Paper 6 Organic Chemistry Question bank

Unit 3 - STEREOCHEMISTRY
Questions carrying 2 marks each:

1.Define plane of symmetry.

2.Define centre of symmetry.
3.Define axis of symmetry.
4.What is meant by the term enantiomers?
5.What is meant by the diastereomers?
6.What is meant by a racemic mixture?
7.What is meant by a meso isomer? Explain with reference to tartaric acid.
8.What is the advantage of the R/S system of assigning configuration, over the D/L system?
9.What is meant by resolution of a racemic mixture?
10. Mention the advantage of the chemical method of resolution over the biochemical method.
11. Mention the conditions necessary for a biphenyl derivative to be optically active.
12. Draw the R and S forms of lactic acid and label the isomers.
13. Which of the following compounds exhibit/s optical isomerism?
(a) nitromethane (b) biphenyl (c) glyceraldehyde (d) ethylene glycol
14. What is the criterion of enantiomerism?
15. How would you distinguish between maleic acid and fumaric acid on the basis of dipole
moment?
16. How would you distinguish between maleic acid and fumaric acid on the basis of pKa
values?
17. Describe the biochemical method of resolution.
18. A meso isomer is optically inactive. Justify the statement.
19. Assign R/S configuration of below compounds and justify your answer.(2 marks each)
Questions carrying 4 marks each:

1. Give the differences between enantiomers and diastereomers.

2. Give a brief account of the optical isomerism of lactic acid.
3. Give any 2 evidences to show that maleic acid is the cis isomer and fumaric
acid is the trans isomer.
4. Discuss the geometrical isomerism of maleic acid and fumaric acid.
5. Explain the terms racemic and meso as applied to optical isomers, taking
tartaric acid as example.
6. Discuss the optical isomerism of biphenyl derivatives.

7. Write a brief note on the optical isomerism due to restricted rotation.

8. Describe the chemical method of resolution of a racemic mixture.
9. Illustrate how the R and S configurations are assigned to a compound
containing 2 stereogenic centres, taking the Fischer projection formulae of the
different isomers of tartaric acid.
10. Write the molecular models of the enantiomers of 1,1 chlorobromoethane and
label them as R and S.
11. Write the molecular models of the enantiomers of lactic acid and label them as
R and S.
12. Write the molecular models of the enantiomers of bromochloroiodomethane
and label them as R and S.
13. Write the molecular models of the enantiomers of glyceraldehyde and label
them as R and S.
14. Write the molecular models of the enantiomers of alanine and label them as
R and S.
15. Write the molecular models of the enantiomers of α - deuteroethyl bromide and
label them as R and S.
16. Write the structures of the isomers of 1-bromo-2-chloroethene and label them
as E and Z.
17. Write the structures of the isomers of butendioic acid and label them as
E and Z.
18. Write the structures of the isomers of 1-iodo-2-methylethene and label them as
E and Z.
19. Draw the chair conformation of methyl cyclohexane and mention the relative
stabilities of the axial and equatorial conformations.
20. Give examples of any 2 compounds exhibiting geometric isomerism. Write
their E and Z configurations.
Questions carrying 6 marks each:

1.Write the structures of the 1,2 dimethylcyclohexanes and discuss their relative stabilities.
2.Write the structures of the 1,3 dimethylcyclohexanes and discuss their relative stabilities.
3.Write a note on geometric isomerism taking maleic acid and fumaric acid as
examples.
4.Discuss the phenomenon of diasteroisomerism taking tartaric acid as example.
5.Define plane of symmetry. Describe how optical isomerism is observed in biphenyl
derivatives, illustrating the absence of plane of symmetry in these compounds.

Unit 4- Carbohydrates
1. What are epimers? Give example.
2. What is mutarotation? Explain with an example.
3. What are anomers? Give example.
4. Explain Killiani Fisher synthesis/ explain with mechanism a method to prepare the next
higher homologue of a carbohydrate.
5. How will you convert glucose to fructose?
6. Draw the Haworth structure of a pair of anomers.
7. Draw the Haworth structure of Lactose, maltose, Sucrose. (both alpha and beta and also
the gyycosidic linkage for each)
8. How will you account for the ring size of glucose by using periodic acid oxidation
method?
9. What are synthetic sweeteners? Give example.
10. How will you convert fructose to glucose?

Unit 5- Heterocyclic compounds

1. State and illustrate Huckel’s rule. (2)
2. Give the structures of two fused ring heterocyclic compounds. (2)
3. Explain the aromatic character of furan/thiophene/pyrrole. (4)
4. Furan is more reactive than benzene towards electrophilic substitution. Explain with the help
of the resonating structures of furan. (2)
5. In furan elctrophilic attack at C-2 is easier than C-3. Explain. (4)
6. Explain the aromatic character of pyridine. (4)
7. Draw the resonating structures of pyridine and predict whether it undergoes electrophilic or
nucleophilic substitution. (2)
8. Explain nucleophilic substitution in pyridine at various positions. OR Nucleophilic
substitution in pyridine takes place preferentially at C-2 and C-4 positions rather than C-3.
Why? (4)
9. Compare the basicity of pyridine , piperidine and pyrrole. (4)
10. Write down the following synthesizes. (4)
i) Furfural to furan
ii) Acetylene to a) pyrrole
b) thiophene
c) pyridine
11. Explain i) Bischler Napieralski synthesis of isoquinoline. ii) Fischer indole synthesis. (4)

12. Write a note on biologically important heterocycles. (2)

Unit 6- CHEMISTRY OF NATURAL PRODUCTS

ALKALOIDS, TERPENOIDS, FLAVANOIDS and ANTHOCYANINS

Alkaloids:
1. Structural elucidation of nicotine. (6)
2. Draw the structure of nicotine.
3. How the following conversions take place. a) nicotine to nicotinic acid b) nicotine
to hygrinic acid (4)
4. How nicotine is synthesized? (4)
5. Give the structure and uses Cocaine (2)
6. Mention the uses of any two alkaloids. (2)

Terpenoids.
1. What is isoprene rule? Explain with an example. (2)
2. Structural elucidation of citral. (6)
3. Write any two reactions to prove the presence of carbonyl group in nicotine. (2)
4. Write down the reactions of citral with KMnO4 and aqueous K2CO3. OR Write any two
reactions to indicate the carbon frame work and position of double bonds of citral (4)
5. What are the products of ozonolysis of citral? (2)
6. Explain the synthesis of citral from methyl heptenone (4)
7. Draw the structure and mention the uses of camphor, limonene, β- carotene, menthol.
(4)

Flavonoids
1. Mention the Functions of flavonoids in plants.
2. Mention some uses (health benefits) of flavanoids.
3. Explain the basic structure of flavanoids.
4. Draw the basic structures of the following.
a) Flavone b) flavonol c) Isoflavone d) Flavanol
5. Write a note on isoflavones.
6. Draw the structure of quercetin. OR Draw the structure of a flavonol and name it.
7. Explain the structure of catechin and epicatechin (any two flavanols)
8. Write a note on the dietary sources of flavanoids.
9. Write any two tests for the detection of flavanoids.

Anthocyanins
1. Give the basic structure of anthocyanins. (2)
2. Are anthocyanins and anthocyanidins same? If not what is the difference? (2)
3. Draw the structures of any two anthocyanins and name them. (Cyanidin and malvidin) (2)
4. Give the basic structure of anthocyanins. Write a note on the functions of anthocyanins in
plants (4)
5. Explain any two applications of anthocyanins. (4)