4. What is the final product, Z, of the following synthesis? Name: Last four numbers of the ID: Part A. 1. LiAlH(O-t-Bu) 3 ether, -78 o C 2.

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1 ame: Last four numbers of the : 4. What is the final product, Z, of the following synthesis Part A 1. The R spectrum of which type of compound will not show evidence of hydrogen bonding Aldehyde Alcohol Carboxylic acid Phenol Primary amine S 2 C 3 1. KMn 4, -, heat X CAl(t-Bu) C 2 2 CC 3 C Y 1. LiAl(-t-Bu) 3 ether, -78 o C 2. 2 CLi C 2. LiAl 4 (LA) cannot be used to convert carboxylic acids to the corresponding aldehydes because: LA is not sufficiently reactive. RC is converted into RCLi. LA is too reactive and RC is reduced to RC 2. RC is reduced to RC 3. RC is converted into R 2C=. 3. A compound with formula C 5 10 gives two signals only, both singlets, in the 1 MR spectrum. Which of these structures is a possible one for this compound C 3 C 2 CC 2 C 3 (C 3 ) 2 CCC 3 (C 3 ) 3 CC C 3 C 2 CC 5. An aldehyde results from the reaction of which of these compounds with aqueous base C 3 C 2 C 2 C 3 CC 2 C 3C=C 2 C 3C 2C 2 C 3C 2C 3 6. The product, K, of the following sequence of reactions C 3 C 3 CC C 3 C 2 Mg 3 Benzene J + Al 3 ether K would be: C 3 (C 3 ) 2 CC 2 C Page 1 Page 2

2 7. What, in general, is the order of decreasing reactivity of these carbonyl compounds towards nucleophilic reagents C 3 CC 3 C 3 C (C 3 ) 3 CCC 3 C (C 3 ) 3 CCC(C 3 ) 3 > > > > > > > > > > > > > > > > > > > > 8. The compound C 6 5-C=- 2 is produced by the reaction of benzaldehyde with which compound Ammonia ydrazine itrogen Phenylhydrazine ydroxylamine 9. What is the major product of the following reaction sequence C 3 i), ii) LA, Et 2 iii) 2, The aldol cyclization of C 3CC 2 C 2 C 2 C= produces which of these C C 3 C 3 C= C= 11. Which of these compounds would have the lowest pka C 3 CC 2 5 C 3 CC 2 CC 3 C 3 CC 3 C 3 C C 3 CC 2 C 2 CC 3 C 3 Page 3 Page 4

3 12. Predict the product of the following reaction sequence. i. ac 2 5 ii. C 3 C 2 C 2 iii. a, 2 iv. 3 +, heat 13. What would be the major product of the following reaction C 6 5 C=CCC +C - A 3 C 6 5 C 2 CCC 3 C C 6 5 CC 2 CC 3 C C 6 5 C 2 C 2 CC 3 C C 6 5 C 2 C 2 CC C 6 5 CC=CC 3 C 14. What final product is expected when toluene (C 6 5 C 3 ) is subjected to the following reaction sequence i) KMn 4, a; ii) 3 + ( product = C 7 6 2); iii) S 2; iv) 3 (product = C 7 7); v) 2, a C 6 5C 2 C 6 5C 2 2 p-c 3C 6 4S 2 2 p-c 3C C Page 5 Page 6

4 15. What would be the product of the following reaction sequence i. C 3 ii. Ag 2, 2 iii. heat and only 18. What reagent can effect the following transformation 2 2 Sn + ; then - 2 3P 2 CuC, then The product, C, of the following reaction sequence, 16. When an equimolar mixture of ammonia and butyl bromide reacts, which of these products will form Butylamine ibutylamine Tributylamine Tetrabutylammonium bromide All of these C 3C 2CC 3 would be: 17. ow would one carry out the following transformation: 2 a 2,, 0-5 C; then 3 a 2,, 0-5 C; then 3P 2 a 2,, 0-5 C; then 2,i C 6 5S 2, - ; then a, MS C 3C=CC one of these Page 7 Page 8

5 20. What would be the major product of the following reaction 22. What would be the product, C, of the following reaction sequence (C 3) 3CC 2C 2C What would be the product of the following reaction C 3C=CC 2C C 3C=CC Page 9 Page 10

6 23. Which reagents would you use to synthesize this compound by an aldol condensation 25. What compound results from the aldol cyclization of 24. What starting compound(s) would you use in an aldol reaction to prepare Both and Page 11 Page 12

7 Which of the following compounds would be the strongest base When cyclizes in basic solution, which of these compounds will be formed 27. What is the final product, C 29. Which would be the weakest base p-methylaniline p-methoxyaniline exylamine p-itroaniline ipropylamine 30. LS is a common abbreviation for: lead stroncium dichromate least square differences method lecithin sulfonium dichloride lithium sulfodioxide lysergic acid diethylamide 31. A correct name for C 6 5 C 2 C 2 C 3-Benzylpropanone 3-Phenylpropanal 3-Benzylpropanal onanone onanal is Page 13 Page 14

8 32. The product, E, of the following reaction sequence, P 5 C 6 6 ab 4 C 3 C 2 C C E Al 3 C 3 would be: 33. C 2 C 2 C 3 CC 2 C 3 CC 2 C 3 CC 2 C 3 Which of the following procedures would not yield (C 3) 2 CC as a product PCC C 2 2 C 2 S 2 3 KMn 4 (heat) 3 + LiAl(-t-Bu) 3 ether, -78 o C Zn Ac C(C 3 ) Which product can be obtained via the following generalized reaction R- + aet C Et Et Et R C Et Et R R R 35. Which compound would be formed when 2,3-dimethylhexanal is treated with a solution of a in Which reagent could be used to separate a mixture of aniline (Ph 2) and toluene (PhC 3) KMn 4 in 2 ilute a ilute ac 3 Ag( 3) 2 ilute R C C Page 15 Page 16

9 37. What compound is likely to be obtained via the following reaction sequence i., 0-5 o C 2 ii. Cu iii. Fe/ 2 iv. a, 2 v., 0-5 o C vi. 3 P Which of the following pairs represent tautomers C 3 C=C and C 3 C C= P Which is the best method to prepare 3 (excess) 2, i 3 C 3 2 2, i o C hν + 3 2, i ame Last four numbers of the Part B 40. (10 marks) Prepare hexane-2,5-dione from acetone and acetoacetic ester (C 3 C()C 2 C 2 C 3 ). Show a mechanism of either the first or the last step. (A tip: α- bromoacetone can be a possible intermediate). 41. (10 marks) Complete the following reaction sequence, giving structural details of all significant intermediates and the mechanism of the first step. i. EtMg i. 3 ii. 3 +, heat ii.zn, C 3 C 2 2 All of these one of these Page 17 Page 18

10 42. (10 marks) When phthalimide (1) is treated with a strong base and 3-bromopentane, two products (2 and 3) are formed. Compound 2 is a liquid with a molecular formula of C 5 10 that showed an infrared peak at 1620 cm -1. Compound 3 has the molecular formula of C When 3 is heated with hydrazine, compound 4 is isolated (C 5 13) and its expected 1 MR spectrum (with integrated peak areas) is shown below. 1 (a) Show structures for 2, 3 and 4. (b) Give an arrow-pushing rationale for the formation of 2 and 3. (c) Assign the 1 MR signals for (10 marks) Show the final product and all intermediates of the following reaction sequence (remember that BAL is Al(i-Bu) 2 and 4 is weakly acidic). Show the arrow pushing mechanism of step (). What intramolecular cyclization could happen in the last step (show the structure for 1 extra mark) C 3 (excess) / + BAL 2 2 heat -78 o C (ether) (ethanol) 4 / Benzaldehyde was treated with nitroethane and dilute base. When worked up, the product A (C 9 9 2) showed 7 signals in the 13 C MR spectrum. Compound A was then subjected to hydrogenation over a platinum catalyst to give B that showed an exact mass measurement of the parent ion of and gave the 1 MR shown below. C a) (7 marks) Justify the formation of A with curved arrows and show structures for A and B. b) (4 marks) Justify the splitting pattern in the 3ppm region of the spectrum Page 19 Page 20

11 Answer Key A 2. C 3. C 4. C B 7. B 8. B 9. E B B 14. E 15. A 16. E 17. B 18. A 19. A 20. E E 26. A 27. C 28. B E 31. B 32. C A 35. E 36. E 37. C 38. C 39. A i. EtMg ii. 3 +, heat C 3 (excess) / + heat 3 C 3 - a+ heat 1)a 2) + i. 3 ii.zn, C 3 C BAL -78 o C(ether) (ethanol) 4 / unstable intermediate A B The splitting is due to unequivalent protons in alpha position to Ph group (diastereotopic protons) which are next to the chiral centre (amino-substituted carbon) Page 21 Page 22

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