CHE-06 Organic Reaction Mechanism
1. a) Differentiate between bond homolysis and bond heterolysis with the help of suitable examples.
b) Draw the potential energy diagram for the reaction and explain, A B C
2. a) List the factors essential for a compound to be aromatic. Why do aromatic compounds mostly undergo electrophilic substitution reactions?
b) How will you convert benzene to the following:
i) p- Bromobenzyl bromide
3. a. What is the effect of a leaving group on SN1 reactions? Compare the effect with that for a SN2 reaction.
4. a) The rate of reaction of primary amine, in presence of an acid, with carbonyl compound increases by an increase in acidity but beyond a certain limit, the rate decreases with further increase of acidity. Explain
b) Give the mechanism of the following reactions:
c) Explain the following:
i) E2 elimination does not give rearranged product;
ii) E1 elimination does not involve isotope effect;
iii) Hofmann elimination gives less substituted alkene.
d) What do you understand by syn-elimination and anti-elimination. Explain with a suitable example.
5. a) What is oxidation state? Calculate the oxidation state of the two carbons in CH3 COOH.
b) Name any two method used to convert an aldehyd or a ketone to corresponding alkene.
c) Give the mechanism of the following reactions:
i) Perkin condensation
6. a) Describe the following:
i) Wolff rearrangement
iii) Hofmann rearrangement
7. a) Discuss various methods of detection of free radicals along with their principles.
b) Write the products and mechanism for the bromination of cyclohexene and ethyl benzene with N-Bromosuccinimide (NBS) in presence of light. What are advantages of such types of reactions.
8. a) Write the mechanism of the following rearrangement reactions:
i) Pinacol-pinacolone rearrangement
ii) Baeyer-Villiger rearrangement
b) Explain the products obtained from photo-induced and thermal-induced reactions of 2E-4Z-6E-octatriene. Write the types of motion responsible for these cyclisations.
9. a) Taking suitable examples discuss the photosensitisation.
b) How will you prepare 3-bromo-4-aminotoluene from p-toluidine? Write all the steps involved in this preparation.
10. How will you prepare following? Write all the steps involved in these preparations.
i) Disperse yellow
ii) Poly (ethylene terephthalate)
iii) Barbituric acid
iv) Quinolines
v) Propanol using Grignard reagent
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