I have been having trouble figuring out the following mechanism

asked by @michellea45 • about 1 year ago • Organic Chemistry • 5 pts
  • https://s3.amazonaws.com/lightcat-files/chat_images/GzvnudeqR0CCePDAzh1r_Screen%20Shot%202017-08-06%20at%203.21.40%20PM.png Michelle commented about 1 year ago
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Hi there! One way you can do this is through this sequence of reactions. The Pr groups here simply represent propyls which are 3 carbon chains. Notice that we would eventually lead to a 3-membered ring. That gives us a clue that we would at some point use cyclopropanation. First, we will use a base to eliminate the halide and form a triple bond. From there we simply need to do a partial reduction. It is very important to notice that the 2 propyl substituents are facing opposite directions which is why we need to reduce the triple bond to a trans alkene using dissolving metal reduction. From there, any version of reagents can be used that we talked about in our carbenes and cyclopropanation section. Here we went with the reagents for Simmons-Smith. I hope that makes sense!enter image description here

answered by @leot1 • 12 months ago