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Carbon–carbon bond formation

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Question 3

In organic synthesis, extending a carbon chain by forming a new carbon–carbon bond is a key step in building complex molecules. A process chemist investigates two different methods to increase the chain length of aliphatic precursors:

  • Transformation 1: Converting 1-bromopropane into butanenitrile.
  • Transformation 2: Converting propanal into 2-hydroxybutanenitrile.

For both transformations:

  • State the name of the reaction mechanism.
  • Draw the complete mechanism, showing:
    • the structures of the organic starting material, intermediate (where appropriate), and organic product,
    • relevant dipoles (δ+\delta+δ+ and δ−\delta-δ−) and lone pairs,
    • curly arrows to show the movement of electron pairs.
[6]
Markscheme

Carbon–carbon bond formation Questions

  1. A Level
  2. /Chemistry
  3. /Carbon–carbon bond formation

4 exam-style questions on OCR A A Level Chemistry Carbon–carbon bond formation. Each one has a worked solution and a mark scheme showing where the marks go.

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