Engg.
Chemistry, AKTU : PYQs UNIT-2
What is Beer-Lambert law in UV-Visible absorption spectroscopy? A
AKTU 2018-2019,
compound having concentration 10-3 g/l resulted absorbance value 0.20 Refer notes-Pg: 12,13,
Q1 2019-2020, 2021-
at λmax =510 nm using 1.0 cm cell. Calculate its absorptivity and molar 14
22
absorptivity values. Molecular weight of compound is 400.
Q2 State and drive the Lambert beer's law. Refer notes-Pg: 12,13 AKTU 2019-2020
Refer notes-Pg: 26,27 AKTU 2018-
What are chromophores and auxochromes? How do auxochromes
175 nm shows that it 2019, 2019-2020-
Q3 increase the colouring power of chromophores? A di-ene has λmax at
is not a conjugated di- 20, 20-21, 2021-
175 nm in its UV spectrum. What inference can be drawn from this data?
ene. 22, 2022-23
The % transmittance of an aqueous solution of unknown compound is
Q4 20% at 25oC and concentration 2 x 10−5 at 300 nm. The length of the cell Solution: Pg 7 AKTU 2022-23
is 4 cm. Calculate the absorbance and molar extinction coefficient.
AKTU 2018-2019,
CH2=CHCOCH3
Explain which one will exhibit higher value of 𝝀max in UV/visible spectra 2019-20202020-
Q5 As it is a conjugated
of CH3COCH3 and CH2=CHCOCH3. 21, 2021-22,
diene.
2022-23
Engg. Chemistry, AKTU : PYQs UNIT-1
Why the λmax for the diene (I) is observed at a lower nm than (II)?
Solution: Pg
AKTU 2018-19,
Q6 7
2022-23
Refer notes- AKTU 2018-19,
What type of electronic transitions is involved in UV-visible spectroscopy? Explain the
Pg: 22-26; 2019-20, 2020-
Q7 absorption and intensity shift in the UV spectroscopy and support with examples.
28-32;35-36 21, 2021-22,
Illustrate, the effect of polar and non-polar solvent on π- π* transition in acetone..
2022-23
How do Auxochromes increase the coloring power of Chromophores? A diene
Solution: Pg
(molecular formula C4H6) shows an intense peak at λmax 217 nm while another diene AKTU 2018-19,
Q8 8
(molecular formula C5H8) shows an intense peak at λmax 175 nm in their UV spectra. 2022-23
Giving proper explanation assign the structures to the two dienes.
Asymmetrically substituted compounds having even number of cumulative double Solution: Pg
AKTU 2022-
Q9 bonds exhibit optical isomerism whereas compounds having odd number of cumulative 8
23
double bonds exhibit geometrical isomerism. Explain giving proper reasons.
Engg. Chemistry, AKTU : PYQs UNIT-2
AKTU 2018-2019,
Give the possible electronic transitions (UV spectra) in- CH3CH2CH3, CH3CH=CH2, Solution: Pg 8
Q10 2019-2020, 2021-
CH3CH=O and CH3-CH=CH-CH=CH-CH3
22
Can ultra-violet spectral data be useful to distinguish between the following
Refer notes-
Q11 compounds? Give reasons. AKTU 2019-2020
Pg: 129
(i) Ethyl benzene and styrene (ii) CH2=CH-CH2-CH=CH2 and CH2=CH-CH=CH-CH3
Refer notes- AKTU 2018-
Explain the principle of IR spectroscopy. For XY2 bent molecule show various
Pg: 63-67; Pg 2019, 2019-2020,
Q12 types of stretching and bending vibrations in IR spectroscopy. Discuss the
70-71 2020-21, 2021-22,
significance of Finger print region.
2022-23
Among H2, HCl, CO2, H2O molecules identify which will be IR active and why?
Refer notes-
Explain different modes of vibrations observed in CO2 molecule. Out of the
Pg: 129-130; AKTU 2018-19,
Q13 following pairs which one is expected to absorb at higher frequency for
Pg 68 2021-22
stretching vibrations? Also state reason.
i) HCHO, CH3CHO ii) C=C, C≡C iii) O-H, C-C
AKTU 2018-2019,
How many fundamental Vibrational degrees of freedom are expected for the Refer notes-
Q14 2020-21, 2021-22,
following molecules: CO2, H2O and C2H4? Pg: 61-62, 139
2022-23
Engg. Chemistry, AKTU : PYQs UNIT-2
AKTU 2018-
Two isomers A and B of the molecular formula C3H6O gives IR absorption at 1650Refer notes-Pg:
Q15 2019, 2019-
cm-1 and 1710 cm-1 respectively. Assign structural formula to A and B isomers. 134
2020, 2022-23
AKTU 2014-
One of the fundamental vibrational modes of H2O occurs at 3652 cm-1.What Solution: Pg 9
Q16 2015, 2019-
would be the frequency of the corresponding vibration for D2O.
2020, 2021-22
On the basis of IR spectra, distinguish between intermolecular and intra-molecular
Refer notes-Pg:
hydrogen bonding. How can you distinguish the following with the help of IR AKTU 2021-
Q17 73
spectroscopy: (i) Formic acid and ethyl alcohol (ii) Formaldehyde and di-methyl 22, 2023-24
ether.
An organic compound having molecular formula C7H6O shows absorption peaks atRefer notes-Pg:
AKTU 2015-
Q18 3010, 2700, 1600, 1580, 1480 and 1270 cm-1 in its IR spectrum. Suggest its 132
16, 2018-19
structure.
Refer notes-Pg:
How will you distinguish between the following pairs of compounds on the basis of AKTU 2015-
Q19 127
IR spectroscopy: i) CH3COOH and CH3COOC2H5 ii) C2H5OH and C2H5OC2H5 16, 2018-19
Discuss the various regions in IR spectrum. Discuss the finger print region.
Refer notes-Pg:
Determine the structure of the compound, C3H6O showing the following AKTU 2015-16,
Q20 69-71, 134.
absorption bands in IR spectrum: i) 2950 cm-1 ii) 1720 cm-1. The compound gives 2018-19
negative test with Tollen’s reagent.
Engg. Chemistry, AKTU : PYQs UNIT-2
A compound having molecular formula C2 H4 O2 gave the following IR peaks :- Refer notes- AKTU 2015-
Q21 2900 – 2950 cm−1 , 1710 cm−1 and 3550 - 3650 cm−1 . The compound also gave Pg: 133, 16, 2018-
effervescence with Na2 CO3 . Identify the compound. Solution: Pg 9 2019
What is the basic principle of 1H NMR spectroscopy? What is the significance of Refer notes-
shielding and deshielding ? A compound having the molecular formula C 10 H 14 Pg: 82, 90-92
AKTU 2014-
Q22 gave the following 1HNMR data: δ 0.88 (6H, doublet), δ 1.86 (1H, multiplet),δ 2.45
Solution: Pg 9 2015
(2H, doublet) and δ 7.12 ( 5H, singled). Giving reasons, assign the structure to the
compound which is consistent with the above data.
Refer notes-
What is shielding and deshielding in NMR spectroscopy? A compound having the 90-92; AKTU
molecular formula C4H9Br gave the following 1H NMR data: δ 1.04 (6H, doublet), δ
Q23 Solution- Pg 2021-22,
1.95 (1H, multiplet) and δ 3.33 (2H, doublet). Giving reasons, assign the structure
10 2023-24
to the compound which is consistent with the above data.
Predict the number of signal and their splitting pattern in 1H NMR spectra of Solution: Pg AKTU 2015-
Q24
(i) CH3CCl2CH3 and (ii) CH3OCH2CH3 10 16, 2018-19
Why is TMS used as an internal standard in NMR spectroscopy? Two isomeric Refer notes-
compounds A and B have molecular formula C10H14. The 1H NMR spectra of these 94,
isomers gave the following data: AKTU 2021-
Q25 Solution: Pg
Isomer A: δ 1.30 (9H,s); δ 7.28 (5H, s) 22, 2023-24
11
Isomer B: δ 0.88 (6H, d); δ 1,86 (1H, m); δ 2.45 (2H, d); δ 7.12 (5H, s).
Giving reasons assign the structures for the two isomers.
Engg. Chemistry, AKTU : PYQs UNIT-2
Predict the number of signal and their splitting pattern in 1H NMR AKTU 2015-16,
Q26 Solution: Pg 10
spectra of CH3CCl2CH3 and CH3OCH2CH3 2022-23
Give five examples of compounds showing optical isomerism without
the presence of chiral carbon. What is E-Z configuration?
Assign E or Z confirmation to the following and draw all its possible
stereo isomers: Refer notes-Pg:
Q27 171-180 AKTU 2022-23
Discuss the stereochemistry of tartaric acid. What will happen when one Solution: Pg 12
Q28 AKTU 2014-15
of the OH group of tartaric acid will be replaced by NH2
Refer notes-Pg: AKTU 2022-23
Q29 What are Chiral Drugs? Give examples of Chiral Drugs
181-182
How can you distinguish the following with the help of IR spectroscopy: Solution: Pg 13
Q30 AKTU 2022-23
(i) Formic acid and ethyl alcohol (ii) Formaldehyde and di-methyl ether
Engg. Chemistry, AKTU : PYQs UNIT-2
% T = 20 So, T = 20/100
Ans. 4 So, Absorbance, A= -log T = - log 20/100 = 0.699
Molar extinction coefficient, Ɛ = A/cl = 0.699 / (2 X 10 -5 X 4)
= 0.087 X 10 -5 l g-1 cm-1
For structure (I): Since it is a-cyclic diene, its base value is 214nm.
Ring residue= 4 × 5 nm = 20 nm
So, 𝜆max = 214 + 20 = 234 nm
For structure (II): As it is also a-cyclic diene, its base value = 214 nm
Exocyclic double bonds= 2 × 5 nm = 10 nm
Ans. 6
Ring residues = 4 × 5 nm = 20 nm
So, 𝜆max = 214 + 10 + 20 = 244 nm
Hence, , 𝜆max for compound II is greater than I.
The addition of auxochrome to the chromophore shifts the absorption towards higher
wavelength region. This occur due ton extended conjugation by sharing their lone pair of
electrons. Hence, auxochrome introduces colour to the chromophore.
217 nm is the absorbance given by simple conjugated di-ene. The given molecular formula is
Ans. 8
C4H6. So, the structure for di-ene will be CH2=CH-CH= CH2.
175 nm is the absorbance given by simple ethene. The given molecular formula is C5H8. So, the
structure for di-ene will be CH2=CH-CH=CH-CH3.
Asymmetrically substituted compounds having even number of cumulative double bonds exhibit
optical isomerism because in this case the groups attached to the terminal carbon atoms are not
in one plane and are perpendicular to each other. As a result, the molecule as a whole have a
Ans. 9 chiral plane and they exhibit optical isomerism.
Asymmetrically substituted compounds having odd number of cumulative double bonds exhibit
geometrical isomerism as terminals lie in the same plane.
CH3CH2CH3 is a saturated aliphatic compound which has only σ and σ* orbitals. Hence, possible
transition is only σ to σ*, though it will not be visible as it lies in vacuum region.
CH3CH=O is a carbonyl compound which have σ, π, σ* and π* and a non bonding n orbital. So,
possible transitions are σ to σ*, π to π*, n to σ* and n to π*. σ to σ* and n to σ* will not be
Ans 10.
visible due to low wavelength region.
CH3-CH=CH-CH=CH-CH3 is an un-saturated. It have σ, π, σ* and π* orbitals. So, possible
transitions are σ to σ* and π to π*. Though σ to σ* will not be visible as it lies in vacuum region
C
C = 3×1010cm/sec
K= 5×105dynes per cm
Ans. 16
mo= 16/6.023×1023gm
mD= 2/6.023×1023gm
In the above formula and calculation, we get
μH2o = 1 × 16/ 1 + 16 = 0.94; μD2o = 2 × 16/ 2 + 16 = 1.78
So, νD2o/ νH2O = (μH2o/ μD2o)1/2
νD2o = νH2o (μH2o/ μD2o)1/2 = 3652 (0.94/1.78) ½ = 265 cm-1
Ans. 22
Structure determination of C4H9Br
C=C Double bond equivalence :
= C - H/2 + N/2 + 1 – X/2
= 4 – 9/2 + 0/2 + 1 – ½
=0
Now, δ = 1.04, there is a doublet for 6 hydrogens i.e. there are two CH3 groups. therefore,
(CH3)2CH-
Ans. 23 Also, δ = 1.95, there is a multiplet because if one hydrogen i.e., a CH- group attached to other
alkyl groups
And, δ = 3.33, there is a doublet due to two hydrogens i.e. a -CH2 group attached to –CH.
(i) CH3CCl2CH3 Signals = 1 and no splitting will be observed.
(ii) CH3OCH2CH3 Signals = 3
Ans. 24
Splitting Pattern: CH3 = no splitting, CH2 = quartet, CH3 = Triplet
CStructure determination of C10H14
Double bond equivalence in isomer A and isomer B
= C - H/2 + 1= 10 – 14/2 + 1 = 4
Molecule will have three double bond and one ring thus part of the molecule will have benzene
ring.
Ans. 25
Ans 28. The structure of tartaric acid is :
If we analyse the structure, we can see that there are
two asymmetric carbon atoms so using the formulae 2n
formula where n is the number of asymmetric carbon
atoms, we can calculate the number of stereoisomers.
Number of stereoisomers=22=4
Compounds (I) and (II) are mirror images of each other and
they are known as enantiomers but in the meso form.
There is a place of symmetry present in tartaric acid.
Tartaric acid shows three isomeric forms one of which is
optically inactive and the other two are optically active i.e.
d (+) and I or (-).
If one of the OH group of Tartaric acid is replaced by NH2,
then meso form of tartaric acid will disappear.
(i) Formic acid and ethyl alcohol
C=O stretch (carboxylic acid) -- 1725−1700 cm−1 is found in formic acid which is not observed in ethyl
alcohol. O−H stretch for formic acid is observed at 3200−2500 cm−1, whereas for ethyl alcohol it is
observed at 3650−3550cm−1
Ans. 30
(ii) Formaldehyde and di-methyl ether
Di methyl ether shows a strong C-O stretch between 1000 and 1300 cm−1, which is not found in
formaldehyde. In Formaldehyde a C=O Stretch is observed at 1750 cm−1 which is not found in di methyl
ether.
