So let's just look at the mechanism first. What I'm starting off with is water as my nucleophile. Water is obviously neutral, so that means it's going to be a weak nucleophile. It's not going to want to do a backside attack or grab a proton right away. It's going to sit back and wait for something to happen. And then the alkyl halide that I have is secondary. Okay? And a secondary alkyl halide is problematic. Remember that I told you guys that it's right in the middle where we don't really know what direction it will go. It could make a carbocation, not so great, but whatever. And it could also do a backside attack, once again, not so great. So how are we going to really know what to do? The answer is the flowchart. Just wait. Just hold on with me. I have a flowchart at the end that's going to change your life. But for right now, because we're combining a secondary with a neutral, we know this is going to favor e1sn1 because it's not going to sn2 and e2 isn't favored with a neutral. So let's go ahead and just say, Sn1, E1. Okay? So let's go ahead and draw these mechanisms out. The first step is the same regardless, which is my leaving group leaves. So what I'm going to get is a carbocation that looks like this. All right? I didn't draw the H because I don't have to. So let's draw the sn1 or I mean sorry, let's draw the e one product first. So the e one product would be that I pull off a beta proton and make a double bond. So the question is how many different types of betas do I have? Well, I have this is a beta carbon here. I'll make that one blue. This is a beta carbon here. I'll make that one green. Okay? Do they both have hydrogens on them? Yes. Are they both exactly the same? No. One is a primary, one is a secondary. One is at the end, one is on the middle of a chain. So these are actually 2 different ways that I could eliminate and now I'm going to have to draw both products. I told you guys this one had more than 2 answers. So I'm not going to draw both mechanisms, but I will just draw one of them. One of the mechanisms, let's say, that I eliminate there would be that I take my water And I pull off this hydrogen and make a double bond. So what that means is that I would have 2 e1 products. I'm going to write here e1 and I'm going to write here e1. Okay? And the 2 e1 products would be that I could get an elimination down, down the left side of that bond. Okay? That would be 1. And then the other e one product would be that I get an elimination down the right side. Okay? So those are my 2 different products. As you can see, they're completely different. Okay? So those are my E ones, but now I also have to figure out the esin one. Okay? So the esin one would be the same water, but it would have attacked directly onto the carbocation. Okay? So what that means is that I would now get a product that looks like this. I'm just going to come over here and draw it out, SN1. Okay? And what I would wind up getting is something that looks like this where now I have water coming off of my chain and that means that I'm going to have a positive charge. So what could I use to take off that proton with the deprotonation step? And the answer is I could use my br negative. So I'm going to use br negative. Oops. Br negative. And I'm going to take off that proton, give it to the o, and now I have an alcohol. So what we can see is that the end product here is going to be an alcohol. Now I have one last question. Will this become a chiral center? The answer is yes because now I'm going to have a methyl. I'm going to have a ring. I'm going to have an alcohol and I'm also going to have an h here. Okay? So that means that now I have to draw 2 different SN1 products. Products. I'm gonna have to draw that I get a product that looks like this with the alcohol facing towards the front. Okay? And I'm also gonna get another s n one product that has the alcohol facing towards the back. I have to include both chiral centers because both are possible because it's racemic. Okay? Cool. So now you guys just saw that I have a possibility of 1, 2, 3, 4 different products here. I took it easy on you guys. I didn't make 5. 5 is the worst case scenario for this. But still, it sucks and basically you guys should know that that's why we don't use this reaction for synthesis because it's terrible. No one wants to get 4 different products. Instead, you'd rather get 1. So that's why we use SN2 and E2 instead of using SN1 and E1. But guess what? You still need to know this reaction for your test and that's why I'm explaining it to you. Alright. So let's move on to the next topic. Let me know if you guys have any questions.

Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

8. Elimination Reactions

E1 Reaction

Organic Chemistry

8. Elimination Reactions

E1 Reaction

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Multiple Choice

Predict the product

Chemical structure depicting an intermediate in the E1 reaction with OH and Br.

Chemical structure showing a product of the E1 reaction with OH and Br in different positions.

Chemical structure illustrating another product of the E1 reaction with Br and OH in different positions.

Chemical structure of a final product in the E1 reaction with OH positioned at the end.

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Verified step by step guidance

Identify the type of reaction: The presence of water (H₂O) suggests a nucleophilic substitution reaction, likely an SN1 or SN2 mechanism.

Analyze the substrate: The substrate is a secondary alkyl bromide, which can undergo either SN1 or SN2 reactions. The presence of a cyclohexane ring may influence the reaction pathway.

Consider the reaction conditions: Water is a polar protic solvent, which typically favors SN1 reactions due to its ability to stabilize carbocations.

Predict the mechanism: In an SN1 reaction, the bromine atom leaves first, forming a carbocation intermediate. Water then acts as a nucleophile, attacking the carbocation to form an alcohol.

Determine stereochemistry: SN1 reactions often lead to racemization due to the planar nature of the carbocation intermediate, resulting in a mixture of stereoisomers.