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CHM 215 Semester Test 2_Memo (2018) Ver 2 DLR Edit
CHM 215 Semester Test 2_Memo (2018) Ver 2 DLR Edit
UNIVERSITY OF PRETORIA
DEPARTMENT OF CHEMISTRY
CHM 215
SEMESTER TEST 2
ORGANIC CHEMISTRY
1 3
2 12
3 18
Total
4 27
60
General Instructions:
1. Answer both Sections directly on the question papers. If an answer is not given in the space provided, clearly
indicate location. Cancel answers that should not be marked with pen.
2. Final answers should be given in blue or black pen.
3. Cell phones must be switched off.,
4. Use line structures where structures are required, unless specified otherwise.
Page 1 of 10
Question 1 (3 marks)
2.2 Consider the following reactions and based on the intermediates formed in step 1, rank the
given compounds according to their increasing reactivity. Fully explain. (NB: Do not give the final
products.) (8)
Page 2 of 10
2.3 Purine occurs commonly in the structure of DNA. Using the template given below, show an
atomic orbital drawing of the π and lone pair electrons of purine. (4)
Page 3 of 10
Question 3 (18 marks)
3.1 Use suitable diagrams and curly arrows to show electron movement to explain why aniline is
ortho-, para- directing. (9)
Page 4 of 10
3.2 Aniline when nitrated affords the unexpected meta-product as the major product.
Page 5 of 10
Question 4 (27 marks)
4.1 The following alkylation of benzene does not give product A as the major product.
a) Give the line structures of products B and C and show mechanistically how both form. (9)
b) Show a synthetic approach (no mechanism) detailing how you might obtain only product A
as the major product. (3)
Page 6 of 10
4.2 Propose a synthetic route for the following conversion. Assume that solvents and any other
reagents are available. Show all steps complete with reagents and products. Mechanisms are not
required. (6)
Page 7 of 10
4.3 Propose a synthetic route for the preparation of benzoic acid from benzene. Assume that solvents
and any other reagents are available. Show all steps complete with reagents and products.
Mechanisms are not required. (5)
Page 8 of 10
4.4 Show the major product formed in each of the following EAS reactions; where appropriate
justify your choice. (4)
Page 9 of 10
CHM 215 Organic Reagents Data Sheet
Page 10 of 10