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).
This page is available to MOC Members only.
Sign up here for about 30 cents/ day!
Real-Life Example:
Org. Synth. 1951, 31, 66
DOI Link: 10.15227/orgsyn.031.0066
Click to Flip
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
From one nitpicker to another, thank you. Easy thing to fix (done). Anything else, just let me know! James
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?
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"]