ORGANIC SYNTHESIS OF ALIPHATIC COMPOUNDS

ORGANIC SYNTHESIS
1. A specialised branch of chemistry concerned with producing organic compounds by chemical reactions
2. May be simple or require more complex, multi-step reactions involving many stages
3. In industry, a multi-step synthesis of a complex organic molecule starts from a commercially availablle raw materia
  1. Crude oil is the raw material for many organic compounds
    1. Compounds derived from crude oil are also used as starting materials
4. Often presented as a puzzle
  1. You may be supplied with reactions you've never seen before
  2. Using familiar + unfamiliar reactions you could be asked to suggest a mult-istep synthesis of an organic compound from a supplied starting material
Stepwise approach to organic synthesis
1. 1.Need a good knowledge of the chemical reactions, reagents and conditions in the specification
  1. 2. Should check carbon skeleton of starting material + product
    1. longer chain usually means that 2 C-containing compounds must be reacted together
    2. 3. Examine the starting material and product to see if you can spot what has changed
      1. 4.Think about working backwards
        5. Finally check you answer and every step of the synthesis
        Retro synthesis
        Synthesis that is planned backwards, starting at the target molecule
        Involves breaking up target molecule into simple, available reactant molecules
Worked Example
1. State the reagents and conditions and give suitable equation for the preparation of 3- aminopropan-1-ol from 3 - chloropropanal
2. Step 1: draw the structures of the starting material and the product
  1. Step 2: Use knowledge of functional groups to propose a route
    1. An alcohol can be made by reducing an aldehyde so 3-chloropropan-1-ol can be made by reducing 3-chloropropanal Reagents: NaBH4/H20 Conditions: heat
      1. Halogenoalkanes can be converted to amines using ammonia Reagents: excess NH3 Conditions: ethanol solvent/reflux
Synthetic routes in aliphatic chemistry

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ORGANIC SYNTHESIS OF ALIPHATIC COMPOUNDS

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	Created by Nicole Chananda about 9 years ago