CHM 215

SEMESTER TEST 1

1/03/2019 Time: 90 min

Marks: 60

Internal examiners: Dr D Riley & Dr M Nkwelo

External examiners: Dr N October

Initials & Surname: __________Memo_________________________________

Student Number: ___________________________________________

Signature: ___________________________________________

_________________________________________________________________

General Instructions:
1. Answer both Sections directly on the question paper. 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.

Page 1 of 6
Question 1 (6 marks)

Provide the IUPAC names for the following compounds. Indicate stereochemistry and double bond
geometry. (6)

(3Z,5Z,8R)-3,4-diethyl-8-iodo-2-methyl-3,5-nonadiene 3-benzyl-5-t-butylphenol

Question 2 (15 marks)

2.1 Write a stepwise mechanism for the radical polymerization of the following monomer: (5)

Page 2 of 6
2.2 (a) Draw the line structure of the monomer needed to synthesize the following polymer: (2)

(b) How many monomers are in this polymer? (2)

(c) Add to the polymer the benzoyl peroxide radical initiator (2).

2.3 Draw the structure of four monomer units of the polymer formed from the following monomer: (4)

Question 3 (26 marks)

3.1 Explain briefly, which of the following reactions is faster? Give the line structure/s of the product/s
formed in each reaction. (6)

Page 3 of 6
3.2 Draw the line structures of the substitution products formed in the following reactions. Explain
briefly, which reaction is faster. (6)

3.3 Draw the line structures of the major products formed in the following reactions. Which reaction
is faster? Explain. (7)

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3.4 Suppose you have compounds A – D at your disposal and any other suitable solvent. Use the
appropriate compounds and solvents to synthesise compound E. Make use of reactions and
short descriptions to explain your choice. (7)

Question 4 (7 marks)

Using line structures, propose a synthetic route for the following compound from the specified starting
material. Assume that solvents and any other reagents are available. Show all steps complete with
reagents and products. No mechanism or stereochemistry is required. (7)

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Question 5 (6 marks)

Draw resonance structures for the following carbocation. Which resonance structure is the
major contributor? Explain your choice and draw the resonance hybrid. (6)

Page 6 of 6