ORGANIC CHEMISTRY
TARGET
D P P Topic - Organic Acids and Bases JEE/NEET
DAILY PRACTICE PROBLEMS
# Subjective Type Of Questions
Direction : These questions are subjective in nature, need to be solved completely on notebook
@
ci)
(ai)
(iv)
w)
wi)
Cyclo hexene has three type of hydrogen
Hea)
din - HW
cr
arrange the reactivity order of these C-H bonds.
Write correct order of acidic strength of following compounds -
° ° ° °
I I Il |
(@)NOMCH=C-O-H (6) F-CH-C-O-H (©) Ph-CH=C-O-H— (@) CH=CH=C-O-H
¢ i i
OCH RCH-FHC-O-1 (CH CHECHEC-O-H (6) CH=CH
F F
i i aa
I
G@)CLCHR=C-O-H (O)CHEH-C-O-H(€)C-7-C-0-1
a a
cH,
(@)CH-CH-O-H —(b)CHCH-O-H—_(¢) CH-t-O-H
cH, cH,
of \ of \ of \
‘COOH ‘COOH ‘COOH
coon COOH CH-COOH
@ I CHS ©
Coon ‘COOH ‘CH-COOH
(a) HF (b) HCI (o) H-Br (He
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(ii)
(ivy
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wi)
(vii)
(viii)
(i)
(@CH, (b) NHs (10 (a) HEF
() F-CHCH.-O-H_——(b) NO-CH-CH,-O-H
€
(©) Br-CH-CH-O-H—— (d) NHy-CH-CH;-O-H
(a) HCOOH (b) CH,CH,OH
(©) CHOW (@) CHSOH
Write increasing order of basic strength of following ~
(Cu. NI ou @p
Ord wd (br wt
(NH, (b) MeNH, (©) MeNH () MeN (In H,0)
(Nu (b) MeN, (©) MeNHs (a) MesN (Gas phase)
(a)R-NH, ——(b) Ph-NH (©) R-C-NU.
§
@ QO oQ © oO
Nit Nii
i
°
Nu, Nu, Ne Na,
, ) © @ oO
NHS cr CH iH
Write correct order of acidic strength following compounds -
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NO:
(a0,
@[O,
9
I
w
tw)
w
(wi)
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on OH
OH OH
o “© “© “© “©
Cuts NOs & Nits
OH on OH on
(i) OL “EL QL, “
NOs F Hy
On OH OH OH
(iit) @) AVOME OL, © “©
JMe
Ome
ou
OH oH OH
® @ © fx “QL
NO
J Nos
ON NO:
6 Write increasing order of basie strength of following ~
a) (a) CH-CH,-NH) (b) CH;-CH=NH (c) CH;-C=N
«
()CH-CH-NH, (©) cHi-¢-ftt
NH
Nu,
Gi) @) LN of ©
N’
i
H
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Sn,
(a) (b) @
No:
Nu,
“© )
NO:
Mey ‘ Me
OMe
(a) (b) (©)
OMe
Me, Me
(a)
CH-CH:
(a)
OO)
H
Nn,
@ )
Select the strongest base in following compounds -
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ci)
(ii)
(iv)
8:
w
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(iii)
10
oO © O ne)
I I
Nits
H
x
a \ [ \ c
°O "© ol a)
H H
uy, H
H H
Nout ,
Me
i i
(@) QO ) QO xO) @ QO
Arrange the following compounds in decreasing order of their basicity.
a3 ee oe ae
(a) H,C=CH-Na_—(b) H,C-CH,Na_(@) H,C-CH,ONa_— (4) HC=C-Na
@ (O>nn () (©>-ctn-nn Qu @ Opn
oO
NO>
(HO (D)NHs— (FLO) HSO,
cm § 8
HO-C-C-OH is stronger acid than 110 -C—CH~C-OH why?
INH
is weaker lewis base then CH ~NH. Why?
Arrange the following in increasing order of basic strength (In aqueous solution)
(NH, HO, HyS, PH; (4) “NHlg, “O11, “CH ,CH3CH-
(ili) “OH, CHs-O-, CH3-OH, CH3-CH-OH (iv) “CH3, CHy=CH>, CH=C~
°
t
(v)0H, H-C-0- 1,0 e (vi) CF, 10, 4-98, CH= C-
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DHL0%.cH-C0*. he,
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(x) o oO Co)
# ‘Only One Option Correct’ Type Of Questions
Direction : Each question has four choices (a), (b), (c) and (d), out of which ONLY ONE is
correct,
2.
13.
MW
5
Vo
2
h Nis
(A) (B) (c)
(A) A is more basic than B_— (B) B is more basic than A
(C)B is more basic than (D) All are aromatic bases
Which of the following will be the increasing order of basic strength of given ion -
chy, Ni, OW, F
1 u i iv
(A)I
) (O)-cH,0n
Which of the following does not contain an active methylene group -
(A) CH3 ~COCH{COCH3 —(B) CH3CH2NO2
(©) CHyCOCHCN (D) PhCOCHCN
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19.
20,
24.
22,
2.
Most acidic aleohol is —
(A)(CHyC-OH——(B) CH,CH.OH
(CcHoH (D) Propanol-2
‘Under suitable conditions CgH,CH.OH (A) CcH,OH (B), and C,H,COOH (C) can act as acids
‘The increasing order of their acidic strength is ~
(A)A I> I> IV (B) I> > > IV.
(QIV>M>M>1 (IVS M>1>11
Among the following compounds, the strongest acid is —
(A)HC=CH {B) NH; (cha=cH2 (D) CH30H
Which is strongest acid -
(A) Ortho iodo benzoic acid —_(B) Ortho bromo benzoic acid
(C) Ortho chlorobenzoic acid _(D) Ortho fluro benzoic acid
(CH,),CCH,COOH is more acidic than (CH,),SiCH;COOH because —
(A) Size of Si is more than that of carbon
(B) Electronegativity of carbon is less than that of silicon
(©) Silicon is more electropositive than carbon due to which (CH3)sSiCH;COO™ becomes less
stable
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26.
27,
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29,
30.
(D) None of the above
Peroxyacetic acid (CHsCOsH) is weaker acid than acetic acid (CHyCOsH) since —
oO
(A) Negative charge in CHy-€-0-0" can't be dlocalise into the carbon group
(B) CH, group in CH,COsH show + effect
(©) Both are correct
(D) None is correct
For the following acids —
(CH)),CCH;CO,H = (CH,);NCH,COH-—— CH,COOH
wo ay ay
pKa value will be in order ~
(A> > (BI M0 (DyM>M>1
Place the following in the correct order of acidity
CH = C-COOH; CH=CH - COOH; OH CH3CH{CO.
c0} ay «amt
(Ay > > (B)M>m>1 (ueiom (DyI>m> 1
Phenol is a weaker acid than acetic acid because
(A) Phenoxide ion is better stabilized by resonance than acetate ion.
(B) Acetate ion is better stabilized by resonance than Phenoxide ion,
(C) Phenol is less soluble in water than acetic acid
(D) Both phenoxide ion and acetate ion are stable
Which aromatic acid among the following is weaker than simple benzoic acid -
“6 “ mo) »
cu,
Which of the following would be expected to be most highly ionised in water —
(A) CHSCH:CH.COOH (B) CH,CHCICH.COOH
(C)CH.CHCCICOOH (D) CH,CH.CHCICOOH,
Assign number 1 for least to 4 for most to indicate the relative base strength of the following~
I u
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32.
33.
CcHSNH p-NO:C\HANH,
m v
m-NO:CcHNHz _p-CHsOCGHNH:
ion om ow
@m 3124
(B) 12 3 4
(c) 23 4 1
O 41 3 2
Highest value of pK will be of
(ANH (B)(CHy).NH (©)(CH)N (D) CHANH
‘Amines are basic in nature because~
(A) They produce OH ions when treated with water
(B) They have replaceable H atoms on N atoms
(©) They have lone pair of electron on N atom
(D) Both (A) & (C)
‘Most acidie alcohol among the following is -
HL
(A) Gs-O-H (BY CHC,
Br-CH,
oH HM
1
CH—CH, — (D)F=CHy—CH,
(Noy
ay Bi, 0s 3 in nerating pi vac
cen, PhSOH > PhCH,OH > PhOH —_(B) PhSOsH > PhOH > PhCO:H > PhCH.OH.
(C) PhCO;H >PhOH > PhCHOH > PhSO,H_—_(D) PhSOH > PhCO;H > PhOH > PhC!
Arrange the following in correct order of acidic strength:
(CHrNO, (1) NOs=CHs—NOs (II) CH)—CH-NOs LV) NOs—Cht—-Nos
Nos
(AVIV> >> (B)IV> >>
(QM>I>0>IV (Dy M>1>1V>1
Which of the following substituted carboxylic acids has the highest K, value
(A)CH,CIh=CH-CooH —_(B)CH, CHCl: CooIt
a a
(©) CH CH, —CH-COOH—_(D)CH,-cH-C
t
a Br
coon
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42.
Which nitrogen in LSD (Lysergic acid diethylamide) is more basic:
om
1 i
HON CN (Cig:
— n
i
cu
wi @u (MD) Allare equally basic
Rank decreasing order of bond dissociation energies of the bonds indicated with the arrow’s,
MOT
u
(Ajema>b (B)a>b>e (C)e>b>a (Dyb>c>a
Which of the following is most basic -
cH git
:
w oF
Which of the following is least alkaline—
“ on
*
l
© (D)AI are equally basic
‘When propionic acid is treated with aqueous NaHCO, COs is librated, The ‘C” of CO; comes
from
(A) Methyl group (B) Carboxylic acid group
(©) Methylene group (D) Bicarbonate
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49.
‘The correct order of basicities of the following compounds is -
aN
(pci-e (2) CH3CH2NHy
‘Nis
°
(3) (CHy),NH (cudnt,
(A)2>1>3>4 — (B)1>3>2>4 — (C)3>1>2>4 (D)1>2>354
Arrange the following compounds according to decreasing order of basic strength
NH
Q ‘ a
NH
@) @
a
(A)2>1>3 (B)1>2>3 (C)2>3>1 (D)3>2>1
Identify most basic compound in the following is -
H
NHL
wma
4
a ow
cool gy
x
ol,
oon
when X is made to react with 2 eq. of NaNH3 the product formed will be:
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Q © Q ©
@“ ®)
Se \
han ow hon"
me) DH Hooc oe
©
© ©)
Si
on Oo 8 oy (Lou
50. HN Nu,
Z YY Y
coon
x
Correct order of acidic strength is
(Ayx>y>z (B)z>y>x (C)y>2>x (D)x>z>y
51. Arrange the following according to decreasing order of acidic strength ?
HS LCN uw
0 aw ay
(AyI> I> (B)I> =m (i>msn — (D)I=
=
52, Which of the following is strongest acid ?”
0. coon CH.OH coon
aC) wo ot (P)
# ‘More than One Options Correct’ Type of questions
Each question has four choices (a), (b), (c) and (d), out of which MORE THAN ONE are correct
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56.
s7.
Consider the following compounds
ome
UG
iW Ni
Pyrtole (1) Pyridene (11) Aniline (111)
which of the following statements are correct?
(A) is more basie than II (B) Il is more basic than I and III
(C) is more basic than I (D)1 is weakly acidic
Which statement is true ~
° °
(A) NHj is stronger base than OH (B) NH:-OH is less basic than NH;
Ni H—NH;
(teh everest, (0)(O) ewer
Which is less acidic than phenol -
oH oH
or or
a (B) CH;-CH-OH © (D) CH=CH
Consider the following acids, which is/are weaker acid than stieast other two of them?
- 00H
Cl. Cha Chew
@) coo (By oO () or
Consider the following neutralisation reaction.
CH,CHFCOONa + CH,CH,COOH = CH,CHFCOOH + CH,CH,COONa
‘The correct statement(s) regarding this neutralisation reaction is/are
(A) The equilibrium lies predominantly to left
(B) Equilibrium constant (K) is less than 1
(C) Itisa spontaneous neutralisation reaction
(D) If equal motes of reactants are mixed to form solution, the major ion present in solution is
CH,CH,COO™ and Na*
Consider the following amines,
CHj—CH,—NHz = CHj—NH—CHy CHly— City N— Clty
1 0 |
CH,
uM
‘Scanned with CamScanner # ‘Match the Column’ Type of Questions
60.
ot.
Which of the following statements is/are correct regarding their basicity?
(A) In aqueous solution, the mereasing basicity is1H> TS 1V (IVE I> >TO n> I> 1V> I (D)I>1V> I>
Which of the following is most acidic —
coott coon cooH coon
OL Os © I)
ot ‘NO; NO;
Consider the following two structures and chose the correct statements ~
320
o ay
(A) Carbon- nitrogen bond length structure I is greater than that in structure I
(B) Carbon-nitrogen bond length in structure 1 is less than than in structure 11
(©) Carbon-nitrogen bond lenght in both structure is same
(D) It can not be compared
# Phenols are converted into their salts by aqueous NaOH but not by aqueous bicarbonates. The
salts are converted into the fiee phenols by aqueous mineral acids, carboxylic acid or carbonic
acids most phenols have K value of about 10°", and are tremendously more acidic than alcohols,
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7.
A-6=0-6
The difference in acidity are due to difference in stabilities of reactants and products. Phenol and
phenoxide ions, contain benzene ring and therefore must be hybrid of Kekule structures
on on
Being basic, oxygen can share more than a pair of electron with the ring
Phenoxide ion
Since energy must be supplied to separate opposite charge, the structure of phenols should
contain more energy. The net effect of resonance is therefore to stabilise the phenoxide ion to a
greater extent than the phenol and thus to shift the equilibrium towards ionization and make Ka
larger than for an alcohol.
Which of the following is strongest acid ?
:
(A) HCO; (B) (C)CH-OH (D)CH-CH.-OH
OH OH Ou OH
(A) HCO; > CH;-OH > (B) oO. >
wneoreren) oT Cha
Choose the correct statement:
(A) Phenol gives effervescence with NaHCO; (B) Pirie acid is weaker acid than carbonic acid
re se sn (OT
(C) Picric acid gives effervescence with NaHCO, (D) R—
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6.
70.
# Amines are basic in nature due to presence of lone pair of electrons on nitrogen atom, Electron
releasing groups increase the basic character of amines and electron withdrawing groups decrease
the basic character of amines.
which of the following is most basic—
(A) CH-NH; (B) CH-NH-CH, (C)CHLN-CH, (D) NHs
cH,
Which of the following reaction is more favourable in forward direction
(A) cit-NH
NH Ni,
® On o— Ojo
(©) Both are equally
(D)Can’t be predicted
1.0 cH,-N,¢ on
Which of the following esha value of Kb
NH, NH NH
(A) "© (D),
och, No: D
Which of the following is most basic
NH: Nis NH
a (B) © (D) Cant’ be predicted
OCH, Ochs Nos
Choose the correct order of character—
Ni NH NH NH
(A) CH NCH an eae oO Oo ‘OQ:
* Gy
NH: NH
oO O: Oo oO” (D) None of these
CH
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4.
76.
7.
# According to Bronsted Lowry concept when acid donate a proton it forms a conjugate base
1
Strength of conjugate base «
In acid base reaction a strong acid can produce weak acid but vice versa is not possible.
All reaction are reversible, Which of the following reaction are possible.
OKO) + NaN — PHC
PhyCH + NaH == PhyC°Na’ + Hy
UJ + CH,—CH)-Li == CU]. CH,—CH,+Li"
Ni 7
t
° 9 “ro
cn, -b-cr, dcr, « pai ct t-te iu
(i) CH=CH + NaOH CH=C-Na* +H,0
(ii) ROH + NaOH (excess) = RO'Na’ + H:0
OH Na’
cin Goon = 6 +Ho
(iy) R-COOH + NaOH == RCOONa’ + HO
(v) RSOsH + NaOH === RSO;Na* +H,0
(i) CH=CH + NaHCO, CH= CNa+ HCO;
(ii) R-OH+ NaHCO, == R-O" Na’ +H,CO,
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ou Na
(ii Oo + NaHCO; == +H,COy
(iv) RCOOH + NaHCO; RCOO™ Na"+ HsCOs
() RSOSH + NaHCO; RSO;Na* +H5CO,
() RSOsH+ Na == RSO\Na + 1/2 H(t)
(il) RCOOH + Na=== RCOO™Na' + 1/2 HL (1)
mH at
ow Na== S + U2 HAT)
(iv) R-OH + Na == RONa’ + 12 HA)
6 '
( ay-t-en, hen, > cy 8 Gt cay sam
(vi) CH= CH + Na==CH = CNa' +12 Hy
(vil) CH= CH+Na 255> CH= CNG +NHy
CH,SO.H +NaHCo, = Product + gas. Determine gas.
(SO, (ii) CO; (iii) "CO
Which of the following will produce effervescence (CO;) on reaction with NaHCOs,
Hi Ht
No» NO NO;
(A) Pierie acid (B)
NO; NO:
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(C(C)] +Naticosexcess) —_(D) None of these
Nos
ANSWERS
1 b>e>d, (i)a>b>e, (ii)e>b>a, (iv)a>b>e, (ve b>a,
(via>b>e,
(xyd>a>c>b
(a>b>e>d,
(vya>b>e,
(iye>d>b>a
(@d>c>a>b,
(v)a>b>e,
@b Ga Gib
(@a>b>e,
(vy) b>a>e,
(iye>b>a
ja ony
(b>ard>e,
(vil) d>e>b>a,
(ii)a>b>e>d,
(iab>e,
(vi) b>a,
(ind
(i)d>e>b>a,
(wi)e>a>b,
(xJa>b>e
Gide
(i)b>a>c>d,
(vill) d>e>b>a,
(ix d>b>a>e,
(ili)e>b>d>a, (ivyaa>b (viii) b> e>a
(iiye>a>b>d (iyd> b> ema
(vil)b>a, (viije>b>a,— (ixye>a>b.
(ii) b> e>a, (ivy d>e>b>a
(vii) b> a, (vill)e>b>a,
(ya
(ii)a>b>e>d,
As we know that - I effect decreases with increasing the length of'C’ chain. In the case of
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12.B
2A
32.D
aA
52.0
®
Il I Il
HO-C—Cll,~€— OH, effect of one OH on another one is nt as stronger as
aa a?
Con. Which causes greater acidic character of HO -C--C—O1 in the comparison
AS it is clear from resonating structure “CO lone pair of 'N' is not localised on 'N’ atom but
'N’ also contain a small (+)ve charge which results lower basic character C) But in the case
‘of CH3 — NHp lone pair is localised on nitrogen atom and it contain a (89) charge which causes
seater basic character.
()IR:D>P
60, AR.B>P;C>Q,DS, 61. A>Q,B>P,C>R.D>S
2D 6.B 64B 658A 66D 67.C 6B 6%.A 70.A TLB 72.€
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79. i) ¥ (ii) ¥ (i) ¥ (iv) ¥ (v) Y (vi) ¥ (vii) ¥_ 80. (iii) 81, ABC
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