Questions tagged [rearrangements]

For questions about specific rearrangements within organic chemistry.

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1answer
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Reaction mechanism for the conversion of acyl hydrazide to acyl azide

How is an an acyl hydrazide converted into an acyl azide in the presence of $\ce{HNO2}$? According to me, the $\ce{-NH2}$ group of hydrazide will get converted into $\ce{-N2+}$ through $\ce{HNO2}$. ...
9
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1answer
1k views

Ring contraction when cyclohexene oxide is treated with methyl Grignard

My book writes that: Recall that epoxides rearrange with Lewis acids in a pinacol-like fashion, and that Grignard reagents in THF exist in the following equilibrium: I approached this ...
1
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0answers
93 views

Number of products on dehydrobromination

Question: The total number of alkene products possible from the dehydrobromination of 3-bromo-3-cyclopentylhexane using alcohol KOH is : This question was asked here before but I am getting more ...
3
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0answers
236 views

Major product of isomerization reaction

I am trying to come up with a logical mechanism for the following transformation, where 2-methylenecyclobutan-1-ol is converted to cyclopentanone under acidic conditions: What I have tried to do was ...
10
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2answers
901 views

Can a six member ring expand to achieve octet completion to stabilize a carbocation?

(Probably unnecessary background: I came up with this carbocation while predicting the major product of $\ce{NaNO2/HCl}$ with 1-(methylamine)cyclohexan-1-ol) Will the following carbocation ...
4
votes
0answers
359 views

Regioselectivity of the Beckmann rearrangement

It seems to be that the Beckmann rearrangement is a nice way to prepare secondary amines. This can be achieved by removal of oxygen via the use of $\ce{HI}$/$\ce{P}$. However, if ketones are used, ...
10
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2answers
2k views

Ring expansion from a given cyclic carbocation

How will the cyclobutane ring behave in the case of cyclobutylmethylium (cyclobutylmethyl cation)? I initially thought there would be ring expansion to a five membered ring so that there may be less ...
19
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1answer
16k views

Migratory aptitude in Baeyer-Villiger reaction

In short, I do not understand how or why the migratory aptitude is as listed in every textbook I've read. Firstly, they talk about a positive charge being built up that is stabilised by the movement ...

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