Predict the major products of the following reactions. (c) o -xylene + H 2 (1000 psi, 100 °C, Rh catalyst)

Hey everyone and welcome back What major product is expected from the reaction shown below. We are starting with nitrobenzene and we are using the following reaction conditions. First of all, that's hygiene gas. Right? So it implies hydrogenation. Whenever we are using that atomic hydrogen. This is governed by the fact that we're using a transition metal catalyst. Whenever we're using a transition metal in combination with the hydrogen, that implies hydrogenation. And it's also really important to understand that the pressure here is really high £1,000 per square inch. So that's an equivalent of around 68 atmospheres and that's high temperature. The conditions are really extreme. And the reason why we're using such a high pressure and such a high temperature is because it's very hard to reduce benzene ring, abnormal or standard conditions. So essentially we're dealing with the reduction reaction. And you may recall that whenever you're reducing double bonds, you end up with single bonds because you're creating saturated chain or basically you're adding hydrogen atoms and breaking the pi bonds to produce corresponding carbon hydrogen sigma bonds. So understand that this is hydrogenation. We are first of all going to introduce our ring, we will not have any of the pi bonds at these harsh conditions, it is possible to reduce the benzene ring. So we have our cyclo hexane ring because all of these three pi box have been reduced. Now think about the nitro group. We also have to be extra careful recall that whenever we have a nitro group at these conditions, we can reduce it into an amino group because we have reduction, there will be no oxygen atoms. Since that we are going to add two hydrogen atoms. So N. O. T group and such a reduction reaction is converted into an NH two group from nitro two amino group. So that means we're going to add our NH two group and this would correspond to our final product because we were asked to write the major product, We are going to label this as our final product or basically cyclo Hexcel, I mean and now just to review everything. Let's keep in mind that because restaurants, because benzene ranges resonance stabilized, it's really hard to reduce the spy bonds. That's the main reason why we're using such extreme conditions, it's really important to recognize that whenever you're trying to reduce benzene ring whenever you have such a high pressure at around 68 atmospheres high temperature and you're using a basic hydrogenation reaction in which hydrogen gas is used along with a transition metal catalysts such as rainy. Um you're going to reduce all of your pi bonds in the benzene ring and produce your cyclo hexane ring. In addition to that of course, if you have a nitro substitution, you're going to reduce it as well into an amino group. And based on our answer, we may conclude that the correct answer to the multiple choice question is c. We are producing cycle hex, I mean I hope you found this video useful and I will see in the next one. Thank you for watching.

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19. Reactions of Aromatics: EAS and Beyond

EAS:Sequence Groups

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

EAS:Sequence Groups

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Problem 32c

Textbook Question

Predict the major products of the following reactions.
(c) o-xylene + H₂ (1000 psi, 100 °C, Rh catalyst)

Verified step by step guidance

Step 1: Analyze the reaction conditions. The reaction involves hydrogen gas (H2) under high pressure (1000 psi) and moderate temperature (100 °C) with a rhodium (Rh) catalyst. These conditions are typical for catalytic hydrogenation reactions.

Step 2: Identify the functional group on the reactant. The reactant is a nitrobenzene derivative, with a nitro group (-NO2) attached to the benzene ring. Nitro groups are susceptible to reduction under hydrogenation conditions.

Step 3: Predict the transformation of the nitro group. Under catalytic hydrogenation, the nitro group (-NO2) is reduced to an amino group (-NH2). This is a common reaction pathway for nitro compounds in the presence of H2 and a metal catalyst.

Step 4: Consider the aromatic ring stability. The benzene ring itself is not hydrogenated under these conditions because aromatic rings are highly stable and require more extreme conditions for hydrogenation.

Step 5: Write the major product structure. The major product will be the benzene ring with the nitro group reduced to an amino group, resulting in aniline (C6H5NH2).

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Catalytic Hydrogenation

Catalytic hydrogenation is a chemical reaction that involves the addition of hydrogen (H2) to unsaturated organic compounds, typically in the presence of a catalyst. In this case, the Rhodium (Rh) catalyst facilitates the reaction, allowing for the conversion of double bonds in o-xylene to single bonds, resulting in the formation of saturated hydrocarbons.

Reaction Conditions

The reaction conditions, including pressure and temperature, significantly influence the outcome of catalytic reactions. Here, the high pressure (1000 psi) and elevated temperature (100 °C) promote the hydrogenation process, enhancing the reactivity of o-xylene and favoring the formation of saturated products over side reactions.

Product Prediction

Predicting the major products of a reaction involves understanding the structure of the starting material and the nature of the reaction conditions. In the case of o-xylene, the hydrogenation will likely lead to the formation of 1,2-dimethylcyclohexane, as the reaction saturates the aromatic ring, converting it into a cycloalkane structure.

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