Acidity Basicity Tautomerism
Acidity Basicity Tautomerism
Acidity Basicity Tautomerism
QUESTION BANK ON
ACIDITY, BASICITY
AND
TAUTOMERISM
CHEMISTRY CLASSES
S-1, 2ND FLOOR, HL PLAZA, SEC-12, DWARKA, NEW DELHI-78
#9811848651, www.chemistryclasses.in
ACIDITY AND BASICITY
O O
|| ||
(c) Ph CH 2 C O H (d) CH 3 CH 2 C O H
O O
|| ||
(ii) (a) CH 3 CH 2 CH C O H (b) CH 3 CH CH 2 C O H
| |
F F
O
||
(c) CH 2 CH 2 CH 2 C O H
|
F
O O Cl O
|| || | ||
(iii) (a) Cl CH 2 C O H (b) Cl CH C O H (c) Cl C C O H
| |
Cl Cl
CH3
(iv) (a) CH3–CH2–O–H (b) CH 3 CH O H (c) CH3–C–O–H
|
CH 3 CH3
(iii) (a) NH3 (b) MeNH2 (c) Me2NH (d) Me3N (in H2O)
(iv) (a) NH3 (b) MeNH2 (c) Me2NH (d) Me3N (Gas phase)
NH2 NH2
N N N
(viii) (a) (b) (c)
O2N Me F
NH2 NH2
NH2 NH2
NO2 Cl CH3
Chemistry Classes Acidity, Basicity & Tautomerism [3]
O–H O O–H O–H O–H
N
(iii) (a) O (b) O (c) (d)
N
O N
O O
O O
C–O–H C–O–H
CH3
(vi) (a) (b)
COOH COOH
Cl Br
(vii) (a) (b)
O
O O
C–O–H
C–O–H C–O–H
OMe
(viii) (a) (b) (c)
OMe OMe
O
C–O–H O O
C–O–H C–O–H
(ix) (a) (b) (c) NO2
N NO2
O O
OH OH OH OH
OH OH OH OH
OMe
(iii) (a) (b) (c) (d)
OMe
OMe
OH OH OH
NO2 OH
NO2
(iv) (a) (b) (c) (d)
NO2 NO2 NO2
NO2 NO2
NO2
(ii) (a) CH 3 C NH 2 (b) CH3–CH2– NH 2 (c) CH 3 C N H 2 (d) N H 2 C NH 2
|| || ||
O N
H N
H
NH2
NMe2 Me Me
NMe2 N
OMe
(vi) (a) (b) (c)
OMe OMe
NH2 NH2
Me Me
NH2 NH2
NH2 H
C H
(ix) (a) (b) H (c)
H C H
H C
H H
H
H H H
H H CH3 H
H H Me
+
N¯Li N N N
(iv) (a) (b) (c) (d)
(i) (a) H2C = CHNa (b) CH3CH2Na (c) CH3CH2ONa (d) HC CNa
(ii) (a) NH2 (b) CH2 – NH2 (c) NH2 (d) C – NH2
NO2 O
Q.10 Which one of the following phenols will show highest acidity?
CH3 CH3
O
Nb
H2N– C – CH2 CH2 – NH – C – CH3
c
NH
a
N
CH3 d CH3
(A) b > d > a > c (B) a > b > d > c (C) a > b > c > d (D) a > c > b > d
O O O O O O
(I) (II) (III)
(A) I > II > III (B) III > II > I (C) III > I > II (D) I > III > II
Q.18 Record the following sets of compounds according to increasing pKa ( = – log Ka)
OH OH
(c) or (d) or
O=C–CH3 O=C–CH3
(e) or
Q.20 Which of the following would you predict to be the stronger acid ?
(a) or
Q.24 In each of the following pair of compounds, which is more basic in aqueous solution? Give an explanation
for your choice:
(a) CH 3NH2 or CF3NH2 (b) CH3CONH2 or H2N NH2
(c) n-PrNH2 or CH3CN (d) C6H5N(CH3)2 or 2,6-dimethyl-N-N-dimethylaniline
(e) m-nitroaniline or p-nitroaniline
Q.26 Choose the member of each of the following pairs of compunds that is likely to be the weaker base.
(a) H 2O or H3O (b) H2S, HS–, S2– (c) Cl–, SH–
(d) F–, OH–, NH2–, CH 3 (e) HF, H2O, NH3 (f) OH–, SH–, SeH–
O O O O
|| || || ||
(c) O C C OH or HO C C OH (d) or
(a)
(b)
(c)
(d)
(e)
TAUTOMERISM
Q.32 Among the following the compounds having the highest enol content :
(A) CH3CHO (B) CH3COCH3
(C) CH 3 C CH 2 CHO (D) CH3–CO–CH2–CO2CH3
||
O
N=O
HO OH
OH
O O
HO O HO OH
(A) (B)
HO OH O O
O OH
O
O O
(C) (D) All of these
HO OH
OH
C – CH2 – C
O OH OH O
OH OH O OH
(a) l (b) l
(c) l (d) l
(e) l
(a) (b)
(c) l (d) l
(e) l
Q.39 In each of the following pairs which will have higher enol content :
(a) and
(b) and
(c) and
(d) and
Q.40 In each of the following pairs which will have less enol content :
Q.42 In each of the following sets of compounds write the decreasing order of % enol content.
(a)
(b)
(c)
(d)
(e)
Q.43
Q.45
Q.1 (i) a > b > c > d, (ii) a > b > c , (iii) c > b > a, (iv) a > b > c, (v) c > b > a, (vi) a > b > c
(vii) d>c>b>a , (viii) d>c>b>a, (ix) d>b>a>c, (x) d > a > c> b
Q.2 (i) a > b> c> d, (ii) a > b > c > d, (iii) c > b> d> a , (iv)a < b< c< d, (v) a > b> c, (vi) a < b < c
(vii) c > a > b, (viii) b > c> a, (ix) c > d> b > a
Q.3 (i) d > c > a > b, (ii) a > b > c, (iii) c > a > b > d, (iv) d > b > c > a, (v) a > b > c, (vi) b > a
(vii) b > a, (viii) c > b > a, (ix) c > a > b
Q.5 (i) a > b > c, (ii) d > c > b > a, (iii) b > c > a, (iv) d > c > b > a, (v) b > a > c, (vi) c > a > b
(vii) b > a, (viii) c > b > a, (ix) c > b > a, (x) a > b > c
Q.7 (i) b > a > d > c, (ii) b > a > c > d, (iii) a > b > c > d
Q.15 A Q.16 A
Q.18 (a) 3<2<1; (b) 1<2<3; (c) 3<2<1; (d) 2<1<3; (e) 2<3<1
Q.19 (a) 2; (b) 2; (c) 1; (d) 1; (e) 1 Q.20 (a) 2; (b) 2; (c) 2
Q.21 A Q.22 A Q.23 A Q.24 (a) i, (b) ii, (c) i, (d) ii, (e) i
Q.25 (a) i, (b) i, (c) ii Q.26 (a) 2; (b) 1; (c) 1; (d) 1; (e) 1; (f) 3
Q.27 (a) 2; (b) 1; (c) 2; (d) 2 Q.28 (a) 3<2<1<4; (b) 1<2<3<4; (c) 3<1<2
Q.29 (a) 1>2>3; (b) 1<2<3; (c) 3<1<2; (d) 2<1<3; (e) 1<2<3
Q.37 (a) 1; (b) 1; (c) 1; (d) 1; (e) 1 Q.38 (a) 2; (b) 2; (c) 1; (d) 2; (e) 1
Q.39 (a)1; (b) 2; (c)1; (d) 2 Q.40 (a) 2; (b) 1; (c) 2; (d) 1; (e) 2
Q.41 (a) 2; (b) 2 Q.42 (a) 3>1>2; (b) 4>2>1>3; (c) 4 > 1 > 3 > 2 ; (d) 3>1>4>2; (e) 3>4>2>1
Q.43 3>1>2
Chemistry Classes Acidity, Basicity & Tautomerism [16]
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