9/5/2014

CHEM 523 Advanced Organic Chemistry – II

DEPARTMENT OF CHEMISTRY
PONDICHERRY UNIVERSITY
M.Sc. Chemical Science and M.Sc. Integrated Program
CHEM 523 Advanced Organic Chemistry – II
1st Session Examination; Date: September 8, 2014; MAXIMUM MARKS = 150; Time: 90 min
Answer all questions; Select correct answer; Marks for right answer = 6; Marks for wrong answer = -2.
Note: Selection with part correct answer will not be considered
1. Identify the major product formed in the following reaction

2. Identify the major product in the following conversion (BPS = tert-butyldiphenylsilyl)

3. Match the conversions with the reagents
1.
2.
3.
4.
5.
6.

A. (X) - (ii); (Y) - (i); (Z) - (iv)
B. (X) - (iii); (Y) - (v); (Z) - (vi)

HgSO4, H2SO4 (dil)
a). mCPBA, b) LAH
OsO4, NaIO4
NaBH4
N2(COOK)2, NaOH
NaBH4, CeCl3

C. (X) - (i); (Y) - (iv); (Z) - (vi)
D. (X) - (iii); (Y) - (v); (Z) - (iv)

4. Which of the statements is/are true for the following oxidation
I. X reacts faster than Y
II. Y reacts faster than X
III. Loss of H of OH is the rate limiting
http://210.212.230.223/a04543zx_/chem_test.php

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X: 3. I and III D.3-carbonyl disposition is A. (ii).230.9/5/2014 CHEM 523 Advanced Organic Chemistry – II step IV. (i). A. Y: 2 B. (iii). (ii) C.223/a04543zx_/chem_test. Identify X and Y. Y: 4 7. (iii) B. Correct order of reagents in the following 1. (ii). (ii) 6. Y: 1 D. X: 1. Identify the major product formed in the following reaction 8. I and IV 5. Y: 3 C. I and III B. While epoxidation of geraneol with mCPBA provides two products X and Y in the ratio of 2:1. with VO(acac)2 and t-BuOOH provides a single product Y. Removal of H of CHOH is the rate limiting step A. (i). X: 2. (iii). (iii). X: 3.212. (i).php 2/7 . Match the following http://210. (i) D. II and IV C.

230. (Z) .(v). tetrahydronaphthalene to naphthalene Y. (X) .(iii). Z . Z . Z . Y . 2. 3.2-dihydroxycyclohexane Z. DMF C.(ii) B. NMO PDC. 5.(i). (X) . 1 and 3 B. Z . Y . Y . 4. (Y) .(v) C. (a) CF3COOOH.(v) B. Z .(ii). (b) dil. Y .(ii) B.(iv). 5. Which of the following ketones can be used for asymmetric epoxidation A. 2 and 4 10. MnO2 CH3CO3H H2 (high pressure). X . benzaldehyde to phenol A. HClO4 OsO4. (Y) . (Z) .(iv) 11.(iii). X . Cyclohexene to trans-1. 4.(i). X . 3. Cyclohexene to 1.(iii).(ii). (Z) . Y .(ii) D. Cu(OAc)2. X .(v).(ii).(iv).(i). PtO2 (a) O2.9/5/2014 CHEM 523 Advanced Organic Chemistry – II A.223/a04543zx_/chem_test. Y .(v) 9. NaOH OsO4. Phenol to cyclohexanol Z.(v). Y . X . Z . (Y) . 1 and 2 D.(ii). Match the following conversion with the reagents X. X .(i).(v) 3/7 .(iii).php 1. (b) Zn.(iii).(ii) 1.(iv). Cyclohexenone to cyclohexenone oxide Y.(iii).(iii).(ii) D. (Y) . AcOH DDQ C. X . (X) .(vi) D.(iii).(iv).(ii) http://210. X . (Z) .(iii). 1 only C. 2.6-hexanedial A. (X) . Z . Match the following X. Z . NaIO4 H2O2. Y .212.

Z . Z .php 4/7 .(ii).(i). Z: (vi) B. X . X . Identify the product formed in the following reaction 13. X . Y: (iii). X . Z: (vi) D. Z .(ii). Y: (iv).(iii). Y .(vi) 15.(iv). Y .(vi) B.(iii). X: (ii). Y: (iii). X: (i). Y: (iii).230.(i). X: (ii). Z .223/a04543zx_/chem_test.(iii). Correct order of reagents for following conversion is http://210. Y . Z: (vi) C.(vi) C.212. Appropriate reagents for the following conversions are A. Z: (v) 14. Match the products with the reactions A. X: (i).9/5/2014 CHEM 523 Advanced Organic Chemistry – II 12.(v) D. Y .

NaCNBH3.223/a04543zx_/chem_test. 4.230. H2O DMF isopropanol xylene dicholormethane C. O3. 3. X .(v) 1. Z . benzyl amine. Y .php 5/7 .212. X . Reduction of acid chloride to aldehyde Z. X . (iii) HOH A. Reduction with sodium borohydride Y.(iv). Z . X .(i).(ii). iii > i > ii D. Me2S. 4. O3. 16.(iii) B. Y .(iii). Me2S.(iv). i > iii > ii 19. 2. Y . Identify the major product 17. i > ii > iii C.(iii). 3. O3.9/5/2014 1. NaCNBH3. Z . CHEM 523 Advanced Organic Chemistry – II benzyl amine. 2. Y . Identify the major products in the following reaction http://210. benzyl amine.(v) D. benzyl amine.(i).(ii) 18. O3. Me2S. Oxidation with cetylammonium permonganate A. 5. NaCNBH3. (ii) HOOH. Identify appropriate solvents for the following reaction X. Z . ii > i > iii B. Arrange the following according to acid strength (i) CF3CO3H. NaCNBH3. Me2S.(iv).

212. Select an appropriate reagent 22.223/a04543zx_/chem_test. Predict the product 23.230. Identify the product 21.9/5/2014 CHEM 523 Advanced Organic Chemistry – II 20. Select appropriate reagent for conversion http://210.php 6/7 . Identify appropriate reagent 24. Identify major product among the following 25.

212.9/5/2014 1. Y: (v) Do well and best of luck http://210. 2. Y: (iv) X: (ii). Y: (vi) X: (iii). CHEM 523 Advanced Organic Chemistry – II X: (i).230. Y: (v) X: (i).php 7/7 . 3.223/a04543zx_/chem_test. 4.