50 votes
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Do molecules with bridges through rings exist?

I'm not sure about the existence of molecules with bridges through rings. However, there are several publications of synthesis of molecules mimicking wheels and axles ([2]rotaxanes; The “[2]” refers ...
Mathew Mahindaratne's user avatar
30 votes

Do molecules with bridges through rings exist?

A variation on this theme is Ice VII, in which two cubic ice structures are intertwined with hydrogen bonds from each component structure passing through the hydrogen-bonded rings formed by the other ...
Oscar Lanzi's user avatar
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22 votes

Has anyone sysnthesized perfluorocubane (AKA octafluorocubane)?

[Caveat: This is not so much a question-and-answer as a desire to share Derek Lowe's article in his inimitable style. Given enough down-votes, I'll delete both Q-&-A. But enjoy the synthesis ...
DrMoishe Pippik's user avatar
20 votes
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What is the mechanism of the reaction between hexane-2,5-dione and nitrous acid?

As you may know from diazotisation reactions, $\ce{HNO2}$ is a generator of the nitrosonium cation, $\ce{NO+}$. Electrophiles like these can react with the enol tautomer of hexanedione: Following ...
orthocresol's user avatar
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19 votes
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What does washing and drying a solution mean?

This is standard for purifying substances. To wash means to add your product solution to an aqueous solution (or just water, but frequently a saturated solution) to a separatory funnel. After shaking, ...
Zhe's user avatar
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18 votes
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Mechanism for basic hydrolysis of α-chloronitrile to ketone?

Your analysis is slightly incorrect, actually. If you do a $\mathrm{S_N2}$ on the chloride, hydrolyse the nitrile, and decarboxylate, you end up with the wrong oxidation state: Instead, if you ...
orthocresol's user avatar
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18 votes
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Understanding the synthesis of twistane

The first step is a conversion of the nitrile into a carboxylic acid, in the literature Martin Olbrich, Peter Mayer, and Dirk Trauner (J. Org. Chem., 2015, 80, 2042-2055) used KOH in ethylene glycol ...
Nuclear Chemist's user avatar
18 votes
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ICHO Synthesis Problem 2018

You have asked quite a number of questions in your post so let's tackle it one by one. Why does the oxidation take place at that particular nitrogen atom? To understand this, we first need to ...
Tan Yong Boon's user avatar
16 votes
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Are there any significant uses of the compound formed by magnesium and anthracene?

It seems like an idea of using magnesium anthracene systems for the $\ce{MgH2}$ production persisted since 1980s [1] till late 2000s, when new more efficient method with better scalability for ...
andselisk's user avatar
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16 votes
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Why doesn't aromatic substitution add at multiple positions in one reaction?

The rate of Aromatic substitution depends upon the activity of the aromatic system, because when the collision happens the aromatic system has to donate electrons to an electrophile. In the example ...
Nisarg Bhavsar's user avatar
15 votes
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Which platonic solids have been built as carbon skeletons?

The previous answer and comments have already listed out the known platonic hydrocarbons, however, since the OP had expressed an interest in the synthesis of these platonic hydrocarbons in one of his ...
getafix's user avatar
  • 8,475
15 votes

What is the mechanism of the reaction between hexane-2,5-dione and nitrous acid?

Orthocresol did a great job describing how to get to the isoxazole methyl ketone. However, nitrous acid can be an oxidant. The methyl ketone in the presence of mineral acid, which you need to get the ...
user55119's user avatar
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15 votes

Why doesn't aromatic substitution add at multiple positions in one reaction?

During a electrophilic aromatic substitution, it is always possible to have multiple substitutions during one reaction. However, your example is not the ideal one for a discussion. As noted, Oscar ...
Mathew Mahindaratne's user avatar
14 votes
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What is the mechanism of azulene synthesis?

The @orthocresol link to the Zincke reaction is a good start to the mechanism. You are correct about the first step. Dimethylamine adds to the electrophilic pyridinium salt 1 as illustrated in 1 $\...
user55119's user avatar
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14 votes

What is the best way to deprotonate a methyl group?

The deprotonation of 1a has been conducted with LDA/THF and subsequently converted to the phosphonate.[1] Alternatively, bromide 3a has been prepared[2] and converted[3] to phosphonate 2a via an ...
user55119's user avatar
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13 votes

How can one synthesise a conjugated alkyne chain?

A carbenoid Fritsch-Buttenberg-Wiechell (FBW) rearrangement of a substituted dibromoolefinic precursor is used to generate a lithium acetylide, and subsequent trapping with carbon-based electrophiles ...
Waylander's user avatar
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13 votes

Does germanium(IV) chloride have to be handled under inert atmosphere?

At times like this, you always refer to the material safety data sheet (MSDS). Have a look: Upon contact with water or moist air this material reacts to release corrosive and toxic hydrogen chloride ...
Nilay Ghosh's user avatar
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12 votes
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Fluorescein synthesis

This reaction is considered a modified Friedel-crafts acylation. The reaction is formally a series of electrophilic aromatic substitutions, with hydroxyl leaving groups picking up protons (1), however ...
gannex's user avatar
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12 votes
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Synthesising Complex Aromatic Compound

An alternative approach might be something like this. The tertiary alcohol product with two identical groups suggests that a Grignard reaction with an ester might be a useful step.
bon's user avatar
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12 votes
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Kolbe Schmitt followed by methylation

Collecting my comment thoughts together, there is an early demethylation step in this synthesis. Structure 1 is the result of carboxylation while methylation provides ester N. Friedel-Crafts ...
user55119's user avatar
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12 votes
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How are organic compounds with radioactive atoms synthesized?

The current methods employed for synthesis fall into the following three categories1: Chemical synthesis Biochemical methods Isotope exchange reactions Chemical Synthesis: Most chemical syntheses ...
Aniruddha Deb's user avatar
11 votes
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How to develop a retrosynthesis plan for 2-[(E)-2-(3-bromophenyl)ethenyl]-1,3-benzoxazole?

Extempore, this should be available by the reaction of 3-bromocinnamaldehyde with 2-aminophenol. Samarium triflate as a catalyst might be a good idea. In any case, I'd start the retrosynthesis at the ...
Klaus-Dieter Warzecha's user avatar
11 votes
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N-fluorosuccinimide: any scope?

Maybe NFS doesn't work well? Bear in mind that bonds from a second-period element to fluorine are generally stronger and less labile than the corresponding bonds to heavier halogens. If that's true, ...
Oscar Lanzi's user avatar
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11 votes

Anthracine blue composition

Springmühl indeed reported Anthracene Blue (orig. "Anthracenblau" (German)) from an intermediate with brutto-formula $\ce{C14H7O3}$. It seems like this method only worked well at a lab scale....
andselisk's user avatar
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11 votes
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Why is tert-butoxide often used in elimination reactions when it is not necessary?

Several reasons: t-BuOK is especially known as a strong base, and a poor nucleophile. Its large, bulky structure causes it to perform exceptionally poorly in substitution, literally eliminating any ...
William R. Ebenezer's user avatar
11 votes
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Why benzenediazonium bromide and iodide are of little interest?

There is indeed very little to be found in the literature. A recent Russian paper (Ref.1) mentions benzenediazonium bromide as a reactant. This thesis from 1975 (Ref.2) contains a preparation of ...
Waylander's user avatar
  • 22.4k
11 votes

Choosing reaction stoichiometry in organic synthesis

The most precious component of the reaction is the starting material you made yourself so the materials used in excess are usually the bought ones, unless you are at the first step of a sequence. In ...
Waylander's user avatar
  • 22.4k
10 votes

Which platonic solids have been built as carbon skeletons?

There are the three painfully obvious platonic hydrocarbons: tetrahedrane, cubane, dodecahedrane. The latter one also exists as a fullerene, i.e. $\ce{C20}$, which is also believed to be the smallest ...
Martin - マーチン's user avatar
10 votes

Bromination of cyclohexene in presence of UV light or heat

Both products are formed although 3-bromocyclohexene is the major product. Formation of major product: 3-bromocyclohexene Under UV light, $\ce{Br2}$ undergoes homolytic splitting to generate $\ce{Br*...
DHMO's user avatar
  • 5,035
10 votes

How to convert ethanol to benzoic acid?

Here is how I would do it. Part I: Blue First, ethanol 1 is oxidised to acetaldehyde 2, which undergoes nucleophilic addition with $\ce{KCN}$ and $\ce{HCN}$ to form the hydroxynitrile 3, and finally ...
Linus Choy's user avatar

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