ChemistryOrganic Chemistry

Hammond Postulate: Energy and Transition-State Structure in HCl Addition

Chloride capture is exergonic. The Hammond postulate predicts an early, carbocation-like transition state with a weakly formed C–Cl bond.

Question

Consider the chloride-capture step of electrophilic HCl addition to an alkene: a chloride ion combines with the carbocation intermediate.

  1. Classify this step as exergonic or endergonic.
  2. Decide whether its transition state is more like the carbocation reactant or the alkyl chloride product.
  3. Sketch an approximate structure for this transition state.

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Evidence boundary

This is a normalized presentation of OpenStax Organic Chemistry Problem 7-20, selected as a complete representative exercise for the truncated Hammond keyword. It is not a reconstruction of the truncated search post. The conclusion concerns chloride capture in the textbook mechanism; the sketch is qualitative and does not specify bond lengths, a barrier height, or an experimental transition-state structure.