Question & Answer Session:~ 
  
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Question:-) When this derivative of cholesterol under treatment with hydroxylamine hydrochloride and followed by para toluene suphonyl chloride in presence of pyridine ,after heating with water, then finally it gives a product, what will be the actual product in given options. 

Answer:-) options:- (a)

-----: Reaction Mechanism :----

Solution:-  First of all the hydroxylamine it will attack on the more electropositive centre on the starting material (1). And after charge neutralization it will gives an  ammonium hydroxide (2). After removal of water molecule, it gives an oxime (3). 

  And  the next reagents PTS-Cl in presence of pyridine. After formation of oxime (3), it can attack on the solid para toluene suphonyl chloride center and chloride ion remove as a leaving group. And pyridine can takes proton from oxime to give an  system (4). After the addition of OTs, it becomes more unstable due to OTs is A very good leaving group. Here, in structure- 4, lone pair on N- atom falls here and valency of this C- atom is increases, for this reason one of the group will migrates, but the question is which group will migrates ? The more priority group i.e., this whole group (four rings) will migrates to N- atom and -OTs group removed from this system to give an isolated highly reactive species (5). So here rearrangement can take place.

   And finally heating with water to give structure- (6). After tautomerism it will gives amide like system and that is the actual product, i.e., structure-7 is the product. So the options- (a) is the correct answer. 

At a glance:-

   

  Hydroxylamine :-  Hydroxylamine is an inorganic compound with the formula NH₂OH. The pure material is a white, unstable crystalline, hygroscopic compound. However, hydroxylamine is almost always provided and used as an aqueous solution. It is used to prepare oximes, an important functional group. 

      Para toluene suphonyl chloride:-  4-Toluenesulfonyl chloride is an organic compound having the formula CH₃C₆H₄SO₂Cl. This white, malodorous solid is a reagent widely used in organic synthesis. Abbreviated TsCl or TosCl, it is a derivative of toluene and contains a sulfonyl chloride functional group.

1. Pure Alcohol and Lithium Aluminium Hydride 

The solid is dangerously reactive toward water, releasing gaseous hydrogen (H₂).

Note:- Both Aluminium Hydride and Borohydride reacts with protic solvents such as water and ethanol.  Lithium Aluminium reacts violently with water to form hydrogen gas, which may burn explosively because of the heat generated in the reaction. Therefore Lithium Aluminium Hydride can only be used in aprotic solvents such as diethyl ether.

Lithium Aluminium Hydride :- 
Lithium Aluminium hydride, commonly known as LAH, is an inorganic compound with the chemical formula LiAlH4.
      It was discovered by Finholt, Bond and Schlesinger in 1947. The compound is used as a reducing agent in Organic synthesis. Actually, it is used especially for the reduction of esters, carboxylic acids, and amides.

Preparation of LiAlH4:- 
Lithium Aluminium Hydride is obtained by the reaction of lithium Hydride and  Aluminium Chloride in presence of dry ether. By this reaction 97% of LiAlH4 is obtained.
      Chemical properties:--- it reacts violently with water or ethanol to release hydrogen gas (H2).

Alcohol in living being: Toxicity:-
     Fuel grade ethanol may contain dangerous impurities and should never be consumed. Ethanol is the alcohol in alcohol beverages, many times it just called "alcohol". However, it is toxic to drink. And methanol sometimes called “wood alcohol”, it is also highly toxic.

Identification of an iridium-containing compound with a formal oxidation state of +9 :--

  

   [IrO4]+  , i.e., The valence electron configuration of iridium in IrO4 is 5d1, with a formal oxidation state of +8. Removal of the remaining d electron from IrO4 would lead to the iridium tetroxide cation ([IrO4]+), which was recently predicted to be stable and in which iridium is in a formal oxidation state of +9 .  

Guanjun Wang, Mingfei  Zhou  &  Sebastian Riedel 

v Nature 514, pages475–477 (23 October 2014) 

  Full text at journal site:- Click here 

At a glance :-- 
     One of the most important classifications in chemistry and within the periodic table is the concepts of formal oxidation States. The preparation and characterization of chemical compounds containing element with unusal oxidation States is of the great interest to Chemists, They use their Chemist Thinking Power. The highest experimentally known formal oxidation state of any Chemical is at present +8. Although higher oxidation States have been postulated. Some compounds with oxidation state +8 include several Xenon compounds (i.e., XeO4 and XeO3F2) and mostly common species RuO4 and OsO4 are also familiar to this category.
      Iridium, which has 9 valence electrons, is predicted to have the greatest chance of being oxidized beyond the +8 oxidation state. In recent matrix-isolation experiments, the IrO4 molecule was characterized as an isolated molecule in rare-gas matrices. The valence electron configuration of iridium is IrO4 is 5d¹, with a formal oxidation State of +8. Removal of the remaining d electron from IrO4 would lead to the iridium tetroxide cation, IrO4+, which was recently predicted to be stable. And in which iridium is in a formal oxidation state of 9. There has been some speculation about the formation of [IrO4]+ species. But these experimental observation have not been structurally confirmed.
       Here we report the formation of [IrO4]+ and it's identification by infrared photo dissociation spectroscopy. Quantum Chemical calculation were carried out at the highest level of theory that is available today. And the predicted Iridium tetroxide cation, with a Tetrahedral symmetrical structure and a d° electron configuration, is the most stable of all possible [IrO4]+ isomers.

Moritz Malischewski
 & Konrad Seppelt

Carbon seen bonding with six other atoms for the first time :-

Angenwandte Chemie, 2017   

For more information, 👉 Click here 

[ When hexamethylbenzene loses two electrons, it rearranges from a flat hexagonal ring into the five-sided pyramid shown here. The carbon atom on top of the pyramid bonds to six other carbon atoms as opposed to the usual four. ] 

    Chemists confirm links to six other atoms in unusual molecule.

      In the 1970s, another group of researchers from Germany made some intriguing observations about “hexamethylbenzene” which can exist in a stable configuration of six carbon atoms arranged in a hexagonal ring flag. 

       Moritz Malischewski and colleagues from the “Free University of Berlin” decided to sweep the dust off old paper and try it out. It was a little bit difficult at first because the original paper was poor on details but the researchers eventually managed to make the charged hexamethylbenzene molecule.

   

      After the molecule was crystalized, a three days mentional map of the Crystal's structure was made by using X-rays. Strikingly, the experiment proved that when hexamethylbenzene lost two electrons. It recorded that itself in the six carbon bond configuration. Specially, one carbon atom jumped out of the flag hexagonal and eventually turning the structure into a five -sided carbon pyramid. The carbon right a top to the pyramid was bonded to six other carbon atoms, five in the ring and one above. 

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Overall description:-
 In this fifth edition of Jack Jie Li's Name Reaction, the author has added twenty seven new name reaction to reflect the recent advances in Organic chemistry. As in previous editions, each reaction is delineated by its detailed stae by step, electron pushing mechanism and supplemented with the original and the latest references, especially from review articles. Now with addition of many synthetic applications, this book is not only an indispensable resource for advanced undergraduate and graduate students. But it is also a good reference books for all Organic chemists in both industry and academia.

           The book on name reaction in Organic Chemistry, name reaction, a collection of detailed reaction mechanism and synthetic applications focuses on the reaction mechanisms. 

        

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Simmons Smith Reaction:-
          It is named after Howard Ensign Simmons, Jr. and Ronald D. Smith.

The Simmons–Smith reaction is an organic cheletropic reaction involving an organozinc carbenoid that reacts with an alkene (or alkyne) to form a cyclopropane.

It uses a methylene free radical intermediate that is delivered to both carbons of the alkene simultaneously, therefore the configuration of the double bond is preserved in the product and the reaction is stereospecific.The Simmons–Smith reaction is generally subject to steric effects, and thus cyclopropanation usually takes place on the less hindered face.

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Kolbe-Schmitt Reaction. A base-promoted carboxylation of phenols that allows the synthesis of salicylic acid derivatives. 

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      The Kolbe–Schmitt reaction or Kolbe process is a carboxylation chemical reaction that proceeds by heating sodium phenoxide with carbon dioxide under pressure, then treating the product with sulfuric acid. The final product is an aromatic hydroxy acid which is also known as salicylic acid.

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  The Gattermann–Koch reaction, named after the German chemists Ludwig Gattermann and julius Arnold koch  is a variant of the Gattermann reaction in which carbon monoxide (CO) is used instead of hydrogen cyanide.

Unlike the Gattermann reaction, this reaction is not applicable to phenol and phenol ether substrates. Additionally, when zinc chloride is used as the catalyst, the presence of traces of copper(1) chloride co-catalyst is often necessary. 

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    The Gattermann reaction, also known as the Gattermann formylation and the Gattermann salicylaldehyde synthesis, is a chemical reaction in which aromatic compounds are formylated by a mixture of hydrogen cyanide (HCN) and hydrogen chloride (HCl) in the presence of a Lewis acid catalyst such as AlCl3. 

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      It is named for the German chemist Ludwig Gattermann  and is similar to the Friedel-Crafts reaction. 

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  The Bucherer reaction in Organic Chemistry is the reversible conversion of a naphthol to a naphthylamine in the presence of ammonia  and sodium bisulfite.

    The reaction is widely used in the synthesis of dye precursors. 

   The French chemist Robert Lepetit was the first to discover the reaction in 1898. The German chemist Hans Theodor Bucherer (1869–1949) discovered (independent from Lepetit) its reversibility and its potential especially in industrial chemistry.

     Bucherer published his results in 1904 and his name is connected to this reaction. The Organic reaction  also goes by the name Bucherer-Lepetit reaction.

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    The Gabriel synthesis is a substitution type Chemical reaction that transforms primary alkyl halides  into primary amines. Traditionally, the reaction uses potassium phthalimide.

  

Gabriel phthalimide synthesis

  The reaction is named after the German chemist Siegmund Gabriel.

Potassium Phthalimide:----
     Potassium Phthalimide is a chemical compound of formula C₈H₄KNO₂. It is the potassium salt of Phthalimide, and usually presents as fluffy, very pale yellow cryslals. It can be prepared by adding a hot solution of Phthalimide in ethanol to a solution of potassium hydroxide in ethanol; the desired product precipitates.

Synthesis of primary amine,
JACS, 1926