SN1 reactions of cyclic ethers

In summary, the question is asking which is more stable, a tertiary carbocation or a primary one. The answer is the tertiary carbocation is more stable due to interaction of σ electrons in an adjacent empty π orbital.
  • #1
baldbrain
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The Attempt at a Solution


Firstly, since -Br is the better leaving group among the three, it's either (a) or (b). Further, since -Br is present at α position in (b), which also has an acidic α hydrogen to the same carbon, it would react better with a weak nucleophile (favouring SN1) than in (a). So, the answer's (b). But is my line of action correct?
 

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  • #2
baldbrain said:
But is my line of action correct?
Not quite. If I had to guess, this question is really asking about carbocation stability. Your leaving group analysis is fine. So out of a and b, which carbocation is more stable?
 
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  • #3
TeethWhitener said:
Not quite. If I had to guess, this question is really asking about carbocation stability. Your leaving group analysis is fine. So out of a and b, which carbocation is more stable?
Well, I can't really decide.
Is molecule (a) more stable because of separation of charges, or, is (b) more stable due to the highly polar C-O bond?
 
  • #4
Why is a tertiary carbocation more stable than a primary one? (ignoring steric considerations)
 
  • #5
Hyperconjugation
 
  • #6
baldbrain said:
Hyperconjugation
Which is?
 
  • #7
TeethWhitener said:
Which is?
Interaction of σ electrons in an adjacent empty π orbital.
 
  • #8
baldbrain said:
Interaction of σ electrons in an adjacent empty π orbital.
Oh, so you mean the σ electrrons of the oxygen would interact with the π orbital of the carbocation, hence leading to more stability?
 
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  • #9
baldbrain said:
Oh, so you mean the σ electrrons of the oxygen would interact with the π orbital of the carbocation?
Yes.
 
  • #10
TeethWhitener said:
Yes.
Ok. Thanks
 
  • #11
@TeethWhitener you didn't reply to my last question on 'How can any of these give the same SN1 & SN2 product'. I'd asked your advice on something
 
  • #12
What question?
 
  • #13
All my concepts are quite clear, but I still **** up during exams (probably due to haste). I also solve a lot of problems, and I can get them quicker when there's no time limit. That ticking clock makes me feel like a guillotine will behead me any moment.
Sometimes, even the opposite happens. I get the good problems, and **** up the easy ones. Can you give me some advice regarding this?
 
  • #14
I don't know if I’m the best one to give advice. Practice is the most important thing. People make mistakes occasionally. If you really understand a concept, then the number of mistakes will drop over time and become a kind of random noise. If you make an undue number of mistakes with particular concepts, it means you don’t quite understand it and you should seek outside help.
 
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  • #15
TeethWhitener said:
I don't know if I’m the best one to give advice. Practice is the most important thing. People make mistakes occasionally. If you really understand a concept, then the number of mistakes will drop over time and become a kind of random noise. If you make an undue number of mistakes with particular concepts, it means you don’t quite understand it and you should seek outside help.
All Right. Thank you again
 

Related to SN1 reactions of cyclic ethers

What is an SN1 reaction?

An SN1 reaction is a type of substitution reaction in which a leaving group is replaced by a nucleophile to form a new compound. It is a two-step process, with the first step being the formation of a carbocation intermediate followed by the attack of the nucleophile in the second step.

What are cyclic ethers?

Cyclic ethers are organic compounds that contain an oxygen atom bonded to two alkyl or aryl groups in a ring structure. These compounds are commonly used as solvents and can undergo SN1 reactions due to the presence of a good leaving group, such as a halogen, on the ring.

How do SN1 reactions of cyclic ethers differ from those of acyclic ethers?

The main difference between SN1 reactions of cyclic and acyclic ethers is the stability of the resulting carbocation intermediate. In cyclic ethers, the ring structure can stabilize the positive charge on the carbocation, making the reaction more favorable. Additionally, the ring structure can also hinder the approach of the nucleophile, leading to regioselectivity in the reaction.

What factors affect the rate of SN1 reactions of cyclic ethers?

The rate of SN1 reactions of cyclic ethers can be affected by several factors, including the stability of the carbocation intermediate, the strength of the leaving group, the strength of the nucleophile, and the solvent used. Additionally, the size and substitution pattern of the cyclic ether ring can also impact the rate of the reaction.

What are some common examples of SN1 reactions of cyclic ethers?

One common example of an SN1 reaction of a cyclic ether is the hydrolysis of tetrahydrofuran (THF) to form 1,4-butanediol. Another example is the reaction of oxacyclopentane with hydrochloric acid to form 1-chloro-3-methylbutane. These reactions are important in organic synthesis and are also used in the production of various pharmaceuticals and industrial chemicals.

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