Spectroscopy Assignment

1. How will you differential the following pairs by IR spectra? (CSE-2010)

(i) R – COOH and R – CO – O - COR

2. What characteristics bands will be observed in the IR spectrum of 1 –

phenylethanone? (CSE-2009)
3. How would you explain the carbonyl stretching frequencies given below the
structure of the following compounds:- (CSE-2011)

4. What is the range of fingerprint region in infrared spectrum? Write the range in
which carbonyl group normally absorbs:- (CSE-2008)
5. How could you use IR spectroscopy to tell if preparation of 5 – cholesten-3- one
cholesterol by Jones oxidation is complete? (CSE-2000)

6. Distinguish between the following pairs IR. (CSE-2000)

7. Which compound A or B is expected to show lower stretching frequency for

C = O group in the IR spectrum? (CSE-2001)

8. Predict the position of absorption bands for the carbonyl group in the IR spectra
of the following compounds: (CSE-2002)
st
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9. Account for the changes in the carbonyl stretching frequency in the following:

(CSE-2003)
10. Infra – red spectrum of (2R, 3S) 2, 3 –dichloro – pentane was recorded. Do you
think that this spectra will be identical with the spectra of (2S, 3R) 2, 3 –dichloro
– pentane & (2R.3R) 2, 3-dichloro – pentane? Give reason for your answer. (CSE-
2004)
11. Normal O –H stretch comes at about 3600 cm-1. What is the reduced mass for O
–H? Happens to the doublet in turn; i.e, when O -H is converted to O – D and S
–H? in fact both O – D and S –H stretch come at about 2500 cm-1 why?
(CSE-2005)
12. How will you use IR and NMR spectroscopy to distinguish 0 – and –p-
hydroxyacetophenones (CSE-2004)
13. Indicated how IR spectrum can be used to distinguish:

(CSE-2005)
14. Indicate main stretch frequencies for functional group present in acetyl acetone.
What would happen to the spectrum if a small amount of organic base is added
to it?
15. Using chemical and / or spectral method (as indicated) Show how the following
can be different. (CSE-2005)

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16. (a) (i) How can NMR/IR be used to estimate enol content of the following?

(CSE-2006)
17. The IR spectrum of p-nitro benzyl alcohol, when recorded in the KBr phas3e,
shows a medium, broad absorption at around 3200 cm-1. The same absorption
shifts to 3450 cm-1 as medium, sharp absorption when recorded in CHCl 3

solution. Explain. (CSE-2007)

18. ) Using IR spectroscopy, indicate how will you ditterentiate between the
following pairs of compound? (CSE-2007)
(i) Benzyl chloride and Benzyl cyanide
(ii) Aniline and N – methyl aniline
(iii) Cyclohexanone and cyclohexanol
(iv) Benzoic acid and Benzaldehyde
(v) Styrene and phenyl acetylene
19. ) CH3COCl, CH3COCH3, CH3CoNH2, CH3COOet arrange in increasing carbonyl
structure frequency with reason?
20. (a) How will you distinguish CH3CH2COCH3 and CH3 – CH = CH – CH2OH by
IR spectra?

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21. Calculate the λmax for the following compounds using woodwork – Fieser
rule. (CSE-2011)

22. (i) Phenol is a week acid with pKa = 10.0. it has λmax = 210 nm in ethanol. When
dil NaOH is added to the solution, the absorption increases to λmax = 235 nm.
How do you account for this shift? (CSE-2000)
23. Calculate λmax for the following:- (CSE-2000)

24. The following dienes in ethanol have λmax,s at 231 nm (ε21,000), 236 nm (ε 18,000),
265 nm (ε 6, 400) and 282 nm (ε 11,900). Indicate which diene corresponds to
which spectrum. (CSE-2001)

25. p – nitro aniline exhibits a pronounced red shift in the k- band, which is not
observed in O or m – isomer. Explain. (CSE-2002)
26. Calculate the λmax for the triene (a) which contains both a heteroannular and
homoannular diene. Your calculation should be based on the homoannular diene.
(CSE-2002)

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27. Calculate the λmax for the following using Woodward – Fieser rule: (CSE-2003)

28. An α, β –unsaturated ketone of relative molecular mass 110 has an absorption

in U.V at λmax 215 (εmax ~ 10,000). A solution of this ketone showed absorbance
A = 2.0 with 1 cm cell calculate concentration of ketone in the solution
expressed ing/l.
29. U.V visible spectrum of an α, β –unsaturated carbonyl compound was recorded
first In Cyclohexane as solvent. What will be the effect on λmax if the spectra of the
same compound is taken in the ethanol as solvent? Give reason for your answer.
30. Predict which of the following pairs of compounds will have higher λmax values
and why? (CSE-2007)
(i) CH3 – CH2 – OH and CH3 CHO

(iii) Trans Ph – CH = CH – CH3 and Ph – CH2 – CH = CH2

31. Grade the following transition according to the amount of energy required and
give explanation for your grading on the basis of Molecular orbital theory in a
qualitative manner:- π → π* ; n→ π* ;σ → σ*. (CSE-2007)
32. How do you assay bulk drugs using UV – visible spectroscopy? (CSE-2007)

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33. An ∝β – unsaturated ketone of relative molecular mass 110 has on absorpation
in U.V. at λmax 215 (Emax ~ 10000). A solution of this ketone is g/l.
(CSE-2004)
34. UV – visible spectrum of an ∝β – unsaturated carbonyl compound was
recorded in cyclohexane and the in ethanol and 80% aqueres ethanol. Discuss
changes on λmax. (CSE-2004)
35. An organic compound of molecular formula C4H9NO showed the following
PMR data in δ (ppm) scale: (CSE-2011)
(t, 4H), 3.8 (broad singlet, exchanged with D2O, 1H).
Suggest the structure of the compound assigning the reasons for the peaks.
36. Room temperature NMR spectrum of aetylacetone exhibits two close by peaks
at δ = 1.97 and 2.14ppm. Explain the reagent for their organic. What other peaks
will be observed. (CSE-2010)
37. 1H NMR spectrum recorder for CH3 – CH = CH2 at 90MHz gave coupling
constant (J) of 5 Hz for vinyl protons. If spectrum is recorder at 500MHz, write
the expected value of coupling constant. (CSE-2010)
38. In H NMR spectra C2H2 and CF3 COOH gives signals at different positions
1

why? (CSE-2010)
39. Decomposition of a diazocompound A in methanol gives a alkane B (C8 H14 O),
whose 1H NMR spectrum shows following signals: (CSE-2002)

δ ppm = 3.50 (3H, S), 5.50 (1H, dd, J = 17.9 and 7.9Hz)
5.80 (1H, ddd, J = 17.9, 9.2 and 4.3 Hz)
4.20 (1H, m) and 1.3 – 2.7 (8H, m)
What is structure?
(i) B is unstable and isomerises at room temperature to another compound C.
(ii) When the diazocompound A is decomposed in presences of a diene (D) it is
trapped as an adduct E.
Explain the reactions which give the products B, C and E.

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40. A carboxylic acid of molecular formula C11 H14 O2 on treatment with SOCl2
followed by the reaction of the product with anhydrous ACl3 in CS2 gave the
compound A of molecular formula C11 H12 O. The IR spectrum of A has a strong
band at 1690 cm-1 and its proton NMR spectrum has three signals in the intensity
ratio 2: 1: 3 (low to high field) on heating A with hydrazine in ethylene glycol, a
hydrocarbon B is obtained whose PMR spectrum gave the following chemical
shifts for the protons in the δ scale:-
1.22 (S, 6H), 1.85 (t, 2H, J = Hz)
2.83t, 2H, J = 7 Hz) and 7.12 (S, 4H).
Write down the reactions giving the structure of all the intermediates and final
products and interpreate the spectra. (CSE-2003)
41. A compound having molecular formula, C10H12O3, exhibited following data in its
1H NMR spectra; (CSE-2004)
δ 1.3 (3H, triplet, J = 7Hz), 3.85 (3H, singlet).
4.3 (2H, quartet, J = 7 Hz), 6.9 (2H, doublet, J = 11 Hz), 7.9
(2H, doublet, J = 11 Hz).
Assign structure to be the possible compound.
42. Indicate how NMR can be used to distinguish:- (CSE-2005
43. )

44. Sketch the high resolution H NMR spectrum of ethyl acetoacetate.

(CSE-2005)
45. Arrange the following in order of increasing magnitude of coupling constant
between HA and HB in the NMR spectrum. Give reasons for your answer:-

(CSE-2006)

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46. (a) Explain why TMS is used as a reference standard in 1H NMR spectroscopy.
(CSE-2007)
(b) Write the structure of the two isomeric alcohols corresponding to a molecular
formula of C3H8O and explain their proton NMR spectra (CSE-2007)
Indicate how you can identify the products of the following reaction using 1H
NMR spectroscopy? (CSE-2007)

47. Explain how can you use 1H NMR to identify the following isomers?

(CSE-2007)
48. The molecular formula of a compound was found to be C3H3Cl5. In its 1H NMR
spectrum, it showed signals at δ4.52 (t) and 6.07 (d). The ratio of integrals was
found be 2 cms: 4 cms. What is the structure of this compound? (CSE-2007)
49. Compound given below dissolves in the acetone to from a brightly coloured
solution whereas in ether, it remains colorless. The proton NMR at δ 1.88 which
on cooling to – 50 0C resolves into two signals at δ 2.07 (6H) and δ 1.29 (3H).
Explain:-

(CSE-2007)
50. Show how would you distinguish between propanal and acetone using NMR.
Label peaks and explain? (CSE-2006)
51. Predict approximate chemical shift and multiplicities for PMR of

52. A compared having molecular formula C10H12O3 has PMR spectra as following.
δ 1.3 (3H, t, J = 7) ; 4.3 (2H qua, J = 7) ; 7.9 (2H, d, J = 71)
3. 85 (3H, s) ; 6.9 (2H, d, J = 11). Assign structure.

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53. (a) How NMR can be used to distinguish aldehyde and ethylene proton?
Discuss study of H – bonding with IR?
54. In what region NMR these compared expected to absorb also give number of
Signal with multiplication.

(CSE-1994)
55. Propose structure for C9H11Br that first the following 1HNMR data:
δ 2.15 (2H, qui, J = 7) ; 2.75 (2H, t, J = 7) ; 338 (2H t, 3 = 7) δ 7.22 (5H, s)
(CSE-1994)
56. The base peak (m/e) appears at 105 for one of the following (A, B and C) and at
m/e =119 for the other two. Match the compounds with appropriate m/e
values for their base peaks. (CSE-2011)

57. How would you determine molecular wt of acetone on the basis of its mass
spectrum? Suggest possible fragmentation pattern. (CSE-2010)
58. How are the following compounds distinguished by mass spectrometry?
(a) DCH2 CH2 COCH3
(b) CH3 CH2 COCH2 D
(c)CH3 CHDCOCH3 (CSE-2009)
59. A characteristic peak at m/z 58 is shown by 2 – Pentanone [M+ 86] in the mass
spectrum. And isomer of this structure of this compound? Another isomer of this
given peaks at m/z 86 and 57. Identify this isomer. (CSE-2001)
60. Predict the structure of a fragment ion which is responsible for the appearance of
a strong characteristic peak at m/z = 149 in the3 mass spectra of the esters of the
phthalic acid. Give the mechanism of its formation from diethyl phthalate.
(CSE-2002)
61. How will you account for following mass peaks in C6H5 – CH2 – OH ?
(M/z): 108, 107, 106. 105, 91, 79
Show the fragmentation pattern. (CSE-2003)
62. The mass spectrum of ethyl phenyl ether has a prominent peak at m/z 66.
Describe mode of formatio0n of the fragment responsible for this peak. (CSE-
2004)
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63. How can one identify from the inspection of mass spectrum of the compound
that is contains: (CSE-2005)
(i) One nitrogen (ii) One chlorine atoms
(iii) Two chlorine atoms (iv) One bromine atom
64. How would mass spectral studies help you to distinguish the following?

(CSE-2006)
65. (i) Using the technique of mass spectrometry, indicate now will you distinguish
between the three identical-mass-compound (mol. Wt. 58) i.e. (CSE-2007)

CH3CH2 CH2 CH3, CH3 – N = N - CH3 AND CH3 - CH2 – CHO?

(ii) In the mass spectrum of acetophenone, a Meta – stable peak was observed at
56.5. Explain what is it due to. (CSE-2007)
66. Spectrum data of a compound (molecular formula C7 H6 O2) are given below.
Suggest a structure to this compound which is consistent to the spectral data.
UV; λmaxEtOH; (εmax) : 256nm (12, 600), 324 nm (3, 400)
IR; (cm -1) : 3175 – 3275 (broad).1667 (strong), 1616, 1580, 1484, 1456,
1383, 1230, 1205, 1151, 1115, and 1029.
(iii) 1H NMR; (δ ppm) : 10.83 (`1H, S) which disappears on addition of D2O 9.59
(1H, S) 7.31 – 6.79 (4H, m)
(iv)Ms; m/z (Relative
Abundance) : 122 (M+ 100%), 121 (96%) 93 (18.5%), 29 (31%)
(CSE-2001)
67. Treatment of phthalinide 1 with bromine in aqueous sodium hydroxide
followed by acidification with acetic acid affords compound 2. Spectrum data 2
are summarized below. Deduce the structure of 2 and provide a mechanism for
its formation. Compound 2 reacts with HNO2 to give an unstable product 3.
When 3 is treated with trans-trans 2, 4 – hexadiene (4), if forms an adduct 5,
identify 3 and explain how 5 is formed from 3. (CSE-2002)

Compound 2:

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 M/S, m/z = 137 (59%), 119 (100%) 932 (79%), 92 (59%)
IR (KBr) = 3940 (m), 3380 (m) 3300 – 2400 (br.) 1665 (s)
1245 (s), 765 (m) cm-1
1H NMR (δppm.) = 6.25 1H, t J = 8.0Hz)
6.77 (1H, d, J = 8.0 Hz)
7.23 (1H, t, J = 8.0 Hz)
7.72 (1H, d, J = 8.0 Hz)
8.60 (3H, br, S, disappears on addition
of D2O)

68. Treatment of A with KOH gives a compound B [C7H10O]. spectral data of B are
given below. What is its structure and how is formed? Explain. (CSE-2002)

IR; = 1710 cm-1

1H NMR; δ ppm = 1.15 (6H, S), 2.1 (2H, S), 6.8 (1H, d), 7.3 (1H, d)
69. Deduce the structure of a compound on the basis of the spectral data given
below: (CSE-2002)
(i) Molecular formula : C12H15NO3
(ii) UV, λmax : <210 nm (ε > 10, 000), 280 nm (ε900)
(iii) IR cm-1 : 3300, 1710, 1670 cm-1
(iv) 1H NMR, δ ppm : 2.21 (3H, s)
3.37 (2H, s), 3.76 (2H, s), 4.34 (2H, d), 6.80 – 7.18 (4H, dd)
(One proton does not show, it exchanges with D2O)
70. Deduce the structure of the following spectral data assigning reason for each
peak: (CSE-2003)
IR (cm-1) : 2875, 1720, 1622, 1310, 725
1H NMR (δ) : 1.23 (S, 3H), 4.25 (S, 2H), 7.2 (m, 5H)
Mass (m/z) : 138, 96, 91, 65, 43
Molecular formula : C9H10O2.
71. The natural product bullatenone was isolated in the 1950s and assigned the
structure A. when compound A was synthesized; it was not identical with the
natural sample. Predict the expected 1H NMR spectrum of A. given the full
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 spectroscopic data available nowadays, but not 1950s say why A was wrong
and suggest a better structure for bullatenone. (CSE-2005)

Spectra of bullatenone:
Mass spectrum : m/z 188 (10%),
Mol. Formula: (C12H22O2),
105 (20%), 102 (100%), 77 (20%)
IR spectrum : 1604 and 1705 cm-1
1H NMR spectrum: 1.45 (6H, s), 5.82 (1H, s)
72. A ketone of molecular formula C8H8O upon treatment with NaBH4 gives (A) of
molecular formula C8H10O. IR spectra of A sulfanyl chloride in the pressure of a
Base gave B. (B) was then treated with NaBH3(CN) give a hydrocarbon with
following PMR data δ 0.9 (t, 3H); δ 2.6 (quartet, 2H) ; δ 7.1(3) indentify ketone
& hydro carbon. (CSE-1999)

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73. A compound containing C, H, O, Cl shows molecular ion peak at m/z 108 and
110 in the ratio of 8:1. The IR spectra are characterized by the presence of strong
absorpation near 1710 cm-1 and a broad band near 2800 cm-1. Its NMR spectra
shows triplets at δ 2.8 & 3.8 and a singlet at about δ 12.0 in ratio of δ 2 : 221.
Deduce structure? (CSE-1996)
74. The intermolecular distance of HCl is 0.13 is 0.13 nm and the bond constant 500
Nm-1 calculate (i) moment of inertia (ii) first calculate energy (in cm-1).
(CSE-2003)
75. Explain why (M +1) ion peak is observed in mass spectrometry. Indicate, which
electron is most likely to be lost in the ionization of following compounds and
write the radical cation formed: (CSE-2013)
(i) CH2 = O (ii) CH2 = CH2
(iii) C6H5CH2CH3 (iv) CH3Cl 20
76. The compound C2H2BrCl exhibits three isomeric structures. The three isomers
in proton NMR exhibit two doublets each having J ~ 1.5, 9 and 14 Hz respectively.
Write the structures of isomers and assign j values to each one of them. 20
: (CSE-2013)
77. How many NMR signals do you expect in:

Explain their nature. : (CSE-2013)

78. An organic compound C4H8O gives a strong absorption band at 1710 cm-1 in IR
spectrum. In proton NMR, it gives signal at δ 1.1 (triplet), 2.1 (singlet) and 2.3
(quartet). Write the, likely, structure of the compound and assign the 8 value.
(CSE-2013)
79. Which of the following two pairs of stereoisomers can be distinguished with the
help of coupling constants in PMR spectroscopy? Account for your choice: (CSE-
2014)

80. Give major m/e peaks for 1-pheny 1-1-butanone. Give rearrangement product
for the same. 10 (CSE-2014)
81. Account for te different carbonyl absorptions [v C = O] for thr following
compounds: (CSE-2014)
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 82. Assign structure to the compound wiyh mol formula C9H10O2, on the basis of the
following spectral data:
(i) UV (EtOH):λmax 268,264,257,243 nm
(ii) IR : 1745 cm-1, 1225 cm-1,749 cm-1,697 cm-1
(iii) 1H NMR:δ7.1-7.3(m,5H), 5.0(s, 2H), 1.96(S,3H)
(iv) Mass : m/e ions : 150,108, 91, 43.
83. Predict the base peaks for the following compounds in mass spectroscopy: 10:
(CSE-2014)

84. Calculate λmax for the following compounds: 5 : (CSE-2014)

85. Distinguish between the following compounds using proton NMR spectra:
10(CSE-2014)
(i) 1-bromopropane and 2-bromopropane
(ii) Propanal and propanone
86. Given below are two isomeric compounds with molecular formula C5H10O. Predict the
base peaks for each of the following:

Show McLafferty fragmentation peak wherever applicable.

87. An unknown compound, C9H10O2 did not dissolve in aqueous NaOH. The IR
spectrum exnibited strong absorption at 1730 cm-1. The 1H NMR spectrum had
signals at 87.2(multiplet), 4.1 (quartile) and 1.3 (triplet). Elucidate the structure of
the unknown compound. (CSE-2017)
88. How many 1H NMR signals do you expect for 1-bromopropane and 2-
bromopropane? Give their splitting pattern. (CSE-2017)
89. How will you distinguish the following compounds by IR spectroscopy? Which
will absorb more wave number in cm1, and why? (CSE-2017)

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90. Predict the M+ peaks and mass spectral fragmentation for the
following compounds. (CSE-2017)

91. How can you distinguish between the following pairs of compounds by using IR
spectroscopy. (CSE-2017)
(i) Salicylic acid and p-Hydroxy benzoic acid
(ii) Propionaldehyde and Acctone
92. How do the UV spectral data λmax 296 nm, εmax 10700 and λmax 281 nm, εmax 20800
help in deciding between structures X and Y? (CSE-2018)

93.An organic compound (MF C5H10O) exhibits the following spectral characteristics:
?
UV(λmax : 280 nm)
IR λmax : 1715 cm-1
1H NMR (δ, ppm) : 0.90 (3H,t), 1.60 (2H, m) 2.20 (3H, s), 2.40 (2H, t)
Mass (m/z) : 86,71, 58, 43 (100%)
Deduce the structure of the compound and explain the principle ions observed in the
mass spectrum. (CSE-2018)
94. The mass spectra of two different cycloalkaners both show a molecularion peak at
m/z =98. One spectrum shows a base peak at m/z =69 and the other shows a base at
m/z = 83. Identify the two cycloalkenes. (CSE-2018)
95.(a) An organic compound having molecular formula C7H5Cl3O exhibited the
following 1H-NMR data (ppm): (CSE-2017)
δ 3.9, s
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δ 6.8, d( J=8.0 Hz)
δ 7.3, d( J=8.0 Hz)
Deduce the structure of the compound
(b) How will you distinguish various isomers of bromochlorethylene on the basis of
1H-NMR spectroscopy?

96. An organic compound with molecular formula C8H4O3 exhibited the following
spectroscopic data:
IR (cm-1) : 1830, 1760, 1120
1H-NMR : δ 8.049 , 2H, s
δ 7.635 , 2H, s
Mass : m/z = 148, 104, 76, 50
Deduce the structure of the compound and justify the formation of the above fragment
ions. (CSE-2017)
97.(a) Predict λmax for the following molecular. (CSE-2019)

(b) How will you distinguish the two using IR-spectroscopy?

98 (a) On the basis of the given spectroscopic data, deduce the structure of C 7H9N:
(CSE-2019)
UV : λmax=290 nm (in ethanol)
IR (v) : 3440 cm-1, 3360 cm-1, 3025 cm-1, 2920 cm-1, 1625 cm-1, 1380 cm-1, 810
cm-1
1H-NMR (ppm) : δ2.16 , s, 3H
δ 3.24 , s, 2H
δ6.37 , d, 2H (J=8.0 Hz)
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 δ6.79 , d, 2H (J=8.0 Hz)
99. An organic compound X was erroneously assigned the following structure: (CSE-
2020)

The spectral data of the organic compound are given below. On the basis of the
spectral data, justify why X is definitely a wrong structure and write the correct
structure compatible with the spectral data:
IR (cm-1) : 1705, 1604
1H NMR : δH (ppm) 1.43 (s, 6H), 5.82 (s. 1H) (m,3H), 7.68 (m, 2H)
MS : m/z 188 (10%) (high resolution confirms C12H12O2), 105 (20%), 102
(100%), 77(20%).
100. (i) What are metastable ions and how are they formed? The mass spectrum of
toluene shows strong molecular ion peak at m/z 91 and its fragment at m/z 65.
Calculate the value for metastable ion peak. (CSE-2020)
(ii) Identify how vibrational spectroscopy might be used to monitor the progress of
the following reaction: (CSE-2020)

101. (i) Dichloromethane has a chemical shift of 532 Hz from TMS(tetramethylsilane)

on a 100 MHz spectrometer. What will be the chemical shift in ppm? What would the
chemical shift be ppm and Hz on a 600 MHz spectrometer? (CSE-2020)
(ii) 3-Buten-2-one gives two peaks in its ultraviolet spectrum at 213 nm(ε=7100) and
320 nm (ε27). What type of transition is responsible for each absorbance? Account for the
difference in molar absorptivity for the two absorptions. (CSE-2020)
102. (i) Calculate C=O stretching frequency, K=12.3⨯105 dyne/cm. (CSE-2020)
(ii) A compound has molecular formula C5H10, showing absorption at 1380 cm-1.
Identify the structure of the compound. (CSE-2020)
103.(a) Arrange the following compounds in increasing order of out of plane C-H
wagging vibrations, as down, and give a suitable explanation to justify your answer:
(CSE-2020)
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(b) Consider the two methyl groups labelled as and in the following
compound, and answer: (CSE-2020)

(i) Which methyl group would exhibit a higher chemical shift in 1H NMR spectrum?
(ii) Offer a suitable explanation to justify your choice of methyl group.
(iii) Predict the approximate chemical shift values for the methyl groups.
104. A molecule with molecular formula C10H14O exhibits a board band at 3464 cm-1
in IR spectrum. Its mass spectrum exhibits base peak at m/z 135 and the 1H NMR
spectrum exhibits the following signals:
δ 1.3 (d, 6H); 2.4 (s, 3H), 3.4(M, 1H), 4.6 (s, D2O exchangeable), 6.6 (s, 1H), 6.8 (d, 1H)
and 7.1 (d, 1H). Deduce the structure. (CSE-2021)
105. 2-Pentanone and 3-Pentanone are structure isomers. Only one of the isomers
exhibits McLafferty rearrangement. Identify and show the McLafferty fragmentation
for this isomer. Also propose bas for the other isomers, which does not exhibit the
McLafferty rearrangement.
6.(a)(i) IR : 1620 cm-1 and 1695 cm-1
1H NMR : δ 1.9(s, 3H), 2.1(s, 6H), 6.15(S, 1H) (CSE-2021)
106. The molecule obtained on treatment of acetone with dilute sodium hydroxide
exhibits the above spectral data. Propose the structure of this molecule. (CSE-2021)
(ii)

Identify the compound in each of the above pairs, that can be expected to exhibit
carbonyl stretching signal at higher frequency.

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107. 2,4-Pentadione exhibits five signal in 1H NMR spectrum. Account for the
observing. Also write the approximate chemical shift. (CSE-2021)
108. (i) Draw the rough- sketch of NMR spectra of CH2Br –CHBr2. (CSE-2012)
(ii) Which bond has higher frequency in IR spectra?
(1) − C  N
(2) − C  C −
109
=. Dihydropentalene (C6H8) is treated with two moles of nbutyl lithium and it
produces a white crystalline compound. A. NMR spectrum of A is as follows: (CSE-
2012)
a double  7.98 J = 3Hz
b triplet  5.73J = 3Hz
and peak ratio of a : b = 2:1. What is the structure of A?

114. Draw the possible structures for the compounds that meet the following
description:
(i) C2H6O; one singlet
(ii) C3H7Cl; one doublet and one septed
(iii) C4H8C12 ; two triplets

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 (iv) C4H8O2; two singlet, one trilet one quartet
115. Pre-dict the McLafferty rearrangement ion (m/c) peak for the following compounds:

116. One of the five compounds shown below was analysed by IR spectrosocopy.
Peaks were observed at 1639 cm-1 (weak) and 1714 cm-1(strong). There was no
singlet between 310 cm-1 to 3500 cm-1. Which compound was analysed?

117. Assign the observed chemical shift value of 1.22’ 1.88, 4.13, 5.81 and 6.95 for the
following compound: (CSE-2016)

118. Which of the following structures has λmax 229 nm? Give the calculations of each:
(CSE-2016)

119.(a) Identify the compound, which can give M + - 1 peak among the
following. Discuss its fragmentation pattern with m/e values: (CSE-2016)
(i) CH3CH2CH2CH2CHO
(ii) CH3CHOHCH2CH2CH3
(iii) CH3 CH2 COOCH2CH3
(iv) CH3 COOCH2 CH2 CH3

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(b) Draw structure, label equivalent protons and indicate the number of
signals in each of the following: (CSE-2016)
(i) Mesitylene
(ii) p-ethylbenzene
(iii) Isopropylbenzene

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