Questions tagged [organic-chemistry]

Use this tag for questions relating to organic molecules and their properties (structure of organic molecules, spectroscopic properties, reaction mechanisms, stereochemistry etc). DO NOT use this tag as the only tag in your question, as this tag by itself cannot appropriately classify your question. Always use this tag in addition to other more specific tags.

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Why does a dough with margarine absorb more oil than one with butter?

My family makes deep-fried cakes. Normally, we use butter in the dough and fry it in canola oil. Recently though, we tried using margarine instead of butter and the cakes absorbed much more of the ...
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Mechanism of toluene oxidation with CrO3

What is the mechanism for the following oxidation of toluene with $\ce{CrO3}$ in acetic anhydride? Use of chromic oxide ($\ce{CrO3}$): Toluene or substituted toluene is converted to benzylidene ...
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Increasing C-alkoxycarbonylation of enolates

I am working with N-tosyl-2-piperidone and attempts to use the lithium enolate of this compound to perform an nucleophilic acyl substitution reaction on an several chloroformate esters in THF has lead ...
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Reaction of alkenes (localised π bond) with nitrating mixture

The nitrating mixture for the nitration of benzene contains many strong electrophiles (e.g $\ce{H2SO4}$, $\ce{NO2+}$). All of these could, presumably, add across the π bond in a molecule containing a ...
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Is there a way to force C-protonation of an enolate?

In another question, I mentioned that O-protonation of an enolate followed by tautomerization may lead to increased amounts of the thermodynamic product over the kinetic product (when those are ...
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Is there a general term for a vertex in a skeletal formula?

When a carbon atom is single bonded to a residue, it is referred to simply as "methyl." When it is single bonded to two attachments, it is methanediyl, or methylene bridge. When it is single bonded to ...
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Formose reaction - mechanism of first step

The following image was taken from wikkipedia's article about the Formose reaction. What is the mechanism of the first step of the reaction sequence? How do the two formaldehyde molecules condense?
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Why do branched hydrocarbons burn more efficiently (complete & clean combustion)?

Branched and cycled hydrocarbons usually a higher octane number than their straight chain counterparts. This is due to a more complete and clean (no residue) combustion. In addition, there is no ...
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Transforming a cis double-bond to a trans double-bond using any mechanisms of my choice

For my final, I need to be able to a trans-double bond from a cis double bond. Here is what I drew: I essentially created a triple bond and oxidized
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Mechanism of reaction between substituted aniline and potassium thiocyanate in presence of bromine and glacial acetic acid

Im currently doing this project where in we are synthesizing 2-amino-6-substituted benzothiazole by using p-substituted aniline with potassium thiocyanate in presence of bromine and glacial acetic ...
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What prevents self-condensation in the Perkin reaction?

An acid anhydride is condensed with an aromatic aldehyde in the Perkin reaction. The latter is non-enolisable, and thus the former forms the enolate which attacks as a nucleophile. If the attack is ...
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What is the degradation mechanism of pyrrole?

A vial of pyrrole (that was occasionally exposed to air) changed its color while degrading from pale yellow to dark orange. What is the mechanism of pyrrole degradation? What are the resulting ...
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Where can I obtain research material on the synthesis of polypyrrole?

I'm studying Chemistry at A-level and a large part of the course is a researcher paper that takes most of the year. Conductive polymers interest me. I'm struggling to find any surfeited researcher on ...
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How does the Kucherov reaction work if the alkyne is aromatic?

I know how the Kucherov reaction works for aliphatic alkynes, but what if the alkyne has a phenyl attached? How will the aromatic ring affect the reaction of alkynes with water?
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Regioselectivity in Ziegler–Natta polymerisation of α-olefins

Why does the Ziegler–Natta polymerization display the regioselectivity shown in the image? Internal nucleophiles (coordinated to the metal) should attack the alkene on the less substituted end, like ...
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964 views

How to dissolve a strong resin in difficult situation?

The resin is made up from two components: Component A: silicic acid, sodium salt (less than 10% sodium silicate) Component B: Diphenylmethane-4,4'-Diisocyanate, isomers and homologs (MDI,Polymer-MDI)...
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Catalyzation in Carbonic Acid

I understand the basics of carbonic acid + 1 kcal breaking down into water and carbon dioxide. However, my professor wants me to draw an energy map showing the catalyst in human blood reducing the ...
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Which has greater +R strength - toluene or anisole?

I read that resonance in toluene is initiated with the help of hyper-conjugation. Also hyper-conjugation is weaker than resonance/mesomeric effect. But, in toluene, its resonance is taking place with ...
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Burning formaldehyde gas for disposal?

Since formaldehyde gas is flammable, is there a safe way to burn it, and can this be done to dispose of the gas or neutralize its harmful effects (tear production, respiratory problems, etc.)? This ...
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Combustion of halo-organic compound

My question is based on the Preparatory Problem Set for the 47th IChO Problem 26 - Holy War against Four Horsemen of the Apocalypse (it is on page 36). It is written that cooling of Y combustion ...
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257 views

When is coal considered to be oxidized?

What amount of oxidization is required to refer to some coal as oxidized coal, and how long does it take for coal to become oxidized in temperatures of roughly 25-40°C? I have found a research ...
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239 views

Why does the trimethylammonium cation have a larger -I effect than the ammonium cation?

Why does $\ce{N(CH_3)_3^+}$ have a larger $-I$ effect than $\ce{NH_3^+}$? Since the methyl group is good at donating electrons it would stabilize the charge on nitrogen atom, decreasing its ...
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Bromination of alkenes

In regard to the mechanism of halogen addition, consider the situation when we add a halogen (say, bromine) to an unsymmetrical alkene about the double bond (say, propene) in the presence of $\ce{CCl4}...
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Protonation of Carbonyl oxygen in Fischer Esterification

In the Fischer Esterification, why is it the acid's carbonyl oxygen getting protonated and not the hydroxyl oxygen? This protonation occurs in Step 1 of the mechanism below. I read in some textbooks ...
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Order of reactivity of carbonyl compounds towards nucleophilic addition

Arrange the following according to reactivity towards nucleophilic addition reaction: I have already seen this post regarding the reactivity. It helped me to some extent. $\ce{Cl}$ increases the ...
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1answer
134 views

Regioselectivity in Diels–Alder reaction between 2-nitrobuta-1,3-diene and acrylonitrile

Since $\ce{-CN}$ shows strong −I effect, there will be δ+ charge on the carbon adjacent to it. Similarly, $\ce{-NO2}$ shows strong −I and –M effects. So, I proposed that π-electrons are being donated ...
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Reaction of 1,3-dibromobutane with zinc dust upon heating

I've studied that when 1,3-dibromopropane (or in general any halogen, not just bromine) is heated with Zn dust, the electrons produced cause the halogens to break away homolytically and two free ...
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Geometry of a free radical at the bridgehead carbon

With reference to J. Am. Chem. Soc. 1968, 90 (19), 5266–5267, they state: The most favorable geometry of aliphatic free radicals remains an unsolved problem, since existing data are consistent with a ...
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Three-membered ring pathway bromination of alkene

Bromination of alkene occurs by the mechanism as shown (source: Master Organic Chemistry — Bromination of Alkenes: The Mechanism): Here $\ce{Br^-}$ attacks bromonium ion from a side which is more ...
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164 views

How to name this compound (Carboxylic acid+amide)?

It's the first one, I know that this solution is a mistake, but what is the true one? can we just use 5-amido?
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What drives the 'internal return' in SNi?

I just learnt that alcohols can undergo $\mathrm{S_N}i$ with $\ce{SOCl2}$ (without pyridine) to achieve retention: However, what I really do not understand is the 'internal return' step (forming '...
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Do tert-butylcyclohexanes with a leaving group locked in the equatorial position undergo E1?

Background Elimination of 1-bromo-tert-butylcyclohexane is a prototypical example of how important the anti periplanar relationship is for E2. From Organic Chemistry: Structure, Mechanism, Synthesis ...
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Why is this compound named (Z)-but-2-ene-1,1-diyldibenzene and not (Z)-1,1-diphenylbut-2-ene

A recent answer of mine involved the synthesis of the following compound: I initially assumed the name of this compound to be (Z)-1,1-diphenylbut-2-ene as the butene is the main chain, with two ...
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Spraying difluoroethane into an enclosed space

I'm working on developing physics lab activities that my students can do at home during the covid quarantines. For an activity involving waves and thermodynamics, I came up with an experiment at home ...
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Covering conformers in a molecular modelling; consider them as a static entity or work with modelling shifts as well?

I am currently working with a molecular docking project, examining potential affinities of a solvent on a protein in an assay to evaluate potential error margin. The solvent is cyclohexanol (referred ...
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How can should one separate and purify benzophenone from salicylic acid?

I am working with two solids and I know that they are benzophenone (s)(ketone) and salicylic acid (s) (carboxylic acid). I am curious to know what is/are the best method of extraction and ...
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Decarboxylation of THCA during CO2 Extraction of Cannabis

We have a strange problem. We are performing CO2 extraction on cannabis and we are seeing considerable decarboxylation of THCA to THC. We have high quality temperature sensors at the heat exchangers, ...
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Condensation reaction between catechol and acetone

I was thinking of ways to synthesize 2,2-bis(dihydroxyphenyl) propane and I thought it could be made by a condensation reaction between dihydroxybenzene (catechol) and acetone in strongly acidic ...
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MO theory used in organic chemistry textbook

I'm currently using Clayden's organic chemistry textbook, and when he shows MO diagrams of functional groups of organic molecules, he sometimes treated it as if only orbitals on two atoms are ...
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Reaction mechanism of thiol to disulfide oxidation under basic conditions?

I have been looking everywhere for an explanation to a reaction mechanism concerning the oxidation of DTT (or just thiols to disulfides in general) using oxygen as the oxidant. I'm aware that ...
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Hofmann and Zaitsev products

It is known that, with regard to the elimination reaction, the Zaitsev product is the thermodynamically more stable product, which is also often the more substituted alkene while the Hofmann product ...
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CuAAC “Click” reaction giving inconsistent results

I apologize in advance for the large amount of text and thank all those who take the time to read it. The "Click" reaction after Fokin and Sharpless is known to achieve high yields without long ...
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Shi Epoxidation Issues - Any help would be appreciated

As part of my PhD project, I'm currently looking into running a Shi Epoxidation reaction. The first step is to reproduce the current literature on this reaction by using trans-stilbene as my substrate....
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What's the mechanism behind mineral oil loosening cyanoacrylate bonds?

Per industry literature I found that mineral oil is used to loosen out "super glue" and aid in removal from skin. I am exploring the chemistry of this loosening and I am intrigued. Please help me find ...
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Mechanism of DPD (N,N-diethyl-p-phenylenediamine) reaction with free chlorine

NOTE: As I've been finding new informations about the question, I've been editing the question to keep it up to date. If some comment doesn't make sense just check the Edit History. DPD (N,N-diethyl-...
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An unknown glassware piece from our cupboard

We have multiple of these. It is a small glass funnel with splits into 3 spouts from it. Now, we are thinking it might be similar to a cow receiver, however, I have never seen one this small or ...
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Unknown possibly handmade glassware- description in information below

Okay, Another random item from the cupboard (unknown users or discipline of life sciences unknown) could be anything up to 40 years old.... This appears to be a 2 neck quickfit adapter (B19 and B14) ...
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Reagents for synthesis of ethyl 2-(2,3-dihydrobenzofuran-2-yl)acetate from naphthalen-1(4H)-one

The following conversion can be performed in a few steps. Show key intermediates and reagents (detailed mechanisms are not required). So I've been looking at this for a while and I can't seem ...
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An unconventional decarboxylation to form bullatenone

I recently had an assessment which required me to draw the mechanism of decarboxylation of a $\beta$-ketoacid. However, it is slightly peculiar because there is the presence of $\alpha$, $\beta$-...
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Nucleophilic nature of ions

Consider the following species: $$ \underset{(\text{A})}{\ce{\overset{⊖}{O}H}} \quad \underset{(\text{B})}{\ce{CH3-\overset{⊖}{O}}} \quad \underset{(\text{C})}{\ce{\overset{⊖}{C}H3}} \quad \...

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