The reactions shown below are unlikely to occur as written. Tell what is wrong with each, and pr

The reactions shown below are unlikely to occur as written....

Key Concepts

Chemical Equation Balancing

This concept involves ensuring that the number of atoms of each element, as well as the total charge, is identical on both sides of the equation. Inaccuracies or omissions during balancing can lead to chemically absurd or non-occurring reactions. Understanding and applying balancing techniques is crucial to verify not only the stoichiometric ratios but also the overall feasibility of a reaction.

Reaction Feasibility and Conditions

Assessing reaction feasibility involves evaluating the thermodynamic and kinetic parameters that favor or disfavor a reaction under the given conditions. A reaction as written may be unlikely if it does not account for necessary factors such as proper catalysts, solvents, temperatures, or if it predicts products inconsistent with the inherent reactivity of the reactants. This concept is key when predicting what products form in real-world scenarios versus what might be naively written on paper.

Mechanistic Prediction of Reaction Products

This concept focuses on understanding the underlying step-by-step processes (mechanisms) by which reactants are transformed into products. By analyzing potential intermediates, reaction pathways, and the influence of reagents, one can identify errors in a proposed reaction and accurately predict the most likely outcomes. Such mechanistic insights help explain why a reaction as originally proposed may not proceed and guide the correction of the reaction to yield the actual product.

Transcript

00:01 All right, so we have the following reactions here, and we are told that these reactions are unlucky to occur.

00:06 So we want to go ahead and figure out what is wrong with each one of these and go ahead and predict the actual product.

00:12 So for our first reaction here, we have looks like we have a tube baromobutane, which is being reacted with the potassium terputoxide to form what it looks like as substituted product.

00:24 And we know that this is not going to occur.

00:28 So we would say we're not going to get this product because we know that when, whenever we react in alkohalide with a big bulky base like potassium turpid toxide, we're actually going to get an elimination reaction that favors the less substituted product.

00:42 So we would say the hoffman product due to steric hindrance.

00:47 And so what is going to actually happen is we are going to get the following reaction.

00:56 So i'm going to abbreviate potassium turpidotoxide as tbuok.

01:04 And then we're going to have an elimination reaction, right? so we're going to have the terminal hydrogen here, which is going to favor our hoffman product.

01:14 So these electrons are coming to come and deprotonate that hydrogen, and the electrons of the hydrogen are going to get pushed towards there and form a new pie bond.

01:22 And now our bromide's going to leave, so it's going to be an et2 elimination reaction.

01:29 And this is going to form our product, our hoffman product.

01:41 All right, so we would say that the hoffman is favored here, due to, due to our big bulky base.

01:50 And now we're given reaction b here, which we have a fluorosyclohexane, which is reacted with the sodium hydroxide to give us what looks like the substituted product.

01:58 Normally we would think, ok, sodium hydroxide's a very strong nucleophile.

02:02 And since fluoride is an alkaliate, it must be a good leaving group, although that is not really the case.

02:08 And we also have sodium hydroxide as a strong base.

02:10 So what is going to actually end up happening is an elimination reaction.

02:14 And we're going to get the following mechanism, right? so we're going to have, let's go ahead and draw our fluorosyclohexane here.

02:27 So we're going to end up deprotonating at one of the beta hydrogens.

02:31 It doesn't really matter which, because whether it's this one or this one, we're going to form the same product...

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