OrganicPhotochemistryandPericyclicReactions

Questions

1. Find out the major product & provide mechanism?

O
a)

b)

vapour phase

vapour phase
O

OH
h

c)

d)

2. Give mechanism for the given transformation.

O
h

a)

OH
h (pyrex)

b)

diethyl ether

O
c)
O

h
CH3OH

OCH3

HO

O
d)

3. Complete the following reaction & give their mechanism?

O
a)

Ph

Ph

O
b)

CO2Et

EtO2C

N
?

c)

O
h

d)

4. Write the possible mechanism for the following photochemical transformation.

OCH3
a)

OCH3

A , CH3 CN

b)

A , CH3 CN

c)
Ph

d)

Ph

H
C6H5

Ph

A , CH3CN ,O2

C6H5
H

5. Write the major product.

Ph
O O

Ph

N
Ph

h
a)
Sensitizer

b)

h
Sensitizer

c)

Sensitizer

6. Write the major product & provide mechanism

S
h

a)
S

Ph
h

b)

7. Find out the products in the following transformation.

a)

100 0C

CO2Me

MeO2C

B
2

b)

D
H

c)

CO2Et

EtO2C

Ph
N

CO2Et

EtO2C

Ph
H N H
Ph

N
CO2Et

N H
CO2Et
C

Ph

8) Suggest mechanism for the following transformation.

a)

h
rose bengal

O
H

O
h

b)

rose bengal
c)

O2

9. Predict the major product.

Et3N
OH

a.

NMe2

b.

c.

d.

H2C CH2

h
cyclohexane

10. Complete the given reaction and give the mechanism.

h

a.

b.

T1 Sens

d.

c.

T1 Sens

11. Write all the four products obtained in the given reaction
h

12. Find out the product A and B in the given transformation and explain the difference in the
photoreaction

Ph
H

Ph
H

(CH3)2CHOH

(CH3)2CHOH
H

13. Find out the product missing in the given transformation

H

h
A

C
D

14. Predict the major product for the given transformation

N N

a.

b.

N
O

c.

N2

15. Predict the product of the following transformations

O

h
a.

CN
b.

COOCH3
OAc
O

O
OAc
c.

16. Find the intermediates formed during the following transformation

S1

S2

S
S

17. Predict the stereochemistry of the following pericyclic reaction

h
a.

h
b.

N
c.

18. Predict the structure of A and B in the given transformation.

Ph
Ph

19. Predict the product

hv

380 oC

a.

dioxane
b.

OH

d.

c.

20. Predict the product.

O
a.

b.
O

c.

21. Write the product and give their mechanism.

a.

b.

H3C H
hv

d.

c.

H
H3C H
22. Write the major product

O
a.

MeO

O
O

Cl
Cl

Cl
Cl

b.

Cl
Cl

OMe
OMe

c.
O

23. Find out the A and B in the following transformation.

OCH3
A

OH

24. Find out A and B in the following transformation.

25. Find out the A and B in the following transformation.

O
Ph
O
S

O
A

Ph

26. Find out the intermediates.

O
RONO

OH

NH2

27. Find out the product.

a.

b.

+
COOEt

c.

+
NEt2
COOMe

d.

+
COOMe

28. Find out the product.

a.

Ph N C O

O2N

A
S

b.

Zn/AcOH

N
Oc.

OHC

H3C

C6H5

NHOH / OH-

H2C CH2

29. Predict the product.

C6H5
a.

CN2 + HC C COOMe
C6H5

b.

N3+

O2N

OCH3
c.
H3C

1 mole
ozone

30. Predict the major photoproduct.

H
O2 / hv ,Rose bengal

a.
H3C

H
H3 C

b.
H

H
CO2H
+

MeOOC

200oC

Problems were taken from

(i)

Modern Molecular Photochemistry: Nicholas J. Turro

(ii)

Organic photochemistry by Jan Kopecky

(iii)

Photochemistry and pericyclic reactions by jagdamba Singh and Jaya Singh