Draw the structures of the two different alkenes from which 3-methyl-3-pentanol, shown in the margin, can be made. Draw them in both condensed and line format.

Question

Structural formula of 3-methyl-3-pentanol with labels for its components.

Accepted Answer

All right. Hi, everyone. So this question says that the following or the structures of the akines from which three methyl, three Hexon all shown below can be made except and here we have four different anti choices for four different, all kids. What I want to point out here is that three of the alkenes in the inter choices are centered around one specific carbon whereas the fourth alkene is not. So let's keep that in mind if I scroll up one more time to examine our product, then three methyl three Hexon all is an alcohol, of course, in which the hydroxy group is on carbon three of the parent chain. Now a common way to produce alcohol is from all kinds. If you recall is acid catalyzed hydration in which water is added across both carbons of the double bond, right? One receives hydrogen and the other receives an oh group, therefore forming an alcohol. However, in the case of an unsymmetrical all keen where one carbon is more substituted than the other, then the question of which carbon receives the hydroxy group depends on Markov Niko's rule because acid catalyze hydration is considered a Markov Niko addition. Now Markov Niko's rule states that in the case of an unsymmetrical all keen, the hydroxy group is going to add itself on to the more substituted carbon. So the hydroxy group is going to be found on the carbon that has more bonds to other atoms or simply less bonds to hydrogen. Now, what's noteworthy about our product here is that the hydroxy group is on the most substituted carbon in the parent chain, right? Because notice how carbon three is tertiary because it's connected to three other carbon atoms. So it already is the most substituted carbon in this molecule. So if I go ahead and I briefly redraw the product, right, any double bond between carbon three and any of the three carbons surrounding it would result the intended alcohol. So in this case, we have a few different options, right? I can either make, I can first erase the hydroxy group and make a double bond in between carbons two and three. So that would be one product or one starting material. I can make a double bond in between carbons three and four of the chain to give me another product. And so my last product would feature a double bond in between carbon three here and the carbon of the methyl substituent, all of these three alkenes would result in the addition of the hydroxy group on carbon three because carbon three is the most substituted carbon in all cases. So if we consider the four different answer choices. Then the first three or the all keen that I drew previously, right? Because notice how all of them are centered on carbon three where the hydroxy group ends up being. So the only one that will not yield the intended product is option d in the multiple choice, right? Because it has a double bond in between carbons, one and two, not involving carbon three at all. And there you have it. So with that being said, thank you so very much for watching and I hope you found this hopeful.

Draw the structures of the two different alkenes from which 3-methyl-3-pentanol, shown in the margin, can be made. Draw them in both condensed and line format.

Verified video answer for a similar problem:

Key Concepts

Alkenes

Condensed Structural Formula

Line-Angle Structural Formula