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ORGANIC CHEMISTRY
GOC
ELECTRONIC DISPLACEMENT EFFECTS
Q.3 In each of the following pairs, determine whether the two represent resonance forms of a single
species or depict different substances. If two structures are not resonance froms, explain why.
(a) and
(b) and
(c) and
GOC [2]
Q.5 Which one of the following pairs of structures does not represent the phenomenon of resonance?
O O
|| |
(A) H 2C CH C H ; CH 2 CH C H
(B) CH 2 CH CH Cl ; CH 2 CH CH Cl
O O
|| |
(C) (CH 3 ) 2 CH C O ; (CH 3 ) 2 CH C O
O O
|| |
(D) CH 3 CH 2 C CH 3 ; CH 3 CH C CH 3
(e) CH2= CH C H 2 (f) CH2 = CH CH = N H
(e) (f)
Q.8 Which of the following is not a valid resonating structure of the other three?
+ + +
NH2 NH2 NH2 NH2
(i) (a) + (b) (c) (d)
O O O O
+ + + + +
NO NO NO NO
(ii) (a) (b) (c) (d)
+ + +
NH2 NH2 NH2 NH2
(iii) (a) CH 2 N O (b) CH 2 N O (c) CH 2 N O (d) CH 2 N O
| | | |
CH 3 CH 3 CH 3 CH 3
GOC [3]
Q.9 Draw the resonance forms to show the delocalization of charges in the following ions
O O
+
(a) CH3 C CH2 (b) H C CH = CH CH2 (c) CH2
(h) (i) CH3 CH = CH CH = CH CH CH3
O
(j) CH3 CH = CH CH = CH CH 2
(iii) (a) (b) (c)
(iv) (a) (b) (c)
(v) (a) (b) (c) (d)
(vi) (a) CF3 CH 2 (b) CCl3 CH 2 (c) CBr3 CH 2
GOC [4]
Q.11 Write stability order of following intermediates:
CH 3
|
(i) (a) CH 3 CH 2 (b) CH 3 CH CH 3 (c) CH 3 C
|
CH 3
(ii) (a) (b) (c)
(iii) (a) (b) (c)
(iv) (a) HC C (b) CH 2 CH (c) CH 3 CH 2
Q.12 Rank the following sets of intermediates in increasing order of their stability.
(i) (a) C6H5+ (b) pNO2(C6H4)+ (c) pCH3(C6H4)+ (d) pClC6H4+
CH2 CH2 CH2
N OMe
O O
GOC [5]
(iii) (a) (b) (c)
(iv) (a) HC C (b) CH 2 CH (c) CH 3 CH 2
Q.14 Among the following molecules, the correct order of C C bond lenght is
(A) C2H6 > C2H4 > C6H6 > C2H2 (B) C2H6 > C6H6 > C2H4 > C2H2(C6H6 is benzene)
(C) C2H4 > C2H6 > C2H2 > C6H6 (D) C2H6 > C2H4 > C2H2 > C6H6
Q.15 Which of the following is (are) the correct order of bond lengths :
(A) C C > C = C > C C > C N (B) C = N > C = O > C = C
(C) C = C > C = N > C = O (D) C C > C = C > C C > C H
Q.18 CH2 = NH
I II III IV
Among these compounds, the correct order of C N bond lengths is :
(A) IV > I > II > III (B) III > I > II > IV
(C) III > II > I > IV (D) III > I > IV > II
GOC [6]
Q.20 CH3O CH = CH NO2 I
CH2 = CH NO2 II
CH2 = CH Cl III
CH2 = CH2 IV
Which of the following is the correct order of C C bond lengths among these compounds :
(A) I > II > III > IV (B) IV > III > II > I
(C) I > III > II > IV (D) II > III > I > IV
Q.21
These are three canonical structures of naphthalene. Examine them and find correct statement
among the following :
(A) All C C bonds are of same length
(B) Cl C2 bond is shorter than C2 C3 bond.
(C) C1 C2 bond is longer than C2 C3 bond
(D) none.
Q.22 In which of the following pairs, indicated bond having less bond dissociation energy :
(a) CH 3 CH 2 Br & CH 3 CH 2 Cl
(b) CH 3 CH CH Br & CH 3 CH CH 3
|
Br
(c) &
(d) &
(e) &
(f) &
GOC [7]
Q.24 A canonical structure will be more stable if
(a) it has more number of bonds than if it has less number of bonds.
(b) the octets of all atoms are complete than if octets of all atoms are not complete.
(c) it involves cyclic delocalization of (4n + 2) electrons than if it involves acyclic delocalization
of (4n + 2) electrons.
(d) it involves cyclic delocalization (4n) electrons than if it involves acyclic delocalizationof
(4n) electrons.
(e) +ve charge is on more electronegative atom than if +ve charge is on less electronegative atoms.
(f) ve charge is on more electronegative atom than if ve charge is on less electronegative atom.
+
(ii) (a) (b) (c) (d)
+
(iii) (a) (b) (c) (d)
N
H
Q.27 Consider the given reaction:
+ 3H2 Pd /C
In the above reaction which one of the given ring will undergo reduction?
Br
Q.28 AgNO
3 A
GOC [8]
Q.29 Which of the following pairs has higher resonance energy :
(e) &
(c) CH 2 CH N H & HN CH N H (d) CH2 = CH F & CH2 = CH Br
(e) & CH2 = CH C H 2
(c) & CH2 = CH CH = CH2 (d) & CH2 = CH C H 2
(e) &
GOC [9]
Q.34 Explain why which compound is aromatic, antiaromatic or nonaromatic.
H
+
(a) N (b) N S (c) (d)
O O O
isoxazole 1,3-thiazole pyran pyrylium ion
O NH2
N
(e) (f) (g)
O N N O
H
1,2-dihydropyridine H
-pyrone
cytosine
Q.35 Identify less stable canonical structure in each of the following pairs :
(a) C H 2 O CH 3
CH 2 O CH 3 (b)
(c) (d)
(e)
CH2 CH2
Q.36 Identify more stable canonical structure in each of the following pairs :
O O CH2 CH2
(a) C C (b)
.. C C
H OH H OH Me2N OMe Me2N OMe
(c) (d)
(e) C H 2 CH CH O
CH 2 CH CH O (f)
GOC [10]
Q.37 Rank the following sets of intermediates in increasing order of their stability.
CH2 CH2
Cl N C N
O O
(iii) (a) CH 2 CH (b) CH 2 CH 3
||
O
Q.38 In each of the following pairs of ions which ion is more stable:
(a) (I) C6H5 CH 2 and (II) CH2=CH CH 2
(b) (I) CH3 CH 2 and (II) CH2 = CH
(e) CH2CH=NH CH2=CHNH
O O
(f) +
CH3C=CHCHCH3 CH3CCH=CHCH3
+
O O O O
(g) CH3CCHCCH3 CH3C=CHCCH3
NH2 NH2
(h) +
CH3CH2CNH2 CH3CH2C = NH2
+
GOC [11]
Q.39 Select the least stable resonating structure in each of the following sets of carbocation.
O O
+ + +
(i) (a) CH2 = CH N (b) CH2 CH N
O O
O O
+ + + +
(c) CH2 CH N (d) CH2 CH = N
O O
(ii) (a) CH 2 CH CH CH NH 2 (b) CH 2 CH CH CH NH 2
(c) CH 2 CH CH CH NH 2 (d) CH 2 CH CH CH NH 2
(iii) (a) H 2 C CH CH = CH O CH3 (b) H 2 C CH = CH CH = O CH3
(c) H2C = CH C H C H O CH3 (d) H2C = CH CH CH = O CH3
Q.40 Rank the following sets of intermediates in increasing order of their stability.
CH2 CH2 CH2
H
(iii) (a) (b) H (c) C H
C H H
H
H C H
H
Me Ph +
| |
(v) (a) Me C (b) Ph C (c) Ph CH 2 (d)
| |
Me Ph
GOC [12]
+
+
(vi) (a) (b) (c)
+
+
(d) (e)
+
Q.41 Which of the following groups cannot participate in resonance with other suitable group :
(a) COOH (b) CO O (c) COCl (d) NH 3
(e) C H 2 (f) C H 2 (g) CH 2 N
|
CH 3
Q.44 Which of the following groups can either donate or withdraw a pair of electrons in resonance
depending upon situation :
(a) NO2 (b) NO (c) CH = CH2 (d) CHO
(e) NH2 (f) N = NH
Q.45 Which of the following groups can only withdraw a pair of electrons in resonance depending
upon situation :
(e) N Me3 (f) CONH2
Q.46 Which of the following group can participate in resonance with other suitable group :
(a) CH 2 O (b) CH 2 C H 2 (c) CH C H2 (d)
2
(e) (f) BH2 (g) P Ph
3
GOC [13]
Q.47 In which of the following molecules electron density in ring is minimum :
Q.51 Which one of the following molecules has all the effect, namely inductive, mesomeric and
hyperconjugative?
(A) CH3Cl (B) CH3CH = CH2
(C) CH 3 CH CH C CH 3 (D) CH2 = CH CH = CH2
||
O
GOC [14]
Q.54 Arrange following compounds in decreasing order of electrophilic substitution.
CH3 CH3 H
CH3 HCCH3 CH3CCH3 HCCH3
(A) i > ii > iii > iv (B) iii > iv > ii > i (C) i > iv > ii > iii (D) i > ii > iv > iii
(c) and CH 3 CH 2 Cl
(d) CH 2 CH CH CH 2 and CH 2 CH 2 CH 2 CH 3
(e) CH 2 CH CH CH 2 and CH 2 CH NO 2
(f) and
Q.57 Choose the more stable alkene in each of the following pairs. Explain your reasoning.
(a) 1-Methylcyclohexene or 3-methylcyclohexene
(b) Isopropenylcyclopentane or allylcyclopentane
(c) or
GOC [15]
Q.59 Compare heat of hydrogenation (Decreasing order)
(i) &
(ii) &
(iii) &
CH3
(iv) CH2 = CH CH & CH3 CH = C
CH3
(i)
A B D
(ii)
Q.62 Among the following pairs identify the one which gives higher heat of hydrogenation :
(a) and
(b) and
(d) and
GOC [16]
Q.63 Write increasing order of heat of hydrogenation :
Q.65 Rank the following sets of intermediates in increasing order of their stability.
+
(i) (a) C (b) Ph CH 2 (c) (d) Me C Me
|
Me
(ii) (a) CH 2 CH (b) CH 2 CH CH 2 (c) CH2 (d) CH3
GOC [17]
CH2
CH2 CH2
+ +
CH2 CH2 +
(iv) (a) (b) (c)
+ + +
(v) (a) (b) (c)
(vi) (a) (b) (c)
Q.66 Which of the following statements would be true about this compound :
GOC [18]
ANSWER KEY
Q.1 (a), (c), (d), (g), (j), (l), (m)
Q.2 a = Resonance form, b= A, c = C, d= A & B, e=B&C, f = 0, g = B, h = B
Q.3 (a) is resonance form; (b) is not resonance form due to different number of l.p. and b.p.;
(c) is not resonance form due to different number of l.p. and b.p
Q.4 A Q.5 D Q.6 (b), (d), (e) Q.7 (b), (d), (e) Q.8 (i) a (ii) c (iii) c
O O
| |
Q.9 (a) CH 3 C CH 2 (b) H C CH CH CH 2
+ +
CH2 CH2 CH2 CH2 CH2
+ +
(c)
+
(d) +
(e) O O O O
+
(f) NH (g) (h)
O+
O
(i) CH3 CH CH CH CH CH CH3 (j) CH3 CH CH CH CH CH 2 ]
Q.12 (i) b < d < a < c (ii) b>c>a (iii) c>a>b (iv) c>a>b
(v) a>b
Q.20 A Q.21 B
GOC [19]
Q.23 (a) Due to resonance C H 2 CH = Cl+
(b) In CH2=CHOCH3, there is single bond character due to resonance
C H 2 CH = O+ CH3
(c) Conjugate base of CH3SH ie, CH3S is more stable than conjugate base of CH3OH, ie CH3O
(d) In CH2=CHNH2 lone pair of N is delocalized C H 2 CH = N H 2
Q.24 (a), (b), (c), (f) Q.25 (a), (b) Q.26 (i) a, b, d (ii) a, c (iii) b, c, d
Q.27 A Q.28 A, B, D Q.29 (a) II, (b) I, (c) II, (d) II, (e) II
Q.30 (a) II, (b) II, (c) II, (d) II, (e) II Q.31 (a) I, (b) II, (c) II, (d) I, (e) I
Q.32 (a) II, (b) I, (c) I, (d) II , (e) I Q.33 (a) II, (b) I, (c) I, (d) I, (e) I
Q.34 (a) A, (b) A, (c) N.A. (d) A, (e) A, (f) N.A. (g) A Q.35 (a) I, (b) II, (c) II, (d) II, (e) I
Q.36 (a) I, (b) I, (c) I, (d) I, (e) II, (f) II
Q.37 (i) a<b (ii) b>c>a>d (iii) a>b
Q.38 (a) I, (b) I, (c) II, (d) II, (e) II, (f) I, (g) II, (h) II Q.39 (i) c (ii) a (iii) c
Q.41 (d) Q.42 (c), (f) Q.43 (a), (b), (c), (d), (f) Q.44 (b), (c), (f)
Q.45 (f) Q.46 (a), (e), (f), (g) Q.47 D Q.48 B Q.49 A
Q.56 (a) I I , (b) I I , (c) I , (d) I , (e) I I , (f) I I Q.57 (a) i , (b) i , (c) ii
Q.58 (a) 4658, (b) 4638, (c) 4632, (d) 4650, (e) 5293 Q.59 (i) 2 > 1 (ii) 2 <1 (iii) 1 < 2 (iv) 1 > 2
Q.60 (i) D > C > B > A (ii) E > C > D > B > A Q.61 (I) d > c > b > a; (II) a > b > c > d
Q.64 (i) c > b > a (ii) a>b>c>d (iii) a>b (iv) c>b>a
Q.65 (i) a c > b > d (ii) d>b>c>a (iii) b>a>c (iv) a>c>b
(v) b>c>a (vi) b>c>a Q.66 C
GOC [20]