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Hydrocarbons

Markovnikov addition of hydrogen bromide and carbocation stability

  • 3 things to know
  • Components 1 and 2

Overview

Recall questions on the two possible products from an unsymmetrical alkene, which predominates and why, the relative stability of primary, secondary and tertiary carbocations, the inductive effect of alkyl groups, and predicting the major product for named alkenes.

What you need to know

Answer each one before you reveal it.

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Key term

Which product predominates when hydrogen bromide adds to propene?

Key term

Explain why the hydrogen bromide molecule acts as an electrophile without needing to be polarised by the alkene.

Key term

Describe the first two curly arrows in the addition of hydrogen bromide to propene.

Questions from this subtopic

Each one with the model answer underneath.

  1. 1

    Name the two products that can be formed when hydrogen bromide adds to propene.

    Model answer

    They are 2-bromopropane and 1-bromopropane.

  2. 2

    Which product predominates when hydrogen bromide adds to propene?

    Model answer

    2-bromopropane is the major product.

  3. 3

    Explain why the hydrogen bromide molecule acts as an electrophile without needing to be polarised by the alkene.

    Model answer

    Bromine is much more electronegative than hydrogen, so the H—Br bond already carries a permanent dipole with the hydrogen atom δ+.

  4. 4

    Describe the first two curly arrows in the addition of hydrogen bromide to propene.

    Model answer

    One arrow runs from the C=C π-bond to the δ+ hydrogen atom, and a second runs from the middle of the H—Br bond to the bromine, releasing a bromide ion.

  5. 5

    Name the two carbocations that can be formed when a proton adds to propene.

    Model answer

    A secondary carbocation forms if the proton adds to the end carbon, and a primary carbocation forms if it adds to the middle carbon.

  6. 6

    Place primary, secondary and tertiary carbocations in order of increasing stability.

    Model answer

    The order is primary, then secondary, then tertiary.

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