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Ethanol reacts with potassium cyanide, followed by dilute acid, to form 2-hydroxypropanenitrile - AQA - A-Level Chemistry - Question 4 - 2019 - Paper 3

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Ethanol reacts with potassium cyanide, followed by dilute acid, to form 2-hydroxypropanenitrile. Name the mechanism for the reaction between potassium cyanide and e... show full transcript

Worked Solution & Example Answer:Ethanol reacts with potassium cyanide, followed by dilute acid, to form 2-hydroxypropanenitrile - AQA - A-Level Chemistry - Question 4 - 2019 - Paper 3

Step 1

Name the mechanism for the reaction between potassium cyanide and ethanol.

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Answer

The mechanism for the reaction between potassium cyanide and ethanol is known as a nucleophilic addition.

Step 2

State the name of this type of mixture.

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Answer

The type of mixture formed by the two isomers is called a racemic mixture.

Step 3

Explain how the structure of ethanol leads to the formation of two isomers.

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Answer

Ethanol has a chiral center at the carbon atom attached to the hydroxyl group and the hydrogen. This allows for two different configurations (R and S forms) as the cyanide ion can attack from either side, leading to the formation of two isomeric products.

Step 4

Draw 3D representations of the two isomers to show the relationship between them.

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Answer

The 3D structures of the two isomers are as follows:

  1. (R)-2-Hydroxypropanenitrile:
    • The -OH group is oriented upwards on the chiral carbon.
    • The CN group is oriented downwards.
  2. (S)-2-Hydroxypropanenitrile:
    • The -OH group is oriented downwards on the chiral carbon.
    • The CN group is oriented upwards.

The two isomers are mirror images of each other, which can be represented by proper 3D diagrams with wedges and dashed bonds for clarity.

Step 5

Suggest a suitable reagent and conditions for the conversion of 2-hydroxypropanenitrile into acrylonitrile.

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Answer

The suitable reagent for the conversion of 2-hydroxypropanenitrile into acrylonitrile is concentrated sulfuric acid (H₂SO₄) at a temperature of approximately 170°C.

Step 6

Draw a section of the polymer polyacrylonitrile, showing three repeating units.

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Answer

The section of the polymer polyacrylonitrile can be represented as follows:

[-C-N≡C-CH₂-]n

This represents three repeating units in polyacrylonitrile, where the polymer backbone consists of alternating carbon and nitrogen atoms.

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