ST.

‌‌BERCHMANS‌C ‌ OLLEGE,‌‌CHANGANACHERRY
MSc Chemistry: Semester 1-Model Exam‌December 2022
BMCH102: MECHANISTIC AND STRUCTURAL ORGANIC CHEMISTRY

Time:‌‌1‌‌½‌‌hrs‌ ‌Marks:‌‌35 ‌‌

Section A
Answer any 5 questions (5 x 2 = 10 marks)

1. What are SET reactions? Narrate a suitable mechanism.

2. Explain internal allylic substitution reaction with suitable reaction.
3. Differentiate between Wheland intermediate and Meisenheimer complex.
4. Give a short account of addition - elimination mechanism.
5. What are ‘ansa’ compounds?
6. Explain the basic principle of chiral chromatography in separating enantiomers.
7. Trans-isomer of 1,3-di-t-butylcyclohexane exists in twist boat conformation. Explain.
8. Draw the conformations of cis and trans isomers of 1,2-dimethylcyclohexanes. Compare
stabilities and optical properties of above compounds.
Section B
Answer any 2 questions (2 x 5 = 10 marks)

9. Show that hydroboration-oxidation is syn addition, regiospecific and stereospecific taking

propene and 1-methylcyclohexene as examples.
10. Explain (i) benzyne mechanism (ii) Gomberg bachmann reaction.
11. Explain the chirality of the allenes with suitable examples.
12. With the help of P.E diagram analyse the conformations of cyclohexane.

Section C
Answer any one question (15 marks)

13. Discuss the effect of neighbouring groups in the rate and stereochemistry of a
nucleophilic substitution process with proper examples (10 marks). (b) Explain the
competition between elimination and substitution reactions in aliphatic compounds. (5
marks)
14. (a) Briefly explain the symmetry and substitution addition criteria for the identification
of homotopic and enantiotopic ligands with suitable examples. (8 marks)
(b) Explain the mechanistic details of (i) Hoesch reaction (ii) Pschorr cyclisation (iii)
Gattermann Koch reaction (7 marks)