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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Stability of extended enolates

I'd expect an extended enolate to be more stable than a normal enolate, when both can form, but my textbook suggests otherwise. What is the stability of an extended enolate compared with a normal ...
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Platt's Notation/Nomenclature for transitions

How do you read Platt's Notation / Nomenclature? Where can I learn this? Some examples where I've seen this mentioned: In Platt's notation the transitions are designated as $\ce{A -> B}$ and $\ce{...
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Series of reactions

The compound given above is subjected to the following reaction (in that order): $\ce{t-BuOK}$; $\ce{CHCl3}$ and $\ce{CH3ONa}$; $\ce{H3O+}$ and heat. Find out the final ...
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Why is enol content higher in non-polar solvents?

Apparently, for keto-enol tautomerism, the enol content of a given carbonyl compound increases when in a non-polar solvent. What is the reason for this?
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Nomenclature for an alkane substituted with a branched alkyl group

Consider, for example: From what I've learned in chemistry class, this molecule would be unofficially named 3-isopropylpentane. What would the official IUPAC name for this molecule be? And what's ...
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Why does the keto tautomer of guanine have lower energy?

Looking at the keto and enol forms of guanine, it would seem as if the enol form is more stable, due to the fact that aromaticity is established with the enol form. However, according to a question on ...
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Why is it easier to add bromine to styrene than cinnamic acid?

Why is it easy to add bromine to styrene and why is it so difficult to add bromine to cinnamic acid? It is obvious that the $\ce{COOH}$ group of cinnamic acid affects the reaction quite a lot, but I ...
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How to theoretically predict thermodynamic stability?

Let's say we have $\ce{CH3-NH2}$ undergoing Hoffman's exhaustive methylation with $\ce{CH3-Cl}$. In which case side reactions such as $\ce{CH3-NH2 + CH3-NH2 -> CH3NHCH3 + NH3}$ would also occur. ...
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Selective sorption of toxins by polymethylsiloxane polyhydrate

Polymethylsiloxane polyhydrate (PMSPH) is used as enterosorbent for a couple of decades (nowadays under the trademark "Enterosgel"), intended for binding in the gastrointestinal tract and excretion of ...
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Protonation of compounds with two or three neighboring nitrogens

I am working with organic compounds. Many of them are similar to this ones: The R group (which I paste for completeness) is: I am a bit confused about the protonation state of those amine-compounds ...
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Which is the stronger base?

I would like to know which of the two is the stronger base, tri-(n-butyl)amine or tri-(tert-butyl)amine? I feel that the one with tert-butyl would be stronger as the inductive effect of tert-butyl ...
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Titration of caffeine using Iodine

I was trying to do an investigation on the variation of caffeine content with temperature. I used 6 Lipton yellow label tea bags (black tea) to brew the tea solution. Next, I perform the extraction of ...
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Why does reduction of naphthalene with nickel/hydrogen lead to trans-decalin?

Is there any reason why $\ce{H2/Ni}$ leads to trans-decalin? I knew from high school that catalytic hydrogenations are always syn.
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Side chain formation in polymerisation of ethylene

I am having difficulty understanding (or at least need confirmation of my understanding) of this diagram regarding the formation of sidechains of polyethylene. If someone could explain it, that would ...
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Symmetry forbidden cycloaddition in the Wittig reaction?

My textbook (Klein) describes the mechanism for the Wittig reaction as a [2+2] cycloaddition, followed by a collapse of the ring. As far as I'm aware, [2+2] cycloadditions are symmetry forbidden, ...
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Is polymeric ethylene glycol conductive?

The other day, when we were doing the chapter Polymer Chemistry my teacher mentioned that Polymeric Ethylene Glycol (PEG) is conductive. [EDIT- By 'conductive', I guess my teacher meant, "...
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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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Asymmetric Suzuki coupling - saturated alkyl chain

9-BBN is applied for Suzuki coupling of a saturated alkyl chain with some alkenyl,alkynyl or even secondary alkyl halide like the modification attached: (Saito, B.; Fu, G. C. Alkyl−Alkyl Suzuki Cross-...
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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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113 views

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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656 views

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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447 views

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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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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783 views

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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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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266 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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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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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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Can secondary alkyl halides be used in the Corey–House synthesis?

I've been told by my teacher that the Corey–House synthesis cannot proceed with secondary alkyl halides; they will prefer to undergo elimination over $\mathrm{S_N2}$ substitution. [used as the pseudo ...
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Does the chlorination of 4-methylcyclopentene generate two enantiomers or two diastereomers?

Does the chlorination of 4-methylcyclopentene generate two enantiomers or two diastereomers? I think it makes two enantiomers (or one pair of enantiomer) since the starting compound is achiral, but ...
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Why is the Suzuki coupling done under inert atmosphere?

There are plenty of sources saying that the Suzuki coupling is air-sensitive (even though there are some versions that require oxygen). However I'd like to know why a typical Suzuki coupling is air-...
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Can bis-quaternary aromatic compounds act directly on acetylcholine receptors?

The book Cholinesterases and Anticholinesterase Agents gives examples of bis-quaternary aromatic compounds that are capable of inhibiting acetylcholinesterase. Page 400 gives examples of some such ...
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Why does equilibrium for the addition of the Claisen enolate to an ester not favor the product?

I am currently reading chapter 26 of Clayden's Organic Chemistry, and a diagram for the elementary steps of the Claisen condensation with ethyl acetate in ethoxide is provided. It is obvious why the ...
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Mechanism for the Formation of DMC

I have recently reviewed the synthesis of the dehydrating agent DMC (7), but I could find no reported mechanisms for its formation. I have proposed the mechanism drawn below, but I am unsure about a ...
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What is the mechanism of benzyl ether hydrogenolysis?

The mechanism for the hydrogenation of alkenes or alkynes using Pd/C is fairly well explained to involve the absorption of hydrogen onto a metal's surface followed by the addition of that hydrogen ...
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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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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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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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