Predict the products of the following reactions.
(c) 1-methylcycl...

Question

Predict the products of the following reactions.
(c) 1-methylcyclohexanol + H2SO4, heat
(d) product of (c) + H2, Pt

Accepted Answer

Hey everyone, Let's do this problem. It says determine the major product of each reaction below. We have one methyl cyclo Penton one all and H two S. 04 with heat. Then we have the major product of part A reacting with hydrogen and a platinum catalyst. Okay, so let's identify what type of reactions these are in part a. We have our ending all. So that's an alcohol reacting with an acid and heat. So this is going to be an acid catalyzed dehydration reaction. Okay. And that's going to oh, acid catalyzed dehydration of alcohol. Right? And that's going to follow an E one mechanism. Okay. And that will form an al keen right? Elimination reactions. We know deep resonate a beta hydrogen to form an alky Okay, E one to form L keen. And then we'll find out that our major product is going to be an al keen, Right? Just like we said. So when al keen with addition of hydrogen will result in in al caine, right? Because in an elk in that's an unsaturated carbon, right? So if we add hydra jen's, we're saturating that carbon back to an al cane. Okay, so let's draw our reactant and I'm going to draw the mechanism just so we know how we are getting from point A to point B to our products. Okay, so one methods cyclo Penton one, All cyclo Penton is our five member carbon ring. We have our alcohol group on carbon number one In a methyl group also on carbon # one. Okay. And we're reacting this with H two s. 04 and heat, which we can know Tate with this little delta symbol. So in an elimination reaction specifically E one, the leaving group should leave 1st. But is alcohol a good leaving group? No. Right. So we need to change our leaving group into water. Right? Water is a good leaving group. So we do this by pro donating that alcohol group and then it will leave. Okay, so that alcohol is going to take one of the protons from our acid to form water, giving it a positive charge. Which means now it's going to want to take those electrons and be on its way. Right? So once we lose the water we are left with our carbo cat on intermediate and this is a tertiary carbon cat on. Right, that's really stable. So are there multiple products that we can have here in our elimination? Right? The next step is that one of the beta hydrogen needs to be deep rotated. So we have this beta hydrogen, let me redraw this hydrogen next to the carbo cat on And we also have this hydrogen, the blue hydrogen next to that carbo cat on. Well, we know there's the potential sites of product which is the more substituted, all keen and the Hoffmann product which is the less substituted elkin. So if we deep renate this hydrogen are alkaline will be in the ring and it will be more substituted. So let's draw that mechanism. And this is going to be depreciated by H S. 04 minus. Okay, So if we remove this hydrogen, those electrons will form an alkaline right here between that tertiary carbon and this hydrogen. Okay. And our Hoffmann product will be our less substituted elkin. So that would be deep resonating this red hydrogen. Right? Because then our al keen is going to end up outside of the ring to give us this product. Okay, so which one is going to be the major product? It will be the more substituted alc in which is the sites of product. So that's our major product. This is our minor product. Okay, so that's it for part A. So now part B says the major product of A and hydrogen with the platinum catalyst and we're simply turning it into an al cane. Right? So let's draw our major product one more time Reacting with H two and Platinum. And we're just going to remove our double bond, giving us this as our product, which makes be the correct answer to this problem. That's it for this one. I hope this video was helpful and thanks for watching

Predict the products of the following reactions. (c) 1-methylcyclohexanol + H2SO4, heat (d) product of (c) + H2, Pt

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