So now we're going to switch gears and move away from talking about strict addition reactions to talking about oxidation reactions. It turns out that double bonds can not only be added to but they can also be oxidized. What that means is that oxygens can be placed directly on them. So, what we're going to talk about is some different ways to do that and what I want to talk about right now is ozonolysis. Ozonolysis would be categorized as a reaction that is a form of weak oxidative cleavage. Basically, cleavage just means to cut something. This entire time we're going to be using our visual scissors to cut things in different pieces. There is a mechanism for ozonolysis; it's very long. If you need to know it for your professor, believe me, I'll teach it to you. But that's not going to be on this page. On this page, I just want to give you a general overview of what ozonolysis does. Ozonolysis basically slices double bonds in half and winds up making a combination of ketones, aldehydes, and formaldehyde. Why does it make each of those things? I'll explain. But think about it this way: imagine that you have a very long carbon chain with one double bond in the middle and you cut it into 2 − how many chains would you expect to have? 2. That's pretty easy. How about if I have a ring and I have a double bond in one part of it and then I snip it right there? What would I expect to get at the end... Two rings? Two chains? No, I would just expect one chain because I have a ring and I cut it in one place, so now I have one chain. These are just simple geometry questions that actually get students confused with ozonolysis. That's exactly the way this works. So here, you can see I have a 7 carbon chain with 2 places to cut. I could use scissors here and I could use scissors here. Please, the scissors reference is just to help you visualize what's going on. What winds up happening is that if we have a 7 carbon chain with 2 cuts, I'm going to wind up getting 3 pieces. I'll get one piece at the end, a piece in the middle, and a piece on the other end. Does that make sense? The number of carbons at each end is going to be the number of carbons in the product. Here along this cut, I'm splitting it off with 1 carbon at the end. Here between the two cuts, I've got 4 carbons in the middle. And then here at the top, I've got 2 carbons being chopped off. So, I'm going to expect 3 different products: a 1 carbon product, a 4 carbon product, and a 2 carbon product. Now let's look at the reagents really quick. The reagents are actually really easy for ozonolysis because it's always just going to be ozone. O3 is ozone. So anytime you see that, you know this is ozonolysis. Sometimes different professors use different reagents as the reductive workup. Some will use zin
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Ozonolysis - Online Tutor, Practice Problems & Exam Prep
Ozonolysis is a weak oxidative cleavage reaction that involves the breaking of double bonds in alkenes, resulting in the formation of ketones, aldehydes, and formaldehyde. The process adds oxygen atoms to both sides of the double bond, effectively converting it into carbonyl groups. For example, a double bond in a carbon chain can yield multiple products based on the number of carbons on either side of the cleavage. The primary reagent used is ozone (O3), with reductive workup often performed using zinc and acetic acid or dimethylsulfide.
Ozonolysis is a form of oxidative cleavage that breaks through alkenes and replaces them with carbonyls on both ends. Just imagine the ozone functioning like tiny atomic scissors, cutting each alkene right in half!
General properties of ozonolysis.
Video transcript
The products of ozonolysis are a mixture of ketones, aldehydes and formaldehyde. You get these with:
- Ends of alkenes with –R groups on both sides = Ketones
- Ends of alkenes with 1 –H = Aldehydes
- Ends of alkenes with 2 –Hs (yielding single carbon fragments) = Formaldehyde
General Reaction:
Predict the products of the following reaction.
Do you want more practice?
More setsHere’s what students ask on this topic:
What is ozonolysis in organic chemistry?
Ozonolysis is a weak oxidative cleavage reaction that involves breaking double bonds in alkenes using ozone (O3). This process results in the formation of carbonyl compounds such as ketones, aldehydes, and formaldehyde. The reaction adds oxygen atoms to both sides of the double bond, effectively converting it into carbonyl groups. The primary reagent is ozone, and the reductive workup is often performed using zinc and acetic acid or dimethylsulfide.
What are the products of ozonolysis?
The products of ozonolysis are typically ketones, aldehydes, and formaldehyde. When a double bond in an alkene is cleaved by ozone, oxygen atoms are added to both sides of the double bond, forming carbonyl groups. The specific products depend on the structure of the original alkene. For example, a double bond in a carbon chain can yield multiple products based on the number of carbons on either side of the cleavage.
What reagents are used in ozonolysis?
The primary reagent used in ozonolysis is ozone (O3). For the reductive workup, common reagents include zinc and acetic acid or dimethylsulfide. These reagents help to reduce the ozonide intermediate formed during the reaction, leading to the final carbonyl products.
How does ozonolysis work?
Ozonolysis works by breaking the double bonds in alkenes through the addition of ozone (O3). The reaction mechanism involves the formation of an ozonide intermediate, which is then cleaved during the reductive workup. This process adds oxygen atoms to both sides of the double bond, converting it into carbonyl groups such as ketones, aldehydes, and formaldehyde. The specific products depend on the structure of the original alkene and the number of carbons on either side of the cleavage.
What is the mechanism of ozonolysis?
The mechanism of ozonolysis involves several steps. First, ozone (O3) reacts with the alkene to form a molozonide intermediate. This intermediate rearranges to form a more stable ozonide. During the reductive workup, the ozonide is cleaved, typically using reagents like zinc and acetic acid or dimethylsulfide, resulting in the formation of carbonyl compounds such as ketones, aldehydes, and formaldehyde. The overall process adds oxygen atoms to both sides of the original double bond.
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- The following product was obtained from the ozonolysis of an alkene followed by treatment with dimethyl sulfid...
- For each compound, show the products obtained from ozonolysis, followed by treatment with dimethyl sulfide. b....
- For each compound, show the products obtained from ozonolysis, followed by treatment with dimethyl sulfide. a....
- What products are formed when the following compounds react with ozone and then with dimethyl sulfide? b.
- What products are formed when the following compounds react with ozone and then with dimethyl sulfide? a.
- What alkene gives the product shown after reaction first with ozone and then with dimethyl sulfide? b.
- For each compound, show the products obtained from ozonolysis, followed by treatment with dimethyl sulfide. d....
- For each compound, show the products obtained from ozonolysis, followed by treatment with dimethyl sulfide. c....
- What is the major product of each of the following reactions? f.
- "Ozonolysis of an alkene, followed by treatment with dimethyl sulfide, forms the following product(s). Identif...
- What hydrocarbon forms the following products after reaction first with ozone and then with dimethyl sulfide?
- Give structures of the alkenes that would give the following products upon ozonolysis–reduction. b. and
- Give structures of the alkenes that would give the following products upon ozonolysis–reduction. a.
- Give the products expected when the following compounds are ozonized and reduced. c. d.
- Give the products expected when the following compounds are ozonized and reduced. a. b.
- Limonene is one of the compounds that give lemons their tangy odor. Show the structures of the products expect...
- Predict the major products of the following reactions, and give the structures of any intermediates. Include s...
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- When compound Z is treated with ozone, followed by dimethyl sulfide and washing with water, the products are...
- Draw the product(s) you'd expect when each of these alkenes is treated first with O₃, then with Ch₃SCH₃ (a)
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- In Solved Assessment 9.30(b), we came up with an alkene that under the conditions of ozonolysis would produce ...
- Suggest a synthesis of the following aldehydes or ketones using the ozonolysis reaction of an alkene. (a)
- (••) Predict the product(s) that would result when the alkenes are allowed to react under the following condit...
- (••) Predict the product(s) that would result when the alkenes are allowed to react under the following condit...
- (••) Predict the product(s) that would result when the alkenes are allowed to react under the following condit...
- (••) Predict the product(s) that would result when the alkenes are allowed to react under the following condit...
- Propose a synthesis of the carbonyl(s) using the (i) ozonolysis pathways. (a)
- Propose a synthesis of the carbonyl(s) using the (i) ozonolysis pathways. (b)
- Predict the reagents or reactant(s) necessary to complete the following syntheses. (b)
- Draw the product(s) you'd expect when each of these alkenes is treated first with O₃, then with Ch₃SCH₃(d) <...
- (••) Predict the product of ozonolysis of the triglyceride shown.<IMAGE>
- Predict the product of the following aldehyde/ketone syntheses.(a) <IMAGE>
- (•••) Ozonolysis of an unknown alkene A gives the products shown. Predict the product that results from hydrog...
- (••) Suggest reagents to carry out the following transformation. [One of the answers should be from Chapter 9....
- Draw the product(s) you'd expect when each of these alkenes is treated first with O₃, then with Ch₃SCH₃ (b) &l...
- Suggest a synthesis of the following aldehydes or ketones using the ozonolysis reaction of an alkene.(b) <I...
- (••) Predict the product(s) that would result when the alkenes are allowed to react under the following condit...
- (••) Predict the product(s) that would result when the alkenes are allowed to react under the following condit...
- Draw the product(s) you'd expect when each of these alkenes is treated first with O₃, then with Ch₃SCH₃(c) <...
- b. What alkenes would give only an aldehyde with four carbons as a product of oxidative cleavage
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- What are the products of the following reactions? Indicate whether each reaction is an oxidation or a reductio...
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- Problem 8-54 describes a new method to perform ozonolysis reactions that used pyridine (py) to generate the fi...
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