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2637, Hudson Lane, Behind Khalsa College, Near G.T.B. Nagar Metro Station Gate No. 3 & 4, New Delhi – 110009 
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Organic Spectroscopy 
 
1. The correct order of the 
1
H NMR chemical shift values (d) for the indicated hydrogens (in 
bold) in the following compounds is: 
 
(I)        (II)     
 
(III)       (IV)  
 (a) I > II > III > IV  (b) II > I > III > IV (c) III > II > I > IV (d) II > III > VI > I 
2. The correct order of the fundamental vibrational frequency of the following diatomic 
molecules is: 
(a) 
1
H
35
Cl > 
1
H
37
Cl > 
2
D
35
Cl   (b) 
2
D
35
Cl > 
1
H
37
Cl > 
1
H
35
Cl 
(c) 
1
H
37
Cl > 
1
H
35
Cl > 
2
D
35
Cl   (d) 
1
H
37
Cl > 
2
D
35
Cl > 
1
H
35
Cl   
3. Which of the following compound show only two signals in 
1
H NMR and a strong IR 
bond at ~ 1690 cm
-1
: 
 
 
 
(a)       (b)      
 
 
 
 
(c)        (d)   
 
 
4. The correct order of 
1
H NMR chemical shift (d) values for the labeled methyl groups in 
the following compound is: 
 
 
 
 
(a) Me
1
 < Me
2
 < Me
3
 < Me
4
    (b) Me
3
 < Me
4
 < Me
1
 < Me
2
 
(c) Me
3
 < Me
1
 < Me
4
 < Me
2
   (d) Me
2
 < Me
4
 < Me
3
 < Me
1 
Page 2


 
2637, Hudson Lane, Behind Khalsa College, Near G.T.B. Nagar Metro Station Gate No. 3 & 4, New Delhi – 110009 
Mob. 011-47455430, 08860929430, e-mail: info@asfinstitute.com, www.asfinstitute.com  
 
 
Organic Spectroscopy 
 
1. The correct order of the 
1
H NMR chemical shift values (d) for the indicated hydrogens (in 
bold) in the following compounds is: 
 
(I)        (II)     
 
(III)       (IV)  
 (a) I > II > III > IV  (b) II > I > III > IV (c) III > II > I > IV (d) II > III > VI > I 
2. The correct order of the fundamental vibrational frequency of the following diatomic 
molecules is: 
(a) 
1
H
35
Cl > 
1
H
37
Cl > 
2
D
35
Cl   (b) 
2
D
35
Cl > 
1
H
37
Cl > 
1
H
35
Cl 
(c) 
1
H
37
Cl > 
1
H
35
Cl > 
2
D
35
Cl   (d) 
1
H
37
Cl > 
2
D
35
Cl > 
1
H
35
Cl   
3. Which of the following compound show only two signals in 
1
H NMR and a strong IR 
bond at ~ 1690 cm
-1
: 
 
 
 
(a)       (b)      
 
 
 
 
(c)        (d)   
 
 
4. The correct order of 
1
H NMR chemical shift (d) values for the labeled methyl groups in 
the following compound is: 
 
 
 
 
(a) Me
1
 < Me
2
 < Me
3
 < Me
4
    (b) Me
3
 < Me
4
 < Me
1
 < Me
2
 
(c) Me
3
 < Me
1
 < Me
4
 < Me
2
   (d) Me
2
 < Me
4
 < Me
3
 < Me
1 
 
2637, Hudson Lane, Behind Khalsa College, Near G.T.B. Nagar Metro Station Gate No. 3 & 4, New Delhi – 110009 
Mob. 011-47455430, 08860929430, e-mail: info@asfinstitute.com, www.asfinstitute.com  
 
 
 
5. The 
1
H NMR spectrum of a compound with molecular formula C 3H7NO shows the 
following features: 
Chemical shift (ppm)  6.50   2.25  1.10 
Shape   broad singlet quartet  triplet 
Which of the following is in agreement with this information: 
(a) (CH3)2C = NOH (b) CH3COCH2NH2 (c) CH3CH2CONH2 (d) HCON(CH3)2 
6. The two fine–structure components of a nuclear magnetic resonance transition are 
observed  at chemical shifts of 2.142 and 2.208 ppm in a 300 MHz NMR spectrometer. 
Calculate the coupling constant: 
(a) 19.8 Hz  (b) 0.066 Hz  (c) 6.6 Hz  (d) date is insufficient  
7. A C5H12O2 compound has strong infrared absorption at 3300 to 3400cm
-1
. The 
1
H NMR 
spectrum has three singlets at d 0.9, d 3.45 and d 3.2 ppm with relative areas 3:2:1. 
Addition of D2O to the sample eliminates the lower field signal. The 
13
C NMR spectrum 
shows three signals all at higher field than d 100 ppm. Which of the following 
compounds best fits this data:  
 (a) 1, 5-pentanediol     (b) 1, 3-dimethoxypropane  
(c) 2, 2-dimethyl-1, 3-propanediol   (d) 2, 4-pentanediol 
8. The 
1
H NMR spectrum of a compound A shows a doublet and a septet. Which one of the 
following statements is true: 
(a) The spectrum is consistent with A containing CH 3CH2CH2 group. 
(b) The spectrum is consistent with A being (CH3)2 CHCl. 
(c) The spectrum is consistent with A containing a CH3CH2 group. 
(d) The spectrum is consistent with A being (CH3)2CCl2. 
9. A compound of formula C5H12 gives one signal in the 
1
H NMR and two signals in the 
13
C 
NMR spectra. The compound is: 
(a) Pentane      (b) 2-methylbutane  
(c) 2, 2-dimethylpropane    (d) Cannot tell without more information  
10. The most appropriate spectroscopy for the identification of a nitrile group is: 
(a) IR   (b) 
1
H NMR  (c) UV   (d) ESR 
11. Compound I gives a strong infrared absorption at 1730 cm
-1
. 
1
H NMR spectrum indicates 
that it has two types of hydrogen atoms; one H atom appearing as signlet at d = 9.7 ppm 
and 9H atoms appearing as a singlet at d = 1.2 ppm. The structure of I is: 
 
(a)    (b)    (c)    (d) 
 
 
 
Page 3


 
2637, Hudson Lane, Behind Khalsa College, Near G.T.B. Nagar Metro Station Gate No. 3 & 4, New Delhi – 110009 
Mob. 011-47455430, 08860929430, e-mail: info@asfinstitute.com, www.asfinstitute.com  
 
 
Organic Spectroscopy 
 
1. The correct order of the 
1
H NMR chemical shift values (d) for the indicated hydrogens (in 
bold) in the following compounds is: 
 
(I)        (II)     
 
(III)       (IV)  
 (a) I > II > III > IV  (b) II > I > III > IV (c) III > II > I > IV (d) II > III > VI > I 
2. The correct order of the fundamental vibrational frequency of the following diatomic 
molecules is: 
(a) 
1
H
35
Cl > 
1
H
37
Cl > 
2
D
35
Cl   (b) 
2
D
35
Cl > 
1
H
37
Cl > 
1
H
35
Cl 
(c) 
1
H
37
Cl > 
1
H
35
Cl > 
2
D
35
Cl   (d) 
1
H
37
Cl > 
2
D
35
Cl > 
1
H
35
Cl   
3. Which of the following compound show only two signals in 
1
H NMR and a strong IR 
bond at ~ 1690 cm
-1
: 
 
 
 
(a)       (b)      
 
 
 
 
(c)        (d)   
 
 
4. The correct order of 
1
H NMR chemical shift (d) values for the labeled methyl groups in 
the following compound is: 
 
 
 
 
(a) Me
1
 < Me
2
 < Me
3
 < Me
4
    (b) Me
3
 < Me
4
 < Me
1
 < Me
2
 
(c) Me
3
 < Me
1
 < Me
4
 < Me
2
   (d) Me
2
 < Me
4
 < Me
3
 < Me
1 
 
2637, Hudson Lane, Behind Khalsa College, Near G.T.B. Nagar Metro Station Gate No. 3 & 4, New Delhi – 110009 
Mob. 011-47455430, 08860929430, e-mail: info@asfinstitute.com, www.asfinstitute.com  
 
 
 
5. The 
1
H NMR spectrum of a compound with molecular formula C 3H7NO shows the 
following features: 
Chemical shift (ppm)  6.50   2.25  1.10 
Shape   broad singlet quartet  triplet 
Which of the following is in agreement with this information: 
(a) (CH3)2C = NOH (b) CH3COCH2NH2 (c) CH3CH2CONH2 (d) HCON(CH3)2 
6. The two fine–structure components of a nuclear magnetic resonance transition are 
observed  at chemical shifts of 2.142 and 2.208 ppm in a 300 MHz NMR spectrometer. 
Calculate the coupling constant: 
(a) 19.8 Hz  (b) 0.066 Hz  (c) 6.6 Hz  (d) date is insufficient  
7. A C5H12O2 compound has strong infrared absorption at 3300 to 3400cm
-1
. The 
1
H NMR 
spectrum has three singlets at d 0.9, d 3.45 and d 3.2 ppm with relative areas 3:2:1. 
Addition of D2O to the sample eliminates the lower field signal. The 
13
C NMR spectrum 
shows three signals all at higher field than d 100 ppm. Which of the following 
compounds best fits this data:  
 (a) 1, 5-pentanediol     (b) 1, 3-dimethoxypropane  
(c) 2, 2-dimethyl-1, 3-propanediol   (d) 2, 4-pentanediol 
8. The 
1
H NMR spectrum of a compound A shows a doublet and a septet. Which one of the 
following statements is true: 
(a) The spectrum is consistent with A containing CH 3CH2CH2 group. 
(b) The spectrum is consistent with A being (CH3)2 CHCl. 
(c) The spectrum is consistent with A containing a CH3CH2 group. 
(d) The spectrum is consistent with A being (CH3)2CCl2. 
9. A compound of formula C5H12 gives one signal in the 
1
H NMR and two signals in the 
13
C 
NMR spectra. The compound is: 
(a) Pentane      (b) 2-methylbutane  
(c) 2, 2-dimethylpropane    (d) Cannot tell without more information  
10. The most appropriate spectroscopy for the identification of a nitrile group is: 
(a) IR   (b) 
1
H NMR  (c) UV   (d) ESR 
11. Compound I gives a strong infrared absorption at 1730 cm
-1
. 
1
H NMR spectrum indicates 
that it has two types of hydrogen atoms; one H atom appearing as signlet at d = 9.7 ppm 
and 9H atoms appearing as a singlet at d = 1.2 ppm. The structure of I is: 
 
(a)    (b)    (c)    (d) 
 
 
 
 
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12. The functionality that shows a typical characteristic peak at 2250 cm
-1
 in IR is: 
 
(a)    (b) CHO  (c) NCO  (d) N3 
13. Consider a 
1
H NMR spectrum in which a quartet and a doublet appeared at 9.72 and 2.40 
ppm, respectively. Which of the following compounds is the most probable one: 
(a) CH3COCH3 (b) CH3CH2CHO (c) CH3CHO  (d) CH3CH2CH2OH 
14. The order of decreasing chemicals shift in 
1
H NMR for the underlined hydrogens is: 
(I) H3C – CH2 – CH3     (II) H3 C – O – CH2 – CH3 
(III) Cl 2 – CH – O – CH2 – CH3   (IV) Cl – CH2 – O – CH2 – CH3 
(a) II > III > I > IV (b) II > III > IV > I  (c) III > II > I > IV  (d) III > IV > II > I  
15. The number of normal modes of vibration in the benzene molecule is: 
(a) 6   (b) 30   (c) 12   (d) 36 
16. An organic compound (MF: C8H10O) exhibited the following 
1
H NMR spectral data: d 
2.5 (3 H,s), 3.8 (3H, s), 6.8 (2 H, d, J 8 Hz), 7.2 (2 H, d, J 8 Hz) ppm. The compound 
among the choices is: 
(a) 4-ethylphenol     (b) 2-ethylphenol   
(c) 4-methylanisole     (d) 4-methylbenzyl alcohol 
17. The 
1
H NMR spectrum of 1, 4-dimethoxybenzene will have: 
(a) Ten singlets    (b) Two singlets 
(c) Two doublets and one singlet  (d) Two doublets and two singlet   
18. Appropriate 
1
H NMR chemical shifts (d) for the protons A-D for the following compound 
are: 
 
 
 
(a) A–6.8; B–5.7; C–3.9; D–2.1ppm  (b) A–6.8; B–5.7; C–2.1; D–3.9ppm 
(c) A–5.7; B–6.8; C–3.9; D–2.1ppm  (d) A–5.7; B–6.8; C–2.1; D–3.9ppm  
19. Compound A and B exhibit two singlets, each in their 
1
H NMR spectra. The expected 
chemical shifts are at d: 
 
(A)      (B)  
(a) 6.9 and 2.1 for A; 7.7 and 3.9 for B (b) 7.7 and 3.9 for A; 6.9 and 2.1 for B 
(c) 6.9 and 3.9 for A; 7.7 and 2.1 for B (d) 7.7 and 2.1 for A; 6.9 and 3.9 for B 
 
Page 4


 
2637, Hudson Lane, Behind Khalsa College, Near G.T.B. Nagar Metro Station Gate No. 3 & 4, New Delhi – 110009 
Mob. 011-47455430, 08860929430, e-mail: info@asfinstitute.com, www.asfinstitute.com  
 
 
Organic Spectroscopy 
 
1. The correct order of the 
1
H NMR chemical shift values (d) for the indicated hydrogens (in 
bold) in the following compounds is: 
 
(I)        (II)     
 
(III)       (IV)  
 (a) I > II > III > IV  (b) II > I > III > IV (c) III > II > I > IV (d) II > III > VI > I 
2. The correct order of the fundamental vibrational frequency of the following diatomic 
molecules is: 
(a) 
1
H
35
Cl > 
1
H
37
Cl > 
2
D
35
Cl   (b) 
2
D
35
Cl > 
1
H
37
Cl > 
1
H
35
Cl 
(c) 
1
H
37
Cl > 
1
H
35
Cl > 
2
D
35
Cl   (d) 
1
H
37
Cl > 
2
D
35
Cl > 
1
H
35
Cl   
3. Which of the following compound show only two signals in 
1
H NMR and a strong IR 
bond at ~ 1690 cm
-1
: 
 
 
 
(a)       (b)      
 
 
 
 
(c)        (d)   
 
 
4. The correct order of 
1
H NMR chemical shift (d) values for the labeled methyl groups in 
the following compound is: 
 
 
 
 
(a) Me
1
 < Me
2
 < Me
3
 < Me
4
    (b) Me
3
 < Me
4
 < Me
1
 < Me
2
 
(c) Me
3
 < Me
1
 < Me
4
 < Me
2
   (d) Me
2
 < Me
4
 < Me
3
 < Me
1 
 
2637, Hudson Lane, Behind Khalsa College, Near G.T.B. Nagar Metro Station Gate No. 3 & 4, New Delhi – 110009 
Mob. 011-47455430, 08860929430, e-mail: info@asfinstitute.com, www.asfinstitute.com  
 
 
 
5. The 
1
H NMR spectrum of a compound with molecular formula C 3H7NO shows the 
following features: 
Chemical shift (ppm)  6.50   2.25  1.10 
Shape   broad singlet quartet  triplet 
Which of the following is in agreement with this information: 
(a) (CH3)2C = NOH (b) CH3COCH2NH2 (c) CH3CH2CONH2 (d) HCON(CH3)2 
6. The two fine–structure components of a nuclear magnetic resonance transition are 
observed  at chemical shifts of 2.142 and 2.208 ppm in a 300 MHz NMR spectrometer. 
Calculate the coupling constant: 
(a) 19.8 Hz  (b) 0.066 Hz  (c) 6.6 Hz  (d) date is insufficient  
7. A C5H12O2 compound has strong infrared absorption at 3300 to 3400cm
-1
. The 
1
H NMR 
spectrum has three singlets at d 0.9, d 3.45 and d 3.2 ppm with relative areas 3:2:1. 
Addition of D2O to the sample eliminates the lower field signal. The 
13
C NMR spectrum 
shows three signals all at higher field than d 100 ppm. Which of the following 
compounds best fits this data:  
 (a) 1, 5-pentanediol     (b) 1, 3-dimethoxypropane  
(c) 2, 2-dimethyl-1, 3-propanediol   (d) 2, 4-pentanediol 
8. The 
1
H NMR spectrum of a compound A shows a doublet and a septet. Which one of the 
following statements is true: 
(a) The spectrum is consistent with A containing CH 3CH2CH2 group. 
(b) The spectrum is consistent with A being (CH3)2 CHCl. 
(c) The spectrum is consistent with A containing a CH3CH2 group. 
(d) The spectrum is consistent with A being (CH3)2CCl2. 
9. A compound of formula C5H12 gives one signal in the 
1
H NMR and two signals in the 
13
C 
NMR spectra. The compound is: 
(a) Pentane      (b) 2-methylbutane  
(c) 2, 2-dimethylpropane    (d) Cannot tell without more information  
10. The most appropriate spectroscopy for the identification of a nitrile group is: 
(a) IR   (b) 
1
H NMR  (c) UV   (d) ESR 
11. Compound I gives a strong infrared absorption at 1730 cm
-1
. 
1
H NMR spectrum indicates 
that it has two types of hydrogen atoms; one H atom appearing as signlet at d = 9.7 ppm 
and 9H atoms appearing as a singlet at d = 1.2 ppm. The structure of I is: 
 
(a)    (b)    (c)    (d) 
 
 
 
 
2637, Hudson Lane, Behind Khalsa College, Near G.T.B. Nagar Metro Station Gate No. 3 & 4, New Delhi – 110009 
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12. The functionality that shows a typical characteristic peak at 2250 cm
-1
 in IR is: 
 
(a)    (b) CHO  (c) NCO  (d) N3 
13. Consider a 
1
H NMR spectrum in which a quartet and a doublet appeared at 9.72 and 2.40 
ppm, respectively. Which of the following compounds is the most probable one: 
(a) CH3COCH3 (b) CH3CH2CHO (c) CH3CHO  (d) CH3CH2CH2OH 
14. The order of decreasing chemicals shift in 
1
H NMR for the underlined hydrogens is: 
(I) H3C – CH2 – CH3     (II) H3 C – O – CH2 – CH3 
(III) Cl 2 – CH – O – CH2 – CH3   (IV) Cl – CH2 – O – CH2 – CH3 
(a) II > III > I > IV (b) II > III > IV > I  (c) III > II > I > IV  (d) III > IV > II > I  
15. The number of normal modes of vibration in the benzene molecule is: 
(a) 6   (b) 30   (c) 12   (d) 36 
16. An organic compound (MF: C8H10O) exhibited the following 
1
H NMR spectral data: d 
2.5 (3 H,s), 3.8 (3H, s), 6.8 (2 H, d, J 8 Hz), 7.2 (2 H, d, J 8 Hz) ppm. The compound 
among the choices is: 
(a) 4-ethylphenol     (b) 2-ethylphenol   
(c) 4-methylanisole     (d) 4-methylbenzyl alcohol 
17. The 
1
H NMR spectrum of 1, 4-dimethoxybenzene will have: 
(a) Ten singlets    (b) Two singlets 
(c) Two doublets and one singlet  (d) Two doublets and two singlet   
18. Appropriate 
1
H NMR chemical shifts (d) for the protons A-D for the following compound 
are: 
 
 
 
(a) A–6.8; B–5.7; C–3.9; D–2.1ppm  (b) A–6.8; B–5.7; C–2.1; D–3.9ppm 
(c) A–5.7; B–6.8; C–3.9; D–2.1ppm  (d) A–5.7; B–6.8; C–2.1; D–3.9ppm  
19. Compound A and B exhibit two singlets, each in their 
1
H NMR spectra. The expected 
chemical shifts are at d: 
 
(A)      (B)  
(a) 6.9 and 2.1 for A; 7.7 and 3.9 for B (b) 7.7 and 3.9 for A; 6.9 and 2.1 for B 
(c) 6.9 and 3.9 for A; 7.7 and 2.1 for B (d) 7.7 and 2.1 for A; 6.9 and 3.9 for B 
 
 
2637, Hudson Lane, Behind Khalsa College, Near G.T.B. Nagar Metro Station Gate No. 3 & 4, New Delhi – 110009 
Mob. 011-47455430, 08860929430, e-mail: info@asfinstitute.com, www.asfinstitute.com  
 
 
 
20. In the 
1
H NMR spectrum recorded at 293 K, an organic compound (C 3H7NO), exhibited 
signals at d 7.8 (1H, s), 2.8 (3H, s) and 2.6 (3H, s). The compound is: 
 
(a)   (b)     (c)    (d) 
 
21. An organic compound exhibited the following 
1
H NMR spectra data: 
d 7.80 (2 H, d, J = 8 Hz), 6.80 (2 H, d, J = 8 Hz), 4.10 (2 H, q, J = 7.2 Hz), 
2.4 (3H, s), 1.25 (3 H, t, J = 7.2 Hz) 
The compound, among the choices given below is, 
 
 
(a)       (b)     
 
 
 
(c)       (d)   
 
22. In NMR spectroscopy the product the nuclear ‘g’ factor (gN), the nuclear magneton (ßN) 
and the magnetic field strength (B0) gives the: 
(a) Energy of transition from a to ß state  (b) Chemical shift 
(c) Spin–Spin coupling constant   (d) Magnetogyric ratio 
23. Among the isomers of C4H6 given below, the compound which exhibits an absorption 
band at 3300 cm
-1
 in the IR spectrum, is: 
(a) 1, 3-butadiene  (b) 1-butyne   (c) 2-butyne   (d) cyclobutane.  
24. Match the compounds P–S with their carbonyl stretching frequencies (cm
-1
) I–VI in IR 
spectroscopy: 
P. Acetone      I. 1870 
Q. Ethyl acetate    II. 1800 
R. Acetamide      III. 1740 
S. Acetyl chloride     IV. 1700 
      V. 1660 
      VI. 1600 
(a) P–IV, Q–III, R–I, S–VI    (b) P–III, Q–VI, R–V, S–II 
(c) P–IV, Q–III, R–V, S–II   (d) P–II, Q–V, R–III, S–VI 
25. Out of the following, the one which is not an excitation source for IR spectra is: 
(a) Tungsten filament lamp   (b) Nernst glower 
(c) Deuterium lamp     (d) Mercury arc.  
Page 5


 
2637, Hudson Lane, Behind Khalsa College, Near G.T.B. Nagar Metro Station Gate No. 3 & 4, New Delhi – 110009 
Mob. 011-47455430, 08860929430, e-mail: info@asfinstitute.com, www.asfinstitute.com  
 
 
Organic Spectroscopy 
 
1. The correct order of the 
1
H NMR chemical shift values (d) for the indicated hydrogens (in 
bold) in the following compounds is: 
 
(I)        (II)     
 
(III)       (IV)  
 (a) I > II > III > IV  (b) II > I > III > IV (c) III > II > I > IV (d) II > III > VI > I 
2. The correct order of the fundamental vibrational frequency of the following diatomic 
molecules is: 
(a) 
1
H
35
Cl > 
1
H
37
Cl > 
2
D
35
Cl   (b) 
2
D
35
Cl > 
1
H
37
Cl > 
1
H
35
Cl 
(c) 
1
H
37
Cl > 
1
H
35
Cl > 
2
D
35
Cl   (d) 
1
H
37
Cl > 
2
D
35
Cl > 
1
H
35
Cl   
3. Which of the following compound show only two signals in 
1
H NMR and a strong IR 
bond at ~ 1690 cm
-1
: 
 
 
 
(a)       (b)      
 
 
 
 
(c)        (d)   
 
 
4. The correct order of 
1
H NMR chemical shift (d) values for the labeled methyl groups in 
the following compound is: 
 
 
 
 
(a) Me
1
 < Me
2
 < Me
3
 < Me
4
    (b) Me
3
 < Me
4
 < Me
1
 < Me
2
 
(c) Me
3
 < Me
1
 < Me
4
 < Me
2
   (d) Me
2
 < Me
4
 < Me
3
 < Me
1 
 
2637, Hudson Lane, Behind Khalsa College, Near G.T.B. Nagar Metro Station Gate No. 3 & 4, New Delhi – 110009 
Mob. 011-47455430, 08860929430, e-mail: info@asfinstitute.com, www.asfinstitute.com  
 
 
 
5. The 
1
H NMR spectrum of a compound with molecular formula C 3H7NO shows the 
following features: 
Chemical shift (ppm)  6.50   2.25  1.10 
Shape   broad singlet quartet  triplet 
Which of the following is in agreement with this information: 
(a) (CH3)2C = NOH (b) CH3COCH2NH2 (c) CH3CH2CONH2 (d) HCON(CH3)2 
6. The two fine–structure components of a nuclear magnetic resonance transition are 
observed  at chemical shifts of 2.142 and 2.208 ppm in a 300 MHz NMR spectrometer. 
Calculate the coupling constant: 
(a) 19.8 Hz  (b) 0.066 Hz  (c) 6.6 Hz  (d) date is insufficient  
7. A C5H12O2 compound has strong infrared absorption at 3300 to 3400cm
-1
. The 
1
H NMR 
spectrum has three singlets at d 0.9, d 3.45 and d 3.2 ppm with relative areas 3:2:1. 
Addition of D2O to the sample eliminates the lower field signal. The 
13
C NMR spectrum 
shows three signals all at higher field than d 100 ppm. Which of the following 
compounds best fits this data:  
 (a) 1, 5-pentanediol     (b) 1, 3-dimethoxypropane  
(c) 2, 2-dimethyl-1, 3-propanediol   (d) 2, 4-pentanediol 
8. The 
1
H NMR spectrum of a compound A shows a doublet and a septet. Which one of the 
following statements is true: 
(a) The spectrum is consistent with A containing CH 3CH2CH2 group. 
(b) The spectrum is consistent with A being (CH3)2 CHCl. 
(c) The spectrum is consistent with A containing a CH3CH2 group. 
(d) The spectrum is consistent with A being (CH3)2CCl2. 
9. A compound of formula C5H12 gives one signal in the 
1
H NMR and two signals in the 
13
C 
NMR spectra. The compound is: 
(a) Pentane      (b) 2-methylbutane  
(c) 2, 2-dimethylpropane    (d) Cannot tell without more information  
10. The most appropriate spectroscopy for the identification of a nitrile group is: 
(a) IR   (b) 
1
H NMR  (c) UV   (d) ESR 
11. Compound I gives a strong infrared absorption at 1730 cm
-1
. 
1
H NMR spectrum indicates 
that it has two types of hydrogen atoms; one H atom appearing as signlet at d = 9.7 ppm 
and 9H atoms appearing as a singlet at d = 1.2 ppm. The structure of I is: 
 
(a)    (b)    (c)    (d) 
 
 
 
 
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12. The functionality that shows a typical characteristic peak at 2250 cm
-1
 in IR is: 
 
(a)    (b) CHO  (c) NCO  (d) N3 
13. Consider a 
1
H NMR spectrum in which a quartet and a doublet appeared at 9.72 and 2.40 
ppm, respectively. Which of the following compounds is the most probable one: 
(a) CH3COCH3 (b) CH3CH2CHO (c) CH3CHO  (d) CH3CH2CH2OH 
14. The order of decreasing chemicals shift in 
1
H NMR for the underlined hydrogens is: 
(I) H3C – CH2 – CH3     (II) H3 C – O – CH2 – CH3 
(III) Cl 2 – CH – O – CH2 – CH3   (IV) Cl – CH2 – O – CH2 – CH3 
(a) II > III > I > IV (b) II > III > IV > I  (c) III > II > I > IV  (d) III > IV > II > I  
15. The number of normal modes of vibration in the benzene molecule is: 
(a) 6   (b) 30   (c) 12   (d) 36 
16. An organic compound (MF: C8H10O) exhibited the following 
1
H NMR spectral data: d 
2.5 (3 H,s), 3.8 (3H, s), 6.8 (2 H, d, J 8 Hz), 7.2 (2 H, d, J 8 Hz) ppm. The compound 
among the choices is: 
(a) 4-ethylphenol     (b) 2-ethylphenol   
(c) 4-methylanisole     (d) 4-methylbenzyl alcohol 
17. The 
1
H NMR spectrum of 1, 4-dimethoxybenzene will have: 
(a) Ten singlets    (b) Two singlets 
(c) Two doublets and one singlet  (d) Two doublets and two singlet   
18. Appropriate 
1
H NMR chemical shifts (d) for the protons A-D for the following compound 
are: 
 
 
 
(a) A–6.8; B–5.7; C–3.9; D–2.1ppm  (b) A–6.8; B–5.7; C–2.1; D–3.9ppm 
(c) A–5.7; B–6.8; C–3.9; D–2.1ppm  (d) A–5.7; B–6.8; C–2.1; D–3.9ppm  
19. Compound A and B exhibit two singlets, each in their 
1
H NMR spectra. The expected 
chemical shifts are at d: 
 
(A)      (B)  
(a) 6.9 and 2.1 for A; 7.7 and 3.9 for B (b) 7.7 and 3.9 for A; 6.9 and 2.1 for B 
(c) 6.9 and 3.9 for A; 7.7 and 2.1 for B (d) 7.7 and 2.1 for A; 6.9 and 3.9 for B 
 
 
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20. In the 
1
H NMR spectrum recorded at 293 K, an organic compound (C 3H7NO), exhibited 
signals at d 7.8 (1H, s), 2.8 (3H, s) and 2.6 (3H, s). The compound is: 
 
(a)   (b)     (c)    (d) 
 
21. An organic compound exhibited the following 
1
H NMR spectra data: 
d 7.80 (2 H, d, J = 8 Hz), 6.80 (2 H, d, J = 8 Hz), 4.10 (2 H, q, J = 7.2 Hz), 
2.4 (3H, s), 1.25 (3 H, t, J = 7.2 Hz) 
The compound, among the choices given below is, 
 
 
(a)       (b)     
 
 
 
(c)       (d)   
 
22. In NMR spectroscopy the product the nuclear ‘g’ factor (gN), the nuclear magneton (ßN) 
and the magnetic field strength (B0) gives the: 
(a) Energy of transition from a to ß state  (b) Chemical shift 
(c) Spin–Spin coupling constant   (d) Magnetogyric ratio 
23. Among the isomers of C4H6 given below, the compound which exhibits an absorption 
band at 3300 cm
-1
 in the IR spectrum, is: 
(a) 1, 3-butadiene  (b) 1-butyne   (c) 2-butyne   (d) cyclobutane.  
24. Match the compounds P–S with their carbonyl stretching frequencies (cm
-1
) I–VI in IR 
spectroscopy: 
P. Acetone      I. 1870 
Q. Ethyl acetate    II. 1800 
R. Acetamide      III. 1740 
S. Acetyl chloride     IV. 1700 
      V. 1660 
      VI. 1600 
(a) P–IV, Q–III, R–I, S–VI    (b) P–III, Q–VI, R–V, S–II 
(c) P–IV, Q–III, R–V, S–II   (d) P–II, Q–V, R–III, S–VI 
25. Out of the following, the one which is not an excitation source for IR spectra is: 
(a) Tungsten filament lamp   (b) Nernst glower 
(c) Deuterium lamp     (d) Mercury arc.  
 
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26. The molecular active in rotational microwave, infrared absorption as well as rotational 
Raman spectra is: 
(a) CO2  (b) SF6   (c) HCl  (d) H2 
27. Which of the following absorptions is shown by 1, 3-butadiene in its UV absorption 
spectrum recorded in n-hexane (
max
? is the molar absorptivity): 
(a) ?max217nm(
max
? = 21,000)  (b) ?max214nm(
max
? = 210) 
(c) ?max253nm(
max
? = 50,000)  (d) ?max250nm(
max
? = 500) 
28. Match the compounds in List –I with the stretching frequencies (cm
-1
) of the principal 
functional groups given in List –II: 
List – I    List – II  
 
 (1)       (i) 2240   
 
  
 (2)       (ii) 1795 
 
 
 (3)       (iii) 1750 
 
 
 (4)     (iv) 1725 
       (v) 1695 
 (a) 1-iii, 2-iv, 3-i, 4-v    (b) 1-iii, 2-iv, 3-ii, 4-v 
 (c) 1-vi, 2-v, 3-ii, 4-i    (d) 1-vi, 2-iii, 3-v, 4-i  
29. Match the observed principal absorptions in the visible spectrum shown in List-I with the 
bond shows this absorption in List –II: 
 
List – I    List – II 
 (1) ? ? 
*
?    (i) C–C   
 (2)   n ? 
*
?    (ii) C–O 
 (3)  n, p*     (iii) C=O 
 (4) p, p*     (iv) C=C 
 
 (a) 1-(i), 2-(ii), 3-(iii), 4-(iv)   (b) 1-(i), 2-(iii), 3-(ii), 4-(iv) 
 (c) 1-(ii), 2-(i), 3-(vi), 4-(iii)   (d) 1-(vi), 2-(ii), 3-(iii), 4-(i) 
 
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FAQs on Practice Questions on Spectroscopy - Organic Chemistry

1. What is spectroscopy and why is it important in chemistry?
Ans. Spectroscopy is the study of the interaction between matter and electromagnetic radiation. It is important in chemistry as it allows scientists to analyze the composition, structure, and properties of substances by studying the way they interact with light. By using spectroscopic techniques, chemists can identify and characterize chemical compounds, determine their concentration, and study their chemical reactions.
2. What are the different types of spectroscopy?
Ans. There are several types of spectroscopy, including: - Absorption Spectroscopy: Measures the absorption of light by a substance to identify its composition and concentration. - Emission Spectroscopy: Measures the emission of light from a substance to study its energy levels and electronic transitions. - Fluorescence Spectroscopy: Measures the emission of light after a substance absorbs light of a specific wavelength, used for studying fluorescent compounds. - Infrared Spectroscopy: Measures the absorption of infrared radiation by a substance to identify functional groups and molecular structures. - Nuclear Magnetic Resonance (NMR) Spectroscopy: Analyzes the magnetic properties of atomic nuclei to determine the chemical structure and composition of a substance.
3. How does spectroscopy work?
Ans. Spectroscopy works by passing a beam of light (or electromagnetic radiation) through a sample and measuring the interaction between the light and the sample. The sample absorbs certain wavelengths of light, which correspond to specific energy levels or vibrations within the molecules. The absorbed or emitted light is then detected and analyzed to determine the composition, structure, or properties of the sample.
4. What are the applications of spectroscopy?
Ans. Spectroscopy has numerous applications in various fields, including: - Analytical Chemistry: Used for qualitative and quantitative analysis of chemical compounds. - Environmental Science: Helps in identifying pollutants and monitoring environmental contaminants. - Pharmaceutical Industry: Used for drug discovery, quality control, and formulation analysis. - Astrophysics: Used for studying the composition and properties of celestial objects. - Forensic Science: Helps in analyzing and identifying unknown substances at crime scenes. - Medical Diagnosis: Used in medical imaging techniques like MRI and PET scans.
5. How can spectroscopy be used to determine molecular structures?
Ans. Spectroscopy can be used to determine molecular structures by analyzing the absorption or emission spectra of a substance. Each molecule has a unique set of energy levels, and the transitions between these levels result in the absorption or emission of specific wavelengths of light. By studying the pattern of absorption or emission lines in the spectrum, scientists can deduce the types of bonds, functional groups, and overall structure of the molecule. Techniques like infrared spectroscopy and NMR spectroscopy are particularly useful for determining molecular structures.
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