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2012 NYJC Preliminary Examination, H2 Chemistry Syllabus 9647, Paper 3 Question 1(d)

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2012 NYJC Preliminary Examination, H2 Chemistry Syllabus 9647, Paper 3 Question 1(d)

  1. 1. www.wewwchemistry.com Page 1 of 5 Example of an Organic Synthesis Question from a School Preliminary Examination Paper (The question stem is highlighted in green.) 2012 Nanyang Junior College / Paper 3 / Question 1(d) Aldehydes and ketones react with primary amines in slightly acidic solution to form imines which have the C=N functional group. For example, propanal reacts with methylamine to give N-methyl-1-propanimine.
  2. 2. www.wewwchemistry.com Page 2 of 5 Suggest the reagents and conditions required to synthesise the following imine derivative. Identify all the intermediate compounds. [5]
  3. 3. www.wewwchemistry.com Page 3 of 5 Proposed Solution Step 1: Examine the starting reagent and final product, and take note of the changes in functional groups.
  4. 4. www.wewwchemistry.com Page 4 of 5 Step 2: Examine the structural changes in the propanal to N-methyl-1-propanimine example given in the question stem to determine the intermediate product required to synthesise the final product. ⇒
  5. 5. www.wewwchemistry.com Page 5 of 5 Step 3: Construct the synthetic pathway, showing clearly all reagents and conditions, and all intermediate compounds formed.

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