General Organic Chemistry

E X E R C IS E 1
1. What are hybridisation states of each carbon atom in the following compound?
CH2=C=O, CH3CH=CH3, (CH3)2CO,CH2=CHCN, C6H6.

2. Indicate the -and -bonds in the following molecules:

C6H6, C6H12, CH2Cl2, CH2=C=CH2, CH3NO2, HCONHCH3

3. Write bond-line formulas for : Isopropyl alcohol, 2,3-dimethylbutanal, heptane-4-one.

4. Which is expected to be more stable, O2NCH2CH2O– or CH3CH2O– and why?

5. Explain why alkyl groups act as electron donors when attached to a -system.

6. Draw the resonance structures for the following compounds. Show the electron shift using curved-
arrow notation.
(a) C6H5OH (b) C6H5NO2 (c) CH3CH=CHCHO
(d) C6H5–CHO (e) C6H5–C H2
+
(f) CH3CH=CHC+H2

7. What are electrophiles and nucleophiles? Explain with examples.

8. Identify the reagents shown in bold in the following equations as nucelophiles or electrophiles
(a) CH3COOH + HO–  CH3COO– + H2O
(b) CH3COCH3 + –CN  (CH3)2C(CN)(OH)
(c) C6H6 + CH3 CO  C6H5COCH3

9. Classify the following reations in one of the reaction type studied:

(a) CH3CH2Br + HS–  CH3CH2SH + Br–
(b) (CH3)2C=CH2 + HCl  (CH3)2 CCl–CH3
(c) CH3CH2Br + HO–  CH2=CH2 + H2O + Br–
(d) (CH3)3C–CH2OH + HBr  (CH3)2CBrCH2CH3+H2O

10. What is the relationship between the members of following pairs of structures? Are they structural or
geometrical isomers or resonance contributors?
O O
(a)

D H D D
(b) C=C C=C
H D H H

OH OH
(c) H—C—OH H—C—OH

ONANCE 1
 General Organic Chemistry

11. Explain the terms inductive and electromeric effects. Which electron displacement effect explains ths
following correct orders of acidity of the carboxylic acids?
(a) Cl3CCOOH > Cl2CHCOOH > ClCH2COOH
(b) CH3CH2COOH > (CH3)2CHCOOH > (CH3)3C.COOH

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

(a) CH3O–CH3  CH3O+OCH3 (b) O + –OH  O + H2O

–
E
(c)  + Br– (d) + E+ 
Br

13. Why is nitric acid added to sodium extract before adding silver nitrate for testing halogens?

14. Explain the reason for the fusion of an organic compound with metallic sodium for testing nitrogen,
sulphur and phosphours.

15. Explain, why an organic liquid vapourises at a temperature below its boiling point in its steam distilla-
tion?

16. Will CCl4 give white precipitate of AgCl on heating it with silver nitrate? Give reason for your answer.

17. Why is a solution of potassium hydroxide used to absorb carbon dioxide evolved during the estimation
of carbon present in an organic compound?

18. Why is it necessary to use acetic acid and not sulphuric acid for acidification of sodium extract for
testing sulphur by lead acetate test?

19. In the organic compound CH2=CH–CH2–CH2–CCH, the C2–C3 bond is formed by the interaction
of a pair of hybridised orbitals:
(A) sp – sp2 (B) sp–sp3 (C) sp2 – sp3 (D) sp3 = sp3

20. Which of the following carbocation is most stable?

(A) (CH3)3C CH2 (B) (CH3)3 C (C) CH3CH2 C H2 (D) CH3CH2CH2CH3

21. The best and latest technique for isolation, purification and separation of organic compounds is:
(A) Crystallisation (B) Distillation (C) Sublimation (D) Chromatography

22. The following reaction is classified as:

CH3CH2I + KOH (aq)  CH3CH2OH + KI
(A) Electrophilic substitution (B) Nucleophilic substitution
(C) Elimination (D) Addition

ONANCE 2
 General Organic Chemistry

[ SINGLE CORRECT ]

1. Which of the following represent the resonating structure of

(A) (B) (C) (D) All of these

2. Which of the following resonance structure is minor contributor to the resonance hybrid ?

O O O
C—O—CH3 C—O—CH3 C==O—CH3
I II III
(A) I (B) II (C) III (D) all contribute equally
3. Which of the following is releasing group when in resonance ?
O O
(A) –NH– C –CH 3 (B) –Cl (C) –NH3 (D) –C–OH
4. Which of the following can show both +M and –M effect ?
O
(A) –NH 2 (B) –CH=CH 2 (C) –F (D) –N
O
5. Least contributing structure in nitroethene is
O O O O
CH2=CH–N CH2–CH–N CH2–CH–N CH2–CH=N
O O O O
(A) (B) (C) (D)

6. Which of the following has longest C=C bond length ?

CH3

(A) CH3–C=CH2 (B) CH3–C–CH=CH2

CH3 CH3
(C) CH 3CH 2–CH=CH 2 (D) all have equal C=C bond length

7. Which of the following is not resonating structure

(A) CH2–CH=CH–CH2 (B) CH2–CH=CH–CH2

(C) CH 2=CH–CH=CH 2 (D) CH2–CH=CH–CH2

8. Arrange the following compounds in decreasing order of C–Cl bond length

(I) CH 3–CH 2–Cl (II) CHC–Cl (III) CH 2=CH–Cl
(A) I > II > III (B) III > II > I (C) I > III > II (D) II = I = III

ONANCE 3
 General Organic Chemistry

9. Which of the following is not a permissible resonating form

(A) CH2–N–O (B) CH2=N–O (C) CH2=N=O (D) CH2–N=O

CH3 CH3 CH3 CH3

10 . Which of the following pairs represent resonating structure?

(A) (B) CH2–N=N and CH 2=N=N

(C) and (D) both (B) and (C)

11 . Which one of the following molecule has longest C=C bond length?
(A) CH 2=C=CH 2 (B) CH 3–CH=CH 2
(C) CH 2=CH–CH 2–CH=CH 2 (D) CH 2=CH–CH=CH 2
12 . Which one of the following has all the effect namely inductive, mesomeric and hyperconjugation?
(A) CH3–Cl (B) CH 2=CH–CH=CH 2
O O
(C) CH2=CH–C– (D) Ph– C –CH 3

13 . Which will be least stable resonating structure ?

(A) CH2=CH–CH–CH–NH2 (B) CH2–CH–CH=CH–NH2

(C) CH2–CH=CH–CH=NH2 (D) CH2=CH–CH–CH=NH2

14 . Which of the following pairs is not a pair of resonating structures ?

(A) ,
O O

(B) CH3 – CH = CH – CH3 , CH3 – CH2 – CH = CH2

(C) CH3 – C = CH – C – CH3 , CH3 – C – CH – C – CH3

O O O O
 
(D) CH3 – CH2 – C = N – CH3 , CH3 – CH2 – C  N – CH3

2
15 . Which of the following statement is true about this molecule . 1 3
4
(A) C1 – C2 and C3 – C4 bonds are of same length
(B) C1 – C2 bond is shorter than C3 – C4 bond
(C) C1 – C2 bond is longer than C3 – C4 bond
(D) C1 – C2 and C2 – C3 bonds are of same length

ONANCE 4
 General Organic Chemistry

16 . Which will be least stable resonating structure ?

O O O O
N N N N
O O O O
(A) (B) (C) (D)

17 . (I) CH2=CH–CH–CH3 (II) CH2–CH=CH–CH3

Br Br
Ionisation of these compounds produces Br and
(A) same cation (B) different cation (C) same anion (D) different anion
18 . Which of the following pairs of structures do not represent resonating structures?
O OH

(A) CH3–C–CH3 CH3–C=CH2

OH OH
(B) CH3–CH2–C–CH2 CH3–CH2–C=CH2

(C) CH 2=C=O

(D) O O

19 . Which of the following canonical form of O3 is not possible

O O O O
(A) O O (B) O O (C) O O (D) O O
20 . Which of the following is most unstable resonating structure of CH2= CH – CH = O.

O
CH2–CH=C–H CH 2=CH–CO CH2=CH–C–H CH2–CH=C–H

(A) (B) (C)O (D)O

21 . I. – CH=CH2 II. – CH=CH–OCH3 III. – CH=CH–NO2
Arrange these groups in decreasing order of their electron-donating power in resonance:
(A) II > III > I (B) III > II > I (C) II > I > III (D) III > I > II
O
||
22 . I. – OH II. – O – C – CH 3 III. – NH2
Arrange these groups in decreasing order of their electron-donating power in resonance :
(A) III > I > II (B) III > II > I (C) I > II > III (D) II > III > I
23 . Resonance is not shown by :
(A) O3 (B) CO2 (C) allene (D) vinyl chloride
24 . Heat of Hydrogenation of benzene and cyclohexene are –208 kJ/mol and –120 kJ/mol respectively.
The resonance energy of benzene is
(A) 102 kJ/mol (B) 32 kJ/mol (C) 152 kJ/mol (D) 88 kJ/mol

ONANCE 5
 General Organic Chemistry

O
25 . The correct order of — C — bond length is:
O

CH 3– C –Cl CH 3– C –OH CH3– C –O– C –CH3 CH3– C –NH2 CH3– C – ONa
|| || || || ||
O O O O O
I II III IV V
(A) IV > V > II > III > I (B) I < II < III < IV < V
(C) IV > II > V > III > I (D) V > IV > II > III > I
26 . Highest heat of hydrogenation is observed with :
(A) 1, 3 – Penta diene (B) 1, 4 – Penta diene (C) 2, 3 – Penta diene (D) Cis – 2 – Pentene
27 . Which one of the following has the smallest heat of hydrogenation per mole of double bond.
(A) 1 – butene (B) trans–2–butene (C) cis–2–butene (D) 1–3–butadiene
O
28 . Correct order of — C — bond length is
O O O O
H—C—H CH3—C—H CH3—C—CH3 CH3—C—Cl
I II III IV
(A) IV < I < II < III (B) IV < I < III < II (C) IV < II < I < III (D) IV < III < I < II
29 . Weakest C  H bond is found in :
CH3
(A) CH3  CH2  CH3 (B) CH3–CH–CH3
(C) CH2 = CH  CH3 (D) Ph  CH2  Ph

30 . Strongest C  Cl bond is found in :

(A) CH2=CHCH2Cl (B) CH3CH2CH2Cl (C) CH2=CHCl (D)

31 . What is the correct order of stability of the following alkenes?

(1) CH2=CH 2 (2) CH2=CHMe (3) Me 2C=CHMe (4) Me 2C=CMe 2
(A) 1 > 2 > 3 > 4 (B) 3 > 4 > 2 > 1 (C) 2 > 4 > 1 > 3 (D) 4 > 3 > 2 > 1
32 . Use the following data to answer the questions below:
H2
Ni H = –28.6 KCal mol–1

excess H2
H = –116.2 Kcal mol–1
(Ni)

Calculate the resonance energy of anthracene,

(A) 84 kcal/mol (B) 100 kcal/mol (C) 110 kcal/mol (D) 116 kcal/mol
33 . Lone pair of pyridine is not delocalized with p-electrons because
(A) it is in p-orbital (B) it is in sp3-orbital
(C) it is in sp -orbital which is oriented at right angle to p-orbitals on carbon atoms.
2

(D) it is in sp-orbital which is orthogonal to p-orbitals on carbon atoms.

ONANCE 6
 General Organic Chemistry

34 . (I) (II) (III)

O O O
Stability order of these compounds is in the order as :
(A) I > II > III (B) I > III > II (C) III > I > II (D) II > I > III
35 . The correct order of heat of hydrogenation is
(I) CH2=CH–CH=CH2 (II) CH 2=C–CH=CH2 (III) CH 3–CH=CH–CH=CH 2

CH3
(A) I > II > III (B) II > I > III (C) II > III > I (D) III > II > I
36 . The most stable carbocation amongst the following is :
   
(A) CH3–CH2– C H 2 (B) CH3– C H –CH2–CH3 (C) (CH3)3 C (D) (CH3)3C – C H 2
37 . Which of the following intermediate have the complete octet around the carbon atom ?
(A) Carbanium ion (B) Carbonion ion (C) Free radical (D) Carbene
38*. Most stable carbanion among the following is :
CH2CH2 CH2 CH2 CH2

(A) (B) (C) (D)

OCH3 NO2
39*. Most stable carbocation is :

(A) CH 2  C H (B) (C) CH2 (D) CH3 – CH
CH3
40 . Correct order of stability of following carbanions is :
O
I CH2 – C – CH3 II CH2 – C  N III CH2 – NO2
(A) I > II > III (B) III > II > I (C) I > III > II (D) III > I > II
41.* The stability of the given carbocations in decreasing order is :

CH2 CH2 CH2 CH2

I II III IV

CH3 OH NH2 NO2

(A) I > II > III > IV (B) IV > III > I > II (C) III > II > I > IV (D) II > III > IV > I
42.* The most unstable carbocation is

(A) CH3–CH2 (B) Cl–CH2–CH2 (C) CH2–CH=O (D) CH2–O–CH3

43 . Which of the following is more stable

(A) CH2=CH (B) (C) CH3–CH–CH3 (D)

ONANCE 7
 General Organic Chemistry

44.* The most stable contributor of the following canonicals are

(A) CH3–NH–C=NH– (B) CH3–NH=C–NH–

NH2 NH2

(C) CH3–NH–C–NH– (D) CH3–NH–C–NH–

NH2 NH2
45.* The species having maximum electron deficiency is

(A) (CH3)3C (B) CH3CH2 (C) (CH3)2CH (D) CH3

46 . The decreasing order of stability of carbanions is :

(I) CH2–CH3 (II) CH2–C(CH3)3 (III) CH2– (IV) CH3

(A) III > IV > I > II (B) III > IV > II > I (C) III > II > IV > II (D) IV > III > I > II
47.* The most stable carbocation is
CH3
(A) CH3–C–CH3 (B) CH2 (C) CH2 (D)

48.* Ease of ionization to produce carbocation and will be maximum in which of the following
compounds :

(A) (B) (C) (D)

49 . Stability order of the following is in the order

(I) (II) (III) (IV)

(A) IV < II < III < I (B) IV < II < I < III (C) I < II < III < IV (D) IV < I < III < II
50 . Which one is most stable free radical ?

 
(A) CH 2  C H (B) (C) (D) CH 2  CH  C H 2

] 51 . Which one of the carbanions is most stable ?

(A) (B) (C) (D)

CN

52 . Which of the following three intermediates have nearly similar geometry?

(I) H2CH3 (II) : H2CH3 (III) : H2COCH3 (IV) CH2=CH– H2
(A) I and III (B) II and IV (C) II , III and IV (D) I , III and IV

ONANCE 8
 General Organic Chemistry

53 . Least stable carbanion is:

   
(A) (CH3)3 C (B) NO2– C H2 (C) (CN)3 C (D) C6H5– C H 2
54 . Which of the following will be least stable ?

(A) (B) (C) (D)

55.* Which of the following carbocation is most stable ?

(A) (B) (C) (D)

56.* Which allylic carbocation is the most stable carbocation ?

 
(A) CH3–CH=CH C H 2 (B) CH 3–CH=CH– C H–CH 3

(C) CH3–CH= (D) All have same stability

(–)
O=C–O (–)
O O
(–)

57 . (I) (II) (III)

Stability order of these anions is :

(A) I > II > III (B) II > I > III (C) III > II > I (D) I > III > II
CH3
C
CH3 CH3
58.* (I) (II) CH3 (III) CH2=CH–CH2
C
CH3
Stability order of these carbocation is:
(A) I > II > III (B) I > III > II (C) III > I > II (D) III > II > I
59 . What is the increasing order of stability : OH– , NH2– , H – C  C– and CH3– CH2– .
(A) CH3–CH2– < NH2– < H–C  C– < OH–. (B) H–C C– < CH3– CH2– < NH2– <OH–
(C) OH < H–C  C < NH2 < CH3–CH2
– – – –
(D) NH2– < H–C  C– < OH– < CH3–CH2–
60 . Least stable carbanion is :
  
(A) C6H5 C H 2 (B) (CH3)3 C (C) C Cl3 (D) CH3–
61 . Which is most stable arenium carbocation?
CH3 CH3 CH3 CH3
NO2 
(A) H (B)  (C) (D) H

 NO2
H NO2 H NO2

ONANCE 9
 General Organic Chemistry
(–) (–)
(–)

62 . I II III

NO2 Cl
Stability order of these carbanions is :
(A) I > II > III (B) III > II > I (C) II > III > I (D) II > I > III
(–) (–) (–)
63 . I CH2 – NO2 II CH2 – CH = O III CH2 – CH = CH2
Stability order of these carbanions is :
(A) I > II > III (B) III > II > I (C) III > I > II (D) II > I > III
64 . Which of the following C – H bond is weakest for homolytic fission?

H CH2 H C H
(A) (B) (C) CH3–H (D)

65 . The correct order of stability of following radicals is

• •
• •
•
I II III IV V
(A) I > II > V > III > IV (B) IV > II > I > IV > III
(C) IV > II > I > III > V (D) II > IV > I > V > III
(–)
(–)

66 . (I) (II) (III) (–)

Cl Cl Cl
Stability order of these carbanions is :
(A) III > II > I (C) I > II > III (C) II > III > I (D) II > I > III

CH—CH— CH2
67 . The order of ease of removal of hydrogen
H1 H2 H3 H4

(A) H1 > H4 > H3 > H2 (B) H2 > H3 > H4 > H1

(C) H3 > H2 > H4 > H1 (D) H4 > H3 > H2 > H1
ANSWER KEY

1. D 2. B 3. A 4. B 5. C 6. A
7. B 8. C 9. C 10. D 11. B 12. D
13 . A 14 . B 15. B 16. C 17. A 18. A
19 . C 20 . A 21. C 22. A 23. C 24. C
25 . D 26 . D 27. C 28. A 29. D 30. C
31 . D 32 . A 33. C 34. B 35. A 36. C
37 . B 38 . D 39. C 40. B 41. C 42. C
43 . B 44 . B 45. D 46. A 47. B 48. B
49 . A 50 . B 51. B 52. C 53. A 54. B
55 . A 56 . C 57. A 58. A 59. A 60. B
61 . C 62 . C 63. A 64. D 65. C 66. A
67 . B
ONANCE 10
 General Organic Chemistry

E X E R C IS E 3
1. Explain the following :
(a) Explain why BF3 exists and BH3 does not .
(b) In carbonate ion, there are two single bonds and one double bond between carbon and
oxygen atom but all bond lengths are equal. Why?
(c) H–O–CN (cyanic acid) and H–N=C=O (isocyanic acid) have same conjugated base
(d) 1,4-pentanediene has Hhydrog = –254 KJ/mole which is approximately twice the value for
1-pentene (Hhydrog = – 126 kJ/mole).
However, 1,2-pentadiene has Hhydrog is –298 kJ/mole
CH2
(e) has higher resonance energy as compared to CH2=CH– CH2

(f) In most amines, the nitrogen atom is sp3 hybridized, with a pyramidal structure and bond
angles close to 109º. In formamide and benzene sulphanamide, the nitrogen atom is found to
be planar with bond angles close to 120º. Explain.
O
O
Ph–S–NH2
H–C–NH2
O
formamide benzene sulphanamide
(g) Compound (A) has higher heat of hydrogenation than compound (B).

(A) (B)

(h) In cyclooctatetraene, two kinds of carbon-carbon bonds are found whereas in benzene all
carbon-carbon bonds are identical.
2. Arrange the following in increasing order of stability of carbanions.
I II III IV

(a) CH2–Cl CH2–CN CH2–NO2 CH2–CH3

O O O O
(d) CH2–C–Cl CH2–S–CH3 CH2–C–CH3 CH2–C–H
O
CH3
(e) CH2–CH3 CH2–C–CH3 CH2– CH3
CH3
CH2 CH2 CH2 CH2

(f)

Cl F NO2 CN

ONANCE 11
 General Organic Chemistry

NO2 Cl CH3
(i)

O O
O O O
(j) H——CH–CH=CH2 H–C–CH–N H——CH——H
O

CH2 CH2 CH2 CH2

(k)

CH3 O NO2 CH3

3.* Arrange in order of decreasing stabilities of carbocations

I II III IV

(a) CH3–CH2 CH2–CH2–Cl CH2–CHCl2 CH3–CH–Cl

CH3
(b) –CH2
CH3–C–CH3

CH2 CH2
CH2 CH2

(d)

OCH3 OCH3 N(CH3)2 N(CH3)2

4. Arrange in decreasing order of stability of radicals
I II III IV

(a)

CH3 CH3

(b) CH2–C–CH=CH2 CH2–CH=CH–CH=CH2 CH2– CH2– –CH=CH2

CH2

CH3
(d) CH3–CH=CH–CH2 CH2=C–CH2
CH3

ONANCE 12
 General Organic Chemistry
5.* Arrange in order of ease of ionisation
I II III

O N
(a)

Br Br Br

(b)

CH3 Cl
Cl Cl

ONANCE 13
 General Organic Chemistry

EX ER C IS E 4
[ SINGLE CORRECT ]

1. In which of the following, the lone pair indicated is involved in resonance.

CH2
(A) (B) (C) CH2=CH– CH2 (D) CH2=CH–CH= NH
N O
2. The electron density at benzene ring in the following compounds follows the order.
COOEt OCOEt CH3 NHCOCH3

(I) (II) (III) (IV)

(A) IV > III > II > I (B) I > II > III > IV (C) IV > II > I > III (D) IV > II > III > I
3. The correct order of resonance energy is
CH3
(I) CH 2=CH–F (II) CH 2 =CH–OCH 3 (III) CH 2=CH– N
CH3
(A) I > II > III (B) II > I > III (C) III > II > I (D) III > I > II
4. Which of the following compounds do not have all C–C bonds of same length

(A) (B) (C) (D)

5. Which of the following compounds do not have all C–O bonds of same length
(A) CO 2 (B) HCOOH (C) CO 3–2 (D) HCOO
6. The correct order of C=C bond length is
H3C H3C
(I) (II) (III) (IV)
CH3
(A) IV > III > II > I (B) II > I > IV > III (C) I > II > IV > III (D) IV > II > I > III
7. The correct order of resonance energy is

(I) (II) (III)

(A) I > III > II (B) I > II > III (C) II > III > I (D) III > I > II

8. Which of the following have delocalised electrons?

CH2–NH2
(A) (B)
O

(C) CH 2=CH–CH 2–CH=CH 2 (D) CH 3–CH=CH–CH=CH– CH2

ONANCE 14
 General Organic Chemistry

OH OH OH

9. (I) (II) (III)

NO2
NO2
The order of the C–O bond lengths among these compound is
(A) I > II > III (B) III > II > I (C) II > I > III (D) III > I > II

NH2 NH2 NH2 NH2

10 . (I) (II) (III) (IV)

CHO
CHO
The order of the C–N bond length among these compounds is
(A) III > I > IV > II (B) II > IV > I > III (C) III > I > II > IV (D) II > III > IV > I
11 . The correct order of resonance energy is

Me Me Me Me Me Me
N N N
H3C CH3
(I) (II) (III) (IV)
H3C CH3
N N
Me Me O O
(A) I > III > IV > II (B) II > III > IV > I (C) IV > I > III > II (D) IV > III > I > II
12 . The correct order of increasing C–O bond length of CO, CO3 , CO2 is –2

(A) CO3–2 < CO2 < CO (B) CO2 < CO3–2 < CO
(C) CO < CO3–2 < CO2 (D) CO < CO2 < CO3–2
13 . Which of the following example has both the resonating structures contributing equal to the resonance
hybrid.

(A) CH3–C–CH=CH–CH3 CH3–C=CH–CH–CH3

CH3 CH3
O O
(B) N N
O O

(C) CH 2=CH–CH=O CH2–CH=CH–O

O
O
C OH OH
(D)

ONANCE 15
 General Organic Chemistry

O O
14 . CH 3—C CH3—C
OH O
The correct order of bond lengths is
(A)  >  >  >  (B)  >  >  >  (C)  >  =  >  (A)  =  >  > 
15 . Among the following compound which has longest C – O bond ?
O O O O
(A) H H (B) H F (C) H NH2 (D) H OH

O O O
16 . (I) CH3–C–NH–CH2–Ph (II) CH3–C–NH–Ph (III) CH3–C–NH– –NO2

The electron density on carbonylic oxygen of these compounds is in order as

(A) III > II >I (B) II > III > I (C) I > II > III (D) I > III > I

17 . For the following reactions , CH3 Cl CH3+ + Cl()  H 1º

CH3 CH2 Cl   CH3 CH2+ + Cl()  H 2º
(CH3)2 CHCl  (CH3)2 CH + Cl
+ ()
 H 3º
(CH3)3 CCl  (CH3)3 C+ + Cl()  H 4º
(A)  H1º >  H2º >  H3º >  H4º (B)  H1º <  H2º <  H3º <  H4º
(C)  H1º >  H2º >  H3º <  H4º (D)  H1º >  H2º <  H3º <  H4º

O–H OH OH
CH3 CH3 CH3
18 . (I) CH3–C–N (II) CH 3–C–N (III) CH 3–C=N
CH3 CH3 CH3

The stability order of these canonical structure is

(A) I > II > III (B) II > III > I (C) I > III > II (D) III > I > II
O

19 . How many electron deficient cites are available in

(A) 1 B) 2 (C) 3 (D) 4

20 . Which of the following statements is true about this molecule ?

(A) C5-N bond is longer than C1-N and C3-N bonds.

(B) C5-N bond is shorter than C1-N bond and latter is shorter than C3-N bond.
(C) All three C-N bonds are of same length.
(D) C1-N and C3-N bonds are of same length but they are longer than C5-N bond.

ONANCE 16
 General Organic Chemistry

21 . The C1– C2 bond length is minimum in : CH3

CH3 H3C—C—CH
2 3
CH3 CH2—CH3 CH 1
2 2
1 1 2 1 CH3
(A) (B) (C) (D)

22 . The most stable canonical structure of this molecule is :

(A) (B) (C) (D)

23 . A highly important canonical structure of this molecule is :

(A) (B) (C) (D)

24 . I II III IV

Among these compounds the order of the -electrons energies is :

(A) IV > II > III > I (B) III > IV > II > I (C) III > I > IV > II (D) I > II > IV > III

25 . I. II. III.

Which of the following choice is the correct order of resonance energy of these molecules:
(A) I > II > III (B) II > I > III (C) III > I > II (D) III > II > I

26 . I. II. III. CH2 = CH2 IV. HC  CH

Rotation about indicated bonds

II is easiest in which of these molecules
I
(A) I (B) II (C) III (D) IV

ONANCE 17
 General Organic Chemistry

27 . CH2=CH–OCH3 CH2—CH = O—CH3 I.

CH2=CH–NHCH 3 CH2—CH = NH—CH3 II.

Which of the following statements is true about the I and II in respective resonance hybrids.
(A) Both I and II have same contribution
(B) I contributes more than II
(C) I contributes less than II
(D) It is not possible to judge their relative contribution
28 . Maximum – CN bond distance in :

O
H O
C–NH2
(A) H 3C–CH 2–NH 2 (B) H3C– C =NH (C) (D) NH2– C –NH2

29 . Write the decreasing order of C – O bond length in the following compounds

O
(I) H3C – OH (II) HCHO (III) H – C – OCH3
(A) I > III > II (B) III > II > I (C) II > I > III (D) III > I > II
30 . Maximum resonance energy is observed in :

(A) (B)

(C) (D)

31 . In formadehyde the C – O bond distance is 1.2 Å and in carbon monoxide, the C – O bond
distance is 1.1 Å. The C–O bond distance in CO2 is :
(A) < 1.1 (B) > 1.2 (C) equal to 1.1 (D) between 1.1 & 1.2
32 . The correct order of resonance energy is

(I) N–H (II) (III) (IV)

O S
(A) IV > III > I > II (B) III > II > I > IV (C) I > II > III > IV (D) IV > III > II > I
33 . Which of the following has shortest C–O bond :

O
(A) (B) (C) (D)

CH 3

ONANCE 18
 General Organic Chemistry

34 . Which set of structures have resonating as well as isomeric structure ?


O–H O OH

(A)

O O O

(B)

• •
(C) H2C C=CH2 CH 2 =CH–CH=CH 2 CH2–CH=CH–CH2
CH2
 
(D) CH 3– C =O CH 2=C=O CH 3 –C O

35 . Vinyl halide is represented in the following resonating structures

.. + + ..
(a) CH2=CH– Cl (b) CH2–CH=Cl (c) H2C–CH=Cl

..
..
..
..

..

.. ..
The order of stability of resonating structure are as follows:
(A) a > b > c (B) a > c > b (C) a = b = c (D) none

36 . CH3 – CH2 – NH2

(I) (II) (III)

Rotation barriers about C – N bond among these compounds will be in order .
(A) I > II > III (B) III > II > I (C) II > III > I (D) III > I > II
37 . Which of the following has C–O highest bond distance

(A) O (B) O (C) O (D) O

38 . The correct O — O bond order in O3, O2 and H2O2 is

(A) H2O2 < O3 < O2 (B) O2 < O3 < H2O2 (C) H2O2 > O2 > O3 (D) O3 < H2O2 > O2

39 . (I) (II) (III) CH2=CH2 (IV) HCCH

Among these compounds the order of heats of hydrogenation is:

(A) II > I > IV > III (B) I > II > III > IV (C) III > IV > II > I (D) IV > III > II > I

40 . Which of the following compounds is not aromatic ?

O O
(A) (B) (C) (D)
O O O
O O

ONANCE 19
 General Organic Chemistry

1 4
N N
41 . In this molecule, lone-pair of which N is involved in aromaticity :
N N
2 3
(A) N1 (B) N2 (C) N3 (D) N4
42 . Which is the most stable resonance form ?

(A) (B)

(C) (D)

43 . Electron density in the ring is maximum in :

(A) (B) (C) (D)

CH3 CH2CH3 CH CH3 C CH3

CH3 CH3
CH3
44 . The most stable carbocation amongst the following is :
   
(A) CH3 – C H 2 (B) CH3 – C H = O (C) CH3 – C = NH (D) CH3 – CH = C H

45 . The most stable resonating structure of the intermediate aremium ion is :


NH2 E


NH2 NH2 NH2 NH2

E E E E
(A) (B) (C) (D)
46.* Resonance energies of these cations are in the order :

(I) O (II) N (III)

H
(A) II > I > III (B) I > II > III (C) III > II > I (D) III > I > II
47.* The most stable carbocation is :
(A) CH3O–CH2– –CH2–CH–CH2 (B) CH3O–CH2– –CH2–C–CH3
CH3 CH3
CH3
(C) CH3O–CH2– –CH–CH–CH3 (D) CH3O–CH– –CH2–CH–CH3
CH3

ONANCE 20
 General Organic Chemistry

48.* The most unstable carbocation is

CH3 CH3 CH3 CH2

(A) (B) (C) (D)

49.* (I) O (II) O (III) N Br

Br Br
CH3
The ease of ionization of these compounds to produce Br is in order as :
(A) I > II > III (B) III > I > II (C) II > III > I (D) III > II > I

50 . (I) CH3–CH2 (II) CH2=CH–CH2 (III) CH2=CH–CH–CH=CH2 (IV) CH2=CH

Which of the following choice is the correct order of resonance energy of these radicals.
(A) I > II > III > IV (B) I > III > II > IV (C) III > I > II > IV (D) III > II > I > IV

51 . Ease of ionization to produce carbocation and will be maximum in which of the following
compounds :

(A) (B) (C) (D)

52*.

I II III IV
Resonance energies of these cations are in the order :
(A) I > II > IV > III (B) IV > III > I > II (C) IV > III > II > I (D) II > I > III > IV
53.* Stability of carbocations is in the order

(i) (ii) (iii)

(iv) (v)
(A) iv > ii > i > v > iii (B) i > ii > iii > iv > v
(C) iii > i > ii > v > iv (D) i > iv > ii > iii > v
54.* Which of the following is most stable ?

CH2
(A) CH2 (B) (C) Ph–CH–Ph (D) CH2–O–CH3

55.* Which one of the most stabilised ?

(A) (B) (C) (D) CH3

ONANCE 21
 General Organic Chemistry
56.* The most stable carbocation is :
() ( ) () ( )
(A) CCl3  C H 2 (B) Cl  C H  CH3 (C) Cl  CH2  C H 2 (D) F– C H – CH3

57. * In the following, the stability order of carbocation is :

CH3
|
I CH (+)
, II CH  C III CH   OCH IV CH   NH  CH
|
2 3 | 3 3 3 3

CH3

(A) III > IV > II > I (B) IV > III > II > I
(C) IV > III > I > II (D) I > IV > III > II

58 . Stability order :

(I) (II) (III) (IV)

|
OCH3

(A) III > II > IV > I (B) III > II > I > IV (C) III > I > IV > II (D) III > IV > I > II

59 . Arrange the following radicals in order of decreasing stablity.

I. (CH3)3C• II. CH2=CH– III CH3• IV. (CH3)2CHCH2• V. (CH3)2CH•

(A) I , II , III , IV , V (B) V , I , III , IV , II (C) II , I , V , IV , III (D) II , V , I , III , V

60 . Rank the following free radicals in order of decreasing stability:

• • •
I C6H5 C HC6H5 II C6H5– C H–CH=CH2 III CH3– C H–CH3
• • •
IV C6H 5 C H–CH 3 V CH3CH=CHCH2 C H 2 VI CH3–CH2– C –(CH3)2
(A) I > II > III > IV > V > VI (B) VI > V > IV > III > II > I
(C) I > II > IV > VI > III > V (D) I > IV > VI > V > II > III

61.* Which of the following is the most stabilized carbocation?

(A) (B) (C) (D)

62.* I. II. III.

N N
H H
Stability order of these cation is:
(A) I > III > II (B) II > I > III (C) III > II > I (D) III > I > II

ONANCE 22
 General Organic Chemistry

63.* (I) (II) (III)

Stability order of these carbocations is:

(A) I > II > III (B) III > II > I (C) II > III > I (D) III > I > II

OCH3 OCH3
CH3O OCH3
64.* (I) (II) (III)
OCH3
OCH3 OCH3

Stability order of these carbocation is :

(A) I > II > III (B) I > III > II (C) III > I > II (D) III > II > I
65 . The most stable carbanion is

O O O O

(A) (B) CH3O OCH3

O O O
(C) CH3O CH3 (D) H
66.* Which of the following two corbonium ions are more stable.
..
  NH2
(a)   (b)

I II I II
(A) a–II , b-II (B) a–I , b–I (C) a–I , b–II (D) a–II , b–I

67.* (I) CH2 (II) CH2 (III)

Stability order of these carbocation is:

(A) I > II > III (B) I > III > II (C) III > I > II (D) III > II > I

CH3
68 . The correct order of CH1, CH2, CH3 bond energies is H3 – CH = CH—C—CH2
H2 H1
(A) C–H3 > C–H1 > C–H2 (B) C–H3 > C–H2 > C–H1
(C) C–H2 > C–H1 > C–H3 (D) C–H1 > C–H3 > C–H2

69 . Hetrolytic cleavage is easiest in

CH3
(I) CH3–Cl (II) CH3–CH2–Cl (III) CH3–CH–Cl (IV) CH3—C—Cl
CH3
(A) I (B) II (C) III (D) IV

ONANCE 23
 General Organic Chemistry

70 . (I) CH3O–CH=CH–CH2–Cl (II) (III)

The order of the ease of ionization of these compounds to produce carbocations and is:
(A) I > III > II (B) III > I > II (C) II > III > I (D) II > I > III

H
H3C
71 . H . Arrange the B.E. of (C – H) bonds indicated by    .
H
H
(A) C–H < C–H < C–H < C–H (B) C–H < C–H < C–H < C–H
(C) C–H > C–H > C–H < C–H (D) C–H < C–H < C–H < C–H

72 . Carbonium ion with highest stability :

CH3
|
(A) CD3 — (B) CD3 — (C) CD3 — (D) CH3 — C
|
CH3

73 . Ease of ionization to produce carbocation and will be maximum in which of the following
compounds :

(A) (B) (C) (D)

Cl
74 . The compound gives :

(A) Cl (B) Cl  (C) Cl (D) none

75.*
H Br
H Br
II III
The order of the ease of ionization of these compounds to produce carbocations and is :
(A) I > II > III (B) II > I > III (C) I > III > II (D) III > II > I

ONANCE 24
 General Organic Chemistry

E X E R C IS E 5
1. Arrange the following in increasing order of electron density in ring
I II III IV
O Na+ NH2 OH CH3

(a)

NO NO2 CN NH2

(b)

NO2 CN NH2 Cl

(c)

OCOCH3 NHCOCH3 OH N(CH3)2

(d)

NH2 NHCH3 OH OCH3

(e)

NH2 NH2 NO2

(f)
NO2
NO2 NO2

Cl F Br I

(g)

NO NH2 OH NO2

(h)

ONANCE 25
 General Organic Chemistry
2. Arrange in decreasing order of heat of hydrogenation
I II III IV

(a)

CH–CH3 CH=CH2 CH=CH2 CH2CH3

(b)

CH3
(c) C=CH2

(d)

(e) CH 2=CH–CH=CH 2 CH 3 –CC–CH 3 CHCH CH 3–CH=C=CH 2

3. Arrange in decreasing order of resonance energy

I II III
O
O O
(a)
CH3–S–OH
CH3–C–OH CH3–S–O Na
O
O
CH=CH2
(b)

CH2
(c)

(d) CH2 CH2 O Na CH2 OH

O O
(e) CH2 CH2 C CH2 N
H O

(f)
NO2
NO2 NO2

(g) CH 3O–CH=CH–CH=CH 2 (H 3C) 2N–CH=CH–CH=CH 2 CH 2=C–CH=CH2

OCH3
(h) CH 2=CH–F CH2=CH–OCH3 CH 2=CH–Cl

ONANCE 26
 General Organic Chemistry
4. Arrange in order of increasing stability of canonicals.
I II III

O O O
(a) O=N N O=N N O=N N
O O O

O O O
(b) H–C–OH H–C=O–H H–C–OH

O NH O NH O NH

(c) H H H H H H

(d) HO–CH=CH–CH=O HO–CH–CH=CH–O HO=CH–CH–CH=O

O O O
(e) S—OH S—OH S==OH
O O O

5. Arrange in order of increasing +M effects

I II III

(a) –CH=CH 2 –CH=CH–OCH 3

CH3 O
(b) –NH 2 –N
–NH–C–CH3
CH3

(c) –O Na —O—C— —NH—C—

O O

(d) –O–H –O–CH 3 O–

O
(e) –O–CH=CH 2 –O–CH=O –O–S–CH3
O

O
(f) –CH=CH–N –CH=CH2 –F
O

(g) –OCH 3 –Cl

ONANCE 27
 General Organic Chemistry
6. Arrange in decreasing –M effects
I II III
O O
(a) –N –N=O –CH=CH–N
O O

O O
(b) –CH=CH–OCH 3 –S–OH –S–Cl
O O
O O O O
(c)
–C–NH2 –C–OH –C–O–C–CH3

O
(d) –CH=O –N
O
O
(e) –CH=CH–C–H CHO

CHO
7. Draw resonating structures for each of the following molecules.
O O
(a) (b) HO N O
O O
CH3
(c) CH2 = O – CH = CH2 (d) H3CO – CH = CH – P CH3
CH3

CH3
P
(e) CH3 (f) Cl C  CH

O
(g) HO – S N=N NH2
O

O
O
(h) H2N – CH = CH – S – OH (i) H2N – CHO (j)
N
O
CH3 H
O
NO2
C
(k) (l) OH
O2N CH3 HO

ONANCE 28
 General Organic Chemistry

(m) (n) CH2 = C = CH

(o) (p) CH2 = CH – N – CH3 (q) O = C = O

N
CH3

CH3 O O
O
H S CH S
(r) (s)
O O O
CH3
8. Arrange the following in increasing order of stability of carbanions.
I II III IV

O O
(a) CH2– CH2– H—– –CH2 CH2–CH=CH2
CH3

O O O O O O
S S
(b)

O
O

(c) CF3–CH2 F–CH2 CCl3 CH3–CH2

O
CH2 CH2 CH2 CH–——H

(d) H

H O
O
9.* Arrange in order of decreasing stabilities of carbocations
I II III IV

(a) –CH– CH2

–CH–

(b) CH2–OCH3 CH2– CH2–

(c) C C6H5–C–C6H5 CH3–C–CH3 C6H5–CH2

C6 H 5 CH3

ONANCE 29
 General Organic Chemistry
10 . Arrange in decreasing order of stability of radicals
I II III IV

(a) –CH2

(b) H2C– –CH=CH2 CH2– CH2– CH2–

(c) Ph–CH2

Ph

11.* Arrange in order of ease of ionisation

I II III

Ph

(a) Cl
Ph Cl Cl

Br
(b)
Br

Br
12 . Explain the following
CH3

(a) CH2=C–CH2 is less stable than CH3–CH=CH– CH2

(b) CH2=CH–CH=CH– CH2 is more stable than CH2–C–CH=CH2

CH2

(c) CH3–CH=C–CH3 is more stable than CH2–O .

ONANCE 30
 General Organic Chemistry

E X E R C IS E 6
NEW IIT-JEE PATTERN QUESTION

MULTIPLE CHOICE ANSWER TYPE

1. Hyperconjugation phenomenon is possible in

(A) CH 3–CH=CH–CH=CH 2 (B) CH=CH2

CH3

(C) H2C (D) H3C C—CH3

CH3
2. Which of the following is true about resonance ?
(A) all resonating structure have same energy level.
(B) all resonating structure have same amount of net charge.
(C) all resonating structure have same number of unpaired electrons
(D) resonating structures have identical arrangement of atoms.
3. M effect takes part in
(A) unsaturated system containing conjugated double bond.
(B) Unsaturated system containing non conjugated double bond.
(C) A double bond in carbon chain adjacent to the lone pair
(D) Saturated system
4. The group which exerts –I, –M & +M effect is/are
(A) –N=NH B) –SO 2H (C) –NO 2 *(D) –N=CH 2
5. Which of the following groups when attached to benzene ring show – M effect
R
(A) –NR3 (B) –P R (C) –CH=CH 2 (D) –OCH 3
R
6. Which of the following have delocalised electrons?

(A) (B) CH 2=CH–O–CH=CH 2

O
CH2–NH2
(C) (D) CH 2–CH=CH–CH=CH 2– CH2

7. Which of the following order of resonance energy is/are correct?

O
O
(A) O >

(B) CH2=CH–O > CH2=CH–OH

ONANCE 31
 General Organic Chemistry

O O
(C) >

(D) CH2=CH–NH–CH=CH 2 > CH 2=CH–O–CH=CH 2

8. The correct order of stabilities are
O O
(A) CH3– C –Cl > CH3– C –F (B) >
NO2 NO2

(C) CH2=CH–NH < HN=CH–NH (D) CO3–2 > HCOO

9. Which of the following molecules exists as a resonance hybrid?

(A) Ph–CH=O (B) CH 2=CH–NO (C) (D) 1,4-cyclohexadiene
O
10 . Which of the following statements is true about the given compounds.
I. CH 2=CH–CH=CH–CH 3 II. CH 3–CH=C=CH–CH 3
(A) There is resonance in I but not in II (B) There is hyperconjugation in I but not in II.
(C) II has more canonical structure than I (D) Hyperconjugation takes place in both I and II
11 . Which of the following is not a resonating contributor for N3H?
  
(A) (B) H  N
. . = N = N: (C) (D) N
12 . Pairs of structure which are resonance structures.

• •
(A) & CH2= –H (B) CH2=CH–CH=CH2 & C H 2 –CH=CH– C H 2

NH 2 NH 2
| |
(C) CH2=CH–OH & CH3– C =O (D) CH3–CH2– C NH2 & CH3–CH2 C 
| 
H
13 . Which of the following pairs of structures does not represent resonance structure ?
O
||
||

(A) & (B) &

||

(C) & (D) &

14 . In which of the following compounds nitrogen does not have sp3 hybridization
SiH3 CH2–NH2
(A) (B) H3Si—N—SiH3 (C) (D)
N N

H
ONANCE 32
 General Organic Chemistry

15 . Which of the following will have delocalisation

CH3
(A) CH3–NH3 (B) CH3–BH2 (C) CH3–CH2 (D)

16 . Which of the following compound(s) is/are aromatic :

N
(A) (B) (C) (D)
N

H
17 . Identify the group(s) which exert  I ,  M & + M effects .
(A)  NO2 (B)  NH  CO  CH3 (C)  N = O (D)  CH = CH2
18 . The group(s) that exert + M effects are :

(A) – O – – CH3 (B) – NH – – CH3 (C) – N = O (D)

19 . Compare heat of combustion

I II

H3C
H3C CH3
H
(A) C C
H CH3 H H

(B)

(C)

(D)

20 . Which of the following carbocations can participate in delocalisation?

(A) (B) H3CO (C) H3C–CH=CH (D)

N
CH2
21 . Which of the following carbocations are more stable than benzyl carbocation ?

(A) CH2–CH=CH–OCH3 (B) CH2–CH=CH–CH=CH2

(C) CH2 (D)

ONANCE 33
 General Organic Chemistry
22 . Which of the following are the correct order of stability:

(A) < (B) H3CO CH2 <

CH2 O

(C) < (D) >

CH2
23 . Planar cation is :
   
(A) N H 4 (B) C H 3 (C) CH3– C =O (D) (CH3)3 C Sb F6(  )

24 . Which of the following statements is incorrect ?

(A) Allyl carbonium ion (CH2=CH– CH2 ) is more stable than propyl carbonium ion.
(B) benzyl carbocation is more stable than t-butyl carbocation.
(C) vinyl carbocation is more stable than cyclohexyl carbocation.
(D) none of these

24 . Which of the following stability orders is correct?

(A) O2N– –CH2 > O2N– –CH–CH=O

(B) CH2–CH2–Cl > CH2–CH2–NO2

(C) –Cl > –F

(D) CH3–CH–CH3 > CH3–CH2–Cl

25 . Which of the following statements are true ?
 
(A) CH3O C H2 is more stable than CH3 C H2,
 
(B) Me2 C H is more stable than CH3CH2 C H2,
 
(C) CH2=CH– C H2 is more stable than CH3CH2 C H2.
 
(D) CH2= C is more stable than CH3 C H2.

26 . In which of the following pairs of ions, the Ist ion is more stable:
   
(A) C6H5– CH2 and CH 2=CH– CH2 (B) CH3– CH2 and CH 2= CH
I II I II
 
CH2 CH2 CH3–CH–CH3 CH3–N–CH 3
(C) and (D) and
CH3–C–CH3 CH3–C–CH3
 
I II I II

ONANCE 34
 General Organic Chemistry

MATRIX MATCH TYPE

27 . Match the following column
Column I (group) Column II (effect)
CH3
(A) –N CH3 (p) –M effect

(B) –CH 2 –CH 3 (q) Hyperconjugation

CH3

(C) –C–CH3 (r) – I effect

CH3
(D) –CN (s) +I effect.
28 . Match the following column
Column I Column–II
(stability) (Effects which can explain
stability order)
(A) CH2–CH=CH–NO2 < CH2–CH=CH2 (p) hyperconjugation

CH3
(B) CH3–C > CH2 (q) +M effect

CH3
(C) CH2–OCH3 > CH2–CH3 (r) –M effect

(D) CH2–NO2 > CH2–Cl (s) – I effect

29. Match the following column

Column I Column–II
(A) R–X + Y  R–Y + X (p) Elimination
(B) RCH 2CH2X  RCH = CH2 + HX (q) Condensation
(C) CH3– CH– CH3  CH3CH2CH2CH3 (r) Substitution
CH3
(D) RCH=O+ H2A  RCH=A + H2O (s) Rearrangement
30. Match the following column
Column I Column–II
(A) A–B  A + + B– (p) Free radical
(B) CH3CH (q) Heterolytic clevage

CH3
• •
(C) A••A  A + A (r) Carbocation.
(D) CH2N2  CH2 + N2 (s) Nucleophile
(E) CH3OH (t) Carbene

ONANCE 35
 General Organic Chemistry

31. Match the following column

Column-I (Reaction) Column–II (Intermediate)
CH3
(A) CH3–CH–CH=CH2 + HBr (p) Transition state

(B) CH3+B2H6 (q) Bromium ion

CH3

(C) CH3–CH–CH3 + Br2/hv (r) Carbocation

(D) CH3–CH=CH2 + Br2/CCl4 (s) Radial

LINKED COMPREHENSION TYPE

PARAGRAPH–I
A covalent bond can cleave either homolytically or heterolytically. Homolytic cleavage forms free
radicals where as heterolytic cleavage produces either carbocations or carbanions. In other words,
during organic reactions the cleavage of bond results in the formation of above species known as
intermediates which play an important role in the mechanism of the reaction. The formation of these
inter-mediates depend on the dissociation energy of covalent bonds. The bond dissociation energy (in
mol–1) ofsome bonds is tabulated below:
Bond x=H Cl OH NH2

X 111 96 111 102

CH3–X 105 85 92 85
CH3CH2–X 100 80 94 84
(CH3)2CH–X 96 81 94 84
(CH3)3C–X 93 82 93 82

CH2–X 88 72 81 —

32. In the potential energy diagram, given below the plot B is due to which of the following species.
CH2

CH2=CH–CH2 CH3 CH2

(1) (2) (3) (4)

D
C
Pot. enerty

B
A

Progress
(A) 1 (B) 2 (C) 3 (D) 4
ONANCE 36
 General Organic Chemistry
33. Arrange the dissociation energy of  and  bonds in the increasing order in the following compound
H H
H3C H
H H
H
H
(A)  <  <  <  (B)  <  <  <  (C)  <  <  <  (D)  <  <  < 
34. Which of the following is most stable carbonium ion?

(A) C6H5–CH2– CH–CH3 (B) (C) C6H5–C–CH3 (D) CH2

CH3

REASONING TYPE
This section contains FIVE questions . Each question contains STATEMENT- 1
(Assertion) and STATEMENT - 2 (Reason). Each question has 4 choices (A), (B), (C) and
(D) out of which ONLY ONE is correct.
(A) ‘S’ is correct but E is wrong
(B) ‘S’ is wrong but E is correct
(C) Both ‘S’ and ‘E’ are correct and ‘E’ is correct explanation of ‘S’.
(D) Both ‘S’ and ‘E’ are correct but ‘E’ is not correct explanation of ‘S’.

35. Statement-1: The hybrid state of carbon atoms in diamond is sp3.

Statement-2: All the carbon atoms in diamond are directly linked to four other carbon atoms
tetrahedrally.

36. Statement-1: C–C bond length in graphite is shorter than the C–C bond length in diamond.
Statement-2: Graphite is good conductor of electricity.

37. Statement-1: CO is a good reducing agent.

Statement-2: CO is a combustible gas

38. Statement-1: Carbonic acid is a dibasic acid.

Statement-2: Carbon monoxide when dissolved in water yields carbonic acid.

39. Statement-1: Carbon exhibits catenation to maximum extent.

Statement-2: Valency of carbon is 4.

FILL IN THE BLANKS

40. Fission of covalent bond is of two types, ......... and ...................
41. Homolytic cleavage of bond produces.........
42. Heterolytic cleavage is more favourable when carbon is attached to an atom of ....

ONANCE 37
 General Organic Chemistry
43. The tert-carbocation is ........... stable than sec-carbocation ion
44. When a reaction is done in the presence of peroxides it proceeds through ............
45. Reaction of ethene with HCl to produce ethyl chloride, is an edample of ................
46. Electron rich species are called ............ and can ............ a ................of electrons.
47. Dehydration of alcohols to alkenes is an example of ............
48. Carbon atom carrying a positive charge has ............ of electrons
49. Inductive effect is ........... effect
50. Two substances having different solubility in a particular solvent, can be separated by. ............
51. The process of distillation is applied to separte a mixture of two liquids having large difference in
their ............
52. The boiling point of a liquid ............ when pressure above the liquid is reduced.

TRUE OR FALSE
53. Dienes may have cumulated or conjugated double bonds in the molecule.
O
54. Propanal, CH3CH2–C is an unsaturated compound.
H
55. Heterolytic cleavage of bond produces free radicals.
56. A carbanion has octet of electrons.
57. Ammonia is an electrophile.
58. Alkenes can give electrophillic as well as nucleophillic addition reactions.
59. Electromeric effect is a temporary effect.
60. The carbenes have six electrons and two positive charges.
61. In tert-carbocation the charge bearing carbon atom is sp3 hybridised.
62. The inductive effect operates along the chain of carbon atoms in an organic compound having any
number of carbon atoms.
63. All the nucleophiles are negativly charged.
64. The conversion of ethyl chloride to ethyl alcohol proceeds through SN2 type of reaction.
65. Napthalene can be purified by sublimation.
66. A mixture of diethylether and ethyl alcohol can be separated by simple distillation.

ONANCE 38
 General Organic Chemistry

E X E R C IS E 7
1. The order of decreasing stability of the carbanions: [CET Kurukshetra 1996]
– – – –
(CH3)3 C (I); (CH3)2 C H (II) ; CH3 C H2 (III); C6H5 C H2 (IV) is
(A) I > II > III > IV (B) IV > III > II > I (C) IV > I > II > III (D) I > II > IV > III
2. Which of the following is correct reagarding the –I effect of the substituents? [CBSE 1998]
(A) –NR2 < –OR < –F (B) –NR2 > –OR < – F
(C) –NR2 < – OR > –F (D) –NR2 > –OR > F
3. Which of the following is a dehydro-halogenation reaction? [M.G.I.M.S. Wardha 2003]
(A) C2H5Cl + aq.KOH  CH2=CH2 + KCl + H2O
(B) BrCH2–CH2Br + Zn  CH2 = CH2 + ZnBr2
(C) CH3COOH + CH3OH  CH3COOCH3 + H2O
(D) Both (A) and (B)
4. Which of the following compounds possesses the C–H bond with the lowest bond dissociation energy
[AIIMS 2003]
(A) Toluene (B) Benzene (C) n-Pentane (D) 2,2-Dimethylpropane
5. Which of the followoing represents the given mode of hybridization sp2–sp2–sp–sp from left to right?
(A) H2C = CH–CN (B) HCC–CCH [IIT 2003]
CH2
(C) H2C=C=C=CH2 (D) H2C

6. The general formula CnH2nO2 could be for ope chain [AIEEE 2003]
(a) dialdehydes (B) diketones (C) carboxylic acid (D) diols
7. Tautomerism is not exhibited by [KJ CET 2004]

(A) O O (B) CH = NOH

(C) (D) O O
O O
8. Which of the following is the most stable cation? [J& K CET 2004]
(A) F3C – CH2+ (B) (CH3)2CH+ (C) CH3 +
(D) CF3+
9. Identify the correct statement from below concerning the structure of CH2=C=CH2
(A) The molecules is planar [Kerala CET 2004]
(B) One of the three carbon atoms is in an sp hybridized state
2

(C) The molecule is non-planar with the two CH2 groups being in planar perpendicular toeach other
(D) All the carbon atoms are sp-hybridized.
(E) The molecule is bent with the —C—C—C— angle being 120º.

ONANCE 39
 General Organic Chemistry
10. Orbital interaction between the sigama bonds of a substituent group and the neighboruing p-orbital is
knonw as [Kerala M.E.E. 2004]
(A) hyperconjutaion (B) inductive effetive
(C) steric effect (D) dipole-dipole interactions
(E) electric quadrruple interactions
11. A molecule of ureas can show [Kerala M.E. 2004]
(A) Chain isomerism (B) Position isomerism
(C) Geometrical isomerism (D) Optical isomeris
(E) Tautomerism
12. Which one of the following resonating structures of 1-methoxy-1, 3-butadiene is leas stable?

(A) C H2–CH=CH–CH= O –CH3 (B) CH2=CH– CH –CH= O –CH3 [IIT 2005]

(C) C H2– C H–CH=CH–O–CH3 (D) CH2=CH– C H– C H–O–CH3

13. Which amongst the following is the most stable carbocation? [CBSE–PMT 2005]

CH3
(A) CH3 (B) CH3CH2 (C) CH3–C (D) CH3–C
CH3 CH3

14. Alcohols are isomeric with [AIEEE 2005]

(A) acids (B) ethers (C) esters (D) aldehydes
15. Of the five isomeric hexanes, the isomers that can given two monochlormated cmpound is:
(A) 2-methyl pentane (B) 2,2-Dimethyl btuane [AIEEE 2005]
(C) 2,3-Dimethyl butane (D) n-hexane
16. In the molecule HCC–CH=CH2, the hybridization of C–C bond is [Orissa JEE 2005]
(A) sp–sp2 (B) sp3–sp3 (c) sp2–sp2 (D) sp –sp.
3

17. How many bonds are there in [DCE 2005]

(A) 14 , 8  (B) 18 , 8  (C) 9 , 4  (D) 14 , 2 

18. Consider the following compounds: [Kerala E.E.E. 2006]
(a) Chloroethene (b) benzene (c) 1,3-butadiene (d) 1,3,5-hexatriene
All the carbon atoms are sp2 hybridised in
(A) a,c,d only (B) a, b only (C) b,c,d only (D) c, d only
(E) a, b, c and d
19. An organic compound which produces a bluish green coloured flame on heating in presence of copper
is [K.C.E.T. 2006]
(A) chlorobenzene (B) benzaldehyde (C) aniline (D) benzoic acid
20. Inductive effec involves [K.C.E.T. 2006]
(A) displacement of -electrons (B) delocalisation of -electrons
(C) delocalisation of -electrons (D) displacement of -electrons.

ONANCE 40
 General Organic Chemistry

21. If there is no rotaion of plane polarized light by a compound in a specific solvent, thought to be chiral,
it may mean that [CBSE AIPMT 2007]
(A) the compound may be a racemic mixture (B) the compound is certainly a chiral
(C) the compound is certainly meso (D) there is no compound in the solvent.

22. Which one of the following conformatin s of cyclohexane is chiral [AIEEE 2007]
(A) Twist boat (B) Rigid (C) Chair (D) Boat

23. 59 g of an amide obtained from a carboxylic acid, RCOOH, liberated 17 g of ammonia upon heating
with alkali. The acid is: [JSM Dhanbad 1994]
(A) formic acid (B) acetic acid (C) propionic acid (D) benzoic acid

24. The property which serves as a criterion of purity of an organic compound is: [BHU 1994]
(A) solubility in water (B) melting point (C) density (D) crystalline nature

ONANCE 41
 General Organic Chemistry

E X E R C IS E 8
[ OBJECTIVE ]
(A) FILL IN THE BLANKS
1. Among the given cations, ............. is most stable. [ JEE - 81 ]
(sec-butyl carbonium ion, tert-butyl carbonium ion; n-butyl carbonium ions) [ JEE - 81 ]
2. The compound having both sp and sp hybridized carbon atom is .............
2

3. ............. ring is most strained. (cyclopropane, Cyclobutane, Cyclopentane) [ JEE - 81 ]

4. The terminal carbon atom in butane is ............. hybridised. [ JEE - 85 ]
5. A ............. diol has two hydroxyl groups on ............. carbon atoms. [ JEE - 85 ]
6. Isomers which are .............mirror images are known as ............. (superimpossible, non-superimoposble,
enatnitomers. [ JEE - 88 ]
7. The shape of (CH3) is .............
+
[ JEE - 90 ]
8. The structure of the enol form of CH3–CO–CH2–CO–CH3 with intermolecular hydrogen bonding is
............. [ JEE - 93 ]
9. The bond dissociation energy needed to form the benzyl radical from toluene is ............. than the
formation of the methyl radical from methane. [ JEE - 94 ]
10. The IUPAC name of succinic acid is ............. [ JEE - 94 ]
11. The valence atomic orbitals on carbon in silver acetylide is .............hybridized. [ JEE - 90 ]
12 The kind of delocalisation involving sigma bond orbitals is called ............. [ JEE - 94 ]
(B) TRUE/FALSE
13. m-chloro-bromobenzene is an isomers of m-bromo-chloro benzene. [ JEE - 85 ]
14. Iodide is a better nucleophile than bromide. [ JEE - 85 ]
15. 2,3,4-trichloropentane has three asymmetric carbon atoms. [ JEE - 90 ]
16. During SN1 reactions, the leaving group leaves the molecule before the incoming group is attached to
the molecule. [ JEE - 90 ]

(C) OBJECTIVE QUESTION

17. Which of the following compounds will exhibit cis-trans (geometrical) isomerism? [ JEE - 83 ]
(A) 2-butene (B) 2-butyne (C) 2- butanol (D) butanal
18. The IUPAC name of the compound having the formula is: [ JEE - 84 ]
CH3

H3C–C–CH=CH2
CH3
(A) 3,3,3-Trimethyl-1-propene (B) 1,1,1-Trimethyl-2-propene
(C) 3,3-Dimehtyl-1-butene (D) 2,2-Dimethyl-3-butene
19. An isomer of ethanol is: [ JEE - 86 ]
(A) methanol (B) diethyl ether (C) acetone (D) dimethyl ether

ONANCE 42
 General Organic Chemistry

20. The bond between carbon atom (1) and carbon atom (2) in compound [ JEE - 87 ]

1 2
involves the hybridization as:
(A) sp2 and sp2 (B) sp3 and sp (C) sp and sp2 (D) sp and sp
21. The IUPAC name of the compound? [ JEE - 87 ]
CH2=CH–CH(CH3)2 is:
(A) 1,1-Dimethyl-2-propene (B) 3-Methyl-1-butene
(C) 2-Vinyl propane (D) none of the above
22. Which of the following will have least hindered rottion about carbon-carbon bond? [ JEE - 87 ]
(A) Ethane (B) Ethylene (C) Acetylene (D) Hexachloroethane
23. If two compounds have the same empirical formula but different molecular formulae, they must have:
(A) different percentage composition (B) different molecular weight [ JEE - 87 ]
(C) same velocity (D) same vapour density
24. The number of isomers of C6H14 is: [ JEE - 87 ]
(A) 4 (B) 5 (C) 6 (D) 7
25. Polarisation of electrons in acrolein may be written as: [ JEE - 88 ]

(A) CH2=CH–C=O (B) CH2=CH–CH=O (C) CH2=CH–CH=O (D) CH2=CH–CH=O

26. Keto-enol tautomerism is observed in: [ JEE - 88 ]
O O O O O
(A) C6H5–C–H (B) C6H5–C–CH3 (C) C6H5–C–C6H5 (D) C6H5–C–CH2–C–CH3

27. The compound which gives the most stable carbonium ion on dehydration is: [ JEE - 88 ]
CH3

(A) CH3–CH–CH2OH (B) CH3–C–OH

CH3 CH3
OH
(C) CH3–C–CH2–CH2OH (D) CH3–CH–CH2–CH3
28. The number of sigma and pi-bonds in 1-butene 3-yne are: [ JEE - 89 ]
(A) 5 sigma and 5 pi (B) 7 sigma and 3 pi
(C) 8 sigma and 2 pi (D) 6 sigma and 4 pi
29. Amongst the following, the most basic compound is: [ JEE - 90 ]
(A) benzylamine (B) aniline (C) acetanilide (D) p-nitroaniline
30. The formation of cyanohydrin from a ketone is an example of: [ JEE - 90 ]
(A) electrophilic addition (B) nucleophilic addition
(C) nucleophilic substitution (D) electrophilic substitution
31. The enolic form of acetone contains: [ JEE - 90 ]
(A) 9 sigma bonds, 1 pi bond and 2 lone pairs (B) 8 sigma bonds, 2 pi- bonds and 2 lone pairs
(C) 10 sigma bonds, 1 pi bond and 1 lone pair (D) 9 sigma bonds, 2 pi bonds and 1 lone pair

ONANCE 43
 General Organic Chemistry

32. The hybridisation of carbon atoms in C–C single bond of [ JEE - 91 ]

H–CC–CH=CH2 is:
(A) sp –sp
3 3
(B) sp2–sp3 (C) sp–sp2 (D) sp3–sp
33. Isomers which can be interconverted through rotation around a single bond are: [ JEE - 92 ]
(A) conformers (B) diastereomers (C) enantiomers (D) positional isomers
34. How many optically active stereoisomers are possible for butane-2,3 diol? [ JEE - 97 ]
(A) 1 (B) 2 (C) 3 (D) 4
35. The optically active tartaric acid is named as D-(+)-tartaric acid because it has a positive :
(A) optical rotation and is derived from D-glucose [ JEE - 99 ]
(B) pH in organic solvent
(C) optical rotation and is derived from D-(+)-glyceraldehyde
(D) optical rotation when substituted by deuterium
36. Which of the following has the highest nucleophilicity? [ JEE - 2K ]
(A) F– (B) OH– (C) CH3– (D) NH2–
37. Which of the following compounds will exhibit geometrical isomerism? [ JEE - 2K ]
(A) 1-phenyl-2-butene (B) 3-phenyl-butene
(C) 2-phenyl-1-butene (D) 1,1-diphenyl-1-propene
38. An SN2 reaction of an asymmetric carbon of a compound always gives: [ JEE - 01 ]
(A) an enantiomer of the substrate (B) a product with opposite optical rotation
(C) a mixture of diastereomers (D) a single stereoisomers
39. The number of isomers for the compound with molecular formula C2Br2ClFI is: [ JEE - 01 ]
(A) 3 (B) 4 (C) 5 (D) 6
40. Identify the correct order of reactivity in nucleophilic substitution reactions of the following compounds:
CH3 Cl NO2

[ JEE - 02 ]
1 2 3 4
(A) 1 > 2 > 3 > 4 (B) 4 > 3 > 2 > 1 (C) 2 > 1 > 3 > 4 (D) 2 > 3 > 1 > 4
41. Which of the following compounds exhibits, stereoisomerism? [ JEE - 02 ]
(A) 2-methyl butene-1 (B) 3-methyl butyen-1
(C) 3-methyl butanoic acid (D) 2-methyl butanoic acid
42. Which of the following hydrocarbons has the lowest dipole moment? [ JEE - 02 ]
H3C CH3
(A) C=C (B) CH3–HC=HC–CH3
H H
(C) CH3–CH2CH=CH2 (D) CH2=CH–CH=CH2
43. Which of the following represent the given mode of hybridization sp2–sp2–sp-sp from left to right?
(A) H2C=CH–CCN (B) HCC–C–CCH [ JEE - 03 ]
CH2
(C) H2C=C=C=CH2 (D)
H2C
ONANCE 44
 General Organic Chemistry
44. Among the following the molecule with the highest dipole moment is: [ JEE - 03 ]
(A) CH3Cl (B) CH2Cl2 (C) CHCl2 (D) CCl4

CH3
H H
3
45. 2 [ JEE - 04 ]
H H
CH3
C2 is rotated anticlockwise 120ºC about C2–C3 bond. The resulting conformer is: [ JEE - 04 ]
(A) partially eclipsed (B) eclipsed (C) gauche (D) staggered

46. Which of the following resonating structures of 1-methoxy-1,3-butadiene is least stable ?

(A) CH2 – CH = CH – CH = O – CH3 (B) CH2 = CH – CH2 – CH = O – CH3

(C) CH2 – CH – CH = CH – O – CH3 (D) CH2 = CH – CH = CH – O – CH3

[ JEE - 05 ]

CH3 CH3 CH3

47. CH3O NO2 compound on hydrolysis in aqueous acetone
H Cl CH3
will give :
CH3 CH3 CH3
(i) CH3O NO2
H OH CH3
CH3 CH3 CH3
(ii) CH3O NO2
OH H CH3

CH3 CH3 CH3

(iii) CH3O NO2
H CH3 OH
(A) Mixture of (i) and (ii) (B) Mixture of (i) and (iii)
(C) Only (iii) (D) Only (i) [ JEE - 05 ]

48. The IUPAC name of C6H5COCl is: [ JEE - 06 ]

(A) Benzoyl chloride (B) Benzene chloro ketone
(C) Benzene carbonyl chloride (D) Chloro phenyl ketone

49. In the following reaction, [ JEE - 07 ]

O
N conc. HNO
  3  X
H conc. H 2SO 4

ONANCE 45
 General Organic Chemistry
The structure of the major product X is
O2N
O O
(A) NO2 (B)
N N
H H

O O
(C) N (D) O2N N
H H
NO2

50. Among the following, the least stable resonance structure is: [ JEE - 07 ]
O O
(A) N (B) N

O O

O O
(C) N (D) N
O
O

51. The number of structural isomers for C6H14 is [ JEE - 07 ]

(A) 3 (B) 4 (C) 5 (D) 6

52. The number of stereoisomers obtained by bromiatnio of trans-2-butene is: [ JEE - 07 ]

(A) 1 (B) 2 (C) 3 (D) 4

53. The correct stability order for the following species is [ JEE - 08 ]

(I) (II) (III) O

(IV)
O
(A) (II) > (IV) > (I) > (III) (B) (I) > (II) > (III) > (IV)
(C) (II) > (I) > (IV) > (III) (D) (I) > (III) > (II) > (IV)

(D) OBJECTIVE QUESTIONS (MORE THAN ONE CORRECT)

54. Only two isomeric monochloro derivative are possible for: [ JEE - 86 ]
(A) n-butane (B) 2,4,dimethyl pentane
(C) benzene (D) 2-methyl propane
55. The compound in which C uses its sp3-hybrid orbitals for bond formation is: [ JEE - 89 ]
(A) HCOOH (B) (H2N)2CO (C) (CH3)3COH (D) CH3CHO
56. Which of the following have asymmetric carbon atom? [ JEE - 89 ]
Cl Br H Cl H Cl H H
(A) H—C—C—H (B) H—C—C—Cl (C) H—C—C—D (D) H—C—C—CH3

H H H H H H Br OH

ONANCE 46
 General Organic Chemistry

57. The molecules that will have dipole moment are: [ JEE - 92 ]
(A) 2,2-Dimethyl propane (B) Trans-2-pentene
(C) cis 3-Hexene (D) 2,2,3,3-Tetramethyl butane
58. What is the decreasing order of strength of the bases: [ JEE - 93 ]
OH–, NH2–, H–CC– and CH3–CH2–?
(A) CH3–CH2– > NH2– > H–C C– > OH–
(B) H–CC– > CH3–CH2– > NH2– > OH–
(C) OH– > NH2– > H–CC– > OH– > CH3–CH2–
(D) NH2– > H–CC– > OH– > CH3–CH2–
59. Which of the following compounds will show geometrical isomerism? [ JEE - 98 ]
(A) 2-Butene (B) Propene (C) 1-Phenyl propane (D) 2-Methyl butene
60. Tautomerism is exhibited by: [ JEE - 98 ]

(A) CH=CH–OH (B) O O

(C) O (D) O

O O
61. Match the following column [ JEE - 06 ]

column–I Column–II
(A) CH3–CHBr–CD3 on treatment with alc. KOH (p) E1 reaction
gives CH2=CH–CD3 as a major product
(B) Ph–CHBr–CH3 reacts faster than Ph–CHBr–CD3 (q) E2 reaction
Ph–CHBr–CD3
(C) Ph–CH2–CH2Br on treatment with (r) E1cb reaction
C2H5OD/C2H5O– gives Ph–CD=CH2 as the
major product
(D) PhCH2CH2Br and PhCH2Br react with same rate (s) First order reaction

62. STATEMENT-1 : Molecules that are not superimposable on their mirror images are chiral
because
STATEMENT-2 : All chiral molecules have chiral centres. [ JEE - 07 ]
(A) Statement–1 is True, Statement-2 is True, Statement-2 is a correct explanation for
Statement-1
(B) Statement–1 is True, Statement-2 is True, Statement-2 is NOT a correct explanation for
Statement-1
(C) Statement-1 is True, Statement-2 is False
(D) Statement-1 is False, Statement-2 is True

ONANCE 47
 General Organic Chemistry

OH

63. In the reaction NaOH(aq.)/Br2) the intermediate(s) is (are) [ JEE - 10 ]

O O O O
Br
(A) (B) (C) (D)
Br
Br Br
Br Br

64. The compound P, Q and S [ JEE - 10 ]

O
COOH OCH3 C
O

HO H3C
P Q S
Were separately subjected to nitration using HNO3 / H2SO4, mixturee. The major product formed in
each case, respectively is:
COOH OCH3
C
(A) HO O
H 3C
NO2 NO2 O2N

OCH3
COOH
C
(B) O
H 3C
HO NO2 NO2 NO2

COOH NO2
OCH3
C
(C) HO O
NO2 H3C NO2

COOH
OCH3
C
(D) HO O NO2
NO2 H3C NO2

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 General Organic Chemistry

65. Amongst the following the total number of compounds soluble in aqueous NaOH is [ JEE - 10 ]
H3C CH3
N COOH OCH2CH2 OH
CH2OH

NO2 OH CH2CH3 COOH

CH2CH3

N
H3C CH3

ONANCE 49
 General Organic Chemistry

E X E R C IS E 9
1. Write structural formulf for all the isomeric alcoholss having the molecular formula C4H10O.
[ JEE - 84 ]
2. Write the structure of all the possible isomers of dichloroethen. Which of them will have zero dipole
moment. [ JEE - 85 ]
3. Arrange the following in the order of their increasing basicity. [ JEE - 86 ]
p-toluidine, N, N-dimethyl-p-toluidine, p-nitroaniline, aniline.
4. Write tautomeric forms of phenol. [ JEE - 92 ]
5. Draw the stereochemical structures of the products in the following reactions: [ JEE - 94 ]
C2H5
NaOH H2
(i) Br H  
 (ii) R–CC–R   
SN 2
Lindlar catalyst
C2H5
6. Write down the structures of the stereoisomers formed when cis-2-butene is reacted with bromine.
[ JEE - 95 ]
7. Discuss the hybridization of carbon atoms in allene (C3H4) and show the p-orbital overlaps.
8. Identify the pairs of enantiomers and diastereomers from the following: [ JEE - 2K ]

CH3 CH3 CH3

H OH H OH HO H
(I) (II) (III)
HO H HO H H OH

CH3 CH3 CH3

9. (a) Draw Newmann’s projection for the less stable staggered form of butane. [ JEE - 04 ]
(b) Relatively less stability of the staggered form is due to:
(i) Torsional strain
(ii) van der Waal’s strain
(iii) Combination of the above two
10. obs = i xi [ JEE - 05 ]
where i is the dipole moment of stable conformer and xi is the mole fraction of that conformer.
(a) Write stable conformer for Z–CH2–CH2–Z in Newmann’s projection.
If solution = 1.0 D and mole fraction of anti form = 0.82, find Gauche
CHDY
(b) Write most stable meso conformer of
CHDY
If (i) Y = CH3 about C2–C3 rotaion and (ii) Y= OH about C1 – C2 rotation

ONANCE 50
 General Organic Chemistry

ANSWERSHEET
Exercise - 01
19. C 20. B 21. D 22. B

Exercise - 02
1. D 2. B 3. A 4. B 5. C 6. A
7. B 8. C 9. C 10. D 11. B 12. D
13 . A 14. B 15. B 16. C 17. A 18. A
19 . C 20. A 21. C 22. A 23. C 24. C
25 . D 26. D 27. C 28. A 29. D 30. C
31 . D 32. A 33. C 34. B 35. A 36. C
37 . B 38. D 39. C 40. B 41. C 42. C
43 . B 44. B 45. D 46. A 47. B 48. B
49 . A 50. B 51. B 52. C 53. A 54. B
55 . A 56. C 57. A 58. A 59. A 60. B
61 . C 62. C 63. A 64. D 65. C 66. A
67 . B

Exercise - 03
1. (a) has octet completed atoms

O O O

(b) O O O O O O
All contribute equally to resonance hybrid.
(c) H–O–CN

H–N=C=O O=C=N The conjugated bases are canonicals to each other

(d) CH 2=CH=CH–CH 2–CH 3 is ustable.
(cumulated diene)

CH2
(e) is more stable due to greater delocalisation

O O
H
(f) H—C—N H—C== N
H sp2 H
H
O O
H
Ph— S— N Ph—S== N
H sp2 H
O H O
Due to delocalisation, the hybridization changes to sp2.

ONANCE 51
 General Organic Chemistry

(g) is aromatic, more stable hence less Hhydrogenation

(h) The compound being non planar, no resonance is possible whereas in

cyclooctatetraene
benzene due to delocalisation all bonds are partial double bonds.
2. (a) IV , I , II , III (d) III , IV , I , II (e) II , I , IV , III
(f) II , I , IV , III (i) IV , I , III , II
(j) I , II , IV , III (k) IV , I , II , III
3. (a) I , IV , II , III (b) II , I , IV , III (d) IV , I , III , II

4. (a) II , I , III , IV (b) IV , III , II , I (d) IV , III , I , II

5. (a) II > I > III (b) II > I > III

Exercise - 04
1. C 2. D 3. C 4. B 5. B 6. B
7. A 8. D 9. B 10. A 11. C 12. D
13 . B 14. C 15. C 16. C 17. A 18. D
19 . B 20. D 21. A 22. A 23. B 24. D
25 . B 26. A 27. C 28. A 29. A 30. C
31 . C 32. A 33. A 34. C 35. A 36. A
37 . B 38. A 39. A 40. D 41. C 42. C
43 . A 44. C 45. D 46. A 47. D 48. A
49 . B 50. D 51. B 52. C 53. A 54. D
55 . C 56. D 57. C 58. A 59. C 60. C
61 . D 62. A 63. C 64. B 65. A 66. A
67 . B 68. A 69. D 70. B 71. A 72. D
73 . B 74. A 75. C

Exercise - 05
1. (a) IV, III, II,I (b) II, III, I, IV (c) I, II, IV, III (d) I, II, III, IV
(e) IV, III, I, II (f) IV, III, I, II (g) IV, III, I, II (h) IV, I, III, II
2. (a) III, II, I, IV (b) III, I, II, IV (c) III, II, I, IV (d) I, III, II, IV
(e) IV, III, II, I
3. (a) II, III, I (b) III, I, II (c) III, I, II (d) II, III, I
(e) III, II, I (f) I, III, II (g) II, I, III (h) II, I, III

4. (a) III, II, I (b) III, II, I (c) III, II, I (d) II, III, I
(e) II, III, I
5. (a) II, I, III (b) III, I, II (c) II, III, I (d) II, I, III (e) III, II, I (f) I, III, II
(g) II, III, I
6. (a) III, I, II (b) III, II, I (c) III, II, I (d) III, II, I (e) III, I, II

ONANCE 52
 General Organic Chemistry

O O

7. (a) (b) HO N O
O O
CH3
(c) CH2–O=CH–CH2 (d) H3CO==CH—CH== P CH3
CH3

CH3
P
(e) (f) Cl C== C— H
CH3

O O
(g) HO—S== == N—N== NH2 (h) H2N== CH—CH== S—OH
O O
CH3
O NO2

(i) H2N== CH—O (j) (k) O

N N CH3
O
H
O
C
(l) OH (m) H3CO== CH—CH==CH2

HO

(n) (o) (p) CH2–CH=N–CH 3

N

O O
H3C O
–S=CH–S–
(q) (r) (s)
O CH3 O O

8. (a) IV , I , II , III (b) II , I , III , IV (c) IV , II , I , III (d) III , II , I , IV

9. (a) II , I , IV , III (b) I , IV , III , II (c) I , II , IV , III
10 . (a) II , III , I , IV (b) I , II , IV , III (c) III , I , II , IV

11 . (a) I > III > II (b) III > I > II

12 . (a) due to hyperconjugation travelling upto carbocation

H H
H–C–CH=CH–CH2 H–C=CH–CH=CH2

H H

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 General Organic Chemistry

(b) Radical can delocalise with both the  bonds

CH2=CH–CH=CH–CH2

CH2=CH–CH–CH=CH2

CH2–CH=CH–CH=CH2
(c) Due to delocalisation

Exercise - 06

1. ACD 2. BCD 3. BC 4. ABD 5. BC 6. ABD

7. ABCD 8. BC 9. AB 10. AD 11. BC 12. AD
13 . AB 14. ABC 15. BCD 16. BCD 17. CD 18. ABCD
19 . (a) I < II (b) I > II (c) I > II (d) I > II
20 . BD 21. ACD 22. BCD 23. BCD 24. BC 24. BCD
25 . ABC 26. AC
27 . a – r, b – q s, c–s , d – pr 28. A - r, B - p, C - q, D - rs.
29. A-r, B-p, C-s, D-q 30. A-q, B-r, C-p, D-t, E-s
31. A-r, B-p, C-s, D-q
32. B 33. B 34. C 35. A 36. B 37. B
38. C 39. B 40. homolytic, heterolytic 41. free radicals
42. different electronegativity 43. more
44. free radical mechanism 45. electrophillic addition
46. nucleophiles, donate, pair 47. elimination reaction 48. sextet
49. permanent 50. crystallisation 51. boiling points
52. decreases 53. T 54. F
55. F 56. T 57. F 58. F 59. T 60. F
61. F 62. F 63. F 64. T 65. T 66. F

Exercise - 07
1. B 2. A 3. A 4. A 5. A 6. C
7. A 8. A 9. C 10. A 11. E 12. C
13. D 14. B 15. C 16. A 17. C 18. E
19. A 20. A 21. C 22. A 23. B 24. B

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 General Organic Chemistry

Exercise - 08

1. tert. butyl carbonium ion 2. propadiene 3. cyclopropane

4. sp3 5. vicinal, adjacent
6. non-superimposbale, enantiomers
7. planar 8. CH3–C=CH–C–CH3 9. Less
OH-----O
10. butane 1,4,-dioic acid 11. sp 12 hyperconjugation
13. F 14. F 15. F 16. T
17. A 18. C 19. D 20. C
21. B 22. A 23. B 24. B
25. D 26. D 27. B 28. B
29. A 30. B 31. A 32. C
33. A 34. B 35. C 36. C
37. A 38. B 39. D 40. C
41. D 42. B 43. A 44. A
45. C 46. D 47. A 48. B
49. B 50. A 51. C 52. A
53. D 54. AD 55. CD 56. CD
57. BC 58. A 59. AC 60. ACD
61. A-q, B-q, C-rs, D-ps 62. C 63. ABC
64. C 65. 4

ONANCE 55