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Master Organic Chemistry Reaction Guide

Iodination of alkenes to give vicinal diiodides (1,2-diiodides)

Description: Treatment of alkenes with iodine (I2) leads to the formation of vicinal diiodides (1,2-diiodides).

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Real-Life Example:

Org. Synth. 1951, 31, 66

DOI Link: 10.15227/orgsyn.031.0066

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2 thoughts on “Iodination of alkenes to give vicinal diiodides (1,2-diiodides)

  1. Since this is anti-additon, in the fourth example, shouldn’t the I’s on the third and fourth Carbon’s be one wedged and one dashed not both wedged and dashed?

    1. If you look closely the central carbon-carbon bond has also rotated. If that rotation had not happened, then the two C-I bonds would be anti.

      This is a very common type of exam problem, where the question will start with an alkyne and then do either Lindlar or Na/NH3 to give a cis- or trans- alkene, and then do either a syn- or anti- selective reaction in the second step.

      [wp_quiz_pro id="19026"]

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