SRI SARADA COLLEGE FOR WOMEN

(Autonomous)
Reaccredited with ‘A’ Grade by NAAC (Affiliated to Periyar
University)
Salem – 636 016, TAMIL NADU

II M.Sc. Chemistry
Productive preparation for CSIR/SET/ JRF-IV (PT4TC)

Multiple Choice Questions

 ADVANCED ORGANIC CHEMISTRY
SECTION A

UNIT-I AROMATICITY

1. Which of the following compounds is aromatic?

a)Cyclooctatetraene b)Azulene c)Cyclobutadiene d)Cycloheptatriene
2. Which of the following compounds is anti - aromatic?
a)Benzene b)Naphthalene c) Azulene d)Cyclobutadiene
3. Which of the following carbocation would you expect to be aromatic?

a) b) c) d)
4. Which of the following is converted to aromatic on loss of hydride ion?

a) b) C) d)
A)

5. Which of the following C6H6 has /have a single set of structurally equivalent
hydrogen atoms?

i) ii) iii) iv)

a)i and ii b)ii and iii c)i and iv d)i and iii
6. Which statement regarding Huckels rule is false?
a)There must be (4n+2)π electrons
b) )There must be (4n) π electrons
c)The molecule must be cyclic
d) The molecule must be planar
7. When benzene undergoes hydrogenation in the presence of a catalyst ,the energy that is
released (heat of hydrogenation ) is
a)the same as for cyclohexatriene b) the same as for 1,3- cyclohexadiene
c) the same as for 1,4- cyclohexadiene d)less than for cyclohexatriene
8. Which of the following molecules is/are aromatic according to Huckle rule
a)[10] annulene b) [12]annulene c)[4] annulene d) [8] annulene
9. How many uncharged structures are there for azulene ?
a)1 b)2 c) 3 d)4
10. Select the compound that would be predicted not to be aromatic
a)Pyrrole b) Pyridine c)Pyrimidine d)Piperazine
 UNIT-II PHOTOCHEMISTRY
11. Photosynthesis is
a)photoreduction of CO2 b)photooxidation of CO2 c) photoreduction ofH2O
b)photooxidation of H2O
12. Which type of electronic transition can be seen in saturated carbonyl compounds
a)→ * b)π→ * c)π→π * d)n→π * and π→π *
13. The excited state having net magnetic moment is called
a)singlet state b)triplet state c)doublet state d)ground state
14. Which of the following decay with change in multiplicity is known as ISC?
a)S1→ S0 b) S1 → T1 c) T2 → T1 d) S2→ S1
15. In fluorescence which one of the following decay takes place
a)S1→ S0 b) S1 → T1 c) T2 → T1 d) S2→ T1
16. In phosphorescence, which one of the following decay takes place
a)S1→ S0 b)T1 → S0 c) T2 → T1 d) S2→ S1
17. Photochemical reactions involving fission of α- carbon and carbonylic carbon followed
by elimination is known as
a)Norrish Type I reaction b) Norrish Type II reaction
c) Norrish Type II I reaction d)Barton reaction
18. Photolysis of ketones involving cyclcic transtition state followed by abstraction of ϓ-
hydrogen and cleavage is known as
a)Norrish Type I reaction b) Norrish Type II reaction c) Norrish Type II I
reaction d)Barton reaction
19. Which one of the following reaction is a photochemical reduction?
a)Benzophenone to benzpinacol b)ketone to oxetane
c)norbornene to dimer d) )ketone to olefin
20. Which one of the following reaction is Paterno-Buchi reaction
a)rearrangement of ketones b)photodimerisation c)photoisomerisation
d)cycloaddition of carbonyl compound to alkene
21. Addition of oxygen to anthracene in presence of light is known as
a)photoreduction b)photooxidation c) photoisomerisation d)photodimerisation
UNIT III FREE RADICALS
22. CH3-N=N-CH3----Δ→ A+B. A and B are
a)CH3. And N2 b)CH3+ and N2 c)CH3_ and N2 d)CH4 and N2
23. (CH3)4Pb →? The products are
a)CH3+ and N2 b)CH3_ and N2 c)CH4 and N2 d) a)CH3. and Pb
24. Which is the most stable free radical among the following
a)(CH3 )3C. b) Ph3C. c) CH2=CH-CH2. d) PhCH2.
25. CH3. is having a)planar b)pyramidal c)linear d)tetrahedral structure
26. CF3. . is having a)planar b)pyramidal c)linear d)tetrahedral structure
27. Ph3C. . is having a)planar b)pyramidal c)propeller-type d)tetrahedral structure
28. Aryl halide on heating with copper powder forms biaryl compounds .This reaction is
known as
 a)sandmeyer reaction b)pschorr reaction c)Ullmann reaction d)gattermann reaction
29. When gomberg-bechmann reaction is performed intramolecularly,either by alkaline
solution or by copper ion procedure it is called

a)sandmeyer reaction b)pschorr reaction c)Ullmann reaction d)gattermann reaction

30. Gomberg-bechmann reaction is

a)acidic solution of aromatic diazonium salt is made alkaline, it forms biaryl
b) alkaline solution of aromatic diazonium salt is made acidic, it forms biaryl
c)acidic solution of aromatic diazonium salt is made neutral, it forms biaryl
d)neutral solution of aromatic diazonium salt is made alkaline it forms biaryl
31. ArN2X+HBF4→A→B . The products are
a) .ArN2X and BF3 b) .ArN2X and N2 c)ArN2BF4 and ArF d) .ArN2X ArF
32. Ph3C . is an example of
a) short lived radical b)long lived radical ) short lived carbocation b)long lived
carbocation
UNIT IV PERICYCLIC REACTIONS
33. Orbital symmetry conservation rule states that
a) Orbital symmetry of reactants and products are conserved in all pericyclic reactions
b) Orbital symmetry of products are conserved in all pericyclic reactions
c) Orbital symmetry of reactants are conserved in all pericyclic reactions
d) ) Orbital symmetry of reactants and products are not conserved in all pericyclic
reaction
34. In all pericyclic reactions ,symmetry correlations are made between
a)HOMO of one molecule and LUMO of another molecule
b) HOMO of one molecule andHOMO of another molecule
c) LUMO of one molecule and LUMO of another molecule
d)HOMO of one molecule and Non bonding orbital of another molecule

35. (2+2) cycloaddition of 2CH2=CH2→ is

a) photochemically allowed b)thermally allowed c) ) photochemically forbidden
d)thermally forbidden

36. (4+2) cycloaddition of CH2=CH2 +CH2=CH-CH=CH2 → is

a) photochemically allowed b)thermally allowed c) ) photochemically forbidden
b)thermally forbidden
37. Suprafacial and Antarafacial interaction of orbitals mean
a)in phase and in phase ineraction b) in phase and out of phase ineraction
c) a)out of phase and in phase ineraction d)out of phase and out of phase
ineraction
38. Diels-Alder reaction is an example of
a)[4+2] b)[2+2] c)[2+3] d)[4+4] cycloaddition
 N2 N N

39. is an example of
a)Electrocyclic reaction b)cycloaddition c)chelotropic reaction d)sigmatropic
rearrangement
40. Photochemical shift of D-CH2-CH=CH2→CH2=CH-CH2-D is
a)supra-supra b)supra-antara c)antara-antara d)antara-supra
41. Photochemical dimerization of ethylene to form cyclobutane is
a)2πa+ 2πa b) 2πs+ 2πa c) 2πa+ 2πs d) 2πs+ 2πs cycloaddition
42. Benzyl –N-ylides rearranging to form aromatic amines is known as
a)cope rearrangement b)sommelet-hauser rearrangement c)wittig rearrangement
d)benzidine rearrangement
UNIT V RETROSYNTHESIS
43. Disconnection is defined as
a) bond making and bond breaking b)real bond cleavage in a reaction
c)imaginary bond cleavage corresponding to the reverse of a reaction
d) real bond cleavage corresponding to the reverse of a reaction
44. A synthon is
a)a generalised fragment , usually an ion real or imaginary produced by
disconnection
b)a generalised fragment , usually an atom real or imaginary produced by
disconnection
c)a generalised fragment , usually an molecule real or imaginary produced by
disconnection
d)a generalised fragment , usually an compound real or imaginary produced by
disconnection
45. Synthetic equivalent is an
a)actual compound which is a logical precursor of a target molecule
b)imaginary compound which is a logical precursor of a target molecule
c)actual compound which is a target molecule
d)imaginary compound which is a target molecule
46. Retrosynthesis is a
a)synthon approach to organic synthesis b)`ionic approach to organic
synthesis
c)free radical approach to organic synthesis d) real approach to organic
synthesis
47. Illogical means a)normal polarity is maintained b) normal polarity is reversed
c) normal polarity is quantised d) normal polarity is reflected
48. The synthetic equivalent for H3C+ is
a)CH3Br b)CH4 c)HCHO d)CH3MgBr
49. The synthetic equivalent for -C H2CH2CH2- is
a)EtO2C(CH2)3COOEt b)CH3CH2CH3 c)H3CCHO d)CH3CH2CH2MgBr
50. FGA is defined as
a)addition of functional group in place of carbon
 b) addition of functional group in place of hydrogen
c) removal of functional group in place of carbon
d) elimination of functional group in place of carbon
51. FGI is defined as
a)writing of one functional group in place of another to do disconnection to get SE
b) addition of functional group in place of hydrogen
c) removal of functional group in place of carbon
d) elimination of functional group in place of carbon
52. Reconnection is
a)addition of functional group in place of carbon
b) addition of functional group in place of hydrogen
c) removal of functional group in place of carbon
d)joining a bond in the target molecule which is broken in forward synthesis

SECTION B
UNIT I AROMATICITY

53. From the following compounds shown below, choose which is not aromatic?

,a) b) c) d
54. In the reaction, the product A is aromatic because

2Na
A

a)C8H82- is formed b) C8H8- is formed c) C8H82+ is formed d) C8H8+ is formed

55. In the reaction, the product A is aromatic because

Cl
2Li
A

a)cyclononatetraenide anion is formed b)cyclononane is formed

c)cycloctatetraene is formed d) cycloctatetraene anion is formed

56. Tropylium Bromide is soluble in water because

a)tropylium cation is present b)cycloheptatriene is present c) cycloheptane is
present
d) cycloheptadiene is present
57. Cyclooctatrienyl cation is an example for
 a)aromaticity b) homoaromaticity c)anti-aromaticity d)non -aromaticity
58. Cyclopropenide anion is an example for
a)aromaticity b) homoaromaticity c)anti-aromaticity d)non -aromaticity
59. [12]Annulene di anion is an example for
a)aromaticity b) homoaromaticity c)anti-aromaticity d)non -aromaticity
60. Cycloheptatrienide anion is an example for
a)aromaticity b) homoaromaticity c)anti-aromaticity d)non -aromaticity
61. Calicene is an example for
a)aromaticity b) homoaromaticity c)anti-aromaticity d)non -aromaticity
62. Heptafulvalene is an example for
a)aromaticity b) homoaromaticity c)anti-aromaticity d)non -aromaticity
63. Which is aromatic
a)triafulvalene b)pentafulvalene c)heptafulvalene d)triafulvene

UNIT II PHOTOCHEMISTRY

64. Acetone sensitized photolysis of norbornene leads to formation of

a)norbornane b)dimer c)bornane d)isobornane
65. Decarbonylation of 2,2-dimethylcyclohexanone may form
a)dimethylcyclopentane b) cyclopentane c) cyclohexane d) cyclopentaneone
66. 2CH3COCH3 +(CH3)2CHOH→ A .The product A is
a) (CH3)2C--C(CH3)2 b)CH3OH C) CH3CH2OH d)CH4
HO OH

67. Benzophenone +2-butene→→ A . .The product A is

a) benzpinacol b)butane c)oxetane d)olefin
68. Irradiation of cyclopentenone forms
a)head to head and head to tail dimers in equal proportions
b) a)head to head and tail to tail dimers in equal proportions
c) a)tail to tail and head to tail dimers in equal proportions
d) a)tail to head and head to tail dimers in equal proportions
69. Di-π-methane rearrangement is a reaction in which
a)1,3-butadiene rearranges to form cyclopropane
b)1,4-dienes carrying alkyl or aryl substituents on C3 rearranges to form
vinylcyclopropanes
c) a)1,4-pentadiene rearranges to form cyclopropane
d) a)1,3-butadiene rearranges to form cyclobutane

UNIT III FREE RADICALS

70. The major cause for the stability of triphenylmethyl-type radicals is

a)resonance stabilization b)steric hindrance to dimerise
c)captodative effect d)+I & _I effect
71. R-N=N-R→ A+B. A and B are
 a)R. and N2 b) R+ and N2 c) R- and N2 d) RH and N2

72. Ar. + Ar Formation of biaryl is an example of

a) coupling reaction b) H abstraction c)disproportionation d)thermal cleavage

73. ArN2Cl +CuCl→ArCl .This reaction is called
a)Sandmeyer reaction b)Barton reaction c)Wolf reaction d)Claisen reaction
74. Gattermann reaction is
a)Aryl diazonium salts are treated with cuprous ion it forms aryl halide
b) Aryl diazonium salts are treated with cuprous ion it forms diaryl
c) Aryl diazonium salts are treated with cuprous ion it forms alkane
d) a)Aryl diazonium salts are treated with cuprous ion it forms halogens

UNIT IV PERICYCLIC REATIONS

75. Which of the following statements is false about pericyclic reactions? They are
a)concerted
b)stereospecific
c)brought by the action of thermal or light energies
d)stepwise mechanism
76. Pick out the reaction which is not a pericyclic reaction
a)Diels-Alder reaction b)Cope rearrangement
c)Electrocyclic reaction d)Hofmann elimination
NH NH

H2N NH2

77.
Is an example of which type of sigmatropic rearrangement
a)[3,3] b)[5,5] c)[2,3] d)[1,5]
78. 2Z,4Z-Hexadiene on photochemical electrocyclic ring closure leads to formation of
a)cis-3,4-dimethyl cyclobutene b)tranis-3,4-dimethyl cyclobutene
c) cis-2,3,-dimethyl cyclobutene d) cis-1,4-dimethyl cyclobutene
79. Electrocyclic reaction may be represented as
a) πm πm-2 + 2 b) πm πm-2 + 4 c) πm πm+2 + 2
d) ) πm πm-2 + 1
NMe2
CH3

CH2
NMe2

80. is known as
a)cope rearrangement b)sommelet-hauser rearrangement
c)wittig rearrangement d)benzidine rearrangement
 UNIT V RETROSYNTHESIS

81. Two group disconnection means

a)using of one functional group to help to disconnect another
b)involves one functional group
c)joining of bond to build target molecule
d)reversal of charge on carbon
82. CH3CO/COCH3 ========= SE
a)2CH3COOEt b)CH3COCH2Cl +Me2CuLi c)2CH3COCH2Cl d)2Me2CuLi
83. CH3CH2COOH========= A+B. Aand B are
a)CH3-CH2(+) ,(-)COOH b) CH3-CH2-CH2(+) ,(-)COOH
c) CH3-CH2(-) ,(+)COOH d) CH3-CH2(+) ,CHO
84. Logical synthons formed during dix of 2,4 –pentadione are
a)CH3CO(-) and CH3-CH2(-) b) CH3-CH2(-) and,(+)COOH c),(+)COOH and
CH3CO(-)
d) )CH3CO(-) and)CH3CO(+)
85. The logical SE for synthesis of Quinine are
a)meroquinine and ethyl quininate b) meroquinine and ethyl quininone
c)quinotoxin and ethyl quininate . d) meroquinine and ethyl benzoate
86.An illogical synthon is
a)one in which normal polarity is preserved
b) one in which normal polarity is reserved
c) one in which is neutral
d) one which is a free radical.
87.α-Bromoacetone is an example of
a)illogical electrophile b) )logical electrophile c) )illogical nucleophile
d) )illogical nucleophile
88.1,3-Dithiane is an example of
a)illogical electrophilic SE b) )logical electrophilic SE
c) )illogical nucleophilicSE d) )logical nucleophilic SE
89.Pick out the nucleophilic synthon from the following
a)CH3COOH b)CH3CHO c)(-)CH3 d)CH3COCH3
90) .Pick out the electrophilic synthon from the following
a)(+)CH2OH b)CH3CHO c)(-)CN d)(-)OH
91.Fullerenes is not aromatic because
a)it is cyclic and planar b)it undergoes substitution reaction
c)bond lengths are equal d)it is not cyclic and planar
92.2Z,4E-Hexadiene on heating undergoes conrotation to give
a)trans-3,4-dimethyl cyclobutene b) cis-3,4-dimethyl cyclobutene
c) trans-2,3-dimethyl cyclobutene d) cis-2,3-diimethyl cyclobutene
93. π2s +π2s cycloaddition of ethylene forms
a)pentene b)butane c)cyclobutane d)cyclopentane
94. π2s +π2s cycloaddition of norbornadiene forms
a)quadricyclane b)semibulvalene c)cyclohexene d)bulvalene
95.Cyclopentadiene + maleic anhydride ----product is an example of
π2s +π2s cycloaddition of ethylene forms
a)π2s+π2s b)π4a+π2a c)π4s+π2s d)π2a+π4a cycloadditon
96.Naphthalene, Anthracene and polyacenes on irradiation undergo
a)photodimerisation b)paterno-buchi reaction
c)photo rearrangement d)isomerisation
97.Direct irradiation of 1,5- cycloheptadienone gives
a)CO and 1,35-hexatriene b) a)CO2 and 1,35-hexatriene
c) a)CO and 2,4,6-hexatriene d) a)CO2 and 2,4,6-hexatriene
98.In cyclicketones, suitably placed double bonds or cyclopropane ring facilitate
a)π -cleavage b) )ϒ-cleavage c) )β -cleavage d) )α -cleavage
99.Paterno-Buchi reaction involves
a)singlet ketone and singlet olefin leading to biradical
b) triplet ketone and singletolefin leading to biradical
c) singlet ketone and triplet olefin leading to biradical
d)triplet ketone and triplet olefin leading to biradical
100.Anti-aromatic compounds will undergo reaction such as
a)electrophilic substitution b)electrophilic addition
c) nucleophilic substitution d) nucleophilic addition
PHYSICAL METHODS IN CHEMISTRY

SECTION A
UNIT 1
 1. The 1s electrons for helium have a binding energy of 2.37 MJ/mol, while the 1s
electrons for lithium have a binding energy of 6.26. What best explains why these
bonding energies are so different?
a) Lithium has a higher nuclear charge than helium. This increases binding energy of core
electrons
b) There is greater shielding of core electrons in lithium
c) There is greater electron-electron repulsion in helium
d) All of the answers are correct.
2. Koopman's theorem states that ionisation energy of an orbital
a) negative value of the energy of the orbital, -j, as calculated within the Hartree–Fock
approximation
b)  negative value of the energy of the orbital, -j , as calculated within the Huckle
approximation
c)  negative value of the energy of the orbital, -j , as calculated within the Density
Functional approximation
d) All of the above
3. The minimum amount of energy needed to eject an electron from the neutral molecule
a) Adiabatic ionisation energy b) Vertical ionisation energy
c) Electron affinity d)None of the above
4. The XPS uses photons of energy range
a)200-2000 ev b) 20-200ev c)10-45 eV d) 20-40 ev
5. The PES technique used to examine core electron is
a)UPS b)ESCA c)XPS d)Auger spectraoscopy
6. --------- is a direct measure of the energy required to just remove the electron
concerned from its initial level to the vacuum level
a) Adiabatic ionisation energy b) Vertical ionisation energy
c) Electron affinity d)None of the above
7. The kinetic energy distribution of the emitted photoelectrons is given as
a)Photelectron spectroscopy b)Vibrational spectroscopy
b)Electronic spectroscopy d) Auger electron spectroscopy
8. -------- is a plot of the number of emitted photoelectrons as a function of their kinetic
energy
a)Photelectron spectroscopy b)Vibrational spectroscopy
b)Electronic spectroscopy d) Auger electron spectroscopy
9. ESCA focusses on which of the following information?
a) Mass of the electron
b) Charge of the electron
c) Binding energy of the electron
d) Mass of atoms
10. Auger electron spectroscopy can be used for surface chemical analysis in a way
similar to which of the following?
a) ESCA
b) SIMS
c) ISS
d) Ion spectroscopy
11. In Flame emission photometers, the measurement of _____________ is used for
qualitative analysis.
a) Colour
b) Intensity
 c) Velocity
d) Frequency
12. In Flame emission photometers, the measurement of _____________ is used for
quantitative analysis.
a) Colour
b) Intensity
c) Velocity
d) Frequency
UNIT 2

13. The values of CO stretching frequencies of (1)Ni(CO)4 (2) Ni(CO)3(PMe3) (3)

Ni(CO)2(PMe3)2 follow the trend
a)(1)>(2)>(3) b) (3)>(2)>(1) c) (1)>(3)>(2) d)(2)>(3)>(1)
14. Which one of the following IR frequencies is the closest to that of a triply bridged CO
group-
a) 1700 cm-1 b)1810 cm-1 c)1920 cm-1 d)2140 cm-1
15. Which one of the following spectroscopic techniques will be useful to distinguish
between M-SCN and M-NCS binding modes?
a)NMR b)IR c)EPR d)Mass
16. The number of IR bands corresponding to  (M-X) modes for geometrical isomers of
type ML4X2 is
a) Trans -2 ;cis-1 b) trans-1 ;Cis-2 c)cis-2; trans-3 d)trans-3;cis-2
17. The number of IR bands corresponding to  (M-X) modes for geometrical isomers of
type ML2X4 is
a) Trans -4 ;cis-2 b) trans-1 ;Cis-4 c)cis-3; trans-4 d)trans-2;cis-2
18. In complexes of type ML3X3,  (M-X) modes for facial and meridional isomers
show ...... bands
a)fac-2;mer-3 b)fac-3;mer-1 c) fac-2;mer-2 d)fac-1; mer-1
19. In IR spectra of [Co(CN)5H]3- the Co-H stretching is observed at 1840 cm-1. The Co-D
stretch in [Co(CN)5D] 3- will appear at nearly
a)1300 cm-1 b)2400 cm-1 c)3500 cm-1 d)8600 cm-1
20. Among the following molecules, one having the highest zero point vibrational energy
is (a) CH4 (b) H2O (c) HF (d) NH3
21. Which of the following has lowest stretching frequency?
(a) V(CO)6+ (b) Co(CO)4- (c) Ni(CO)4(d) Fe(CO)4-2
UNIT 3

22. The 1H-NMR of (η5-C5H5)2Fe recorded at room temperature has

a)one singlet b)one multiplet c)Two singlet d)Two multiplet
23. The values of CO stretching frequencies of (1)Ni(CO)4 (2) Ni(CO)3(PMe3) (3) )
Ni(CO)2(PMe3)2 follow the trend
a)(1)>(2)>(3) b) (3)>(2)>(1) c) (1)>(3)>(2) d)(2)>(3)>(1)
24. Which one of the following IR frequencies is the closest to that of a triply bridged CO
group-
a) 1700 cm-1 b)1810 cm-1 c)1920 cm-1 d)2140 cm-1
25. JC-H coupling between H1 and C13 in methane is less than 119Sn-H coupling in SnH4
a) γ( 119Sn) is much larger than γ( 13C). b) γ(13C) is much larger than γ(119Sn)
b) percentage abundance is lesser for Carbon d)percentage abundance is more for tin
26. The 19F NMR spectrum of ClF3 shows
a)doublet and triplet for a T-shaped structure
b) Singlet for trigonal planar structure
c) Singlet for a trigonal pyramidal structure
d)doublet and singlet for a T-shaped structure.
27. The low temperature (-98oC) 19F NMR spectrum of SF4shows doublet of triplets. It is
consistent with the point group symmetry-
a)C3v b)C4v c)Td d)C2v

28. shows how many signals are obtained in 19F NMR spectrum
a)2 b)1 c)3 d)4

29. In the figure comment on 2JPH and 1JPH

a) 2JPH > 1JPH b) 2JPH <1JPH c) 2JPH = 1JPH d) 2JPH >>> 1JPH
30. 19F NMR spectrum of PF3 is
a)singlet b)doublet c)triplet d)quartet
31
31. P NMR spectrum of PF3 is
a)singlet b)doublet c)sextet d)quartet
31
32. P NMR spectrum of PF5 is
a)singlet b)doublet c)sextet d)quartet
19
33. F NMR spectrum of PF5 is
a)singlet b)doublet c)triplet d)quartet

UNIT 4

34. . Electron spin resonance is also known as which of the following?

a) Electron paramagnetic resonance
b) Electron diamagnetic resonance
c) Electron paramagnetic reoccurrence
d) Electron diamagnetic reoccurrence

35. The value of magnetic moment is known as which of the following?

a) Thompson magneton
b) Bohr magneton
c) Goldstein magneton
d) Rutherford magneton
36. When the electrons are aligned either parallel or antiparallel to the direction of external
magnetic field, the electrons will precess about the axis at a frequency that is
proportional to which of the following?
a) Applied magnetic field
b) Electron magnetic moment
 c) Applied magnetic field and electron magnetic moment
d) Neither applied magnetic field not electron magnetic moment
37. . If a weaker radiofrequency alternating magnetic field, having the frequency of
precession of the electron is applied at right angles to fixed magnetic field, which of
the following occurs?
a) Fragmentation
b) Scattering
c) Resonance
d) Absorption
.
38. The population ratio can be given by which of the following laws?
a) Bohr law
b) Beer-Lambert law
c) Kelvin law
d) Boltzmann law
39. The sensitivity of measurement is greatly enhanced by using which of the following?
a) High magnetic field
b) Low magnetic field
c) High electric field
d) Low electric field
40. ESR sensitivity increases with __________ temperature and with _________ magnetic
field strength.
a) Increasing, increasing
b) Increasing, decreasing
c) Decreasing, increasing
d) Decreasing, decreasing
41. Reflex klystron is used in which of the following frequency ranges?
a) 1000 to 2000 MHz
b) 1000 to 10000 MHz
c) 1000 to 15000 MHz
d) 1000 to 20000 MHz

42. Which of the following sensor is used in ESR spectrometer?

a) Hall-effect sensor
b) Load cell
c) Strain gauge
d) Bourdon gauge
43. The number of lines that appear in the EPR spectra of [C6H6]-is:
a. a)5 b)11 c)7 d)13
44. The total numbers of fine and hyperfine EPR lines expected for octahederal high-spin
Mn(II) complexes are respectively (l=5/2 for Mn)
b. a)3 and 30 b)5 and 33 c) 5 and 30 d) 4 and 24
45. Bohr magneton is equal to
 a)eh/2m b)ep/2m c)2ehm d)2m/eh
46. What is the value of g value of free electron
a) 2.323 b)2.000232 c)2.00232 d)20.32

UNIT 5

47. Which of the following terms refers to the molecular modelling computational
method that uses equations obeying the laws of classical physics?
a. Quantum mechanics
b. Molecular calculations
c. Molecular mechanics
d. Quantum theory
48. Which of the following terms refers to the molecular modelling computational
method that uses quantum physics?
a. Quantum mechanics
b. Molecular calculations
c. Molecular mechanics
d. Quantum theory
49. Which of the following statements is true?
a. Energy minimisation is carried out using quantum mechanics.
b. Energy minimisation is used to find a stable conformation for a molecule.
c. Energy minimisation is carried out by varying only bond angles and bond
lengths.
d. Energy minimisation stops when a structure is formed with a much greater
stability than the previous one in the process.
50. Which of the following needs to be known before two drugs can be overlaid to
compare their structures?
a. The pharmacophore of each drug
b. The active conformation of each drug
c. Both of the above
d. Neither of the above
51. Which of the following statements is true?
a. The most stable conformation of a drug is also the active conformation.
b. The active conformation is the most reactive conformation of a structure.
c. The active conformation is the conformation adopted by a drug when it binds
to its target binding site.
d. The active conformation can be determined by conformational analysis.
52. Which of the following statements is not true of cyclic structures?
a. They are normally more rigid than acyclic structures.
b. They are locked into the active conformation.
c. They are useful in determining the active conformation of a series of related
compounds.
d. They are normally more difficult to synthesise than acyclic molecules.
53. What is meant by docking?
a. The process by which two different structures are compared by molecular
modelling.
b. The process by which a lead compound is simplified by removing excess
functional groups.
c. The process by which drugs are fitted into their target binding sites using
molecular modelling.
d. The process by which a pharmacophore is identified.
54. What is meant by de novo drug design?
a. The synthesis of a compound from simple starting materials.
b. The design of the synthesis required to generate a novel range of structures.
c. The design of a novel drug based on molecular modelling studies of a binding
site.
d. The modification of a drug based on molecular modelling studies into how it
binds to its target binding site.
55. Which of the following statements is true in de novo drug design?
a. The design of rigid molecules is superior to flexible ones.
b. Molecules should be designed to fit as snugly as possible into the target
binding site.
c. Molecules that have to adopt an unstable conformation in order to bind should
be rejected.
d. Desolvation energies can be ignored since they are likely to be the same for
different molecules having the same pharmacophore.
56. Which of the following software programmes is used for automated de novo drug
design?
a. DOCK
b. LUDI
c. CHEM3D
d. CoMFA

SECTION B
UNIT 1

57. The PES shown above belongs to which element

a)K b)Ca c)C d)N
58. Identify the molecule that shows the above PES
a) HCl b)HF c)HBr d) HI
59. Given below is the diagram of Flame emission photometers. Identify the unmarked
component.

a) Filter
b) Atomiser
c) Pressure regulator
d) Burner
60. In PES if the vibrational frequency in ion shifts relative to neutral molecule it
indicates which of the following
A) The electron is from bonding orbital
B) The electron is from anti bonding orbital
C) The electron is from non bonding orbital
a) Only A b) A and B c) A,B and C d) B and C
61. Which of the following is an Auger transition starting from a hole in 1s levels which
would be filled up from the 2p level?
a) KLM transition
b) KLL transition
c) LMN transition
d) LLM transition
 UNIT 2

62. trans-[Os(bipy)2(O)2] has one nM=O IR band at 872 cm−1, whilst cis-[Os(bipy)2(O)2]

(bipy = 2,2′-bipyridine) has two nM=O IR bands at 863 and 833 cm−1 because:
a) For the trans isomer the symmetric nM=Omode results in no change in the dipole
moment and hence this is IR inactive while for cis isomer both symmetric and
antisymmetric have change in dipole moment and hence IR active
b) For the cis isomer the symmetric nM=Omode results in no change in the dipole moment
and hence this is IR inactive while for trans isomer both symmetric and antisymmetric
have change in dipole moment and hence IR active
c) For both the cis and trans isomers the symmetric nM=Omodes results in no change in
the dipole moment and hence are IR inactive
d) For both the cis and trans isomers both symmetric and antisymmetric have change in
dipole moment and hence IR active

63. The solid state IR spectrum of [Co2(CO)8] displays nCO bands at 2071, 2044, 2042,
1866 and 1857 cm−1, but in a non-coordinating solvent there are only nCO bands at
2069, 2055 and 2032 cm−1
a) In solid state there are only terminal ligands while there are both terminal and
bridging ligands CO bonds for non coordinating solvent.
b) In solid state there are both terminal and bridging ligand while there are only terminal
CO bonds for non coordinating solvent
c) In solid state there are terminal ligands while there are only bridging CO bonds for
non coordinating solvent
d) In solid state there are both terminal and bridging ligand while there are only bridging
CO bonds for non coordinating solvent
64. Arrrange the following vCO in complexes: [Ni(CO)3(PMe3)], [Ni(CO)3(PPh3)],
[Ni(CO)3(PF3)] in the increasing order of wave number
a) [Ni(CO)3(PMe3)]< [Ni(CO)3(PPh3)]< [Ni(CO)3(PF3)]
b)[Ni(CO)3(PF3)]< [Ni(CO)3(PPh3)]< [Ni(CO)3(PMe3)]
c)[Ni(CO)3(PPh3)]< [Ni(CO)3(PMe3)]< [Ni(CO)3(PF3)]
d)[Ni(CO)3(PMe3)]< [Ni(CO)3(PF3)]< [Ni(CO)3(PPh3)]

65. Arrange the following in increasing order ofνC-Ostretching frequency: (I)

[Mo(CO)3(PF3)3] (II) [Mo(CO)3(PCl3)3] (III) [Mo(CO)3P{Cl(Ph)2}3] (IV)
[Mo(CO)3(PMe3)3]
(a) IV < III < II < I (b) III < II < I (c) I < II < III < IV (d) II < III < I < IV
66. Which of the following IR frequencies is the closest to that of the triply bridged CO
group?
(a) 1700 cm-1 (b) 1810 cm-1 (c) 1920 cm-1 (d) 2140 cm-1
67. Arrange the following in increasing order of CO stretching frequencies :
I. Cr(CO)6 II. [V(CO)6] - III. [Mo(CO)6]+ IV. CO
(a) I > II > III > IV (b) II < I < III < IV (c) IV< II < III (d) I < III < IV
68. Solid Co2(CO)8 shows infrared CO stretching bands at 1857,1886, 2001, 2031, 2044,
2059, 2071 and 2112 cm-1 . When dissolved in hexane, the carbonyl bands at 1887
and 1856 cm-1 disappears. These changes in infrared spectrum are due to:
(a) Loss of terminal CO (b) Structural changes of Co2(CO)8 involving conversion of
terminal CO to bridging CO. (c) Dissociation of Co2(CO)8 to Co(CO)4. (d) Structural
changes of Co2(CO)8 involving conversion of bridging CO to terminal CO.
 UNIT 3

69. Na[5-C5H5)Fe(CO)2] reacts with Br2 to give A. Reaction of A with LiAlH4 gives B.
The 1H NMR of B consists of 2 singlets of relative intensity 5:1 compounds A and
B respectively are:
a) [5-C5H5)Fe(CO)2]Br and [5-C5H5)Fe(CO)2]H
b) [4-C5H5)Fe(CO)2]Br2 and [4-C5H5)Fe(CO)2]HBr
c) [5-C5H5)Fe(CO)2]Br and [4-C5H5)Fe(CO)2]H2
d) [5-C5H5)Fe(CO)2]Br and [5-C5H5)Fe(CO)2]HBr
70. 1H NMR spectrum of free benzene shows a peak at around 7.2 ppm. The expected
chemical shift of benznene ligand in 1H NMR spectrum of (6-C6H6)Cr(CO)3 and the
reason for it if any are
a)4.5; disruption of ring current b)9.0; inductive effect c)7.2 d) 2.5;
combination of inductive effect and disruption of ring current.
71. The 119Sn NMR chemical shift (approximately in ppm) corresponding to (η5- Cp)2Sn
(relative to Me4Sn ) is
a)-4 b)+137 c)+364 d)-2200
31
72. The P NMR of PF4(N(CH3)2) at room temperature and low temperature (173K)
respectively show (assume that N and H do not couple)
a) Triplet and quintet b) quintet and triplet
c)Quintet and triplet of triplets d) triplets and triplets of triplets
73. The metal complex that exhibits a triplet as well as a doublet in its 31P NMR is
a)mer-{IrCl3(PPh3)3} b)trans-{IrCl(CO)(PPh3)2]
c)fac-{IrCl3 (PPh3)3} d)[Ir(PPh3)4]+
74. 1H and 19F NMR of HF2- ion shows
a) Triplet and doublet b)doublet and triplet
c)triplet of triplet d)doublet of doublet
75. 19F NMR spectrum of meriodional isomer of octahedral RhCl3F3 complex, [103Rh
(I=1/2); 19F ( I=1/2) assuming JRh-F> JF-F} will show
(a) One doublet (b) Two doublets and one triplet
(c) Two doublets and two triplets (d) One singlet and two triplets
76. A borane (X) is reacted with ammonia to give a salt of borohydride (Y). The 11B
NMR spectrum of Y consists of a triplet and a quintet. The borane X is:
(a) B2H6(b) B3H9 (c) B4H8 (d) B5H9. In the proton decoupled 13C and 31P NMR
spectrum of (CH3)3P=O, the number of lines observed respectively are:
(a) Two and one (b) One and two (c) Three and One (d) Two and two
77. The 31P NMR spectrum of P4S3 consists of:
(a) A doublet and a quartet (b) Two doublets (c) A doublet and a triplet (d) A singlet

UNIT 4

78. The number of lines that appear in the EPR spectra of [C6H6]-is:
a)5 b)11 c)7 d)13
79. Which of the following technique is used to differentiate M-SCN and M-NC
complexes
a)NMR b)IR c)ESR d)MB
80. If Mossbauer spectrum of Fe(CO)5 is recorded in the presence of a magnetic field, the
original spectrum with two lines changes into the one with:
 (a) Three Lines (b) Four Lines (c) Five Lines (d) Six Lines

81. The number of EPR signals observed for octahedral Ni(II) complex is:
(a) One (b) Two (c) Three (d) Zero
82. Among the following, those can act as Mossbauer nuclei are: (I) 129I (II) 57CO (III)
57
Fe (IV) 121Sb

(a) I,II,III and IV (b) II,III and IV (c) I,II and IV (d) I,III and IV

83. The correct order of the isomeric shift in Mossbauer spectra (57Fe source) of iron
compounds is:
(a) Fe(II) > Fe(III) > Fe(IV) (b) Fe(III) > Fe(II) > Fe(IV) (c) Fe(IV) > Fe(III) > Fe(II)
(d) Fe(IV) > Fe(II) > Fe(III)
84. The number of hyperfine split lines observed in ESR spectrum of methyl radical is:
(a) 1 (b) 6 (c) 8 (d) 4
85. The number of hyper lines in the EPR spectrum of a one electron reduced product of
[Co3(CO)6Se] ( I= 7/2 for Co nucleus) is: (a) 22 (b) 19 (c) 15 (d) 18
86. Among the following diatomic molecules, the one that shows EPR signals is:

(a) B2 (b) N2 (c) C2 (d) Li2

87. Which of the following species is ESR active?

(a) KMnO4 (b) K2Cr2O7 (c) VOSO4 (d) [Co(NH3)6]Cl2
88. The number of lines in the ESR spectrum of CD3 is (the spin of D is 1)
(a) 4 (b) 1 (c) 7 (d) 3
89. The total number of fine and hyperfine EPR lines expected for octahedral high spin
Mn(II) complex are :
(a) 3 and 30 (b) 5 and 33 (c) 4 and 24 (d) 5 and 30
90. The correct value of isomer shift ( in Mossbauer spectra) and its explanation for Fe(II)
– TPP and Fe(III) – TPP respectively from the following are: (TPP =
Tetraphenylporphyrinate) (A) 0.52mms-1 (B) 0.45 mms-1 (C) Increase in s electron
density (D) Decrease in s electron density (a) A and D, B and C (b) A and C, B and C
(c) B and D, A and D (d) B and D, A and C
91. The oxidation state of metal ion in the catalyst can be deducted by:
(a) Atomic Adsorption Spectroscopy (b) HPLC (c) Gas Chromatography (d)
Mossbauer Spectroscopy

UNIT 5

92. Which of the following statements is untrue when using molecular modelling to
design a combinatorial library?
a. Pharmacophore triangles can be used to design a library.
b. The aim is to synthesise the minimum number of structures likely to produce
the maximum number of pharmacophores.
c. Flexible structures should be analysed before rigid ones.
 d. Structures should only be included in the library if they represent at least 10%
additional new pharmacophores compared with the total represented by
structures already present in the library.
93. Which of the following operations or calculations would generally be carried out
using molecular mechanics?
a. Molecular orbital energies
b. Energy minimisation
c. Electrostatic potentials
d. Transition-state geometrie
94. The following graph shows the stability of a molecule as its structure is varied during
conformational analysis.

What term is used to describe the point on the graph marked X?

a. Global energy minimum
b. Transition state
c. Local energy minimum
d. Conformational minimum
95. The following graph shows the stability of a molecule as its structure is varied during
conformational analysis.

What term is used to describe the point on the graph marked Z?

a. Global energy minimum
b. Transition state
 c. Local energy minimum
d. Conformational minimum
96. The following graph shows the stability of a molecule as its structure is varied during
conformational analysis.

If energy minimisation was carried out on a starting structure appearing as shown on

the graph, at which point would energy minimisation stop?
a. V
b. X
c. Y
d. Z
 PHOTOCHEMISTRY AND ORGANIC SPECTROSCOPY

SECTION A

UNIT I

1. Which of the following factors will diminish fluorescence?

a. electron donating groups b. rigidity of the molecule
c. conjugation d. electron withdrawing groups

2. In which of the following compounds, the fluorescence is activated by H-bonding

a. anthracene b. naphthalene c. o-hydroxy benzophenone d. vitamin A

3. Which of the following statement is true?

a. as number of condensed ring increases, fluorescence decreases
b. fluorescence property of anthracene decreases in its dissolved state
c. as concentration increases, fluorescence decreases
d. as temperature increases fluorescence increases

4. Which of the following statement is not related to the excimer formation?

a. two molecules should be in parallel configuration
b. molecules should be planar
c. interaction between the molecules should occur within the excited life time
d. excited state enthalpy should be lesser than thermal energy

5. Which of the following compound forms both excimer and excited state dimer?
a.pyrene b. naphthalene c. 2-methyl anthracene d. 9-methyl anthracene

6. Which of the following operator will couple the two energy states in non radiative
transfer?
a. nuclear kinetic energy operator b. dipolemoment operator
d. Hermition operator d. linear operator

7. The forbidden transition ST is possible at shorter distance by

a. dipole-dipole interaction b. exchange interaction
c. long range transfer d. exciplex formation

8. The transition D*(s) + A(s)  D(s) + A*(s) is detected by

a. sensitisation of acceptor fluorescence b. quenching of acceptor fluorescence
c. sensitisation of acceptor phosphorescence d. quenching of acceptor phosphorescence

9. What happens during quenching by short range energy transfer mechanism, if the donor
is naphthalene and the acceptor is biacetyl?
a. quenching rate drops suddenly because of the back transfer
b. quenching rate is million times lower than diffusion controlled rate
 c. transfer is exothermic and diffusion controlled
d. transfer is endothermic and diffusion controlled

10. In which of the following case, quenching rate is million times lower than diffusion
controlled rate?
a. ETD > ETA b. ETD ~ ETA c. ETD < ETA d. ETD > ESA
UNIT II
11. Which of the following ratio does not express the quantum yield ϕ
a. no. of reactants reacted/no. of photons of radiations absorbed
b. no. of products formed/no. of photons of radiations absorbed
c. no. of moles reacting in a given time/ no. of product formed
d. no. of molecules reacting in a given time/ no. of Einstein absorbed in same time

12. The quantum yield (ϕ) of the photochemical reaction, 2HI + hν  H2 + I2 is

a. ϕ > 1 b. ϕ < 1 c. ϕ = 1 d. ϕ =0

13. Which of the following equation has the quantum yield ϕ < 1
a. b.
hv hv C28H20
C14H10
H2 + Cl2 2HCl

c. hv d. hv
H2O2 CO + Cl2 COCl2
H2 + O2
14. The quantum yield of photolysis of ammonia is
a. ϕ = 1.5 b. ϕ = 0.2 c. ϕ = 2 d. ϕ =1.0

15. Which of the following reaction have the quantum yield ϕ =0.1
a. combination of hydrogen and bromine
b. dissociation of hydrogen peroxide
c. photo dissociation of acetone
d. combination of hydrogen and chlorine

16. Which of the following factor is responsible for higher quantum yield?
a. recombination of dissociated fragments
b. occurrence of reverse reaction
c. deactivation of reacting molecules
d. formation of chain reactions

17. Identify the reaction involved in uranyl oxalate actinometer

a. photoredox reaction of ammonium oxalate
b. photoisomerisation of oxalic acid
c. photodecomposition of oxalic acid
d. photodecomposition of ammonium oxalate

18. In which of the following actinometer, the intensity of radiation is determined by the
weight of CO2 evolved,
a. EDER’s actinometer
b. Photomultipler
 c. Thermopiles
d. Uranyl phosphate actinometer

19. The reactants used in EDER’s actinometer are

a. UO22+, oxalic acid b. HgCl2, (NH4)2C2O4 c.UO22+, (NH4)2C2O4 d. HgCl2, oxalic acid

20. In photolysis of water, the materials used for electrodes are

a. anode – TlO2; cathode – Platinum b. anode – TiO2; cathode – Au
c. anode – TiO2; cathode – Platinum d. anode – Platinum; cathode – TlO2

UNIT III

21. The calculated λmax for the following triene is

C8H17

a. 323nm b. 253nm c. 290nm d. 303nm

22. The λmax values 227nm & 254nm, corresponds to which of the following isomers
a. CH3 b.
&
& O O
O O
CH3 CH3
CH3

CH3
c. d. &
& O O
O O
CH3

23. Assign the λmax values of 234 nm and 273 nm to the dienes given below:
a. b.
& &

c. d.
&
&

24. The introduction of an α-halogen atom in an alicyclic ketone causes ______ shift in the
λmax value of the parent ketone
a. bathochromic shift (when equatorial) or a hypsochromic shift (when axial)
b. hyperchromic shift (when equatorial) or a hypsochromic shift (when axial)
 c. bathochromic shift (when axial) or a hypsochromic shift (when equatorial)
d. hyperchromic shift (when equatorial) or a hypochromic shift (when axial)

25. Substitution of the carbonyl group by an auxochrome with a lone pair of electrons
produces
a. a pronounced hyperchromic shift b. a pronounced hypsochromic shift
c. a pronounced hypochromic shift d. a pronounced shoulder

26. The relative stretching frequencies for C C, C C & C bonds

C are
a. 1650 cm , 2150 cm , & 1200cm b. 2150 cm-1, 1200 cm-1, & 1650 cm-1
-1 -1 -1

c. 2150 cm-1, 1650 cm-1, & 1200cm-1 d. 1200 cm-1, 1650 cm-1, & 2150 cm-1

27. Deduce which of the following compounds would give a spectrum showing strong
absorption at 1720 cm-1?
a. O b. O c. O d. O

28. Arrange the following carbonyl compounds in order of their increasing carbonyl
stretching frequency.
O O
C
O

I II III
a. I < II < III b. II < I < III c. III < II < I d. I < III < II

29. Using IR spectra, acetaldehyde can be easily distinguished from acetone,

a. by the appearance of triplet in the region 2500-3000cm-1
b. by the appearance of doublet in the region 2600-2800cm-1
c. by the appearance of weak band in the region 750-950cm-1
d. by the appearance of doublet in the region 3040-3085cm-1

30. The C=O absorption in the S-trans and S-cis isomer of benzalactone are shown below;
O CH3
CH C CH C
C CH3 C O
H H
S-trans S-cis

νC=O 1674 cm-1 < νC=O 1699 cm-1

Which of the following statement is true related to the above illustration?
a. The effect of conjugation is maximum when chromophores are non-planar
b. Loss of coplanarity will reduce the effect of conjugation thus causes the C=O
absorption to occur at higher frequency.
c. Loss of coplanarity will increase the effect of conjugation thus causes the C=O
absorption to occur at higher frequency.
d. Loss of coplanarity will increase the effect of conjugation thus causes the C=O
absorption to occur at lower frequency.
 UNIT IV
31. A compound (I) having the molecular formula C 10H14 gave the following PMR data: (i)
0.88δ (9H,s) and 7.28δ (5H, s). The compound (I) may be,
CH3
C2H5 CH3 C2H5
a. b. c. d.
H3C C H
C H C CH3 H3C C H
H
CH3 CH3 H

32. Which of the following NMR result is correct to distinguish the primary, secondary and
tertiary alcohols on the basis of PMR spectroscopy,
a. proton of OH group appears as a singlet, doublet and a triplet respectively
b. proton of OH group appears as a triplet, doublet and a singlet respectively
c. proton of OH group appears as a singlet, doublet and no signal respectively
d. proton of OH group appears as a singlet, triplet and a doublet respectively

33. A compound (I) having molecular formula C 2H2BrCl exhibits two doublets (J = 16 Hz)
in its PMR spectrum. The compound (I) may be,
Br H Br H Br Cl Br Cl
a. C C b. C C c. C C d. C C
H Cl Cl H H H Cl H

34. Compound C4H10O gave PMR spectrum consisting of two groups of lines (multiplets)
with relative intensities in the ratio 3:2. Other compound of the same formula exhibited
two lines with relative are of 9:1. Compounds are
a. diethyl ether b. t-butyl alcohol c. both (a) & (b) d. methyl alcohol

35. The peaks expected in low resolution NMR spectrum of vinyl chloride and ethyl
cyclopropane are
a. 3, 5 b. 5, 3 c. 6, 3 d. 3, 6

36. The compound with a molecular formula C6H6 shows two signals each in H 1nmr and C13
nmr. The structure of the compound is
CH CH2
a. b. c. d. H2CHC C CHC CH2

37. Consider the following H1nmr spectral data: 7.25 δ, broad singlet, 5H; 2.90 δ, septet, J =
7 Hz. 1H; and 2.25 δ, doublet, J = 7 Hz, 6H. Which one of the following structures
would have the above mentioned nmr spectrum?
CH3
a. CH3 b. H C CH2CH3 c. H3C CH3d.
3
CH
CH3 CH2CH3
H3C
38. The NMR spectrum of a compound C3H6O shows a three-proton triplet (J = 7cps) at δ
1.05 ppm, a two-proton quadruplet (J = 7 cps) at δ 2.3 ppm and a one-proton singlet at δ
9.77 ppm downfield from TMS. Its structure is

O HO HOH2CHC CH2 CH3CH2CHO

a. CH3
b. c. d.

39. In the broad band decoupled 13C NMR spectrum, the number of signals appear for (i)
catechol, (ii) resorcinol and (iii) hydroquinone respectively, are
a. six, four and two b. six, six and four c. three, four and four d. three, four and two

40. In the broad band decoupled 13C NMR spectrum, the number of signals appearing for
the bicyclooctane A-C, respectively, are

A B C

a. five, four and eight b. three, two and five

c. five, four and five d. three, two and eight

UNIT V

41. In the mass spectrum of the compound given below, during the α-cleavage, the order of
preferential loss of group is
Me
OH
Et
C3H7

a. Me ˃ C3H7 ˃ Et b. C3H7 ˃ Et ˃ Me c. Et ˃ C3H7 ˃ Me d. Et ˃ Me ˃ C3H7

42. In the mass spectrum of dichlorobenzene, the ratio of the peaks at m/z 146, 148 and 150,
is
a. 1:1:1 b. 3:3:1 c. 1:2:1 d. 9:6:1

43. Which of the following mass spectral data corresponds to the base peak of three isomeric
butanols - 1-butanol, 2-butanol and 2-methyl-2-propanol?
a. m/z 56, m/z 45 and m/z 59 b. m/z 59, m/z 45 and m/z 56
c. m/z 45, m/z 56 and m/z 59 d. m/z 59, m/z 56 and m/z 45

44. The ethylamine, diethylamine and triethylamine can be distinguished by which of the
following pairs of base peak in their mass spectra?
a. m/z 58, m/z 30 and m/z 86 b. m/z 30, m/z 58 and m/z 86
c. m/z 86, m/z 58 and m/z 30 d. m/z 30, m/z 86 and m/z 58
45. Which of the following factors is not an unusual aspects of amines in their mass spectra?
a. An odd integral molecular weight of the compound indicates the presence of Nitrogen
b. they have high tendency to capture protons and the normally low (M+1) peak will
increase in intensity if the pressure in the ion source is increased.
c. if the amine is present in the form of salt, it volatilize in the mass spectrometer.
d. if the amine is present in the form of salt, it does not volatilize in the mass
spectrometer. but decompose to give the free amine and the acid. If the acid
component is HCl or HBr, then strong peaks at m/z 36 and 38 (for HCl) and m/z 80
and 82 (for HBr) will be obtained.

46. McLafferty rearrangement is

a. β-cleavage of a bond with γ-hydrogen rearrangement to form a cation radical
and a neutral molecule
b. γ-cleavage of a bond with β-hydrogen rearrangement to form a cation radical and a
neutral molecule
c. β-cleavage of a bond with γ-hydrogen rearrangement to form a anion radical and a
neutral molecule
d. γ -cleavage of a bond with β-hydrogen rearrangement to form a anion radical and a
neutral molecule

47. Scrambling takes place by

a. β-cleavage of a bond with γ-hydrogen rearrangement to form a anion radical and a
neutral molecule
b. rupture and reformation of C-C bonds
c. elimination of neutral molecules
d. ortho effect

48. The most characteristic cleavage of alkylbenzenes occurs at

a. the bond β to the aromatic ring resulting in the formation of tropylium cation
b. the bond β to the aromatic ring resulting in the formation of phenyl cation
c. the bond α to the aromatic ring resulting in the formation of tropylium cation
d. the bond γ to the aromatic ring resulting in the formation of phenyl cation

49. The most characteristic peaks of benzaldehyde, in its mass spectra are
a. m/z 106, 105, 99, 64 b. m/z 106, 105, 43, 29
c. m/z 106, 105, 79, 52 d. m/z 106, 105, 77, 51

50. Which of the following peak will appear in the mass spectra of butanone?
a. m/z 59 b. m/z 45 c. m/z 57 d. m/z 77
 SECTION B

UNIT I

1. Match the following

I. - i. photochemical reaction
Hg + hν  Hg*
Hg* + H2  H2* + Hg
H2*  2H
II. - ii. photosensitisation
Hg + hν  Hg*
Hg* + O2  HgO + O

III. - iii. prompt fluorescence

Hg + hν  Hg*
Hg* + Tl  Hg + Tl*
Tl*  Tl + hν
IV. short lived emission from S1S0 + hν - iv. sensitised fluorescence
a. I – ii, II – i, III – iv, IV – iii b. I – iii, II – i, III – iv, IV – ii
c. I – iv, II – i, III – ii, IV – iii d. I – ii, II – iii, III – iv, IV – i

2. Which of the following pairs are true?

I. static quenching – formation of excited state dimer
II. dynamic quenching – formation of exciplex
III. concentration dependence of quenching – formation of excimer
IV. static quenching – formation of photodimer
a. I, II & IV b. I, II & III c. I, III & IV d. II, III & IV
3. Match the following equation to their appropriate complex name
hv
I. A+Q (AQ) (AQ)* - i. excimer
hv
II. A A* + Q (AQ)* - ii. excited state dimer
hv
III. A A* + A (AA)* [dis=0.3nm] - iii. photodimer
hv
IV. A A* + A (AA)* [dis 0.3nm] - iv. exciplex
a. I – ii, II – i, III – iv, IV – iii b. I – iii, II – i, III – iv, IV – ii
c. I – ii, II – iv, III – i, IV – iii d. I – ii, II – iii, III – iv, IV – i

4. Which of the following factors will govern the radiationless transition?

i. density of states
ii. energy gap between interacting electronic state
iii. vibronic overlap
iv. exciplex formation
a. i, ii & iv b. ii, iii & iv c. i, ii & iii d. i, iii & iv
5. A long range T-S transfer are detected by which of the following factors?
i. enhancement of phosphorescence life time of donor in presence of acceptor
ii. appearance of acceptor fluorescence
iii. reduction of phosphorescence life time of donor in presence of acceptor
iv. disappearance of acceptor fluorescence
a. iii & iv b. ii, iii c. i & iv d. i, ii
UNIT II

6. Match the following

i. quantum yield less than 1 - I. photogalvanic cell
ii. weight of CO2 evolved - II. photovoltaic cell
iii. photobleaching of thionine - III. Uranyl oxalate actinometer
iv. silicon solar cell - IV. Photolysis of ammonia
a. i – III, ii – IV, iii – I, iv – II b. i – II, ii – III, iii – IV, iv – I
c. i – IV, ii – III, iii – I, iv – II d. i – IV, ii – I, iii – II, iv – III

7. For a photochemical reaction AB, the quantum yield ϕ can be expressed as

a. k1k2/(k2+k3[A]) b. k1k3/k2 [A] c. k1/k2+k3[A] d. k1k2/(k2.k3[A])

8. The rate of combination of H2 and Cl2 to form HCl can be written as

a. d[HCl]/dt = 2k1k2Iabs [H2]/k4 b. d[HCl]/dt = 2k1k3Iabs [H2]/k2
c. d[HCl]/dt = 2k1k2k3Iabs [H2]/k4 d. d[HCl]/dt = 2k2k1Iabs [H2]/k3

9. The reactions involved in photogalvanic cell are

a. during charging, thionine gets reduced and ferrous ion gets oxidised;
during discharging, thionine gets oxidised and ferric ion gets reduced
b. during charging, thionine gets oxidised and ferric ion gets reduced;
during discharging, thionine gets reduced and ferrous ion gets oxidised
c. during charging, thionine and ferrous ion gets reduced;
during discharging, thionine and ferric ion gets oxidised
d. during charging, thionine gets reduced and ferrous ion gets oxidised;
during discharging, thionine gets reduced and ferric ion gets reduced

10. Which of the following statement is not related to photovoltaic cell?

a. light energy is directly converted into electrical energy without the
intermediate chemical reaction
b. light energy is directly converted into electrical energy with the intermediate
chemical reaction
c. light energy is indirectly converted into electrical energy without the intermediate
chemical reaction
d. light energy is indirectly converted into electrical energy with the intermediate
chemical reaction
 UNIT III

11. Match the appropriate reason relating UV spectrum results of following compounds:

I. deep orange-red colour of azobenzene - i. nσ* transition

II. differentiation in UV spectra of CH3Cl,

CH3Br & CH3I - ii. chromophore conjugated
with phenyl ring
III. differentiation in UV spectra of ethylene &
butadiene - iii. λmax 357 nm (ε = 4000)
IV. blue colour of azulene - iv. blue shift of * transition

a. I-ii, II-iv, III-i & IV- iii

b. I-iv, II-i, III-ii & IV- iii
c. I-iii, II-iv, III-i & IV- ii
d. I-ii, II-i, III-iv & IV-iii

12. Compound A has the formula C11H16O and reduced to B, C11H18O with hydrogen in
presence of palladium. Compound B was found to have the following structure. The
ultraviolet spectrum of A showed strong absorption with λmax at 225nm and this
absorption was not present in the ultraviolet spectrum of B. What is the structure of
A?
O

a. b. c. d.
O O O O
CH3 CH3 CH3

13. Match the appropriate reason for the IR spectrum results of following compounds:
I. Exceptionally low νC=O (1650 cm-1) stretching
frequency of 2,4,6-cycloheptatrienone - i. rotational isomerism
II. νC=O of 1-acetyl-2-methylcyclohexene >1-acetyl
cyclohexene - ii. conformational
rigidity
III. acyclic α-chloroketones exhibit 2 C=O
stretching frequencies - iii. conjugation
IV. νC-O( str).of 4-tert-butylcyclohexanol;
trans isomer > cis isomer - iv. steric effect

a. I-ii, II-iv, III-i & IV- iii

b. I-iv, II-i, III-ii & IV- iii
c. I-iii, II-iv, III-i & IV- ii
 d. I-iii, II-iv, III-ii & IV- i

14. The dehydration of 1,2-dimethyl cyclohexanol (cis or trans) can lead to the formation of
three alkene A, B & C. Which of the following results of IR spectra is true to differentiate
the three alkenes?

OH

H+ + +
-H2O
A B C
a. A – shows no absorption in IR region; B – 895-885 cm-1 & C – 840-790 cm-1
b. A – 840-790 cm-1; B – no absorption in IR region & C – 895-885 cm-1
c. A – 895-885 cm-1; B – no absorption in IR region & C – 840-790 cm-1
d. A – 895-885 cm-1; B – 840-790 cm-1& C – no absorption in IR region
15. Arrange the following non conjugated carbonyl compounds in order of increasing
Carbonyl frequency:
Aldehydes (I), esters (II), amides (III), acyclic ketones (IV), acid fluorides (V) and acid
chlorides (VI).

a. V < VI < I < III < II < IV

b. II < V < I < III < VI < IV
c. I < V < II < III < IV < VI
d. III < IV < I < II < VI < V

UNIT IV

16. Match the appropriate concept used to distinguish the following compounds by using
PMR spectrum.
I. equatorial and axial protons – i. trifluoroacetylation
II. cis and trans decalin – ii. concentration and temperature
III. inter and intra molecular H-bonding – iii. co-planarity
IV. cyclohexanol and cyclohexane – iv. anisotropic effect
V. cis and trans stilbenes – v. flexible system and rigid framework

a. I-ii, II-v, III-i, IV-iii & V-iv

b. I-iv, II-v, III-ii, IV-i & V-iii
c. I-v, II-iii, III-i & IV-ii & V-iv
d. I-iii, II-iv, III-ii, IV-v & V-i

17. An organic compound of molecular formula C8H10O showed its H1 nmr spectrum with the
following features: 2.15δ (s, 3H); 3.85δ (s, 3H) and 7.1 δ (m, 4H). The most likely structure
for the compound is

a. H C b. H C c. H3C d. H3C CH3

3 OCH3 3 OCH2CH3
OH H2C O CH2
H3C
18. In the proton NMR spectrum, an organic compound exhibited the following spectral data
δ 7.2 (1H, dd, J = 8 and 1.5 Hz), 6.8 (1H, d, J = 1.5 Hz), 6.7 (1H, d, J = 8Hz), 4.9 (2H,s), 3.9
(3H,s), 3.85 (3H, s) 3.5 (1H, br s, exchangeable with D 2O).The compound among the choices
given below is

a. b. HO c. d. MeO
OMe OH
OH
OMe
OH MeO
OMe OMe OMe
OMe

19. An organic compound A (C8H16O2) on treatment with an excess of methylmagnesium

chloride generated two alcohols B abd C, whereas reaction of A with lithium aluminium
hydride generated only a single alcohol C. Compound B on treatment with an acid yielded an
olefin (C6H12), which exhibited only a singlet at δ 1.6 ppm in the H1 NMR spectrum. The
compound A is

a. b. O c. O d.
O O
O O
O O

20. An organic compound (C7H12O2) exhibited the following data in the 1H NMR spectrum
δ 7.10 (1H, dt, J = 1.6 & 7.2 Hz), 5.90 (1H dt, J = 16 & 2 Hz), 4.1 (2H, q, J = 7.2 Hz), 2.10
(2 H m), 1.25 (3 H, t, J = 7.2 Hz), 0.90 (3 H t, J = 7.2 Hz) ppm.
O
a. b. O
O

O
O O
c. d. O
O

UNIT V

21. An organic compound A (Mol.formula C9H10O2) exhibits the following spectral data:
IR: 1745 cm-1(s), 1225 cm-1 (br. s), 749 cm-1 (s), 697 cm-1 (s)
UV: λmax 268, 364, 262, 257 nm
1
H NMR: δ 1.96 (3H, s), 5 (2H, s), 7.22 (5H, s)
The compound, among the choices given below, is

a. CH2CH3
b. c. CH2COCH3 d.
CH2COOH CH2COOCH3

OH CH3 CH2CH3
22. An organic compound with molecular formula C4H6O shows the following spectral
data:
UV, λmax nm : 218 (εmax 18000), 320 (εmax 30)
IR, cm-1 : 2855 (w), 2740 (w), 1700 (s), 1650 (m)
1
H NMR, δ ppm : 9.7 (1H, d), 6.7 (1H, m dq), 6.9 (1H, dd (J = 7 and 17 Hz), 2.5 (3H, d)
The compound, among the choices given below, is
a. b. c. d.
CHO
CHO
O O

23. An organic compound shows the following spectral characteristics:

UV, λmax nm: 256 (εmax 12000), 322 (εmax 200)
IR, cm-1 : 3350, 2833, 2760, 1667, 1616, 1580
1
H NMR, δ ppm : 10.83 (1H, s) (disappears on shaking with D2O)
9.59 (1H, s), 7.31 (2H, m), 6.79 (2H, m)
M.S m/z : 29, 39, 65, 93, 121, 122
The compound, among the choices given below, is
a. b. c. OH d.
CHO CH2COCH3
CH2COOCH3

CH3
OH CHO
24. When acetone is treated with a base, a product A is formed. It showed the following
spectral properties:
UV, λmax nm: 238 (εmax 11700)
IR, cm-1 : 1620 (m), 1695 (s)
1
H NMR, δ ppm : 1.90 (s, 3H), 2.10 (s, 6H), 6.0 (s, 1H)
M.S m/z : 98, 83, 55, 53, 43, 41, 39, 29, 28, 27.
The structure of the compound A is,
O O O

a. b. c. d.

25. An organic compound (Mol. wt. 160) exhibits the following spectral data:
UV, λmax nm: 212 (εmax 60)
IR, cm-1 :2941-2857 (m), 1742 (s), 1460 (m), 1380 (m), 1260 (s), 1056 (s)
1
H NMR, δ ppm : 1.29 (6H, t (J = 7.2 Hz), 2.5 (2H, s), 4.16 (4H, q, J = 7.2 Hz)
The structure of the compound may be,
a. C2H5OOC COOH b. C2H5OOC COOC2H5

d. H3COOC COOCH3
c. C2H5OOC COOCH3