All Questions
45
questions
-5
votes
1
answer
83
views
Why can't the diene in a diels-alder also be a dienophile [closed]
why can't the diene react with itself like this
0
votes
0
answers
46
views
How does the Eschweiler Clarke reaction occur with sodium cyanoborohydride as a reducing agent?
I am specifically confused with 2 concepts.
How sodium cyanoborohydride acts as a reducing agent. I read that it acts as a source of hydride but I am not sure how this works. If anything, I assumed ...
- 9
1
vote
0
answers
42
views
Reactivity of Alkyl Halides with E2 with same number of substituents in the end
I have a question regarding the reactivity of alkyl halide for E2. I know that the general rule is tertiary alkyl halide reacts the fastest with E2, and primary alkyl halide reacts the slowest.
I was ...
- 105
1
vote
0
answers
75
views
Order of radical dimerization ability
In a question I came across recently, it was asked to arrange the following radicals in the ascending order of dimerization ability.
I have read about the triphenylmethyl radical undergoing Gomberg ...
- 371
0
votes
0
answers
31
views
Improve the leaving capability of a leaving group (F-) with electron density donating groups (EDP) in close proximity (neighboring group effect)?
I have a situation in which I want to hydrolyze a phosphonic acid halide under basic conditions. In my specific case, the halide is a fluorine substituent. Other halides like chlorine and bromine are ...
2
votes
0
answers
63
views
Why bromoacetone is more reactive towards SN2 than alkyl bromides? [duplicate]
Compare the rates towards SN2 reaction:
I got the point that 2-bromobutane d is a secondary halide, so the steric hinderance is highest making it least reactive among the four. Both b and c are ...
4
votes
0
answers
75
views
How should the reactivity of 1-propanesulfonyl chloride be expected to compare to tosyl chloride for sulfonylation?
I've come across some scientific literature (e.g., https://doi.org/10.1021/jm400751p) that notably feature 1-propanesulfonyl chloride (PsCl) in the selective activation of hydroxy groups, such as a ...
- 111
3
votes
1
answer
240
views
The dependency on electron density in the reactivity order of electrophilic and nucleophilic additions
It is well-known that for electrophilic addition across an alkene, the reactivity increases when intermediate carbocation is more stable (eg. addition of $\ce{HBr}$ or acid-catalyzed addition of $\ce{...
- 1,817
2
votes
1
answer
435
views
Reaction of unsaturated lactone and alcohol
Image source
I found this equation to turn this compound into an ketoester but I am unsure of the reaction mechanism.
I postulate that the alcohol attacks the carboxyl carbon, the O becomes formally ...
- 748
3
votes
1
answer
786
views
Why can't Grignard reagents react like Organolithium does (with acids)?
I'd read yesterday that Grignard reagents can't give ketones on reaction with carboxylic acids. It is because of the fact that Grignard reagent is a "super-base", and it will deprotonate the ...
- 3,071
2
votes
0
answers
55
views
Reactivity comparison between benzaldehyde and acetaldehyde [duplicate]
One of my teacher says that $\ce{Ph-CHO}$ is more reactive than $\ce{CH3-CHO}$ in performing nucleophillic addition reaction because $\ce{—Ph}$ is planar and thus offers less steric hindrance as ...
- 71
4
votes
1
answer
3k
views
Beckmann rearrangement v/s dehydration of Oximes
In the above question, A is an oxime, which is then reacted with phosphorus pentoxide. Now, phosphorus pentoxide is both a dehydrating reagent and a reagent used for Beckmenn rearrangement, but which ...
user92687
4
votes
2
answers
2k
views
Why are Friedel Crafts reaction not possible for molecules less activated than benzene?
I know that Friedel Crafts alkylation reaction are not possible for aniline and phenol since they form complexes with Lewis Acids. But our teacher told us that Friedel Crafts reactions aren't possible ...
- 41
4
votes
1
answer
3k
views
Reactivity of different alcohols with NaNH2 and CH3I
Identify the final product (B) in the following reaction:
I'm not sure how $\ce{NaNH2}$ and $\ce{CH3I}$ will react with the different types of alcohol present here. According to my solution,ether was ...
- 105
1
vote
1
answer
3k
views
Friedel-Crafts Alkylation of Pyrrole [duplicate]
I thought that I already know how the Electrophilic Aromatic Substitution (EArs) for Aromatic rings work but then this reaction was shown to me and I was really sure that my professors didn't bothered ...
