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Ch.21 - Organic Chemistry

Chapter 21, Problem 74a

List the products of each alcohol reaction.

a.

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Welcome back, everyone provide the expected products of the reaction between the given alcohol and sulfuric acid. Whenever an alcohol reacts with sulfuric acid, we have to recall that we're observing an acid catalyzed dehydration, which produces an LK, right? In addition to that, we're also producing water ac by product, having recognized this reaction, we can just include the water immediately as our by-product. And now we want to get our LK. Now, the question is, how do we get it? Well, essentially, our first goal is to break the carbon oxygen bond and release that. Oh and this leaves us with our carbon chain. Our next step is to remove the so called beta hydrogen. Now, the beta hydrogens belong to the two metal groups bonded to the central carbon atom. The question is which one should we remove? Well, generally we remove the beta hydrogen that is bonded to the more substituted carbon. But these beta hydrogens are equivalent since they belong to the same metal groups. So we can remove any of them. Essentially, we can choose the bottom metal group and we want to introduce a double bond between our carbon atoms. So what we're going to do to get the alkin product is just redraw the metal group on the left, introduce a single carbon carbon bond at the original hydrogen. And now our next goal is to introduce a double bond between the bottom and the central carbon atom. Since we have also removed the beta hydrogen, the bottom CH three becomes CH two, right, it loses that beta hydrogen. And this is how we have got our products. Thank you for watching.