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(1)

General Organic Chemistry

Assignment-5
stability of
Q1. Arrange the following in the increasing order of
carbocation
CH2
CH2 CH2

ocH3
D3
(C) (D)
() (B)

[Link] the following in the increasing order

of their carbonyl
stretching frequency

(B) (C)
(A)

03. What will be the decreasing order of C=C stretching frequency?

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(C) (D)
(A) (B)

order of acidity of the following compunds

Chemisu
Q4. Arrange in increasing
is

COOH COOH
OCH3

OCH3
(
ÓCH3
(C) (D)
(A)

Q5. Which proton is more acidic?

Ha
Hb

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order of stability of
Q6. Arrange the following in the increasing
carbocation
CH
CH,
CH, CH2
OCH3

(4)

(a)

ÇH2 ÇH2
(
hemisty (c)

CH2
OCH3
OCH3
(d)

NO2
(B)

OCH3
C)

(C)
(b)

D)

(b) (c)
(a)

(a)
(e)

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Which of the following is the most and least acidic?

(a) (b)

H H

(c) (d)

Q8/The correct order of acidity of the following conpound A-C is:

Fa
CF3
hert Me
[NET June 2011]

Me

-Me

FsC
Me
CFa
Me

(A) (B) (C)

(a) B> C> A (b) C> B> A

>
(c) A C> B (d) A > B> C
Q9. The increasing order of pK, values of the circled hydrogens in the
following compounds is [NET Dec 2014]

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Me

N
CN

BF41

H,N NH,
Me Me

(0 () ()

<
a) I
<II<II b) I< III <II c) II

compounds is JCheras
Q10. The correct order of heat of hydrogenation for the following
[NET June 2015]

()

Me

Me. Me

Me.

(III) Me (IV) Me
I> b) I> IIl > >
a)
I> II> IV I| IVh
IV > d) IV >
c)
I> IIM> II
I> >
II

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The correct order of pK, values for the

compounds X, Y and Z is
[NET June 2016]

CN
CN
-H H
H
NH -CN

NG

CN

(X) (n
a)
X> Y> Z b) Y >
Z>X c) Z> d) Y > X> Z
Q12. côrrect order of the acidity for the following compounds 1s
The

[NET Dec 2016]

(A) (B) (C)

a) B > C> A b) C> B> A c) B> A >C

d)
C> A> B

Q13. Among the following compounds the one that undergoes

deprotonation most readily in the presence of a base to form carbanion
1S: (GATE 2003)

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b) Meo OMe
a)

c) Meo

hemisty d)

Q14. Steric inhibition of resonance can be expected in

(a)

-N

(d)

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one of the following compounds would you expect to

Q15. Which
be the strongest carbon acid?

(a) (b)

(c) CH;COCH;CO0CHs

(d) CHa(COOC;Hs)2

Cher
16. In this, which hydrogen is the
coOH
most

-y2)
acitie

OH (3)

(a) (1) (b) (2) (c) (3) (d) (4)

017. In the given pair identify the most acidic compound in (A) and
(B). Most basic in (C) and (D)

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CO,H CO,H Co,H

CO,H

CHg
CH3

-(1) (2)
(B)
3(A) (1)

NH,
(2)

NH, NH2 NH,

(1) (2)
PhermiBly
CH3

(D)
(C)

(a) A-LB2,C-1,D-2 b) A-2,B-1,C-1,D-2

3
(c) A
2,B 2C-2,D-2 (d) A-1,B-2,C-1,D-1

Q18. Circle epresents most acidic hydrogens in these molecules.

Which of the following is Correct representation?
OH

MeO,C

OH

CF3 CO,H
(a) (b)

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(d) Allof these

(c)
Rank the following in decreasing order of their acidic strength.
Q19.

OH
H H

(a)
(c)
(A)

A>C>B>
A> DC>B
Qhem
D
(B)

(b) A
(d)
>
D> B>
D> A> C>B
(D)
C

Q20. Which of the following acids would have a STRONGER

Conjugate Base?

(A) H,S vs H,0

2

NH NH
VS

(B) CH,C = CH vs CH,CH-CH, (C)

3 4

(a) 2,4,6 (b) 1,3,5 (c) 2,3,5 (d) 1,3,6

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Q21. Rank the following compounds in order of increasing acidity

(weakest acid first).
CH3 NO2

-OH NO, -OH

-OH CH3

Q22.
(1)

(a) 2<3<1
Jehemisty
(b)3<1<2
(2)
CH3

(c) 1<2<3
(3)
NO2

sH (3)
H

Identify tae most aidic hydrogen in given compound.

(a) 1 (b) 2 (c) 3 (d) 4

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Q23. Product A will be:

Bec OH
2 moles of NaNH,

MOhemitty
O,N
CH

OH

-00C
OH
OH

(a) (b) OH

HOOC
HOOC
OH

O,N
SCH Q,N

(c) ()

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following is:
Q24. The correct acidity order of the
COOH COOH
OH OH

CI
CH3

(2) (3) (4)

(1)

(b
(a) 3>4>2>1
(c) 3>2>1>4 (d) 2>34>1
compoundsin the order of decreasing

heri
Q25. Arrange the following
acidity:
OH OH OH

CHs OCH3
CI

(2) (3) (4)

(1)

(b) 1>2>3>4
(a) 2>4>
(d) 4>3>1>3
(c) 3>1>2>4 ohoebos oiott
decreasing
Q26. Arrange the following compounds in the order of
acidity of hydrogen indicated in italic:
CH;COCH,COCH; CH,00CCH;COOCH, CH,COCH;NO2
CH;COCH;
(2) (3) (4)
(1)

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(b) 4>2>3>1
(a) 2>3>1>4
(d) 2>4>3>1
(c) 4>3>2>1
Q27. Acidic strength is greater in:
OH

(a)
OH

Chemisty (b)

NO2

NH2
(c) (d)

Q28. The acidity in decreasing order of different acids is:

(a) Formicacid>Chloroacetic acid> Acetic acid>Propanoic acid
(b) Formic acid> Propanoic acid >Chloroacetic acid> Acetic acid
(c) Chloroacetic acid> Acetic acid> Formic acid> Propanoic acid
(d) Chloroacetic acid> Formicacid> Acetic acid> Propanoic acid

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Q29. Rank the following alcohols in order of increasing acidity:

OH OH OH OH
C

(1) (2) (3) (4)

(a) 1<2<3<4 (b) 1<2<4<3 (c) 1<3<4<2

Q30. Which of the following has the most stable conjugate acid:
(a) (CH:)eNH (b) (CH3)3N (c) CoHSNH (d) CoHsNHCH;
Q31. Wh ch of the following will not soluble in aqueous NaOH
(through nOin water and given red golor with FeCl3 solution?

(a) (b) H

OEt

H
(c) H
(d)

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hydrogen present in the compound:

Q32. Identify the most acidic

Ha
H,

H,
H H, H

(a) a (b) b (c) c

H0 JChem
Write the pKa order of the following acids.

O- H
H0

(a) X>Y>Z

(b) X>Z>Y

(c) Z>Y>X

(d) Y>X>Z

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carbonic acid in the increasing order of acidic

Q34. Arange the given
strength:

Chemistiy
Me Me
D

B
A

(a) AB<D<C
(b DCB<A
(c) C<B<DA
(d) C<A<B<D

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Assignmn ent o5 (Goc)

C-HChiecebond
(-D

A) )
C<B<ALS

CooH Co oH

(4M,2)

) Gng(*-1)
o)

ha is acil
•pchst
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.6.
(41,-1)
G
(-5)

I) HOa(-t,3)

(-1)

a)

-I

)
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b)

lest
acidle

S=o
most ceidl

(ro shs)

ophon

oriditg

hect of hydusma'a
\

22

tras> cis.
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PraaU

o.

glehephileey

c)
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bdge

onO
tho
(0,M +I

rutonaa
6.18.
an of thes
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9.2.
(A

Shans

Q.22.

923(0
2
9.24. >
4)
4
3))27

9-26.

-4 -1
9.21
-
9.26
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C9.29.
ogah ban
30 Srong cald hon weale Conj
Weale

orjusah (Cns,

3)
Noon basr s

G.32

S33 Acla'ty

9.34