MSc Chemistry (Organic And Analytical) SEM II 2018 19 May 2018-19 CHEMISTRY PAPER III ORGANIC CHEMISTRY 29 (OLD) Question Paper - Mumbai University | munotes

Questions asked in this paper

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1. Q1 (A) Attempt any two of the following :
   • (a) What is Hell-Volhard-Zelinsky reaction? Give its mechanism with 4
   • (b) What is major enolate formed in each of the following condition? 4 Explain their formation
   • (c) What is Mannich reaction? Explain its mechanism with suitable example. 4
   • (d) Complete the following reaction and give the mechanism involved. 4
   • (B) Attempt any one of the following:
   • (a) Complete the following reaction and explain its mechanism. 4 Complete the following reaction, name it and explain its mechanism. 4 ii)
2. Q2 (A) Attempt any two of the following :
   • (a) Explain Von Richter rearrangement with its mechanism. 4
   • (b) Complete the following reactions and name them. 4
3. Q1 Pyridine
   • ii) NaOEt
   • (c) What is Curtius rearrangement? Explain its mechanism. 4
   • (d) Predict the product and name the following reactions. 4
   • (B) Attempt any one of the following:
   • (a) Give the mechanism for following conversion. 4
   • i) o-diazoketone ketene
   • (b) Explain Dienone-Phenol rearrangement with suitable example. Explain 4 Attempt any two of the following :
   • (a) Explain the following mechanisms with suitable examples 4
4. Q1 ii) SN2'
   • (b). Explain the following 4
   • i)NGP of aryl rings in nucleophilic substitution reaction and combination bands in IR spectra
   • (c) Explain n transition of acetone appears at 279 nm inhexane and 4 264 nm in water
   • (d) Aromatic nucleophilic substitution reaction with the help of 4
   • (B) Attempt any one of the following:
   • (a) Calculate the Amax of the following compounds 4
   • i) ii) [ Note: Increments for alkyl substituents on enonechromophore a = 10
   • (b) Explain in the following : 4
5. Q1 Vibrational coupling effect and hypsochromic effect
6. Q4 (A) Attempt any two of the following :
   • (a) a) An Organic Compound having M.F. showed following 4 exchange withD2O). Deduce the structure of the compound and justify
   • (b) Explain the following in Mass spectroscopy with one example each. 4
   • (c) How will you distinguish between 2-pentanone and 3-pentanone by Mass 4
   • (d) Write the number of signals and splitting pattern observed in the 4 spectra of following molecules: Attempt any one of the following:
   • (a) the fragmentation pattern of the following molecules in Mass 4
   • (b) An Organic Compound having M.F. showed following spectral 4
7. Q1 R. 2970 , 1735 1250 cm'! 7.5Hz), 6 7.7 (2H, d, J and 6 2.3 (3H, s ). Deduce the structure of the compound and justify your answer
8. Q5 Attempt any four of the following : Complete the following reaction,name it and explain the mechanism. 3 B the following reaction and explain its mechanism. 3 Explain Brook rearrangement with its mechanism. 3 Complete the following reactions. 3
   • ii) HNO,
   • iii) os Give the mechanism of ester hydrolysis via tetrahedral intermediate. 3 F Which of the two molecules 1, 3 butadiene or ethene will have a greater 3 Amax value and why? Explain the term chemical shift and write the chemical shift values for 3 Explain the term Metastable ion peak and Base peak in Mass 3

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