
AgNO3 , otherwise black ppt. due to Na2 S or white precipitate due to AgCN will be formed and thus
white precipitate of AgCl will not be identified easily.
Na2 S + 2AgNO3 ⟶ 2NaNO3 + Ag 2 S ↓
Black
NaCN + AgNO3 ⟶ NaNO3 + AgCN ↓
White
NaCl + AgNO3 ⟶ NaNO3 + AgCl ↓
White
boil
Na2 S + 2HNO3 → 2NaNO3 + H2 S ↑
boil
NaCN + HNO3 → NaNO3 + HCN ↑
93. (d) Anhydrous CaCl2 is moisture absorber. CO2 absorbing in KOH solution forms potassium bicarbonate.
94. (d) Kjeldahl method is not applicable to any of the given compounds. As nitrogen of these compounds
does not change to ammonium sulphate on heating with conc. H2 SO4 .
95. (b)
𝑦
C𝑥 H𝑦 N𝑧 + (2𝑥 + ) CuO ⟶
2
𝑦 𝑧 𝑦
𝑥CO2 + H2 O + N2 + (2𝑥 + ) Cu
2 2 2
96. (b) In Kjeldahl's method nitrogen is converted into (NH4 )2 SO4 , then to NH3 .
97. (b) 120 mL1.0 mNaOH ≅ 60 mL2 . 0 mH2 SO4
Volume of excess of acid used to neutralise NH3 = 100 − 60 = 40 mL
Normality of acid used = 1.0 × 2 = 2 N
1.4×V×N 1.4×40×2
Percentage of N = m = 5.0 = 22.4%
98. (b) Percentage of N in a compound
1.4 × Normality of acid × Volume of acid used
=
Mass of the substance tak 4
Mass of the substance taken
Given, 0.5MH2 SO4 is used.
Mol. mass 98
Normality = Molarity × 𝑛 where 𝑛 = Eq. mass = 49 = 2
∴ Normality = 0.5 × 2 = 1NH2 SO4
Volume of acid used to neutralise NH3 = 10 cm3
Mass of organic compound taken = 0.25 g
1.4×1×10
∴ % N = 0.25 = 56.
3. (d)
Note : Carboxylic acid (−COOH) has more priority than ketone ( > C = O ).
4. (b) For tri or higher substituted benzene derivatives, the compounds are named by identifying
substituent positions on the ring by following the lowest locant rule.
5. (c) Electronegativity of carbon atom depends on its state of hybridisation. More the 𝑠-character more
will be the electronegativity.
𝑠𝑝3 < 𝑠𝑝2 < 𝑠𝑝
𝑠-character : 25% 33% 50%
Thus, 𝑠𝑝-carbon (CH3 − CH2 − C ≡ ∗ CH) has the highest electronegativity.
6. (c) Two or more compounds having the same molecular formula but different functional groups are
called functional isomers. Functional isomer of alcohol is ether, aldehyde is ketone and cyanide is
isocyanide. But alkyl halides do not show functional isomerism.
7. (d) Essential oils are insoluble in water and have high vapour pressure at 37.3 K but are miscible with
water vapour in vapour phase, it means these are steam volatile. Thus, steam distillation technique is a
suitable method for the extraction of essential oils.
8. (d) Thin layer chromatography (TLC) involves separation of substances of a mixture over a thin layer of
an adsorbent coated on a glass plate.
A thin layer of an adsorbent is spread over a glass plate and glass plate is placed in an eluant. As eluant
rises, components of the mixture move up along with the eluant to different distances depending on
their degree of adsorption and separation takes place. Therefore, TLC technique will give the best
results in identifying the different types of ink used at different places in the documents.
9. (b) 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.
10. (a) Stability of the given cations can be understood by the following structures:
Hence, the correct order of decreasing stability of carbocation will be : II > I > III
11. (a) Electronegativity of Cl, Br, C and Mg follows the order Cl > Br > C > Mg, thus chlorine has the
greatest-I-effect and disperse the positive charge on ' C ' atom most effectively.
Hence, ∗ CH3 − CH2 − Cl has the greatest positive charge.
12. (d) In all the given ionic species, the negative charge is dispersed which stabilises them. Here, the
negative charge is dispersed by two factors, i.e., +R-effect of the carboxylate ion (conjugation) and - I-
effect of the halogens.
As it can be clearly seen in the given structures, that +R-effect is common in all the four species, therefore,
overall dispersal of negative charge depends upon the number of halogen atoms and their
electronegativity. Since, fluorine has the highest electronegativity and two F-atoms are present in option
(d), thus, dispersal of negative charge will be maximum in it, thus it is most stable.
13. (c) When an electrophile attacks CH3 − CH = CH2 , there are two possibilities of an intermediate
formed:
As 2∘ carbocation is more stable than 1∘ carbocation thus first addition is more feasible.
Note : Stability of carbocations is the basis of Markownikoff's rule.
Since, Br is more electronegative than carbon, hence heterolytic fission occurs in such a way that CH3 gets a
positive charge and Br gets a negative charge.
15. (b) Addition of HCl to an alkene takes place in two steps as follows:
Step I : 𝜋-bonds creates an electron cloud, electrophile (H + )from H − Cl attacks the electron cloud and a
carbocation is formed.
16. (d) In case, nitrogen and sulphur both are present in organic compound, sodium thiocyanate is formed.
It gives blood red colour and no Prussian blue since there are no free cyanide ions.
Na + C + N + S ⟶ NaSCN
Fe3+ + SCN− ⟶ [Fe(SCN)]2+ Blood red
17. (c)
18. (d)
20. (a) Compounds with formula C4 H10 O can be ethers which may exhibit metamerism. For example
(More stable due to less e− withdrawing effect of −NO2 ) greater no. of resonating structures.
25. (d) Priority order : −CHO > −CH = O
26. (d) CH3 − C ≡ C−
No. of 𝜎bp − 1
] → 2 and hybridisation is 𝑠𝑝.
ℓp − 1
EXERCISE - 3
1. (b) A − (s), B − (p), C − (q), D − (r)
2. (c) A − (q), B − (s), C − (p), D − (r)
3. (a) 4. (c) 5. (d)
4. (a) It is fact that aniline is better nucleophile than anilium ion. Anilium ion possesses +ve
C6 H5 NH3+ charge, which Anilium ion
reduces the tendency to donate lone pair of electrons.
7. (c) The assertion that trans-2 butene reacts with Br2 to produce meso-2, 3-dibromobutane is correct but
it involves anti addition of Br2 .
8. (d) Resonating structures contain the same number of paired electrons. However, they differ in the way
of distribution of electrons.