Questions tagged [synthesis]

Synthesis is a purposeful execution of chemical reactions to obtain the desired product. Applies to long and complex natural product syntheses as much as to short one or two-step syntheses. This also covers synthetic problem sets and retrosynthetic analyses.

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Buchwald-Hartwig coupling troubleshooting

I am conducting a synthesis using below scheme. And Below is some information about my reaction history. The basic condition is 1 eq of 1-aza-18-crown-6, 1.4 eq of 3-bromothiophene, 1 mol% of ...
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How to synthesize anhydrous zinc(II) nitrate?

I'm interested in making anhydrous zinc nitrate. I know it decomposes fairly rapidly if you heat it. It is also soluble in ethanol. Would another desiccant or a molecular sieve do the trick? Or maybe ...
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Converting benzaldehyde to benzophenone in no more than two steps

This is a question from my book, as stated in the title: How will you convert benzaldehyde to benzophenone in no more than two steps? I can do it in three steps - first using $\ce{PhMgBr}$ on ...
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Can I synthesize 4-aminophenol and/or acetic anhydride at home? [closed]

I am going to try to synthesize acetaminophen as a possible science fair project, or just for fun, but doing it with precursors to the precursors of it might be more fun for myself then just using the ...
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Reduction of unsymmetrical ketones using BINAL-H (Enantioselectivity)

I am struggling with a problem regarding the enantioselectivity of BINAL-H for quite some time now. The reaction scheme shows the reaction with (S)-BINAL-H as it is observed plus the transition state ...
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Has tellurium(II) iodide been properly characterized ever?

According to Wikipedia, tellurium tetraiodide decomposes on heating: $$\ce{TeI4 ->[\Delta] TeI2 + I2}$$ However, the reaction is somewhat wrong as according to this 2008 paper: Solid tellurium ...
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Amides from carboxylic acid and ammonia?

Would it be possible to synthesize amide by simply reacting carboxylic acid with ammonia and then driving off water at higher temperatures? Or would ammonia be also driven off in the process? Google ...
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Partial reduction of anthraquinone to anthrone using stannous chloride?

I've heard of using $\ce{SnCl2}$ in the Stephen's reaction where you reduce a nitrile down to an aldehyde. I've come across a laboratory manual that discusses using tin in the partial reduction of ...
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Does the halogenation of an alkane also produce haloalkanes of a longer chain length?

Take a typical halogenation of an alkane reaction (the bromination of methane). $$\ce{Br_2->Br· + Br· (in the presence of UV light)} $$ $$\ce{Br· + CH4->·CH3 + HBr} $$ One of the possible ...
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Can all 20 H atoms of pentagonal dodecahedrane be substituted with high yield and a wide range of substituents? What limits full substitution?

I first came across dodecahedrane in comments below What dodecahedral molecule is Linus Pauling likely holding in this photograph? Does it have 40 carbon atoms? Wikipedia's Dodecahedrane; Derivatives; ...
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Has a fully methylated pentagonal dodecahedrane been synthesized or at least attempted? If not, is there some reason it could not exist?

I first came across dodecahedrane in comments below What dodecahedral molecule is Linus Pauling likely holding in this photograph? Does it have 40 carbon atoms? Wikipedia's Dodecahedrane; Derivatives; ...
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Why is S-alanine acetylated in the synthesis of S-cathinone?

I came across a method of synthesizing enantiomerically pure S-cathinone using S-alanine which is chlorinated to the corresponding acid chloride which is used in a Friedel-Crafts acylation of benzene. ...
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Making C14 or C13 chlorobenzene site specific label

Imagine that you want to make chlorobenzene with a carbon-14 label in one site only, the only site you want it to be in is on the carbon bearing the chlorine. Can you think of a better and shorter ...
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Diels-Alder and Synthesis Problem: Confused about how to add carbon chain and double bonded oxygen

I am working on this synthesis problem. My first step was converting the dienophile given into a diene via E2 elimination. From the product given, I concluded that the dienophile will carry the double ...
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3 answers
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How to get tin(II) oxide from tin(IV) oxide? [closed]

How to get $\ce{SnO}$ from the deposited $\ce{SnO2}$? Any method is ok. If just heat the $\ce{SnO2}$, can it change to $\ce{SnO}$?
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4 answers
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Why are strong oxidizing agents "incompatible" with ferrocyanide according to SDS?

As I've mentioned in this question, I am making $\ce{Na3Fe(CN)6}$ from $\ce{Na4Fe(CN)6}$ by oxidizing the ferrocyanide using sodium permanganate. The SDS of sodium ferrocyanide as well as potassium ...
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Synthesis of sodium ferricyanide

I need to synthesize sodium ferricyanide, $\ce{Na3Fe(CN)6}$, for some benchtop experiments where I don't want any potassium ions in solution. The way I am doing that right now is oxidizing $\ce{Na4Fe(...
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Preparation of m-nitroaniline from m-dinitrobenzene [duplicate]

Consulting various Organic Chemistry resources, I have found two reactions for the purpose stated in the subject: First reaction: Second reaction: But, I cannot find the reaction mechanism by which ...
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Are there any organic compounds with three or more oxygen atoms bonded together in a straight chain?

Recently, there was a question which enquired about some oxygen rich compounds that burn themselves completely and thus not requiring any external atmospheric oxygen. The author came up with the ...
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Mechanism of this addition-elimination process

In Part 1 of the synthesis of Maoecrystal V (found on synarchive), the last step subjects a $\ce {\alpha, \beta}$-unsaturated ketone to $\ce {I2}$ and pyridine, as shown below: I am wondering what is ...
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2 votes
1 answer
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Dimerization of aniline to biphenyl

I've been looking for ways to synthesize biphenyl - $\ce{(C6H5)2}$. The Ullmann coupling is inaccessible, as bromobenzene is inaccessible in my country due to the manufacture of PCP. I had the idea to ...
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Potassium from Potassium superoxide [closed]

Is it possible to get $\ce K$ from $\ce K{O_2}$ using a synthesis reaction? If yes, can you describe it?
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What is the protocol for esterification reaction between nanocellulose and tartaric acid?

I am trying to prepare nanocellulose esters via esterification with Tartaric acid. I know that the traditional method employs a strong acid such as sulfuric acid. What would the process look like in ...
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1 answer
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Selective secondary amide/lactam hydrolysis

I am working on a synthesis for a compound (4-aminophenol with alkyl chain and lactam at carbon 2). The final step of the synthesis involves hydroylsis of the secondary amide at carbon 4. My problem ...
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2 answers
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Substitution in aryl halides

I need to propose a route for the synthesis of 2-(bromomethyl)benzonitrile from 1-bromo-2-(bromomethyl)benzene. In the attached figure, the structure of the starting compound and the species to be ...
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Accidental hydrolysis of tert-butyl chloride

Yesterday, I performed the synthesis of tert-butyl chloride from tert-butyl alcohole in my practical organic chemistry class. However, I only obtained a relatively low yield of about 30 %. Since I ...
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6 votes
1 answer
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What is the maximum amount of carbon atoms that can comprise a fullerene?

As the fullerene sum formula can be defined as $\ce{C_n}$ with $n$ being any even integer number, is there any fundamental theoretical limit as to how big $n$ can get? If there is no limit to the ...
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1 answer
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pKa of the alpha proton of an alpha amino ester [closed]

Is there a theoretical pKa value for the proton on the alpha carbon of a methylated amino acid, or just a general alpha amino methyl ester?
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Degradation of Pd catalyst in Buchwald-Hartwig amination

I am conducting Buchwald-Hartwig amination. I use $\ce{Pd_2(dba)3}$ and $\ce{P(o-tol)_3}$ as catalyst and toluene as solvent. Temperature is 100 ℃ and reaction time is 24 hours. During the reaction, ...
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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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Can amide form Schiff base?

Can amide ($\ce{RCONH2}$) form Schiff base? When I searched for it, most papers deal with aliphatic amines. Some paper conducted synthesis with amide-containing compound, but iminization occured at β-...
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Struggling to make SMCC

I have attempted to synthesize SMCC (succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate) following the lit protocol in J. Org. Chem. 2011, 76, 21, 9169–9174. Except for the scale, I followed ...
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5 votes
2 answers
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How can we synthesize this cycloester, starting with methyl 4-phenylbutanoate?

I was wondering how to realize following synthesis: I am struggling with this one; for sure, this has something to do with the benzyl position which is particularly reactive, and something ...
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2 votes
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Synthesis of allylic ether, starting with phenalene

I stumbled across a retro-synthesis question, for which I don't know the exact answer; I prepared two synthesis ways, but I don't know if they could be realized in a lab. The question is the following:...
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1 vote
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Reason for adding TFAA in this synthesis pathway?

I have included a short part from a synthetic pathway from: https://synarchive.com/syn/112 $\ce{Mg3N2}$ reacts with $\ce{MeOH}$ to liberate $\ce{NH3}$ which I believe is used in nucleophilic ...
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Reasons for scratching the wall of a flask when precipitate crystals [closed]

I heard that scratching the wall of the flask helps precipitate crystals when obtaining crystals. By scratching the wall of the flask, the crystals from it fall in the center and act as seeds to help ...
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Side-chain Oxidation vs Oxidative Cleavage

When the above compound is subjected to acidified $\ce{KMnO4}$, can both side chain oxidation and oxidative cleavage of $\ce{C=C}$ bond occur? Or will one have priority over the other?
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Method to remove impurities from acetaminophen synthesis experiment

I'd like to know about impurities from acetaminophen synthesis experiment. Are there any impurities produced by oxidation of p-aminophenol? If there is any impurity produced by oxidation of p-...
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3 votes
1 answer
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What is the maximum length of peptide which considered to be hard for synthesis by the current technology?

I am a molecular biologist and work with recombinant proteins. I am wondering what the cut point, in terms of length, is at which I should produce the peptide using heterologous expression rather than ...
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1 vote
0 answers
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Differences in activated manganese dioxide synthesis

I've looked into preparations of activated manganese dioxide for some time now, and what confused me is the contrast between the original Attenborough method and some of the alternatives. A solution ...
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Can two two-material composite precipitation methods be used to make one three-material composite?

There are many methods used in the synthesis of cellulose nanocomposites, including Fe₃O₄@Cellulose in urea, ammonia, and water solution and immersing the product in sulfuric acid, or somewhat ...
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1 answer
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Sodium acetate stoichiometry from baking soda and vinegar

I want to make sodium acetate from sodium bicarbonate and vinegar. I'm a bit stumped at calculating amounts of each reagent. I'm starting with 8% acetic acid vinegar. I was going to add, to 1 L of the ...
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7 votes
3 answers
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Choosing reaction stoichiometry in organic synthesis

Reading papers about organic synthesis, I see many cases like setting one material as 1.2 eq. I presume that reagents used more than 1 equiv are relatively inexpensive or less reactive than other ...
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Problem about TLC solvent and staining

I am conducting an organic synthesis involving 1-aza-18-crown-6-ether. I tried TLC, but they didn't work well. I have tried: (1) hexane+ethyl acetate in various ratio, (2) dichloromethane:methanol=3:1,...
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Setting up reactor in inert atmosphere

I am searching for reactor set-up that can maintain inert atmosphere, and found that many organic synthesis labs use Schlenk line. But organic synthesis is not main thing of my lab, so there is some ...
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2 votes
2 answers
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Synthesis of active chemical manganese dioxide (CMD) for primary alcohol oxidation

This paper1 uses chemical manganese dioxide (CMD) instead of activated manganese dioxide for mild alcohol oxidation. I'm looking for a route on how to synthesize active CMD. Could this work? $$\ce{...
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4 votes
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2-Iodoxybenzoic acid oxidation reaction

I was thinking about using 2-Iodoxybenzoic acid to selectively oxidize primary alcohols to aldehydes. I've found papers using various solvents like acetone/water mixture1, 2-methyl-2-propanol2, DMSO ...
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1 vote
2 answers
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How can I make cerium(IV) chloride? [closed]

How can I make CeCl4? I have some ideas but am worried I'm going to mess it up since this is the first time I've worked with lanthanides.
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3 votes
3 answers
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Decarboxylation of primary amino acids

Since primary amino acids like glycine, alanine can't be decarboxylated under oxidative conditions, what would be the best catalyst for this reaction? I was thinking about copying decarboxylases with $...
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3 votes
1 answer
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Can I synthesize potassium hydroxide from readily available materials?

Where I live, KOH is not readily available and is cost prohibitive to ship. A number of other materials are available, however. I have read similar questions and their answers here, but most are too ...
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