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

  1. How is the 5th example a meso compound when there is no internal line of symmetry? one iodine is on a wedge while the other is on a dashed line.

  2. I hate to nitpick little things like this (this resource is amazing I really appreciate it). I noticed the formation of the Iodonium ion in the main mechanism uses lines for the C-I connections, while in other examples a wedge was used

  3. 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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