Skip to main content

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.

0 votes
0 answers
24 views

Bromination with NBS and AIBN

I reacted 3-pyridylacetic acid (6 fluoro) with NBS and AIBN in CCl4. I refluxed the reaction mixture for 4 hours at 80 degrees. No reaction occurred, and the starting material remained (based on TLC ...
Ella's user avatar
  • 47
2 votes
0 answers
57 views

Clean *di* protection of phosphonic acid dichloride with a suitable protection group with clean deprotection

For some time I am struggling with a tricky synthesis problem in my pHD. I think I came closer now, but I still need a link in the chain to make my idea work. The principle goal here is access a free ...
raptorlane's user avatar
9 votes
3 answers
551 views

Synthesis of racemic nicotine

In my advanced organic chemistry course, we were asked to fill the following scheme for the synthesis of racemic nicotine, starting with ethyl nicotinate: Exercise 6: Complete the following scheme ...
Mäßige's user avatar
  • 383
1 vote
0 answers
28 views

How to avoid side reactions when making boronic esters (Homocoupling, Hydrogen specie)?

I have been working with suzuki couplings using substituted naphtalenes (typically 2-bromo-7-R-naphtalene) for a while now, and making the boronic specie is always a pain. I can't make the boronic ...
The Red Man Jolan Bonelli's user avatar
3 votes
1 answer
180 views

Will a nitro aryl resist an halogen exchange using nBuLi?

I would like to boronate 2-bromo-6-nitro-naphtalene using nBuLi and quenching with 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. Since there is no alpha proton to the nitro, and that the nitro ...
The Red Man Jolan Bonelli's user avatar
1 vote
0 answers
31 views

After adding the electrophile (BOMe3) in an halogen exchange (nBuLi) reaction, why do we leave the reaction stir overnight?

Very basic question. In all the procedures for halogen exchange reactions reported using boronic compounds, the reaction is left to run ON at room temperature after addition of the boronic specie. In ...
The Red Man Jolan Bonelli's user avatar
2 votes
1 answer
60 views

(Di)chlorination of phosphonic acid ester

What is the best way to do this reaction to form the dichloride as an reactive intermediate when the substituent R is acid sensitive? In the literature the reaction is either performed with PCl5, a ...
raptorlane's user avatar
4 votes
1 answer
107 views

Compatibility of DCM/CCl3 with sodium hydride

In our undergraduate studies we were told that chlorinated solvents should not get in contact with alkaline elements like sodium, potassium etc., due to the violent reaction that will form the ...
raptorlane's user avatar
1 vote
1 answer
92 views

Are there methods of synthesizing rubber from plant materials?

First and foremost, I am not talking about natural rubber. I am asking if there are any industrially used methods of synthesizing rubber from agricultural products as opposed to synthesis of rubber ...
EMS's user avatar
  • 113
5 votes
2 answers
131 views

Synthesis of (S)-2-hydroxy-4-oxohex-5-enal

I am currently working on a total synthesis strategy, but I was told that a key step in my total synthesis probably wouldn't work, so now I am trying to figure out a way around it. The compound that I ...
Noor van den Berg's user avatar
1 vote
0 answers
56 views

Quenching reagents for specific reaction

A reaction general procedure is given as follows: A mixture of 2-fluoro-5-iodo pyridine $(\pu{1.0 mmol})$, methyl acetoacetate $(\pu{3.0 mmol})$, $\ce{CuI}$ $(\pu{10 mol\%})$, $\ce{K3PO4}$ $(\pu{3.0 ...
Ella's user avatar
  • 47
1 vote
0 answers
34 views

Synthesis of 1-phenyl-2-buten-1-one using an aldol condensation

I asked my students to suggest a route of synthesis for 1-phenyl-2-buten-1-one [1], using a Claisen or aldol condensation. One student had the idea of forming the aromatic ring as part of the reaction,...
Karsten's user avatar
  • 41.2k
2 votes
0 answers
31 views

What is the purpose of chloromercuration of HgOAc group?

In some reactions using $\ce{Hg(OAc)_2}$, I saw some cases that convert $\ce{-HgOAc}$ group into $\ce{-HgCl}$ group by adding $\ce{NaCl}$. Below is one example, the synthesis of (+)-preussin. Mercury(...
Krang Lee's user avatar
  • 1,101
0 votes
0 answers
33 views

Synthesis of polypropylene

So, I have two questions regarding the synthesis of polypropylene: I have tried looking everywhere but couldn't find a detailed mechanism for the termination step of the synthesis of polypropylene (...
Guy Weizman's user avatar
5 votes
2 answers
197 views

Synthesizing Cyclotetrazane from Hydrazine and Diazene?

Could cyclotetrazane — a compound with nitrogen atoms arranged in a square configuration — be synthesized? A hydrogen atom would be bonded to each vertex (nitrogen atom): Could cyclotetrazane be made ...
user avatar
2 votes
0 answers
50 views

Palladium coupling reactions and purification

I tried to synthesize 2-(6-fluoropyridin-3-yl) acetic acid from 5-(Chloromethyl)-2-fluoropyridine using Pd(OAc)2/PPh3 catalyst,Na2CO3 and DCC. I eluted my product on TLC with Ethyl acetate/hexane/...
Ella's user avatar
  • 47
2 votes
0 answers
35 views

Electrophilic fluorination power: selectfluor vs NFSI

I want to fluorinate the methylene hydrogens between an aryl group and a phosponate ester. The reaction is similar (not identical) to this one: For some reason on the literature people are using very ...
raptorlane's user avatar
2 votes
0 answers
71 views

Could a de-commissioned synthetic ammonia plant be adapted for use in removing CO2 from the atmosphere (DAC)?

I was prompted to ask this question by viewing a disused $\ce{NH3}$ plant in the harbour near where I live. Like many it functioned using a methane feedstock from a natural gas find off the coast. I ...
RetroFan's user avatar
4 votes
0 answers
100 views

With two reagents common on Mars, fluorite and CO2, how would I produce carbon tetrafluoride?

The hypothetical terraforming of Mars would require the heating of the atmosphere. A commonly suggested method is the in-situ production of fluorocarbons, powerful greenhouse gases. For example, ...
Galerita's user avatar
  • 141
2 votes
0 answers
37 views

Synthesize pivaloyloxymethyl ester, but with a substrate that is a terrible nucleophile

I want to synthesize an pivaloyloxymethyl ester from a fluorophosphonic acid. The idea is, to make a compound cell permeable that than be cleaved in the cell by enzymes. Apparently, the acid is a very ...
raptorlane's user avatar
4 votes
0 answers
50 views

Why cool a reaction down when adding reagents if you're only going to reflux subsequently?

I've seen several procedures using thionyl chloride (SOCl2) to make an ester, where the first step is to add the thionyl chloride to the reagent/solvent on ice or subzero temperature, followed ...
sat0ri's user avatar
  • 161
1 vote
0 answers
32 views

Why does hydrogen peroxide decompose during the oxidation of an aryl amine to and nitroarene (rt) and what are the possible overoxidation products?

Small scale: I attempted the oxidation of an aryl amine (2-amino-6-bromonaphtalene) to the nitroarene using hydrogen peroxide (ArNH2, H2O2, MeCN (15 mL as solvent). After trying it on small scale (0.1 ...
The Red Man Jolan Bonelli's user avatar
3 votes
0 answers
50 views

What is the difference in reactivity between the various borates (trimethyl, triethyl, triisopropyl borate) to form boronic acids?

For the transformation of 1,3-dibromobenzene to bromobenzene boronic acid, different groups use different boration reagents namely trimethylborate, triethyborate and triisopropylborate). The reaction ...
The Red Man Jolan Bonelli's user avatar
0 votes
0 answers
39 views

Need Suggestion for Picking the Right Solvent for Column Chromatography

I've completed my reactions, and based on the stoichiometry and TLC analysis, I think my mixture should contain 3-4 compounds: Ethyl gallate (my product) Gallic acid (the reagent/starting material) ...
Jonathan's user avatar
  • 155
4 votes
0 answers
273 views

Exchange of Fluorine to Oxygen for Fluorophosphonic acid by silylating agents or other methods?

[Warning, long post!] Dear all, I am confronted with a seemingly easy transformation. I want to remove a fluorine atom at a fluor phosphonic acid salt. The usual method to achieve this is the basic ...
raptorlane's user avatar
1 vote
1 answer
125 views

How does the following cyclization reaction work?

The following is a reaction from a school provided lab manual. However, I am unable to find anything similar to the cyclization reaction taking place. All of the reactions I have found online make use ...
Marethyu's user avatar
2 votes
0 answers
32 views

TMSBr and 2,4,6 Collidin in Acetonitrile leads to white precipitate

I want to hydrolyse a phosphonic acid ester with TMSBr. I think this reaction works only with the addition of base. Without base, the product in my specific case is prone to deterioation due to acid ...
raptorlane's user avatar
2 votes
0 answers
41 views

What is this gel byproduct of acetylsalicylic acid recrystallization?

I did a very simple acetylsalicylic acid synthesis from salicylic acid and acetic anhydride (with phosphoric acid as a catalyst). After rinsing, filtering and drying the product I dissolved it in ...
Thomas's user avatar
  • 31
2 votes
0 answers
151 views

Removing DCC and its by-product from Steglich Esterfication

In my small research, I want to synthesize 3 alkyl gallates (ethyl gallate, butyl gallate, and hexyl gallate), and here's my overall reaction using Steglich esterification): However, from reading ...
Jonathan's user avatar
  • 155
7 votes
2 answers
642 views

Question about the differences of white and grey NaH properties

We are having some problems with the next reaction in our lab. As you can see, is the sulfonylation of an indole in which we use NaH (60% dispersion in mineral oil) as a base. This reaction goes with ...
Alicia's user avatar
  • 81
4 votes
0 answers
114 views

Hydrolyse a fluorophosphonic compound / Which protective group strategy can I use for phosphonate esters to access the free acid after a reaction?

I have a synthetic problem in my PhD thesis, in which I synthesize a phosphonate ester. To be more precise, it is a phosphonofluoridic compound. In my specific case, the fluorine attached to the ...
raptorlane's user avatar
0 votes
0 answers
78 views

Steglich Esterification in Alkyl Gallates

Based on my research (reading some articles), some alkyl gallate syntheses used Steglich esterification instead of the usual esterification (Fischer esterification). The reason why Steglich ...
Jonathan's user avatar
  • 155
2 votes
2 answers
257 views

Should I remove inhibitor from methyl acrylate?

I need to run multiple aza-Michael additions of methyl acrylate with various amines (dimethylamine, benzylamine, phenylethylamine, aniline, etc.) in order to get the bis-ester. I was wondering if the ...
Matt's user avatar
  • 21
0 votes
0 answers
39 views

Breakdown of addition polymers

We know that condensation polymers can be broken down by hydrolysis with the elimination of small water molecules. Then what about addition polymers? How can they be broken down into their monomers? I ...
Freeby Freeby's user avatar
-3 votes
1 answer
75 views

Synthesizing "Methyl 2-(2-oxopyrrolidin-1-yl)-2-phenylacetate" [closed]

I am a chemistry student, here I mapped out the steps one might take to synthesize Methyl2-(2-oxopyrrolidin-1-yl)-2-phenylacetate, a piracetam dirivitive. Please add any steps I might be missing and ...
Tom's user avatar
  • 1
0 votes
0 answers
50 views

Advise on performance vs cost of the Berkland-Eyde Process for direct synthesis of Nitric Acid from atrmospheric air

I am new to chemistry, having gone down an electronics route in my career, so I decided to pick up where my 'O' levels ended (many years ago) and make a better understanding of the topic a sort of ...
Jay M's user avatar
  • 101
0 votes
0 answers
54 views

Methanisation in the Haber Porcess

I've been reading up on the Haber process lately. In one such industrial case of ammonia synthesis, hydrogen is created through steam reforming, which creates some carbon monoxide. As the reaction ...
Jay Chen's user avatar
2 votes
0 answers
82 views

What is the product and mechanism of reducing a cyclohexanone derrivative with LAH?

I've been trying to figure out the product and mechanism of the reaction pictured below for a while now: I'm fairly sure that the first step is the reduction of the ketone by LAH, which results in a ...
HWABAG's user avatar
  • 29
3 votes
0 answers
119 views

Hydrolyse Phosphonate diester to free phosphonic acid under relatively mild conditions?

I want to hydrolyse a phosphonic acid diethylester to the corresponding free phosphonic acid. In the literature, it is described, that usually strongly basic or acidic conditions are utilized to ...
raptorlane's user avatar
1 vote
0 answers
149 views

Why did this synthesis of Aspirin fail?

I tried to synthesize acetylsalicylic acid(aspirin) by the method below. However, I definitely failed and got something unknown. The method used was: Add 2.5 g of salicylic acid(about 2494 mg), 3.0 ...
user139437's user avatar
-3 votes
1 answer
200 views

Production of sulphuric acid

To my knowledge, sulphuric acid is produced by complex industrial processes like contact process. The following structure shows a sulphate ion. I wonder why sulphuric acid cannot be produced through ...
Freeby Freeby's user avatar
2 votes
0 answers
89 views

Reduction of benzylic alcohol and halide using H2 and Pd

I am studying drug synthesis, and I found some examples that uses $\ce{H_2}$ and Pd/C or Pd/$\ce{BaSO_4}$ as catalytic hydrogenation reagents for reduction of alcohol or halide in benzylic position. ...
Krang Lee's user avatar
  • 1,101
2 votes
0 answers
50 views

Degradation of 4-MeO-Tetrahydrocarbazole

I recently synthesized 4-Methoxy-Tetrahydroxarbazole from 4-MeO-Phenylhydrazine and Cyclohexanone. The product had a off-white color directly after synthesis but was brown after standing over night at ...
arausch's user avatar
  • 31
1 vote
0 answers
59 views

Synthesis of 1-ethylcyclohexane-1,2-diol from cyclohexylethene

Here's my synthesis: HBr NaEtO OsO4/NMO But the problem is that for step 2, there are 3 possible alkene locations, with all of them having 3 substituents, so I would have all 3 forming (although 2 ...
Toast's user avatar
  • 11
0 votes
0 answers
72 views

Find the missing chemical structures in the reaction sequence

I came across the following question, where a set of reagents are used, starting from a carbohydrate derivative. I understand that this is some total synthesis reaction, but I cannot find which one. ...
Cyclopropanol's user avatar
5 votes
1 answer
267 views

Selective formation of enolates

I saw the following reaction on Modern methods of Organic Synthesis by Carruthers. The reaction is about the selective alkylation of trimethylsilyl enolates, and is shown below. However, I have some ...
Cyclopropanol's user avatar
1 vote
0 answers
63 views

Amidine synthesis from nitrile and dimethylamine using n-Buli as a base

I am making LiNMe2 using n-Buli (5.5 equiv.) and dimethylamine (5.0 equiv), -15 ºC, dry THF and under nitrogen atmosphere. I have been doing the reaction and I can observe conversion of starting ...
Bree's user avatar
  • 11
-1 votes
3 answers
123 views

Can any compound form into an amorphous solid?

I am curious whether it is possible or not to make any solution of a specific compound into a crystal lattice or into an amorphous solid? I know that crystals form under specific conditions but seem ...
Brian Blumberg's user avatar
1 vote
0 answers
56 views

TMSiBr and Oxalylchloride for ester cleavage

I am wondering what is the advantage of using TMSiBr do perform an ester cleavage in comparison to perform chlorination first for example with oxalylchloride or thionylchloride and than add water?
raptorlane's user avatar
1 vote
0 answers
45 views

Esterification of phosphonic acid chloride is working with isoprenol but not with prenol

I am performing an esterfication reaction between an activated phosphonic acid (chloride) and a series of alcohols. Until now, I was not able to make the reaction work with prenol, while isoprenol is ...
raptorlane's user avatar

15 30 50 per page
1
2 3 4 5
17