Professional Documents
Culture Documents
Contents
Topic Page No.
Theory 01 - 03
Exercise - 1 04 - 20
Exercise - 2 21 - 35
Exercise - 3 36 - 40
Exercise - 4 41 - 41
Answer Key 42 - 45
Syllabus
Resonance and hyperconjugation, Polarity and inductive effects in alkyl halides; Reactive
intermediates produced during homolytic and heterolytic bond cleavage; Formation, structure
and stability of carbocations, carbanions and free radicals, acidic strength & basic strength.
C ---- C ---- C -- G
But the effect is insignificant beyond third carbon atom.
This effect is transmitted through the chain of bonds and diminishes. with increasing chain
length.
I group :
The group which withdraws electrons is known as I group and its effect is known as I effect.
I power of various group & cation.
> > > NO2 > SO2R > CN > CHO > COOH > F > Cl > Br >
I > OR > OH > C CH > NH2 > C6H5 > CH = CH2 > H.
I power of groups in decreasing order with respect to the reference H
+ I group :
The group which donates or gives electron is known as + I group and effect is known as + I effect.
Alkyl groups, O , CO O are + I groups.
> > C(CH3)3 > CH (CH3)2 > CH2 CH3 > CH3 > D > H
+ I power in decreasing order with reference to H
(b) + I power of same type of alkyl groups :
+ I power number of Cs in same type of alkyl group
For example
Resonance
When a molecule or ion can be represented by two or more structures which have the same
arrangement of atomic nuclei but differ in distribution of electrons, the phenomenon is called as
Resonance. The various structures are called contributing or resonating structures. None of these
structures truly represents all the properties of that molecule or ion. The actual structure is a resonance
hybrid of several contributing structures.
+ M effect (+R) :
C or
When flow of e pair (movement) starts from the group (G). It takes place when G has a lone pair
or an extra electron (in ion).
Groups which shows '+ m' effect are :
> NH2 > NHR > NR2 > OH > OR > NH C R > O C R > Ph, CH3 > F >
|| ||
O O
Cl > Br > I, N = O.
M effect ( R) :
C C G or
Hyperconjugation
When (C H) sigma electrons are in conjugation to pi bond, this conjugation is known as (CH),
conjugation, excessive conjugation or hyperconjugatioon.
Structural requirement for hyperconjugation:
(A) Compound should have at least one sp 2 -hybrid carbon of either alkene alkyl carbocation or alkyl
free radical.
(B) -carbon with respect to sp 2 hybrid carbon should have at least one hydrogen.
If both these conditions are fulfilled then hyperconjugation will take place in the moelucle.
(C) Hyperconjugation is of three types :
(i) (C H), conjugation : This type of conjugation occurs in alkenes.
(ii) (CH), positive charge conjugation : This type of conjugation occurs in alkyl carbocation.
(iii) (CH), odd electron conjugation : This type of conjugation occurs in alkyl free radicals-
X
|
C C = C where X - halogen
|
Aromaticity :
Aromatic Character : [The Huckel (4n + 2) rule]
The following three rules are useful in predicting whether a particular compound is aromatic or nonaromatic.
A-2. Which of the following orbital overlaps is involved in the formation of the carboncarbon single bond in
the molecule HC C CH = CH2
(A) sp3 - sp3 (B) sp2 - sp3 (C) sp - sp2 (D) sp3 - sp
CH3 O O
-
C OH C O
+
(B) CH3 C NH2 CH 3 C = NH 2
|| |
O
O-
-
O O
(C) CH3 C CH3 C
O- O
+ -
(D) CH2 = CH CH = O CH 2 CH = CH O
(A) (B)
B-3. Which of the following statements is not true about the resonance contributing structures of a resonance
hybrid -
(A) Contributing structures contribute to the resonance hybrid in proportion of their energies
(B) Equivalent contributing structures make the resonance very important
(C) Contributing structures represent hypothetical molecules having no real existence
(D) Contributing structures are less stable than the resonance hybrid
(C) ; (D) ;
B-7. The type of hybrid orbitals used by C and N in the formation of CN bond in pyrrole NH is :
(A) sp2 and sp3 (B) sp2 and sp (C) sp2 and sp2 (D) sp2 and s
B-8. Which type of orbitals C and O use in the formation of CO bond in furan, O
(A) sp2 and sp3 (B) sp2 and sp (C) sp2 and sp2 (D) sp2 and p
(A) (B)
(C) (D)
B-11. I II III
C-2. Which of the following molecule has longest C=C bond length ?
CH3
|
(A) CH2 = C = CH2 (B) CH3 CH = CH2 (C) CH3 C CH CH2 (D) CH3 C CH2
| |
CH3 CH3
C-5. The decreasing order of bond length of C = C bond in the following compounds is:
I II III IV
(A) II > I > IV > III (B) III > I > II > IV (C) IV > II > I > III (D) IV > I > II > III
C-6. Which one of the following compounds maximum electron density on aromatic ring :
a b c
C-9. Which of the CC single bond is strongest in H 3C CH CH CH CH CH 3 :
(A) a (B) b (C) c (D) All equal
a
C-10. Predict the relative bond lengths a and b, in napthalene b
(A) (B)
N
H
(A) (B)
N S
H
N S O N
(A) (CH3)3 C+ (B) CH3 CH2CH2 (C) CH3 CH 2 (D) CH3
(A) (C 6 H 5 )3 C (B) (C) (D) CH 2 CH
I II III IV
(A) I > II > III > IV (B) III > II > I > IV (C) IV > I > II > III (D) II > III > I > IV
CH3
CH3 + CH3 CH3
+ C CH3 + +
(A) C CH3 (B) (C) C CH3 (D) C
H3C H3C HO H3C OH
OH
I II III IV
(A) I > II > IV > III (B) III > I > II > IV (C) IV > II > III > I (D) II > IV > III > I
(A) IV > I > III > II (B) IV > III > II > I (C) I > II > III > IV (D) IV > III > I > II
I II III IV
(A) III > I > IV > I (B) III > II > I > IV (C) I > III > II > IV (D) III > I > II > IV
(A) III > II > IV > I (B) III > IV > II > I (C) III > II > I > IV (D) II > III > IV > I
I II III IV
(A) III > II > I > IV (B) III > II < I < IV (C) II > III > II > IV (D) III < II < I < IV
F-4. In following acid, the correct increasing order of acidic strength acid
I. HCOOH II. CH3COOH III. C6H5COOH
(A) I < II < III (B) II < I < III (C) III < II < I (D) II < III < I
F-5.
I II III
Arrange following phenol in increasing order of Pka value
(A) I < II < III (B) III < I < II (C) III < II < I (D) I < III < II
F-6. Which of the following shows the correct order of decreasing acidity -
(A) PhCO2H > PhSO3H > PhCH2OH > PhOH
(B) PhSO3H > PhOH > PhCH2OH > PhCH2OH
(C) PhCO2H > PhOH > PhCH2OH > PhSO3H
(D) PhSO3H > PhCO 2H > PhOH > PhCH2OH
(I) (II)
(III) (IV)
(A) II < I < IV < III (B) IV < II < I < III (C) I < II < IV < III (D) IV < I < II < III
(A) (B)
H3 C CH3 H3 C CH3
|
|
CH3
|
|
|
(C) (D)
|
|
|
H3C H3C H
||
|
CH3
|
H3C CH3
|
H CH3
(A) 1 > 2 > 3 (B) 3 > 2 > 1 (C) 3 > 1 > 2 (D) 2 > 3 > 1
F-15. Use resonance arguments to rank the following in order of increasing acidity .
(A) Hc < Ha < Hb (B) Ha < Hb < Hc (C) Hb < Hc < Ha (D) Hc < Hb < Ha
F-16. 1,3-cyclopentadiene has a pK a = 15 whereas simple cycloalkanes have pK a > 50 with respect to
their conjugate bases . This is because :
(A) 1, 3-cyclopentadiene is aromatic.
(Z)
(W) HO OH
H
F-17. The most acidic H CH2OH(X) is :
O O
OH
(Y)
Vitamin-C
(A) X (B) Y (C) Z (D) W
(A) (B)
(C) (D)
||
|
H
|
G-2. Select the decreasing order of relative basic strengths of following species :
OH, NH2, H C C, CH3 CH2
(A) CH3 CH2 > NH2 > H C C > OH (B) H C C > CH3 CH2 > NH2 > OH
(C) OH > NH2 > H C C > CH3 CH2 (D) NH2 > H C C > OH > CH3 CH2
G-3. Select the decreasing order of relative basic strengths of following species :
(I) (CH3)3 (II) (CH3)2 (III) (CH3)3 (IV)
(A) (I) > (II) > (III) > (IV) (B) (III) > (IV) > (II) > (I) (C) (I) > (II) > (IV) > (III) (D) (II) > (IV) > (III) > (I)
G-5. Which of the following shows the correct order of decreasing basicity in aqueous medium ?
(A) (CH3)3N > (CH3)2NH > CH3NH2 > NH3 (B) (CH3)2NH > (CH3)3N > CH3NH2 > NH3
(C) (CH3)2NH > CH3NH2 > (CH3)3N > NH3 (D) (CH3)2NH > CH3NH2 > NH3 > (CH3)3N
G-6. Give the correct order of decreasing basicity of the following compounds ?
C6H5NH2 (C6H5)2NH (C6H5)3N C6H11NH2
I II III IV
(A) I > II > III > IV (B) IV > III > II > I (C) IV > I > II > III (D) III > II > I > IV
(III) (IV)
(A) b > a > c > d (B) a > c > b > d (C) c > a > b > d (D) a > b > c > d
(A) II > I > III (B) I > II > III (C) III > II > I (D) II > III > I
O
NH2 C CH3 NH2
Cl NH2 CH3
I II III
(A) I > II > III (B) III > I > II (C) III > II > I (D) II > I > III
NH2 NH NH2
(A) III > I > II (B) III > II > I (C) I > II > III (D) II > I > III
(1)
O
HN (3)
(2) CN(C2H5)2
N
CH3
(A) 1 (B) 2 (C) 3 (D) All are same basic
COMPREHENSION
Comprehension # 1
But-1-ene (A) and Buta-1,3-diene (B) differ not only in the number of bonds, but (B) also has and
bonds at alternate positions. This type of the system is called conjugated system. Following are some of
the conjugate system
In such systems, electron shifting result into permanent polarity. This type of -electron shift in the conjugate
systems is called mesomeric effect.
O
||
(C) < (D) > CF3 C O
3. Which of the following alkenes have maximum number of hyper conjugation structure.
Comprehension # 3
Hyperconugation describes the orbital interaction between the -system and the adjacent -bond of the
substituent group (s) in organic compounds. Hyperconjugation is also called as Baker and Nathan
effect. The necessary and sufficient condition for the hyperconjugation are :
(i) compound should have at least on sp2-hybrid carbon of either alkene, carbocation or alkyl free
radical.
(ii) -carbon with respect to sp2-hybrid carbon should have at least one hydrogen.
Hyperconjugation are three types :-
(i) (CH), -conjugation
(ii) (CH), positive charge conjugation
(iii) (CH), odd electron conjugation
H H
|
H C CH = CH2 H C = CH CH2
| |
H H
H
|
H C = CH CH2
|
H
H
|
H C = CH CH2
H
Number of resonating structures due to hyperconjugation = (n + 1 ) where n is number of -hydrogen.
Greater is the number of such forms, more is the stability of species under consideration.
Physical & Inorganic By A-479 Indra vihar, kota Organic Chemistry By
NV Sir Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) VKP Sir
B.Tech. IIT Delhi
ELECTRONIC EFFECT # 18
M.Sc. IT-BHU
6. Hyperconjugation is possible in which of the following species ?
CH3
|
(A) CH CH (B) C6H5CH3 (C) CH2=CH2 (D) CH3 C CH = CH2
3 2 |
CH3
7. Which of the following carbonium ions will show highest number of hyperconjugation forms ?
CH3 CH3
| |
(A) CH3CH 2 (B) CH3 CH (C) CH3 C (D) CH3 CH2 C
| | |
CH3 CH3 CH3
8. Which of the following alkenes will show maximum number of hyperconjugation forms ?
(A) CH2 = CH2 (B) CH3 CH = CH2
CH3
|
(C) CH3 CH2 CH = CH2 (D) CH3 CH CH = CH2
ASSERTION / REASONING
DIRECTIONS :
Each question has 5 choices (A), (B), (C), (D) and (E) out of which ONLY ONE is correct.
(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.
(E) Statement-1 and Statement-2 both are False.
12. Statement-1 : Ortho substituted benzoic acids are stronger than benzoic acid
Statement-2 : Ortho substituent tends to prevent coplanarity of COOH with ring. Thus resonance is
diminished which increases acidic strength (ortho effect)
13. Statement-1 : Salicylic acid is much stronger than its m-, p-isomers and benzoic acid itself.
Statement-2 : It is due to steric inhibition of resonance, as OH group forces COOH out of the plane of ring
15. Statement-1 : The Pka value of acetic acid is lower than that of phenol.
Statement-2 : Phenoxide ion is more resonance stabilized.
16. Statement-1 : Acetate ion is more basic than the methoxide ion.
Statement-2 : The acetate ion is resonance stabilized.
CH2
Cl
(A) CH3CH2 CH2 (B) CH3CC (C) CH3CH= CH (D) CH3 C =CH2
(A) CH3 < NH2 < OH < F (B) F < OH < CH3 < NH2
(C) OH < NH2 < F < CH3 (D) F < OH < NH2 < CH3
11. In a reaction of C6H5Y, the major product (>60%) is m-isomer, so the group Y is
(A) COOH (B) Cl (C) OH (D) NH2
12. Which one of the following orders is correct regarding the I effect of the substituents ?
(A) NR2 < OR > F (B) NR2 > OR > F
(C) NR2 < OR < F (D) NR2 > OR < F
13. Which one of the following compounds will be most easily attacked by an electrophile ?
15. The correct order of boiling point for primary (1), secondary (2) and tertiary (3) alcohols is
(A) 2 > 1 > 3 (B) 3 > 2 > 1 (C) 1 > 2 > 3 (D) 2 > 3 > 1
19. Increasing order of acid strength among p-methoxyphenol, p-methylphenol, and p-nitrophenol is
(A)p-nitrophenol, p-methoxyphenol, p-methylphenol
(B) p-methylphenol, p-methoxyphenol, p-nitrophenol
(C)p-nitorphenol, p-methylphenol, p-methoxyphenol
(D) p-methoxyphenol, p-methylphenol, p-nitorphenol
23. Increasing order of acidity in para methyl (I), chloro (II), amino (III), and nitro (IV) benzoic acids is
(A) III < II < I < IV (B) I < II < IV < III (C) III < I < II < IV (D) II < I < III < IV
(a) CH3NH2 (b) (c) Cl CH2 NH2 (d) CH2 NH2 (e) NH3
Correct answer is -
(A) (a) < (b) < (c) < (e) < (d) (B) (a) < (b) < (c) < (d) < (e)
(C) (b) < (c) < (d) < (e) < (a) (D) (c) < (b) < (e) < (d) < (a)
32. What is the correct increasing order of bond lengths of the bonds indicated as I, II, III and IV in
following coumpounds -
(A) I < II < III < IV (B) II < III < IV < I (C) IV < II < III < I (D) IV < I < II < III
(A) (CH3)3C (B) CH3CH2 C H2 (C) CH3 C H2 (D) CH3
43. Which of the following alkenes will react fastest with H2 under catalytic hydrogenation conditions -
C H2 = C H C H = C H2
1 2 3 4
increasing order is -
(A) a > b > c > d (B) d > c > b > a (C) a > c > b > d (D) a > d > c > b
52. In which of the following pairs the first one is the stronger base than second.
55. In which of the following first carbocation is more stable than second one.
(A) , (B) ,
(C) , (D) ,
56. In which of the pair of carbanion have first more stable than second.
(A) (B)
(C) (D)
COONa COOH
CH3
(P) (Q) (R) (S)
COOH OH NaO
(P) (Q)
(R) (S)
b. g.
c. h. CH3CH2NHCH2CH = CHCH3
d. i. CH3CH2NHCH = CHCH3
e. CH2=CHCH2CH = CH2 j. k.
(E) and
8. In the following sets of resonating structure, label the major and minor contributors towards resonance
hybrid.
(a) (b)
(c)
(d)
NH 2 NH 2
| |
(a) NH2 C NH2 NH2 C
(I) (II)
O O O
|| || ||
(b) CH3 C C CH3 & CH3 C CH= CH3
(I) (II)
(c) &
(I) (II)
(I) (II)
I II III IV
(a) (b) CH3 CHCH2CH3
15. The central carbon-carbon bond in 1, 3-butadiene is shorter than that of n-butane. Why ? [JEE-98]
(11) (12)
19. Benzene and [10] Annulene both have (4n + 2) -electron in ring and all bonds are conjugated even then
only benzene is aromatic explain.
+ + +
H
H H
(i)
H H
H
26. Rank the following free radical in increasing order of their stability and give appropriate reasons.
CH3 CH3
| |
(C) CH3 O CH2 CH CH CH3 (D) CH3 O C H CH 2 CH CH3
(P)
(Q)
(R)
(S)
30. Although phenoxide ion has more number of resonating structures than benzoate ion, benzoic acid is a
stronger acid than phenol. Why ? [JEE-97]
(a) (b)
37. What is the effect of electron releasing and electron withdrawing groups on the basic strength of aniline.
2. Which of the following acids has the lowest value of acid dissociation constant : [JEE-02(S), 3/90]
(A) CH3CHFCOOH (B) FCH2CH2COOH (C) BrCH2CH2COOH (D) CH3CHBrCOOH
5. Which of the following represent the given mode of hybridisation sp2 sp2 sp sp from left to right.
[JEE-03(S), 3/84]
(A) x > y > z (B) x > z > y (C) y > z > x (D) z > y > x
Excess of CH COONa
8. 3
[JEE-05(S), 3/84]
10. NaHCO
3 ; NaHCO
3 [JEE-06, 3/184]
A mixture of benzene sulphonic acid and paranitrophenol react with NaHCO3 separately. The gases produced
are respectively.
(A) SO2, CO2 (B) SO2, CO (C) SO2, NO2 (D) CO2, CO2
11. Among the following, the least stable resonating structure is : [JEE-07, 3/162]
O
+ O +
(A) (B) N (C) + N (D)
+
O O
13. The correct stability order for the following species is : [JEE-08, 3/163]
(A) (II) > (IV) > (I) > (III) (B) (I) > (II) > (III) > (IV)
(C) (II) > (I) > (IV) > (III) (D) (I) > (III) > (II) > (IV)
15. The correct stability order of the following resonating structures is : [JEE-09, 3/160]
(A) (I) > (II) > (IV) > (III) (B) (I) > (III) > (II) > (IV)
(C) (II) > (I) > (III) > (IV) (D) (III) > (I) > (IV) > (II)
(A) (III) > (IV) > (II) > (I) (B) (IV) > (III) > (I) > (II)
(C) (III) > (II) > (I) > (IV) (D) (II) > (III) > (IV) > (I)
17. The total number of basic groups in the following form of lysine is : [JEE-10, 3/163]
19. The total number of contributing structures showing hyperconjugation (involving C-H bonds) for the follow-
ing carbocation is : [JEE-2011]
20. Which of the following molecules, in pure form, is (are) unstable at room temperature ? [JEE-12, 3/136]
O
O
1. In which of the following species is the underlined carbon having sp3 hybridisation ? [AIEEE 2002]
(1) CH3COOH (2) CH3CH2OH (3) CH3COCH3 (4) CH2=CHCH3.
2. Which of the following compounds has wrong IUPAC name ? [AIEEE 2002]
(1) CH3CH2CH2COOCH2CH3 Ethylbutanoate (2) 3Methylbutanal
O
||
(3) 2Methyl-3-butanol (4) CH3CHCCH2CH3 2Methyl-3-pentanone
|
CH3
R CH = CH2 and
(R is alkyl group)
decreasing order of inductive effect is : [AIEEE-2002]
(1) (CH3)3 C > (CH3)2CH > CH3CH2 (2) CH3CH2 > (CH3)2CH > (CH3)3C
(3) (CH3)2CH > CH3CH2 > (CH3)3C (4) (CH3)2C > CH3CH2 > (CH3)3CH
5. The correct order of increasing basic nature for the bases NH3, CH3NH2 and (CH3)2NH is : [AIEEE-2003]
(1) CH3NH2 < NH3 < (CH3)2NH (2) (CH3)2NH < NH3 < CH3NH2
(3) NH3 < CH3NH2 < (CH3)2NH (4) CH3NH2 < (CH3)2NH < NH3
7. Which one of the following does not have sp2 hybridized carbon ? [AIEEE 2004]
(1) Acetone (2) Acetic acid (3) Acetonitrile (4) Acetamide
8. Among the following acid which has the lowest pKa value ? [AIEEE-2005]
(1) CH3CH2COOH (2) (CH3)2CH COOH (3) HCOOH (4) CH3COOH
10. The IUPAC name of the compound shown below is [AIEEE 2006]
12. The correct order of increasing acid strength of the compounds [AIEEE-2006, 3/220]
(1) d < a < c < b (2) d < a < b < c (3) a < d < c < b (4) b < d < a < c
14. Which one of the following is the strongest base in aqueous solution ? [AIEEE-2007, 3/120]
(1) Trimethylamine (2) Aniline (3) Dimethylamine (4) Methylamine
16. Arrange the carbanions, (CH3)3 C , C Cl3, (CH3)2 C H, C6H5 C H2 in order of their decreasing stability :
[AIEEE-2009, 4/144]
(1) (CH3)2 C H > C Cl3 > C6H5 C H2 > (CH3)3 C (2) C Cl3 > C6H5 C H2 > (CH3)2 C H > (CH3)3 C
(3) (CH3)3 C > (CH3)2 CH > C6H5 CH2 > CCCl3 (4) C6H5 CH2 > CCl3 > (CH3)3 C > (CH3)2 CH
17. The correct order of increasing basicity of the given conjugate bases (R = CH3) is : [AIEEE-2010, 4/144]
(1) RCO O HC C R N H2 (2) R HC C RCO O N H2
4. By drawing resonating structures of following molecules, Judge whether the group attatched to ring exerts
+ m or m effect.
(a) (b)
1. H2.
2.
10. Resonance energy of benzene is 36 Kcal mol, but that of toluene is 37.5 Kcal mol. Why ?
PART - II
1. (A) 2. (C) 3. (D) 4. (C) 5. (D) 6. (B) 7. (C)
8. (B) 9. (A) - W, S ; (B) - Z, R ; (C) - Y, Q ; (D) - X, P
10. (A) - r ; (B) - p ; (C) - q 11. (C) 12. (A) 13. (C) 14. (C) 15. (C)
16. (D)
Exercise # 2
PART - I
1. (A) 2. (C) 3. (A) 4. (B) 5. (A) 6. (A) 7. (B)
8. (D) 9. (A) 10. (D) 11. (A) 12. (C) 13. (D) 14. (B)
15. (C) 16. (A) 17. (D) 18. (B) 19. (D) 20. (D) 21. (D)
22. (B) 23. (C) 24. (B) 25. (A) 26. (C) 27. (A) 28. (C)
29. (A) 30. (A) 31. (A) 32. (D) 33. (A) 34. (A) 35. (C)
36. (A) 37. (D) 38. (A) 39. (A) 40. (A) 41. (C) 42. (A)
43. (A) 44. (C) 45. (A) 46. (A) 47. (A) 48. (C) 49. (A)
50. (A) 51. (C) 52. (ACD) 53. (ABD) 54. (ACD) 55. (BCD) 56. (BC)
PART - II
CH = CH2
COOH
CH3 COONa
1. (P) (Q) (R) (S)
COOH
OH NaO
C CH
2. Decreasing order of dipolemoment for given compounds
(x) : I > IV > III > II ; (y) : I > III > II > IV
CH2 = CH CH = CH2 CH = CH
So bond between second & third C-atoms show partial double bond character. Hence bond length is
shorter than C C bond in n-butane.
16. Aromaticity comes through resonance. Only those molecules can be aromatic which have very high
resonance energy. Only those molecules has sufficiently high amount of resonance energy to becomes
aromatic which
(a) are cyclic (b) are planar (c) contains (4n +2) number of -electrons in ring.
(d) Does cyclic resonance between (4n + 2) number of -electrons
Where n = 0,1,2,3,4 ..........
17. (i) It has sp3 carbon in ring. (ii) One C is sp3 hybridised. (iii) It has 8 electrons. It is Antiaromatic.
19. Benzene has all 6 hydrogen atoms in the plane. It does not have any vander waal or steric repulsions. So
it remains planar and aromatic. On the other hand [10]-annulene has inner hydrogen atoms (1, 6) which
are very close to each other causing steric or vander waal's repulsion. To minimise this the ring is twisted
this destroys coplanarity of all 2p-orbitals. So annulene is non aromatic.
21. All are aromtic 22. > > > H2O 23. III > II > I > IV 24. B>A
25. (i) (A) > (C) > (D) > (B) (ii) (C) > (B) > (A) > (D). (iii) (A) > (D) > (C) > (B)
(iv) (C) > (B) > (D) > (A) (v) ((D) > (C) > (B) > (A)
29. 1>4>2>3
Acidic strength order is SO 3 H > COOH > CCH > CH 3
30.
31. (p) A>B>C>D (Order of Ka) (q) A > B > C ~_ D (Order of Ka)
(r) (A) > (D) > (C) > (B) (s) (A) > (B) > (D) > (C)
32. (a) X (b) X
33. (p) C>B>A (q) B>C>A (s) (D) > (B) > (C) > (A)
(t) (D) > (A) > (C) > (B) (u) (C) > (B) > (A) > (D) (w) (A) > (C) > (D) > (B)
34. Due to better solvation in polar protic solvent.
35. (P) I > II > III ; (Q) I > II > III ; (R) I > II > III
36. CH3 < NH2 < OH < F
37. ERG increases the basic strength because they tend to stabilise protonated aniline, on the other hand,
EWG decrease the basic strength they tend to destabilise the protonated aniline.
2. (C)
3. (a) (ii) (b) (iii) (c) (iv) (d) (i) (e) (v)
10. (D) 11. (A) 12. (B) 13. (D) 14. (B) 15. (B) 16. (A)
PART - II
8. (3) 9. (4) 10. (3) 11. (4) 12. (2) 13. (2) 14. (3)
O
-
+ + - -
1. (a) CH 3 CH CH NO2 (b)
- -
3.
+ + .. 2
C H2 C O , N = N = N N N N
..
+
CH 2 = C = O
NHCCH3 NHCCH3
O O
4. (a) NH C CH3 (+M group)
||
O
O
CCH3 O O CH3 O
O CH3 O CH3 CH3
C C C C
CCH3
+
9. (1) CH 2 = CH CH 2 > >
+
+ +
(2) > >