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Organic Synthesis

Functional group interconversions and lengthening the chain

  • 2 things to know
  • Components 02 and 03

Overview

Recall questions on haloalkane to amine and to nitrile, nitrile to amine and to carboxylic acid, and how HCN addition and Friedel-Crafts reactions change the carbon skeleton.

What you need to know

Answer each one before you reveal it.

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Process

What is a multi-stage synthetic route, and how do HCN addition and Friedel-Crafts acylation change the carbon skeleton?

Key term

Which reaction converts benzene into a substituted aromatic compound, what forms when a carbonyl compound undergoes nucleophilic addition with HCN, and which reagent turns a carboxylic acid into an ester?

Questions from this subtopic

Each one with the model answer underneath.

  1. 1

    What reagent and conditions convert a haloalkane into an amine via nucleophilic substitution?

    Model answer

    Excess ethanolic ammonia.

  2. 2

    How is a haloalkane converted into a nitrile?

    Model answer

    By nucleophilic substitution using cyanide ions (e.g. KCN) in ethanol.

  3. 3

    What reagents reduce a nitrile to a primary amine?

    Model answer

    Hydrogen gas with a nickel catalyst (or LiAlH₄).

  4. 4

    How is a nitrile converted into a carboxylic acid?

    Model answer

    By acid hydrolysis (heating with dilute acid such as HCl or H₂SO₄).

  5. 5

    What happens to the carbon chain length when a carbonyl compound reacts with HCN?

    Model answer

    The carbon chain increases by one carbon atom.

  6. 6

    What does Friedel-Crafts alkylation achieve in terms of carbon chain modification?

    Model answer

    It attaches an alkyl group to a benzene ring, increasing the carbon chain.

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AThe first step is Cl• + O₃ → ClO• + O₂.
BThe second step is ClO• + O → Cl• + O₂.
CThe overall equation is O₃ + O → 2O₂.

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In ClO⁻, chlorine has oxidation number +1.
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