Questions tagged [rearrangements]
For questions about specific rearrangements within organic chemistry.
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Stereochemistry of Rearrangements of carbocations [closed]
Suppose in a carbocation ,rearrangement of methyl has to to place to a chiral carbon, forming a stabler cation in the process.But what will be the stereochemistry of the rxn? Will the chiral carbon on ...
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1
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What shold be the answer to the given reaction? [closed]
Q.75 The final product A, formed in the following reaction sequence is:
$$\ce{ Ph-CH=CH2 ->[(i) BH3 (ii) H2O2,OH- (iii) HBr][(iv) Mg, ether, then HCHO/H3O+] A }$$
Options
$\ce{Ph-CH2-CH2-CH2-OH}$
$...
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Electrolytic reduction of nitrobenzene in differing media
In my lecture notes it is given that in a weakly acidic medium, nitrobenzene on electrolytic reduction gives aniline, which makes sense to me because there is ample H+ in the medium to continue adding ...
2
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1
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Explain the mechanism of the following reaction, which involves a 1,2-alkyl migration with double inversion of configuration
I came across the following reaction, whose mechanism is said to involve a 1,2-alkyl migration with a double inversion in configuration. The reagents used were nitrous acid (generated in situ) ...
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What nucleophilic reaction takes place in case of bad leaving group as well as 1* alpha carbon?
If we add HI to a substrate Ph-C-C-OH what will be the major product and what reaction mechn. will be followed?
My attempt: as -OH is bad Leaving Group, we cannot just simply proceed with Sn2 and ...
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Does boric acid really rearrange phenols?
This reaction was on prepchem.com and I want to know whether it could work. Most of their reactions are well sourced but this is rather scant (and can't find the patent referenced).
It is possible ...
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Carbocation rearrangement in dehydration of an alcohol [closed]
In this problem, I know that initially a positive charge is formed at the carbon bearing the hydroxyl group , yielding a secondary carbocation.
But, I can't go any further with that. What kind of ring ...
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Carbocation rearrangement with ring expansion
I was solving a particular question which landed me to a position where I have to decide whether the following ring expansion would take place or not by carbocation rearrangement:
If the expansion ...
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1
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Sigmatropic Rearrangement along with oxidation [closed]
I was going through an organic chemistry book I came along this question it's solution used sigmatropic rearrangement along with oxidation in Jones reagent, how does this rearrangement work??
6
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3-Step Transformation to Humulone
I have some ideas on how this transformation may occur. We're currently studying Ch. 3 (Polar Rxn's under Acidic Conditions) from Grossman's book.
I've found some data online that shows we can perform ...
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7
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1
answer
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Reaction between 1,2-bis(buta-1,3-dien-1-yl)cyclohexan-1-ol and potassium hydride in THF
Which product is formed in the following reaction?
I am quite certain that we deal with an oxy-Cope rearrangement that works at room temperature, but I don’t know how to draw the product given the ...
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Acidification of a vicinal diol [duplicate]
The following is a question from Advanced problems in organic chemistry by MS Chouhan:
The options given are:
My initial thought was that this could be a pinacol–pinacolone rearrangement. However ...
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Mechanism of terpene alcohol rearrangement [closed]
I thought about all kinds of hydride shifts that could be possible here, but I still could not figure out how the mechanism would work.
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3
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4
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Hydride shift or Methyl shift
For the carbocation (A) given in the reaction, first we can rearrange it by ring expansion (4 to 5) then we have two choices either H-shift or methyl-shift. My teacher told me that Hydrogen is the ...
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Does the Oxy or Alkoxy Claisen Rearrangement Exist?
@Waylander's cogent Comment to the query of @Random Guy inspired me to post a problem in synthesis to test a question I have pondered for some time. The activation energy (AE) for the Cope ...
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