EXERCISE 2.

2 (MCQ1 or >1 option correct, Passage based, Matching, A/R)

DIRECTIONS for Q. 1 to Q. 27: Multiple choice questions with J0. Dipole moment is shown by:
one or more than one correct option(s). (a) 1,4-dichlorobenzene
(b) cis 1,2-dichloroethane
(c) trans 1,2-dichloroethene
1. Pick up the correct statement (d) trans 1,2-dichloro-2-pentene
(a) The k of maleic acid is high than that of fumaric acid, 11. C-C and C =C bond lengths are equal in
while the k, of maleic acid is very low than that of fumaric
(a) benzene (b) 1,3- butadiene
acid
(c) 1,3cyclohexadiene (d) none
(b) Fluorine forms stronger H-bond than oxygen, hence HF
should boil at a higher temperature than Resonance stabilised compounds are
H,O
Delocalisation of n electrons does not always lead to
(c)
stabilisation
(d) Delocalisation of r electrons always leads to stabilisatior
(a) (b) CH2 =CH-C
2. In which of the following pairs of carbocations, the second
carbocation is less stable than the first?
(c) -CT (d)
a CH = CHCH and CH2 = CHCH2 CH2

b) CH3NHCH2 and CH,OH CH

j3. The compounds which is(are) isomeric with diethyl ether is (are)
( CH CHCH,CH,CH3 and CH3CH2 CHCHCH3
(a) n-propyl methyl ether (b) butan-1-ol
(d) CHCH, CH2 and CH,OCH2 (c) 2-methylpropan-2-ol (d) butanone
Which of the following compounds show tautomerism? 14. Out of the following compounds, which will not have a zero
OH dipole moment?
(a) 1,1-dichloroethylene
(b) cis-1,2-dichloroethylene
(a) (b) H2N-C-NH2 (c) trans-1,2-dichloroethylene
(d) All have zero dipole moments
O 15. The type of hydrogen present in the above structure is
(a) 2° allylic (b)vinylic
OH (c) 3 allylic (d) benzylic
16 Select the correct order among the following.
(a) Order of heat of hydrogenation
(c) H2N-C-NH2 (d)
HO OH
Enolic form ofmethyl3-oxobutanoate is more stable than its keto
form, this is due to
(a) resonance stabilization of the ernol form
(b) Order of heat of combustion
(b) intermolecular hydrogen bonding
(c) intramolecular hydrogen bonding
d) carbonyl group on each side of-CH group
5. All of the given structures show ring-chain tautomerism, in which
of the following cyclic form is more stable than the open chain
form? (c) Order of resonance energy
(a) CHOCH,CH,OH
(b) CHCOCH,CH,OH
(c) CHOCHOHCHOHCH,OH
(d) CHOHCOCHOHCHÖHCH,OH
. Which of the following compounds have only one type of hybrid
(d) Order of basic strength
carbon?
(a) CH-CH-CH-CH2 (b) HC =C-C=CH NH NH NH
(c) CH-CH, CH-CH, (d) CH, C=CCH,
In which of the following compounds are all the carbon atoms HN NH
n the sp state of hybridization
(a) CH (b) CH
(c) CH (d) C4H10 17. Correct
orderofbond lengthofp,q, r,s&ygiven in the following
kesonance structure of a molecule should have compound is
(a) identical arrangement of atoms
(b) nearly the same energy content
(c) the same number of paired electrons
(d) identical bonding CH,C CH-C OH CH,0
9. CHOH
Hydrogen bonding is possible in
(a) Ethers (b) Hydrocarbons (a) y> X>p>q>r (b) y>p>x>q>r
(c) Water (d) Alcohols (c) p>y> x> q>r (d) p> y>x>q>r
18. Which of the foliowing reactions(s) follow the same pattern of
energy graph for the formation of major product only.
NO, -O0

(b) O COOH OH

O
.(Strength of intramolecular hydrogen bonding)
P.E COOH COOH
OCH,
(c) (Acid-strength)
Reaction progress

COO ÇOO
IOH
CH . (Stability)
(d)
(a) H
for histidine are:
22. The correct orders and statements

OH
(P)
NH
(b) C H , - C H - COOH

r)
(q)
QH
(a) qP ..basic nature
H (b) r>P . basic nature
(c) A (c) Histidine has 6t-electrons delocalized in the ring
All stereoisomers of histidine have same pKj values
CH CH (d)
state of the reaction
23. Homolytic cleavage of covalent bond at some
(d)O H-H-H-CH,-OH isobserved in:

(a) HBr/(PhCOO)2
The correct statements about the following two compounds are
(6) SO2C2
R202
(c) D2/Pd-C
HQ OH
HO OH (d) CH-CH2COOK- electrolysis
24. Which of the following is/are correct according to property
mentioned in the parentheses?
(1) (11)
CI CI

(a) Melting point (i <II) CI. CI

(b) Boiling point (I< I) (a) (dipole moment)
intramolecular hydrogen bonding
(c) (II) may have
(d) (1) and (1) are
geometrical diastereomers
Select the correct optionsfor molecular formulaC,H,Cl,. CI
20. isomers is 4
The total number of
(a) are geometrical isomers
(b) Only two compounds
(cAll isomers have 5o bonds and one rbond Ci H CI
(d) Its has
linear shape (b) C=C =C - C=C =C=C
21. Select the correct statement(s)/ order(s) about I, I1, Il and IV H
ÇOOH COOH (dipole moment)
CH, OH
I. II. (c)BF>BF (B-F, bond length)
(d) PFCI, > PF,Clg (dipole moment)
25. Which of the following statements is/are correct ?
ÇOOH COOH
(a) Vinyl chloride has higher dipole moment than allyl chloride
OCH NO, (6) The relative values of dipole moment of vinyl chloride and
III.
[OT allyl chloride is due to resonance which here decreases dipoe
moment.
(c) The meta-directing influence of
benzotrichloride is due to inductive as well as
-CCl3 group in
OH
(a) hyperconjugation.
..(Stability) (d) Both CH, CHCH,CH3 and CH, CHCH3 are2
carbocations, hence equally stable.
 0Wilhof tUhe tollowing statementsis/are correct
(a) Maleic and fumarie acids have similar acidic character, PASSAGE2
Tautomerism may be defined as a phenomenon in whicha single
while fumarate ion is a stronyger acid than mal e ion
compound exists in two readily interconvertible structures that differ
in the relative position of hydrogen. It is broadly of two types: dyad
b) CHOC is morestablethan CH,OCH, CH2. system in which hydrogen migratesfrom atom one to atom two, and
() Reonaneefftectinvolves delcalisationof rorpelectrons, similarly defined triad system. Keto-enol tautomerism is the most
while inductive ettet ivolves deocalisation of o electrons. important and its most usual example is ethyl acetoacetate.
O OH O
( ) n H2 -CUNH1, the n electrons are delocalised in the
tollowing way CH-C-CH2 -C-OC2Hs =CH3 -C = CH-C-OC;Hs
The two forms are readily interconvertible under ordinary
CH, CH wu >
CU,- CH =NH, conditions by acid or base catalyst.
viz. its
Stability of the enolic form depends upon several factors,
Whih ot the tollonving staternntsis/arecorrect? stabilization (throigh resonance) and nature of solvent. Non-polar
(a) 1,3-Butadiene is stabilised by resonance, while solvents generally stabilise the enolic form, while polar protonic soBvent
cvelobutadiene isdestabilised by resonance. stabilises the ketonic form.
Roiling points of hydrogen halides follow the order HF>
of triad system of
HCI> HBr>HI 31. Which of the following is not an example
Chelation may explain increasing acidic character as well tautomerism?
as decreasing acidic character of certain compounds. OH
sd) Stability of enolic formof acetylacetone is due to resonance
(a) CH -C-CH3 CH2 = C -CH3
as well as hydrogen bonding.
OH

INSTRUCTION forQ. 28 to 48: Read the passages given below and (b) CHs-C-NH2 CHs -C =NH
answer the questions that tollow.
H
(c) CH, -N CH, =N
PASSAGE1
Hydrogen bond is an electrostatic attractive force between
covalently bonded hydrogen atemofonemolecule and electronegative H -0 - N =0
atom of small size of another noiecule. The three atoms satistying (d) H-N
these conditions are F, O and N. Hydrogen bonding may be two samples of acetylacetone,
32. You are given
intermolecular as well as intr melecular. Intramolecular hydrogen
bonding also knownaschelation is possible whena6- or5-membered O O
ringcan be formed. Intermole lar hydrogen bonding increases the CH3-C-CH2-C-CH3 in different solvents, namely ethyl
boiling point of the compound ond also solubility ofthecompound in
alcohol and n-hexane. Which of the following statement is true?
water. Intramolecular hydrogern bonding decreases boiling point and
also its solubility in water. (a) Both samples have equal percentage of the keto form
(b) Sample in ethanol has higher percentage of the keto formn
28. Which of the following compound is soluble in water? than that in the n-hexane sample
(c) Sample in n-hexane has percentage of the keto form
higher
than that in ethanol sample
(d) Sample in ethanol does not have keto form at all
(a) (b) 33. Phenols and amines undergo methylation when treated with CHl
How many methylated products can be formed when isatin is
methylated?

(c) (d) nOne

Among the following pairs, pick up the incorrect order with

eference to boiling points
OH
(a) CH CHCH,> CH, CCH (a) One (b) Two
(c) Thne (d) Four
(b) H , >H,S
OH
PASSAGE-3
(c) CHC CHCOOC2H > C1,CC1,CO0C,15 Conditions for hydrogen bonding
(d) None of the three () The molecule must possess a higher electronegative atoms such as F, O
or N, directly linked to hydrogen atom.
J0, Which hydrogen atom of 2,6-dihydroxybenzoate can torm
(i) The stze of the electronegative atom shouldbesmall.
intramolecular hydrogen bond? Types of hydrogen bonding. Generally, the hydrogen bonds are
011
classified into two groups, viz. intermolecular and intramolecular.
1 Intermolecular hydrogen bonding. In such type of linkage the
O0 two or more than two molecules of the same compound combine
together to give a polymeric aggregate.
[OI OH
Intramolecular hydrogen bonding. In this type, hydrogen
bonding occurs within two atoms of the same molecule.
(a)
()
(b) Intramolecular hydrogen bonding is possihle when a six or five-
membered ring can be formed.
both (d) ne
 34. Hydrogen bonding is possible in 41. Observe the following structures
(a) 0-chlorobenzoic acid (b) HCI
(c) HF (d) KF H2C =
NH2 CH2 -NH2
35. Which of the following explains the high boiling point of m-
chlorophenol than theo-chlorophenol? Structure I is major contributor in the two resonating
(a)
(a) Intermolecular H-bond structures

Intramolecular H-bonding contributor in the two resonating

(b) (b) Structure II is major
() Both structures
(d) None Both are equal stable
36. Which of the following factor explains insolubility of salicyclic (c)
Resonance is not possible
acid in water? (d) can be drawn for 2, 4-pentadienyl
42. How many resonating structures
(a) Its bulky aryi group
radical?
(b) Chemical reaction between OH and -COOH groups 2
(a) (b)
(c) Chelation (d) 4
(d) Association (c)

PASSAGE4
PASSAGE6
t or n electrons and a
A molecule having polar bonds should be polar, however this is R Resonance involves
can be
movement of

derived from another

only
a series of one or
by
not true in all cases. A molecule is said to be polar when the center of resonar.ce structure
is possible only when one double
electron shifts. Thus
resonance
negative charge does not coincide with the center of positive charge. A more
unshared pair
polar molecule has a dipole moment, u, which is equal tothe multiple with another double bond or a n
bond is in conjugation
of magnitude of the charge (e) and distance (d) between the centers of o r a n electron
deficient atom
of electrons
essential that the skeleton should be
charge. Further for resonance, it is
=e x d Thus any structural feature that destroys
planar in conjugated system. will inhibit r e s o n a n c e . This
37. The correct order of the dipole moments of the four alkyl halides this coplanarity of the conjugated system
should be inhibition is referred to as steric inhibition of resonance.

octet of electrons
CHF CHC CH3Br CH3l Structures in which all atoms have a comnplete
IV
are especiallystable and make large contribution to the hybrid.
I> II> I I > IV IV> III >II>I
(b)
(a) II> III > I> IV
(c) II > I> III > IV(d)
38. Which of the following statement is false about BCl,?
chloride which of the -NO2 group (as indicated by
(a) It has three polar bonds 43. In picryl
a, b, c) is involved in resonance.
It is a polar molecule
(b)
It is a non-polar molecule
(c) lone pair of electrons CI b
(d) Its central atom has no
used for NO,
39. Dipole moment can be between two concerned polar atoms
(a) calculating bond length ionic character of the concerned
(b) calculating the percentage
bond
between ionic and covalernt bond
NO
(c) differentiating
all the above three purposes
(d) (a) (b) b
(c) (d) all
PASSAGE -5 44. TheCC-CI bond length in CH, = CHCI and CH=CHCH,C
be taken in consideration for resonance.
Following criteria should respectively is most likely to be
the one with the lowest energy. Good
The major contributor is (b) longer, shorter
have all octets satisfied, as many bonds as (a) shorter, longer
contributors generally (d) shorter, shorter
separation as possible. Negative charges (c) equal
possible and as little charge atoms. 45. Which of the following is more stable than others
are more
stable on the
more electronegative
it to
Resonance stabilization is most important when serves

more atoms. NH :NH

delocalize a charge over two or

40. The two important resonating structures of nitromethane are:

H
CH -N CH,-N H H
o I
the resonance hybrid of nitromethane can be written as

:NH NH
(a) CH (b) CH3

H X H
CH, - N,
() CH -N (d)
(a) (b)
(c) V (d) all equal
 PASSAGEL7 51 Colum ColumnI
hvdrogen atom when bomded with highly ele tn negative atom (A) Irnductive effect (a) femporary effect
tch as fluorine, oxyVgen ete acquires a positive charge. In (B) lyperconjugation (b) LuKas's test for the three

consequem of this, such a

hydrogen atom exerts an
electro types of alkohols
statio attraction on other highly elextronegative atom like fluorine, (C)Mesomericeffect (c) Involves g electrors
or oxvgen. There is actually a
dipole-dipole or dipole (D) Electronic effect (d) Involves nelectrons
ian attractio. which has been named as hydrogen bond This 52. Column Column I
be represented
as, (A) H0 (a) Protophilic solvent
may
(B) Liquid ammonia (b) Amphiprotic solvernt
HYA (C) BernzEne (c) Aprotic solvent
Protogeric solverit
where X and Y are strongly electronegati ve atoms like fluorine, (D) CH,OH (d)
oxygen and nitrogen. 53. Column Column I
Such a bonding is signification only with hydrogen because of (A) sphybridization (a) square planar
thesmallsize of ihe hydroger which ehables Y to make a close (B) sphybridization (b) tetrahedral

approach to the positive charge. (C)sp hybridization

(D) dsp hybridization
(c) oxtahedron
Maximum energy of H bond = 45 k}/mol. (d) trigonal bipyramidal
(E) dsp' hybridization (e) linear
46
Hvdrogen bonding with chlorine is rarely observed because: (F) dsp' hybridization ( triangluar planar
(a) Chiorine atom is not sufticiently electronegative to form 54. ColumnI Column
hydrogen bond. (A) o-Hydroxybenzoic (a) Tautomerism
The charge density of the chlorine atom is greater. acid
(b) Intramolecular H- bonding
The electron affinity of chlorine is highest among the (B) p-hydroxyberzoic (b)
(c) acid
haiogens. Intermolecular H- bonding
(d) The size of the chlorine is greater. (C) Acetylacetone c)
(D) Avetoacetic ester (d) Soluble in water
47 Whih of the following statement is true regarding the existence
55. ColumnI Column li
ofX-H-Ytype
(a)
bond:
The given type of bond rarely occurs because atom can (A) CH=CH (a) Markownikoff addition
accommodate two electrons only in the 1s orbital. The use
of 2s is not possible due to much higher energy. (B) (b) Acidic hydrogen
(b) The hydrogen atom has metal like properties. The valency
ofhydrogen is always limitedto one. Thus X -H-Y type C) CH,COCH,COOC,H, (c) Wohl-Ziegler reaction
of bond never exists. (D) CH,NO, (d) Tautomerism
(c)X - H - Y type of bonding may occur in the electron 56. Match the number of isomers shown in column-I with the
H - Y type of corresponding compounds of molecular formula shown in
deficient molecules. The formation of X
bond occurs like the three - centre- two- electron bond in column-I (exclude all kind of stereoisomerism).
Column-I Column-lI
the electron deficiernt inolecules.
(M.F.) No. of Isomers
(d) Both (a) and (c) are correct
(A) CioH20 (all trans decenes) (a) 3
48. Whichoffollowing statement is incorrect about H-bonding?
(a) Boric acid has sheet like layer structure in solid state due to (B) CH00 (aldehydes) (b) 4
(C) CzH13N (3° amines) (c) 2
intermolecular H-bonding. (D) CsH,,O (three membered (d) 5
(b) NaHC0, (9) has dineric structure whereas KiHCO,(6) has
cyclic epoxides) (e)
polymeric structure due to H-bond. Column-I Column-I
(c)Enol form 57.
ofacetoaceticesterofis intramolecular
more
stable in comparison
H-bonding (Compounds) (Charactristics)
tOketo form due to presence (A) CH, = C =O (a) Mesomeric eftect/ resonance
with stable 6 membered ring
(d) Order of strength of H-bond is (B) (b) Inductive effect
(C) CH, = C = CH, (c) Hyperconjugative eitect
O-H N>0-H 0N-H-0
CH
tructions for Q. 49 to 60: Following questions are Multiple
Matching type Questions: (D) (d) NonpoBar
49 HC H
Column Column
(A) Enol form of resonance stabilization (e) Conjugation
(a) Match the reaction intermediates tormed during the reactions
58.
(B) CH,COCH,COOC,H5
Higher acidity of given in column-1
(b) Hydration
maleic acid than
Column- Column-
fumaric acid (A) Propyne ti/ , (a) Carbocation
(C)
Higher acidity of (c) lntramolecular (Non classical)
potassium fumarate hydrogen bonding
(B) 2Chlorobutane (b) Carbocation
than sodium maleate
(Classical)
(D)Solubilityof NaCT
in water
(d) Intermolecular
hydrogen-bondin (C)But-I
ene BeH (c) Carbanion
50.
(A)
Column I
O= C - O
ColumnIi
NattiCat H,
(a) Cis sp hybridised
(B) OH O has two lone pair ot (D) ,COO
(b)
electrons KOH >CH,-CH,
(d) Alkyl free radical
C) HCHO (c) Cis spéhybridised electrolySis
(D) CH, =C =CH2 (d) O is »p' bybridised (e) Carbene
 59. Match the compounds of column-I with the reaction
Instructions for Q. 61 to 72: Following questions are Assertion and
characteristics of column-l1.
Column-I Column-1I Reasoning Type Questions :

Note
Each question contains STATEMENT-1 (Assertion) and
A. Ph-C-CH,- C-OEt (a) Reduction with ILiAlH STATEMENT-2 (Reason). Each question has 5 choices (a), (b), (
(d) and (e) out of which ONLY ONE is correct.
(a) Statement-1 is True, Statement-2 is True; Staternent-2 is a correct
Me Me explanation for Statement-1.
OH Statement-1 is True, Statement-2 is True; Statement-2 is NOTa
(b)
B. OJ b) Nucleophilic addition correct explanation for Statement-1.
Statement -1 is True, Statement-2 is False.
(c)
(d) Statement -1 is False, Statement-2 is True.
Me OH
(e) Statement -1 is False, Statement-2 is False.

(c) Hydrolysis

C H = CH- CHO
61. Statement - 1: Dipole moment of Azulene
D.
(d) a-Halogenation
more than naphthalene.
CN Statement-2: Azulene exists as dipolarion due to the aromatic
nature obtained in both rings.
(e) Phenyl-1, 2-shift
62. StatementI:3-Phenylbutan-2-one racemises in presence of dilute
possible by using H*
acid or dilute base.
60. Match the following column.
Statement II : Its keto form is thermodynamically more stable
Column-I Column-II form then the enol form.
(Compounds) (Order) 63. Statement-1: CH,OH boiling point is more than CH,SH while
CH-0-CH, boiling point is less than CH-S-CH
A (a) II>I >II Statement-2: Hydrogen bonding is stronger in CH,OH than
CH SH while no hydrogen bonding exist in
(1) (II) CH-0-CH and CH SCH3
64. Statement I:2,4,6 trinitro N,
N-diemethylaniline is 40,000 times
more basic than 2,4,6-trinitroaniline.
Statement II: In the former steric inhibition or resonance causes
the availability of lp on N whereas in the later due to H-bonding
(III) of NH, with NO,
groups make NH planar with benzene ring, so
decreasing order of easy delocalisation of electron pair of N in benzene ring.
carbocation stability 65. Statement 1: p-Hydroxybenzoic acid has a lower boiling point
than o-hydroxybenzoic acid.
because
B. CH3--CH (b) I> II > III Statement 2 : o-Hydroxybenzoic acid has intramolecular
hydrogen bonding.
66. Statement 1:Trichloroacetic acid is
CH3-N=CH-CH3 stronger than acetic acid.
(11)
Statement 2: Electron withdrawing substituents decrease the
activity.
NH 67. Statement 1:
Neopentane forms one mono substituted
compound.
CH3-C-CH Statement2:Neopentane is isomer of pentane.
(111) 68. Statement-1:Free radicals are
decreasing order of pK,a Statement-2: Free radicals paramagnetic.
contain an unpaired electron.
69. Statement-1: Like simple
OH OH
alkyl carbanions, allyl carbanion 15
QH Pyramidal.
Statement-2 : All the carbon atoms in
C. allyl carbanion are
(c) III > II>I sp-hybridized.
70. Statement-1: Toluene is o,
p-directing.
Statement-2: The hyperconjugation effect of the
CI Br
increases the electron density at o-and methyl group
(1) (11) (III)
ring.
p-positions in the benzene
Increasing order of pK, 71. Statement-1: Benzyne contains a carbon-carbon
D. HO Statement-2: Two of its carbon atoms are triple bond.
OF2 O,Cl2 (d) II > IlI>I sp-hybridized.
) (11) (III) 72. Statement-1 : Addition of bromine to
Decreasing order of (O-0) trans-2-butene yields
bond length meso-2,3-dibromobutane.
Statement-2: Bromine addition to an alkene is an
addition. electrophilie
 ctions for Q. 73 to 78: Following questions are Integer Type
Instru 75.
Questions
OCH,
Write the maximum number of atoms having same hybridisation
73.
in 2,5-di-N-chloridothioimino-3, 4-dicyanothiophene as shown -OCH,
below:
N OCH, O=
CH
C
The positive charge of carbocation can be delocalized over how
many oxygen atoms in the resonating structures.
76. The number ofenolizable H atoms is
N
Ph
CH3 Ph
CH- -G-CH-
Find the number of carbon including the given structure which H O O CHCH
74.
structures. (The structures
CH3 O
can havenegative charge in resonating
with charge separation are not acceptable).
77.
HC=C-C-CH = C =CH2
carbon atoms)
C=N How many carbon atoms (including the given
can have unpaired electrons).
possible for molecular
78. How many carbocation isomers are
formula CH5".
H3
EXERCISE 2.3 (Subjective Problem s)
isomers of
8. (a) Write the structural formulae of all the possible
1. Predict the shape of the following species. indicate which of them is non-polar.
(ii) CH3 C,H,Cl,and
i) (CH)B (ii) CH What effect should the following
resonance of vinyl chloride
(b)
(iv) NH (o) BF (vi) (CH,),0. have on its dipole moment?
2. Write the conjugate acid and conjugate
base ofthe following: CH2CH= C1
(a) HNO (b) H: (c) :CH CH, =CH-CI
(d) C (e) HC = CH CHO (c)
Write the tautomeric forms for phenol.
o z o n e which satisfy the
in nature? r e s o n a n c e structures of
Which of the following species is amphoteric 9. (a) Write the two
the following pairs?
3. Which is the stronger base in each of octet rule.
structures of the following that
(a) NH and PH2 (b) Write all possible resonance
(b) NH, and OH satisfy the octet rule.
(c) HS and F. NO and Ng
and ethanol has n-hexane in
form hydrogen bond 3-methylpentane and
Ethanol and water both water boils at a 1 0 . Arrange 2, 2-dimethylbutane,
weight than water, e v e n then Explain your a n s w e r
with proper
high molecular order of decreasing boiling point.
than ethanol. Explain
5.
much higher temperature in increasing order
of stability. reasonin8
in order of increasing boiling point
alkenes
Arrange the following 11. Arrange the following
Explain you answer with proper reason. chloride and isobutane
(CH,),C CHCH =
() n-butane, n-butanol, n-butyl
CH,CH CH,0 2=CH2, (CH3) =CH2,
C
n-butane, ethanol, water and propane.
(CH), C = C (CH3)2 (i) enol content
6. 12. Arrange the following
in increasing order ot expected
Explain the following: CH,COCH,COCH
i) Guanidine behaves a s a strong base. in CH,CH,CHO, CHCOCH,CH,CHO, three structures?
between following
(i) Vinyl alcohol is acidic in nature 13. Is there any relationship
and ketones
aldehydes
Acidic nature of a-hydrogen of reactive in dimethyl
NaF is m o r e
o T h e F of dissolved than in methanol.
o r acetonitrile
sulphoxide, (CH),SO than that of AlCl3
is much higher NI NH
Melting point of NaCl R C = 0 " : is m o r e stable
than HN
acylium ion, the
structure
In
R - C = O. atom in the =
indicate the type of hybridisation of each carbon HO OH
following compounds. (ii) CHCH = CH2
) CH,CN HC=C-CH =CH.
)CH-C=C-CH (iv)
EXERCISE 2.2

1(a.c) 2 (a,b,c) 3
(a,bcd) 4 (a,c) 5 (cd) 6 (a,b,c)
>1 CORRECT
7
(a,b.c,d) 8
(a,bc)|9 (cd) 10 (b,d) 11 (a,b) 12 (a,b.cd)
13 (a,b,c) 14 (a,b)
OPTION | 15 (a,b,c) 16 (b,c.d) 17 (b) 18
(a,bcd
19
(a,d)20 (bc) 21 (a) 22 (acd) 23
(a,bd) 24 (a,b,d)
25 (b,c) 2 26 (b) 27 (a,c,d)
PASSAGE 1 28 (b) 29 (d) 30 (a,bc)
PASSAGE 2 31 (d) 32 (b) 33 (b)
PASSAGE3 34 (a, c) 35 (a) 36 (c)
PASSAGE 4 37 (c) 38 (6) 39 (d)
PASSAGE5 40 (c) 41 (a) 42 (c)
PASSAGE 6 43 (c) 44 (a) 45 (C)
PASSAGE7 46 (b) 47 (a) 48 (a)
49 (A)- a, c; (B) - c; (C) - c; (D) - b, d
50 (A) a, b; (B) -d; (C) - b, c; (D) - a
51 (A) -b, c; (B)
MATCHING -C,d;(C)-d (D) a,d52 -

(A)-a,b,d; (B) a,b; (C) - c; (D) a,b

-
-

53 (A)-e; (B)-f; (C)-b; (D)-a; (E)-c; (F)-d 54 (A) -b; (B) -c, d;(C) -a, b (D) -a, b
TYPE
QUESTIONS55(A)-a,b; (B)-a, c ; (C)-b, d; (D)-b, d 56 (A)-b; (B) - b; (C)-a (D) -d
57 (A)-a, b; (B)-a, e; (C)-d; (D)-a,b,.c.d.e 58 (A)- a; (B) -a; (C)-a (D)-cd
59 (A)-a,b.c.d; (B)-cd; (C)-a,e; (D)-a,b, c 60 (A)-b; (B) -b; (C)-a (D) -d
61 (a) 62
A/R (b) 63 (a) 64 (a) 65 (d) 66 (c)
67 (b) 68 (a) 69 (d) 70 (a) (c) 72 (b)
71
INTEGER 73 6 74 6 75 2 76977 4 78

16. (b, c, d) 18. (a, b, c, d)

OH

(a) Correct order K

(a)
(b)
L
Heat of combustion No. of C atoms.
H
OH

NH NH NH
(6)
(d) HN NH

Conjugate acid Conjugate acid

(most stable) (least stable)
17. (6) xhas partial double bond character
p has partial double bond character
qhas partial single bond character
rhas pure double bond character
y has pure single bond character
. Order of bond length will be -H
y>p>x>q>r
 H (d) Stability

H®. SOo
(
CH,

22. (a, C,
(due to steric
inhibition of resonance)
(O)
d) qhas
H highest electron density since it
density by +M effect, hence receives electro
q> p>r. Histidine
imidazole substituent which K,:has 6-electrons ha
CH CH 24. (a, b, d)
aromaticity. involvedi
CH, CH
CH-H-CH, -OH H Ph -CH- (a)
CI C

(i)
C
(ii)
-
CH, CH CH, CH3 two of C
CH, CH3 Cl bonds cancel each other in (ii) and henc
=
i) > (ii)]
Ph-C
-CH,Hh- Cl H
-CH,Ph--`-CH
H (b) =
are
,two CI - atoms not in the
19. (a, d) sam
H CI
CI
COOH plane but in = C =C =
both C-Cl bonds ar
H Ci
COOH coOH COOH in the same
plane and acting at 180°C, so u of (ii) 0. =

cis So, (b) is also correct.

trans -

(a) M.P. II >I True (c) In BF, B F bond

lengths is smaller due to pt pt back -

(b) False bonding whihc is not in

possible BF4 [hence (C) is nes
(c) False correct.
(d) Iand II are geometrical isomers (d) F
20. (b c)
(a) Total number of isomers are 3.
H H H
H2C =CCl2 (H>0) (H =0)
CI CI C
(b) Yes orly 2 are geometricalisomers.
H Hence, (d) is also correct.
46. (d) Clhas high
(c) Yes all isomers has 5o and one t bond. 48. electronegativity but have size.
(b) HCOg ions exist as dimer in KHCO greater
(d) Noo
1. (a) 0-H-- O
(a) Stability O = = O
O --- H - 0
In ions are
O== NatHCO, the HCO linked in to an infinit
O= chain through intermolecular
56. A -

-(b), B - (b), C (a), D- (d) H-bonding.

(A) Cota0: C-C-C-C-C-C-C-C-C-C

(due to intramolecular H-bonding) Total 4 trans decenes

(b) Strength of H-bonding :

(B) C5H0O: C-C-C-C-CHO; C-C-C-CHO =4

O=q O=C-H
N (C) CgH3N: C-C-N-C; C-c-N-C; C-C-N-C=*
(Since anions have stronger H-bonding and six membered C
intramolecular H-bonding more stable than 7 membered).
(c) Acid strength: C

COOH (D)
ÇOOH CH1oO: - -C-C-C; C-Ç-Ç-C-C
OCH,
(due to steric inhibition of resonance) -C- C; C-
S-C: C--C-¢=5
 B (a, e); C- (d); D- (a, b, c, d, e)
(a, b); 73
-

eA-
O

(inductive effect and resonance)

CHCHYCHLH, < CU,-CH- CH-C1,

(conjugated, resonance)
(c) CH,=C=CH, (nonpolar)

(d) C C
CH Pour carbon atoms and two nitrogen atoms which have
HC
been encirced aresp hybridized.
(resonance, inductive, hyperconjugated, nonpolar) 74. 6

Ph 6
OHS Ph HC C-Ç-CH C = CH
62. CH- - Me 2 CH1- - Me
tautomerisation 2 N
H
Statement-1 is True, Statement-2 is True but reason is not the
correct explanation of assertion. CH
carbon atomns
65. p-Hydroxybenzoic higher boiling point than
acid has The negative charge is delocalised on the marked
o-hydroxybenzoic acid due to intermolecular hydrogen bonding (1-6).
Thus, statement-1 is false. o-Hydroxybezoic acid shows 75. 2
intramolecular H-bonding thus, statement-2 is true.

H-cH
H oCH
66. Trichloro acedic acid is stronger acid as three chloro substituents OCH
are electron withdrawing CH
67. Neopentane forms one mono substituted compound as shown
76. 9
below

CH3 CH3 H
H
Ph
CH-C-CH 2H,C-C-CH,C CH Ph
CH3 CH3 -CH- H
It is 1-chloro 2, 2-dimethyl propane.
t Torms only substituted compound not because it
one mono
is CH,O H O o CH
the
of pentane but because its structure is symmetrical (all 77. 4
Somer carbon).
carbons are symmetrically situated around central
( bTOrm
) With trans-2-butene, the product of Br, addition is optically
reason are correct.
nactive. Even though, both assertion and
the correct reason for the formation
of meso-2,
78. 4
trans-2-butene is anti addition of
dibromobutane from C=C-C, C=C-C, C=C-C
Br2

EXERCISE 2.3 O
CH
(o) (vi)
1. i) B-CH (ii) ..
(ii)
HC
CH H CH,
(CH),B, Trigonal H (CH),0, Tetrahedral
BF,Tetrahedral
C H , Tetrahedral
Conjugate acid Conugate base
Species
(a) HNO H,NO, NO,
(b) H: H2 None
H (io) (c) :CH CH :CH22
(d) C HCI None
H
CH,Trigonal (e) CH, = CH,
CH-CH CH = H
NH, Tetrahedral
 ) CH,O CH OH :CH,02- (ii) -Hydrogen atom of aldehydes and ketones acidic is
However, practically conjugate bases in (c) and (f) are difficult too nature because the carbanion tormed by its los is stablis
form, hence it can
be said that CH,O and: CH3 have no by resonance.
conjugate bases.
Thus HNO, and
3. (a)
CH, CH, are amphoteric. =

NH is stronger base than PH, because of smaller size of N.

(b) NH, is stronger base than OH because of less H,C-C-R -H H, Y -R H,C =C-R
electronegativity of N than that of O. Moreover in Resonance stabilization of
Aldehydes/ketones
: carbanion of aldehydes/ketones
NH,electron density is dispersed over one-third (33%)
of the
(No resonance)
surface wkile in OH electron density is
In methanol, fluoride ion is linked to CH,OH via H-bona
over half (50%) of the surface. dispersed (iv)
(c) Basic character of (CHOH--- F) with the result reactivity of F is decrease
HS and F cannot be compared because
Fand S are in different
The other two solvents are incapable of forming H-bond
covalent.
groups and different
periods of the () NaCl is electrovalent, while AlCl, is
periodic table.
4.
Degree of association is very high inwater as In ion, R-C=0*: is more stable than R-C =0
ethanol because presence of bulky alkyl groupscompared to that in (vi) theacylium
ordinary carbonium ion, because in the former the octes
formation of intermolecular hinders the of every atom is complete while in the later, the carbon
5. hydrogen
Relative stability of alkenes can be bonding.
explained on the basis of atom has only 6 electrons.
hyperconjugation,
structures
the number of
more
hyperconjugative 7. (i) sp, sp (ii) sp*, sp', sp<
(i.e. O-H atoms, written, below the each (iii) sp, sp, sp, sp3 (i0) sp, sp, spé, sp-
more will be the member),
stability of the alkene. H-C-CI H C-CI
8. (a)
CH3 H-C-CI CI-C-H
CH3-CH = CH2 HC = CH C CH2 cis-1,2-Dichloroethylene(Polar) trans-1,2-Dichloroethylene(Non-polar
(b) Resonance decreases the dipole moment of vinyl chloride
The positive charge on Cl and a negative charge on C
(developed by resonance) oppose each other and hence
3-Hyperconjugative No 6-Hyperconjugative diminish the electronegativity of Cl and thus polarity (and
structures structures dipole moment) of the bond. The dipole moments of vinyl
CH chloride and chlorobenzene are 1.4Dand 1.7D respectively,
CH3 CH3 CH3
C =C< while the dipole moment of alkyl halides is 2-2.2 D.
C =C
CH H OH
CH CH3
9 Hyperconjugate structures 12 Hyperconjugative structures
Hence order of stability is
(CH)C = C(CH)2 > (CH,)C = CHCH,> (c)
CH,C=CH2 > CH,CH =CH,> CH, = CH,.
end
6. (i) Guanidine is a strong base because it can accept proton keto
very easily and the protonated guanidine is quite stable as
it is a resonance hybrid of three equivalent structures.
9. (a) :0-ö-o: --o:
NH H2 :
:
H
(b) O-N :Ö= N

HN NH HN NH
NH o-N
and

N- N =N:
HN NH, HN NH2 N =N-N N =N-N
Three equivalent resonating structures 10.
Note that protonation occurs
Branching decreases the surface area of the molecule with
only at
sp<hybridised nitrogen result vander Waal forces the
becomes less and hence the molecule
atom because this leads to a species very much stabilised by boils at lower
three equivalent resonating structures. Protonation b.p. Thus the boiling point order
hybridisedtoN atomgives species which is not stabilised sp° n-Hexane > is
resonance
on

by
11. (i) 3-Methylpentane>
iso-Butane < n-Butane < 2, 2-Dimethylbutane
any significant extent. n-Butyyl <n-Butanol
(ii) Vinyl alcohol behaves as a weakacid because Intermolecular Weaker chloride
deprotonation is more stable than the parentthe ion formed by forces Stronger Dipole-dipole Hbond
compound. vander Waal vander Waal
cH,CH . CH-CH = OH
forces
i) Propane
Intermolecular Weaker <n-Butane < Ethanol
Stronger Weaker
<Water
Less stable due to vander Waal vander Waal Stronger
12. Hbond H-bond
charge separation CH,CHO CH,COCH, CHCOCH,CHO
<
<

13. I and II are <CH COCH,COCH3

tautomers (lactam-lactim
CHCH More stable due CH-CH = 0
resonating structures. type); II and IIl are

to absence of charge separation