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  1. Practice problems
  2. Orgo 1
  3. Electron-flow fundamentals
  4. Name the arrow pattern for ionization

Organic Chemistry 1 · Electron-flow fundamentals

Name the arrow pattern for ionization

Classify · Application

Conditions: (CH3)3C–Br → (CH3)3C⁺ + Br⁻ in water

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The question

One curved arrow goes from the C–Br bond to bromine, giving the tert-butyl cation and bromide. Which arrow-pushing pattern is this?

Reveal the answer and explanation

Answer and explanation

  1. Correct answer Loss of a leaving group

    Correct: a bond breaks and its electrons leave with Br.

  2. Not this one Nucleophilic attack

    Attack forms a new bond from a lone pair or π bond; here a bond only breaks.

  3. Not this one Proton transfer

    No hydrogen moves in this step.

  4. Not this one Carbocation rearrangement

    A rearrangement moves H or an alkyl group within a cation; this step creates the cation.

Worked solution

The arrow starts on a σ bond and ends on the more electronegative atom, which leaves with the pair: loss of a leaving group. No new bond forms, no proton moves and the skeleton does not change.

What you'll practice

Classify a mechanistic step as one of the four basic arrow-pushing patterns.

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Tags

  • #MechanismDrawing
  • #LewisStructures

More Electron-flow fundamentals problems

  • What came before the cyanohydrin alkoxide?
  • Follow a migrating carbon group
  • Add hydroxide to a carbonyl
  • Identify the donor in an adduct
  • Repair a carbonyl arrow set
  • Separate a contributor from a reaction
  • Choose an electron-count convention
  • Count a protonated oxygen

Keep practicing

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