Worksheet on chapter 21 and 22 PDF

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Chapter 21 and 22 from Organic chem work sheet ...

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Recitation worksheet on Chapter 21 and 22 1. What are the criteria of a molecule to be aromatic? Circle aromatic molecules amongst the following.

2. What are the criteria of a molecule to be anti-aromatic and non-aromatic?. Specify antiaromatic and nonaromatic molecule amongst the following.

3. Draw molecular orbital diagram using π molecular orbital and designate bonding, antibonding and non-bonding electrons for the following molecules.

4.

From the concept of aromaticity explain why Pyridine is more basic than Pyrrole?

5. Circle aromatic compounds amongst the following.

6. Explain why the PKa value of the hydrogens shown below in cyclopentadiene is as low as alcohol?-Explain your answer based on the concept of aromaticity.

7. Which one amongst the following reaction is feasible- Explain your answer

8. Napthalene and azulene are constitutional isomers of each other. However, dipolemoment value of one is much higher than others- explain why?

9. Which one amongst the following carbocation has highest stability?

10. Use the following data to answer the question below.

Resonance energies of benzene is 36 Kcal mol -1and Napthalene is 61 Kcal mol -1 (a) Calculate the resonance energy of anthracene? (b) Anthracene is known to react with maleic anhydride in a Diels-Alder reaction. Predict which of the products shown is obtained- Why ?

11. Write down the product and show the mechanism for each step

12. Write down the missing products in the following transformation.

13. Para substituted benzyl halide reacts with methanol to give a benzyl ether. Account for the following order of reactivity under these conditions.

14. Arrange these compounds in order of increasing acidity.

15. Rank the carbocation in order of increasing stability.

16. Which one amongst the following substituted benzene rings would undergo an electrophilic aromatic substitution reaction faster? Circle your answer.

17. Circle the most stable cation

18. Write down the following functional groups mentioned below is ortho-para or meta directing when attached to the benzene ring.

19. Propose a mechanism for the formation of bisphenol A.

20. Write down the product A and B for the following transformation and then answer the question below.

a. Account for the selectivity of nitration in Step 1. b. Propose a mechanism for the substitution reaction in Step 2.

21. Arrange the compounds in each set in order of decreasing reactivity towards electrophilic aromatic substitution.

22. Write down the products for the following reaction and mention about major and minor product.

23. In a reaction mixture in dichloromethane you have an alcohol, phenol, and a carboxylic acid (shown below). How would you isolate (separate) and purify each from the mixture?

24. Write down the product for the following reaction.

25. To carry out the multistep synthesis below, what would be the best reaction sequence (choose one of them amongst four)?

1. (i) Et3N, CH3CH2Cl, (ii) OSO4, Aq. NaHSO3, (iii) H2/Pd-C 2. (i) Et3N, PhCH2Cl, (ii) OSO4, Aq. NaHSO3, (iii) H2/Pd-C 3. (i) OSO4, Aq. NaHSO3, (ii) Et3N, PhCH2Cl, (iii) H2/Pd-C 4. (i) MCPBA, (ii) H3O+...