We could also put it on this carbon connected the metal and then three. There's three unique places on the ring that we could put it. So we have five possible products and they look like this. And then part be asked which product would be obtained in the greatest yield and figure that out. We're going to add up each of the types of hydrogen and used this little chart here to figure out to do a little math to figure that out.
So remember that a tertiary is five times more likely than a primary to be replaced for Corinne and the secondary, 3. Um, so we'll use those numbers so we'll look at the structure and look at the number of hydrogen of each types of the metal has three. Hydrogen is right there. So three times one is three. Um, the next structure that I did actually put that under the product. Okay, three times when I was three, The next structure that I did was that tertiary carbon.
So there is only one of those. The one time five is five. The next one AM is that secondary one? There's two carbon, but are identical there. So the total four times the re Four times they were in a Um and then same thing for the next structure is also for those hydrogen. And for the last one down here, there is two of those secondary hydrogen. So we'll do two times two point there, and that is 7.
So because these two have the greatest number, these air numbers are like relative probability of those being formed. Thes two will be our greatest yields products. Um, there equals of each other.
So well, get those and equal amounts. And then part c asked us how maney model chlorination products. There will be if we included stereo. I summers. So starting with the 1st 1 there are no stereo centers on that one. So we're not gonna add any products before that? Um, the 2nd 1 each time the ring is the same.
So that is not a stairs center right there. But now, on this one, the bull says bring are not the same. So we do have to Stereos enters there so we can have a total of four stereo I summers of that product. So each of those metal and chlorine can you to be up. They both up both down, one up, one down on the opposite of that one up, one down and same thing for the snack structure again to Syria centers there for a total of four possible stereo. I simmers. And then for the last one, we don't have any Kyrill centers here because now both says the rear the same.
We have that symmetry. So that will give us two possible serialize murders there. So if we add all of those up, we have to 6 10 12 possible total products if we include the stereo ice MERS. How many stereoisomers are formed from the reaction of cyclohexene with N… How many stereoisomers are obtained from the reaction of 2 -pentanone wit… What is the major monobromination product of the following reaction?
Disr… The following compounds have the same molecular formula as benzene. How m… Draw the major product s of the reaction of 1 -methylcyclohexene with th… Assume that you have carried out a radical chlorination reaction on R ch… What stereoisomers are obtained from the reaction of each of the following a… What is the major product of the reaction in Problem 7 when the alkane re… Problem a.
What five-carbon alkene forms the same product…. Start at one end and work towards the other. We have 3 possibilities for constitutional isomers: 1-chloropentane, 2-chloropentane, and 3-chloropentane.
Here, we have 5 constitutional isomers possible not counting stereoisomers. It is impossible to capture the variety of potential questions with these three examples, but the general thrust is the same. It also helps to have a systematic approach — starting the exchange of hydrogen for chlorine at one side of the molecule, and gradually working to the other side. Question answer: If the chlorination of propane was completely random, what yields of 1-propane and 2-propane would you expect to see?
How many constitutional isomers would you expect to see for the mono-chlorination of each of these molecules? Under free radical conditions we will obtain a racemic mixture of these two compounds i.
I believe you referred to initiation as a step at which radicals are created, not propagation. Is that incorrect? Your email address will not be published. Save my name, email, and website in this browser for the next time I comment. Notify me via e-mail if anyone answers my comment. This site uses Akismet to reduce spam. Learn how your comment data is processed. Previous Initiation, Propagation, Termination.
Likewise, mono-chlorination of ethane also gives just one product: chloroethane. What about more complicated cases, like propane, butane, pentane, or even 2-methylpentane?
These two products 1-chloropropane and 2-chloropropane are constitutional isomers. Answer below] 3. A More Complex Example: Monochlorination of Pentane Similarly, what do we get for the slightly more complicated example of pentane?
Why that might be? Hass, E. Chlorination of Paraffins B. The first five of these rules are summarized below: 1. If the temperature is controlled to prevent pyrolysis, no skeletal rearrangements will occur , and every possible monochloride will form.
As temperature increases, selectivity of chlorination decreases it approaches tertiary:secondary:primary 4.
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