Question

In chapter 9 we learned how to make acetylide anions and use them as nucleophiles. In order to use this method, we will need to transform the alcohol to a different functional group that would make the carbon a better electrophile. Come up with a method (can be done in 2 steps) to produce the desired product from cyclopentanol (6 points)

4) The following image shows the general structure of a steroid: Steroids can be utilized in the biological systems for a multitude of purposes. One common use is as a signaling molecule. Signaling molecules are also known as hormones. Some medications are analogues of naturally occurring hormones such as the oral contraceptive Mestranol. OH OH H H н H HO H H Estradiol The major female sex hormone in humans Mestranol Let's use this example to start thinking about synthesis using reactions we currently know. Let's isolate the change in the bottom right hand corner. Show the reagents and mechanism that would allow the following transformation (2 points reagent, 2 points mechanism: HO Now let's isolate the changes to the top right position. This change is a bit more complex, but we can use concepts we now understand to hypothesize a way forward. OH HO HO In chapter 9 we learned how to make acetylide anions and use them as nucleophiles. In order to use this method, we will need to transform the alcohol to a different functional group that would make the carbon a better electrophile. Come up with a method (can be done in 2 steps) to produce the desired product from cyclopentanol (6 points)