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Organic Chemistry I

Rates of hydrolysis and the SN1 and SN2 mechanisms

  • 3 things to know
  • Papers 2 and 3

Overview

Comparing hydrolysis rates with silver nitrate in ethanol, the reactivity order of primary, secondary and tertiary halogenoalkanes and of chloro-, bromo- and iodoalkanes explained by C–X bond enthalpy, the Sₙ2 mechanism and its transition state, and aqueous against ethanolic potassium hydroxide for substitution or elimination.

What you need to know

Answer each one before you reveal it.

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Process

What separates the two nucleophilic substitution mechanisms?

Process

Why are iodoalkanes the most reactive halogenoalkanes towards hydrolysis?

Key term

Which reagent lets you compare how fast primary, secondary and tertiary halogenoalkanes are hydrolysed?

Questions from this subtopic

Each one with the model answer underneath.

  1. 1

    Which reagent lets you compare how fast primary, secondary and tertiary halogenoalkanes are hydrolysed?

    Model answer

    Aqueous silver nitrate in ethanol.

  2. 2

    How would you compare, in the lab, how fast chloro-, bromo- and iodoalkanes hydrolyse?

    Model answer

    Warm each with silver nitrate solution in ethanol and time how quickly a precipitate appears.

  3. 3

    What observation indicates that hydrolysis of a halogenoalkane has occurred when using aqueous silver nitrate?

    Model answer

    The formation of a precipitate of silver halide.

  4. 4

    How does the rate of precipitate formation relate to the rate of hydrolysis in the silver nitrate test?

    Model answer

    The faster the precipitate forms, the faster the rate of hydrolysis.

  5. 5

    Place primary, secondary, and tertiary halogenoalkanes in order of increasing reactivity towards nucleophilic substitution.

    Model answer

    Primary < secondary < tertiary.

  6. 6

    Place chloroalkanes, bromoalkanes, and iodoalkanes in order of increasing reactivity towards hydrolysis.

    Model answer

    Chloroalkanes < bromoalkanes < iodoalkanes.

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