Photo Chemistry 1

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 Photo Chemistry 2

1. Thermolysis of allyl phenyl ether generates [NET JUNE 2011]

(a) o–allylphenol only (b) o– and p–allylphenols
(c) o–, m– and p–allylphenols (d) m-allylphenol only
2. The structures of the major products X and Y in the following transformation are [NET JUNE 2011]

3. Match the following starting compounds with corresponding products in photochemical reactions:
[NET DEC 2011]

(a) (i)–(E) (ii) –(A) (iii)–(B) (b) (i)–(A)(ii)–(C)(iii)–(b)

(c) (i)–(D) (ii)–(C) (iii)–(A) (d) (i)–(E) (ii)–(A) (iii)–(D)
4. The two step conversion of 7–dehydrocholesterol to viramin D3 proceeds through [NET JUNE 2012]
 Photo Chemistry 3

(a) Photochemical electrocyclic distrotatory ring opening; and thermal antarafacial [1,7]–H shift.
(b) Photochemical electrocyclic conrotatory ring opening; and thermal antarafacial [1,7]–H shift.
(c) Thermal electrocyclic conrotatory ring opening; and photochemical superafacial [1,7]–H shift.
(d) Thermal electrocyclic distrotatory ring opening; and thermal suprafacial [1,7]–H shift.
5. Structure of the starting material A in the following photochemical Norrish reaction, is
[NET JUNE 2012]

6. The following photochemical transformation proceeds through [NET DEC 2012]

(a) Norrish type I reaction (b) Norrish type II reaction

(c) Barton reaction (d) Paterno–Buchi reaction
7. The major product formed in the following reaction is [NET JUNE 2013]

8. The major product formed in the following photochemical reaction is [NET DEC 2013]
 Photo Chemistry 4

9. The major product formed in the following photochemical reaction is [NET JUNE 2014]

g
10. Amongst the following, the major products formed in the following photochemical reactions are
[NET JUNE 2014]

(a) A and C (b) B and C (c) A and D (d) A and B

11. The cyclic product(s) of the following photochemical reaction is (are) [NET DEC 2014]

(a) Only cis-1, 2-dimethylcyclopentane

(b) Only trans-1, 2-dimethylcyclophentane
 Photo Chemistry 5

(c) a mixture of cis-and trans-1,2-dimethylcyclopentanes

(d) Only 2, 6-dimethylcyclohexanol
12. The major product of the following reactions is [NET DEC 2014]

13. The major product Formed in the following reaction is [NET JUNE 2015]

14. The major products A and B in the following reaction sequence are [NET DEC 2015]
 Photo Chemistry 6

15. The major product formed in the following reaction is [NET DEC 2015]

16. The correct match for the following transformations P-S with the processes I-IV is[NET JUNE 2016]
Reactions :
 Photo Chemistry 7

Processes :
(I) Diels-Alder
(II) Norrish Type–I
(III) Photocycloaddition followed by Diels-Alder
(IV) Norrish Type-II
(a) P–II; Q–IV;R–III; S–I (b) P–II; Q–IV; R–I; S–II
(c) P–IV; Q–II; R–III; S–I (d) P–IV; Q–II; R–I; S–III
17. The major product Formed in the following reaction is [NET DEC 2016]

18. The major products formed in the following photochemical reaction are [NET JUNE 2018]
 Photo Chemistry 8

19. Irradiation of either cis – or trans – stilbene at 313 nm results in the formation of a mixture of 93% cis
and 7% trans olefin because. [NET JUNE 2018]
1. Trans – stilbene is more stable than cis – stilbene.
2. The extinction coefficient of trans – stilbene is greater than cis – stilbene at exciting wavelength
3. The transition state structures of cis and trans – stilbenes are different
4. The triplet excited states of cis – and trans – stilbenes are at different energy levels
20. The major product formed in the following photochemical reaction is [NET DEC 2018]

21. Structures of the products (A) and (B) in the following photo-deprotection reactions are [NET JUNE 2019]
 Photo Chemistry 9

22. The major product formed in the following reaction is [NET JUNE 2019]

23. The major product formed in the following reaction is [NET DEC 2019]

24. The major products A and B formed in the following reactions are [NET NOV 2020]
 Photo Chemistry 10

25. The following transformation involves [NET SEP 2022]

(a) Norrish type-II; ii) fragmentation of a cyclopropyl diradical

(b) i) Norrish type-I; ii) fragmentation of a cyclopropyl diradical -methane rearrangement
(c) i) Norrish type-I; ii) di- -methane rearrangement
(d) Norrish type-II; ii) di- methane rearrangement
 Photo Chemistry 11

ANSWER KEY
1. A 2. C 3. A 4. B 5. C 6. B 7. D 8. B 9. A 10. D

11. C 12. A 13. A 14. C 15. B 16. C 17. A 18. B 19. C 20. C

21. A 22. B 23. D 24. C 25. B

SOLUTION
1.
Ans. (a)
Sol. Chemical reaction involved in the above transformation can be illustrated as

2.
Ans. (c)
Sol. Chemical reaction involved in the above transformation can be illustrated as

3.
Ans. (a)
Sol. Chemical reaction involved in the above transformation can be illustrated as
 Photo Chemistry 12

4.
Ans. (b)
Sol. Chemical reaction involved in the above transformation can be illustrated as

Since there is a trans ring junction, so it is a photochemical conrotatory process.

5.
Ans. (c)
Sol. Chemical reaction involved in the above transformation can be illustrated as
 Photo Chemistry 13

6.
Ans. (b)
Sol. Chemical reaction involved in the above transformation can be illustrated as

Then reaction proceeds through H –transfer

7.
Ans. (d)
Sol. Conformational preference is seen in the phtotolysis of cyclodecanone where transannular hydrogen
abstraction takes place for te E-carbon, i.e. a 1, 7-hydrogen transfer to form the cyclodecanol.

H and OH trans to each other. Because trans decalin is more stable than cis-decalin.
8.
Ans. (b)
Sol. Chemical reaction involved in the above transformation can be illustrated as
 Photo Chemistry 14

9.
Ans. (a)
Sol.

10.
Ans. (d)
Sol.

11.
Ans. (c)
Sol.

It will produce a mixture of product, becuse during the reaction caurse C–C  bond rotation can
 Photo Chemistry 15

takes place
12.
Ans. (a)
Sol. Hofmann Lofflar Freytag reaction

13.
Ans. (a)
Sol.

14.
Ans. (c)
Sol.
 Photo Chemistry 16

15.
Ans. (b)
Sol.

16.
Ans. (c)
Sol.
 Photo Chemistry 17

17.
Ans. (a)
Sol.

18.
 Photo Chemistry 18

Ans. (b)
Sol.

19.
Ans. (c)
Sol.

20.
Ans. (c)
Sol.
 Photo Chemistry 19

21.
Ans. (a)
Sol. Norrish type –II mechanism for the photocleavage of a 2–nitrobenzyl based photolabile protecting group.

22.
Ans. (b)
Sol.
 Photo Chemistry 20

23.
Ans. (d)
Sol.

24.
Ans. (c)
Sol.
 Photo Chemistry 21

25.
Ans. (b)
Sol.
 Photo Chemistry 22

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