Practice Exam 4
VCE Chemistry | Advanced Organic Chemistry, Reaction Pathways, Spectroscopy & Analysis
✎ Complete ALL questions on paper before opening the Model Answers lesson. No notes. Aim for 1 minute per mark.
SHORT ANSWER
Question 1 (4 marks)
Outline a three-step synthesis of ethyl ethanoate from ethene. Include reagents, conditions and reaction types for each step.
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Question 2 (4 marks)
A compound has molecular formula CโHโO and shows an IR absorption at 1715 cmโปยน. The ยนH NMR shows two peaks: a triplet (3H) and a quartet (2H)… Actually for CโHโO: describe the structural identification.
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Question 3 (4 marks)
Explain the difference between SN1 and SN2 mechanisms with reference to the substrate and stereochemistry.
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Question 4 (4 marks)
In a mass spectrum of pentan-2-one (CHโCOCHโCHโCHโ, M=86), predict the m/z values of two likely fragment ions and explain their origin.
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Question 5 (4 marks)
Describe the structure and bonding in the alpha-helix of a protein. What type of bond maintains the helical structure?
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Question 6 (4 marks)
A sample contains a mixture of two organic compounds. Describe how you would use TLC and then preparative HPLC to separate and identify them.
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Question 7 (4 marks)
Outline the mechanism for the acid-catalysed esterification of ethanoic acid with ethanol.
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Question 8 (4 marks)
The ยนH NMR of ethanol (CHโCHโOH) shows three peaks. Describe the expected splitting patterns and relative integrations.
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EXTENDED RESPONSE
Extended Response 1: Organic Synthesis Pathway
Question 9 (5 marks)
Extended Response 1: Organic Synthesis Pathway (a)
Starting from propan-1-ol, outline a synthesis of propanoic acid, then propanoyl chloride, and finally N-methylpropanamide. For each step, give reagents, conditions and the reaction type.
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Extended Response 1: Organic Synthesis Pathway
Question 10 (3 marks)
Extended Response 1: Organic Synthesis Pathway (b)
Describe two methods used to confirm the identity of a pure organic compound.
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Extended Response 1: Organic Synthesis Pathway
Question 11 (2 marks)
Extended Response 1: Organic Synthesis Pathway (c)
Explain what is meant by a ‘green chemistry’ approach to organic synthesis and give one example.
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Extended Response 2: Spectroscopic Analysis
Question 12 (5 marks)
Extended Response 2: Spectroscopic Analysis (a)
An unknown compound CโHโOโ has: IR peak at 1735 cmโปยน (strong); ยนH NMR shows peaks at ฮด 1.2 (triplet, 3H), ฮด 2.0 (singlet, 3H), ฮด 4.1 (quartet, 2H).
Identify the compound and justify your answer using all spectroscopic data.
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Extended Response 2: Spectroscopic Analysis
Question 13 (3 marks)
Extended Response 2: Spectroscopic Analysis (b)
Explain how mass spectrometry (MS) can be used alongside NMR to provide complementary information in structure determination.
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✓ Finished? Open the next lesson – Model Answers – to mark your work.