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Questions tagged [elimination]

Questions whose main focus is on E1, E2, E1cb, or any other type of elimination reaction.

3 votes
0 answers
50 views

What constitutes something being designated as big, bulky in terms of SN2 vs E2

When deciding between $\mathrm{S_N2}$ and $\mathrm{E2}$ for primary and secondary alkyl halides, is there a particular method or molecular size or any other threshold, which allows us to designate ...
Please Delete Me's user avatar
5 votes
2 answers
462 views

Predicting product of amine elimination

From section 'Nitrogen Containing Compounds' I spent quite a lot of time here but could not figure out the answer. It's not mentioned in my school text book either. The solution given in my book is: ...
paracetamol's user avatar
  • 18.8k
2 votes
1 answer
5k views

1,2-dibromopropane reaction with OH and NaNH2 [duplicate]

We have the reaction of the alkyl halide $\ce{CH3-CHBr-CH2Br}$ with 1) $\ce{OH-}$ 2) $\ce{NaNH2}$ The answer is propyne. I am unable to understand why we have performed an elimination reaction here. ...
Mo Samani's user avatar
  • 133
11 votes
2 answers
12k views

What is the major product in the reaction of 2,3-dichlorobutane with sodium amide in liquid ammonia?

I am not able to decide which among 1,3-butadiene and 2-butyne is the major product of this reaction. Will there be even a major product out of the two or will there be a mixture? According to me, ...
chemhead's user avatar
  • 161
3 votes
1 answer
562 views

E1 elimination and alkyne formation

Are E1 elimination reactions possible from a trans dihalide alkane (like 1,2-dibromoethane) all the way to the alkyne (like acetylene)? Or is only E2 possible from the alkene to alkyne? What is the ...
David's user avatar
  • 105
9 votes
1 answer
155k views

Use of aqueous KOH and alcoholic KOH in dehydrohalogenation reactions [duplicate]

What is the difference between aqueous KOH and alcoholic KOH? How do they react differently in dehydrohalogenation?
Chloritone_360's user avatar
3 votes
1 answer
2k views

Why does this E2 reaction occur on the less substituted carbon?

In compound C it eliminates the beta hydrogen attached to the less substituted carbon, rather than attacking the beta hydrogen attached to the tertiary carbon. Why is this the case?
john clastings's user avatar
13 votes
1 answer
4k views

Why does treatment of a geminal dihalide with sodium amide lead to an alkyne and not an allene?

I've come across the following problem in Klein's Organic Chemistry, 2nd edition: However, I'm a little bit confused about why the terminal alkyne is produced. I believe that an allene should be ...
Will Pike's user avatar
  • 437
6 votes
1 answer
1k views

Elimination of HCl from isomeric chlorocyclohexadienes

Which of these is most easily dehydrohalogenated? a. 5-Chlorocyclohexa-1,3-diene (1) b. 3-Chlorocyclohexa-1,4-diene (2) c. 1-Chlorocyclohexa-1,4-diene (3) d. Both 1 and 3 I encountered this question ...
user90870's user avatar
6 votes
2 answers
2k views

Origin of alkenes from Wurtz Reaction

According to Wikipedia: Also, since the reaction involves free radical species, a side reaction occurs to produce an alkene. This side-reaction becomes more significant when the alkyl halides are ...
Dissenter's user avatar
  • 19k
3 votes
1 answer
9k views

What conditions would make SN1 products the major products over E1 products, and vice versa?

It seems that if a carbocation intermediate is formed through solvolysis, then the product(s) are going to always be a pretty even mix of SN1 and E1 products. Are there any conditions that greatly ...
Kevin's user avatar
  • 31
47 votes
5 answers
52k views

Why does alcoholic KOH prefer elimination whereas aqueous KOH prefers substitution?

What is the basic difference between aqueous and alcoholic $\ce{KOH}$? Why does alcoholic $\ce{KOH}$ prefer elimination whereas aqueous $\ce{KOH}$ prefers substitution?
humble's user avatar
  • 647
14 votes
2 answers
4k views

What will be the product when 3,4-dibromocyclohexene is reacted with sodium followed by heating with selenium?

I'm tutoring few Class 12 students for their chemistry exams. I'm stuck with few problems. I don't know, if the key is wrong or I am wrong. According to me product (A) must be the cyclic diene, ...
claws's user avatar
  • 963

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