Show how the following compounds can be synthesized from cyclohex...

Question

Show how the following compounds can be synthesized from cyclohexanol. a.

b.

c.

Accepted Answer

Hey, everyone and welcome back to another video, propose a synthesis scheme for the formation of one methyl cyclo one in from Cyclo Pan. As the problem suggests, the starting material is cyp. So let's draw a five member ring and let's add an alcohol group to one of our carbon atoms. Now, we want to synthesize one mel cyclo band one in. So we're going to draw another five member ring because we have cyclopse. And now according to the problem, we basically have a metal group at carbon number one. And in addition to that, there's a double bonds starting at that carbon. OK. So we got our starting material and our product, we just have to think about the formation of the king. The most important part for us to understand is that we're adding one carbon to the final product. So we will need a source of carbon atoms and specifically, we're adding a metal group. So to do that, the best idea is to use the Green Yard reaction. But to use the Green Yard reaction, we first of all want to make sure that we get a carbonyl compound to get the carbonyl compound we can oxidize our secondary alcohol because we have a secondary alcohol, we will oxidize it using chromium six oxide in the presence of sulfuric acid. So basically, we can use the jones right in the course of the reaction, we will generate the chromic acid, which is a strong oxidizing agent. And therefore, we can form a ke zone out of the secondary alcohol. Meaning we are going to essentially turn our alcohol grew up into a carbonyl group. From here. When we have performed the oxidation reaction, we are going to use the proposed gray reaction specifically. If we want to add a methyl group, we want to use number one, methyl magnesium bromide. And number two, when we form our al oxide and iron, we always want to use mild acidic work up. So that oxide turns into an alcohol and essentially what we're going to get here using the Ard reaction is an alcohol. Simple. Let's recall that if we have methyl magnesium bromide, then the very first step is the attack at the electrophysics position, followed by the cleavage of the pi bond. And the oxide anion is then proton using the acid. So we obtain our tertiary alcohol, we are going to add the resultant methyl group and our alcohol group obtained after the protonation stopped. And finally, if we have our alcohol, we can easily turn it into an al. Now, let's understand that the algae that we're forming is the Z of product because we have a more substituted alkene, we specifically have two unique beta hygienes to remove and we are removing the wand that will form a more substituted alkene. So for that purpose, we can have a single step which is an acid catalyzed dehydration. So we're going to use sulfuric acid in the presence of heat to essentially observe an E one elimination. During the elimination. We are simply going to turn our O H group into water and we will have the loss of the living group formation of a tertiary carbo ion. And then the beta hydrogen will be removed to give us the required alkin well done. So let's summarize our steps to perform the required conversion. We would need the first reaction which is addition of chromium six oxide and sulfuric acid. Right. So that would allow us to oxidize the alcohol into a ketone. Number two, we will add methyl magnesium bromide. Number three, we are going to use mild acidic water cup to proton the oxide and produce a new tertiary alcohol. And number four, we are going to use an acid catalyzed dehydration to form the required alkin. Let's label our synthesis stops and conclude the video. Thank you for watching.

Show how the following compounds can be synthesized from cyclohexanol. a. b. c.

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Show how the following compounds can be synthesized from cyclohexanol. a.
b.
c.