PRACTICE SHEET - 08 (Chemistry)

Basic Concept of Organic Chemistry

76. Guanidine is among the strongest neutral base

NH
C
H2N NH2
Guanidine
The reason for the greater basicity of guanidine is
(1) Presence of three nitrogen atoms in the compound
(2) The delocalization of lone pairs of N
(3) The planar structure of guanidine molecule
(4) The stability of conjugate acid due to resonance

77. In which of the following species lone pair of e– at Nitrogen atom is not involved in delocalization?

N R


N


(1) (2)
|
O H


H


(3) (4) N
N H


78. Which of the following species will have highest resonance energy?
H H H O
–C—C –C—C



(1) (2)
H H H
C H
H
O O
O O
C C


(3) C C (4) H3C –C CH3



H3C CH CH3
– C
H3C O
79. Least basic species among the following is

(1) (2)
N
N
H

(3) (4)
N N
H
80. Given set of resonating structures and their stability is provided in bracket. Select which one is incorrectly
matched?
—
 
(1) CH2  CH — CH  CH2  CH2 — CH  CH2 — CH2 (I  II)

  
(2) CH2 — O— CH3  CH2  O— CH3 (II  I)
  


 
(3) CH2  CH — Cl  CH2 — CHCl  (II  I)



I
(4) All of the above are correctly matched
81. Arrange following three given aromatic compounds in increasing order of resonance energy per ring.

I II III

(1) III < II < I (2) II > III > I

(3) I < II < III (4) I < III < II

82. Select the correct option for stability of following structures.

– +
O CH2 O CH2 O CH2

I II III
(1) I > II > III (2) II > I > III
(3) II > III > I (4) III > I > II
83. Which of the following compounds will not show resonance?
+
CH2

(1) (2) CH2 = CH—CH = CH — CH2

+
NH3

(3) (4)

84. Among the following three canonical structures what would be their relative contribution in hybrid?
I. CH2  CH — CH — CH — CH  CH2
 


II. CH2  CH — CH — CH  CH — CH2

III. CH2 — CH  CH — CH  CH — CH2
(1) I > II > III (2) III > II > I
(3) I > III > II (4) III > I > II

85. The most stable resonating structure of methoxyethene is

    
(1) CH3 — O — CH — CH2 (2) CH3 — O  CH — CH2


  
(3) CH3 — O — CH  CH2 (4) CH3 — O— CH — CH2

86. Which of the following is pair of resonance structure?

(1) (2) and

O OH

(3) (4)

87. The C—Cl bond length is shortest in

(1) CH3 — Cl (2) C6H5 — CH2 — Cl

(3) CH2 = CH — CH2 — Cl (4) CH2  CH — Cl 


88. The correct stability order of the following resonance structure is

       
H2 C  N  N H2 C— N  N H2 C— N  N H2 C— N  N
I II III IV
(1) I > II > IV > III (2) I > III > II > IV
(3) II > I > III > IV (4) III > I > IV > II

89. Which of the following has maximum number of resonating structures?

(1) (2)

(3) (4)

90. Most unstable resonating structure of phenol is

+
OH O—H
(1) (2) –

+ +
O—H O—H
(3) (4) –

91. Which of the following pairs are resonance structures?

I. CH3CH = CH2 and

+
O O
II. CH3 — C — H and CH 3 — C– — H

–
O O
III. CH3 — C — H and CH 3 — C+ — H

IV. CH3 — O — CH3 and CH3CH2OH

(1) I (2) II
(3) III (4) IV
92. Which of the following contains only aromatic species?

 
(1) , and (2) , and


  O
(3) , and (4) , and
N N
N
H
H
93. Pick out the most acidic species from the following.

H H
(1) (2)

H H

(3) (4)
H H H H

94. Which of the following will give light yellow precipitate of AgBr with AgNO3?

Br

(1) (2)

Br

Br
(3) (4) H2C = CH – Br

95. In which of the following alkene hyperconjugation does not take place?

(1) (2)

(3) (4)

96. In which of the following alkenes hyperconjugation is not possible?

H H
CH2
(1) (2) H
H

(3) H2C = CH2 (4)

97. In which of the following molecules all the effects namely inductive, mesomeric and hyperconjugation operate?

(1) Cl (2) CH3

H3C

O
(3) C CH3 (4)

CH3

98. Which of the following is most stabilised by hyperconjugation?

CH3 CH2CH3

(1) (2)

CH3
H3C CH3 H3C CH3
CH C

(3) (4)

99. Which one of the following compounds is not aromatic?

H
H
(1) (2)

(3) (4)

100. Choose the nonaromatic compound among the following.

O
O
(1) (2)

+
(3) N (4)
H H
101. The compound which is not aromatic is

(1) N N—H (2)

+ N
H

(3) O (4)
N O
H
102. Select the aromatic species among following.

(1) (2)

(3) (4)

103. Which of the following carbocations will show highest no. of hyperconjugative forms?

CH3 CH3
| |
(1) CH3 CH2 — C (2) CH3 — C
| |
CH3 CH3

 
(3) CH3 CH2 (4) CH3 —CH — CH3

104. Heterocyclic aromatic compound is

(1) (2)
N N
H H

(3) (4)
N
H

105. Hyperconjugation involves overlap of the following orbitals

(1) - (2) p-p
(3) - (4) - p