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 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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162 views

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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51 views

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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386 views

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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163 views

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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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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111 views

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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613 views

Diazo Coupling reaction with para-substituted phenol?

Usually Diazo coupling occurs at para-position unless the para-position is occupied, in which case coupling occurs at ortho-position. While solving questions I found in both the cases as shown, the ...
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334 views

Mechanisms of Birch and Bouveault-Blanc Reductions

The question is all about the sequence of a possible Birch- and Bouvault-Blanc-Reduction in this exemplary substrate. With which reduction the mechanism begin? My first attempt was to classify the ...
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187 views

How could you accomplish the following transformation in sufficient yield?

I've considered Riley oxidation but the major product would have a hydroxyl group at the benzylic carbon to the left of the double bond instead of the methyl group as shown. Is there a way to make the ...
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Analytics of a paramagnetic complexes

I am working with salophene iron[III] complexes. Unfortunately, my 5th ligand cannot be determined via MS. I performed a 1H-NMR in methanol, but it's not a suitable method for a paramagnetic compound. ...
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1answer
450 views

Why is ethanol distilled off before adding water in the first step of a malonic synthesis?

I am doing a malonic synthesis shown below, and I wonder why I should distill ethanol off before adding water in the first step of the reaction (First I add absolute ethanol and solid sodium).
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Rationalising diastereoselectivity of hydroboration using stereoelectronics

Using bulky reagents such as 9-BBN, hydroboration is often highly diastereoselective, giving rise to the 1,2-anti diastereomer: This is easily explained using a steric argument, with the major ...
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288 views

Reaction of alpha hydroxyketone with KOH

What happens when 2-hydroxycyclohexan-1-one (an alpha hydroxyketone) reacts with aqueous $\ce{KOH}$? I tried something like Favorskii rearrangement, but it's wrong because OH isn't a good enough ...
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74 views

Activation of alcohols by forming sulphonate ester

In activation of alcohol by tosyl chloride, why does the chloride ion not displace the poor leaving group? I think that's because chlorine is a poorer base than that thing which will be formed. But ...
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358 views

Mechanism for reaction of enol ether with HBr

Please refer to the image for the question. I tried two different mechanisms for the reaction (1 and 2) and ended up with two different products. Now I can't decide which of the two mechanisms would ...
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4k views

How to calculate the resonance energy of thiophene?

How to calculate the Resonance energy of Thiophene? I know how to calculate the resonance energy of Benzene. I am applying same procedure for thiophene, too. (Wikipedia: Resonance energy) The values ...
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652 views

Hydrogen bond strength of trichloromethane and chloromethane

Chloromethane has a larger dipole moment than trichloromethane. Does that mean that the hydrogen bond (C-H...O type) between chloromethane and acetone is stronger than that of trichloromethane and ...
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182 views

What is a good solvent for pentacene?

I am doing an experiment with pentacene molecule ($\ce{C22H14}$). I want to clean my sample reservoir after using it. But I show in some literature that it is slightly soluble in organic solvent. ...
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111 views

Directing nature of the -SOR substituent in electrophilic aromatic substitution

This is (alkanesulfinyl)benzene: I didn't draw it, but we know that the sulphur atom also has a lone pair. So, the sulphur atom can increase electron density in the ring by donating a lone pair. ...
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327 views

Sigma bond behaving as stronger nucleophile despite presence of pi bond?

In my book, the following reaction is given The solution states that the sigma bond between hydrogen and carbon (3 degree) in isobutane attacks $\ce{H+}$ from $\ce{HF}$ to generate tert-butyl ...
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270 views

Substitution of a cyclic diether by a halogen

I’m in an organic synthesis class and I have to draw a mechanism for the reaction in the picture. At first I thought it was just forming a free radical but I haven’t been able to find any way to do ...
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159 views

Rationalise the Relative Reactivity of Borane and DIBAL as Reductants

In Clayden's Organic Chemistry (Second Edition) it is written that borane is useful in chemoselectively reducing the most nucleophilic carbonyl to its corresponding alcohol. It is later said that ...
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839 views

Comparison of the rate of SN1 and SN2 reaction

It is known that $\mathrm{S_N1}$ (Substitution Nucleophilic Unimolecular) follows the order of rate of reaction: Tertiary ($3^\circ$) > Secondary ($2^\circ$) > Primary ($1^\circ$) For $\mathrm{...
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228 views

Why is this step exothermic?

From Wade's "Organic Chemistry" [1, p. 1003-1004]: MECHANISM 21-7 Conversion of an Ester to an Amide (Ammonolysis of an Ester) Step 2, loss of a poor leaving group is justified by claiming ...
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Which is the correct mechanism for the ozonolysis of an alkyne?

According to Organic Chemistry by Jonathan Clayden, Nick Greeves and Stuart Warren (2nd edition), the mechanism for alkene ozonolysis is given as In Advanced Organic Chemistry, Part B: Reactions and ...
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225 views

Reaction of bicyclic diol with periodic acid

I'm in an organic 1 class, and we learned about using periodic acid (HIO4) to cleave a glycol into two carbonyl groups, oxidizing the glycol. However, in the given reaction (see picture below), I'm ...
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Kinetics of nitric oxide production

Several articles affirm that NO can enhance the glutamate release from the presynaptic site; moreover, glutamate has been recognized as a major brain neurotransmitter and is considered to mediate ...
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214 views

Waterproofing and recycling paper

I've recently begun studying about waterproofing paper. Through what I learned is that the reason why paper absorbs water so easily is mainly because of it's material composition. Paper is generally ...
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513 views

Number of intermediates and transition states in hydration of given alkene

What is the number of transition states and intermediates formed in the following reaction? My thought: First the alkene extracts $\ce {H^+}$ from the acid to form a carbocation. This step involves ...
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52 views

Pd-catalysed hydrogenation of imines

Hydrogenation of imines to amines by $\ce{H2}$ on $\ce{Pd/C}$ has been used e.g. in the synthesis of Pumiliotoxin. By contrast, carbonyl groups are rarely reduced in this way, which I though was due ...
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In-vivo racemization of thalidomide

In 1961, thalidomide was first introduced as an over-the-counter cure for morning sickness. Pregnant women across the country began to take the drug, which worked well, but shortly after, babies began ...
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328 views

Mechanism for conversion of gem-dihalide to carbonyl compound

How does nucleophilic substitution work in a compound consisting of two leaving groups? I understand that hydroxide ions will attack the carbon centre (which bears a partial positive charge) and ...
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262 views

On the directing nature of these groups in electrophilic aromatic substitution

These three groups are listed in our workbook. I don't know the answer and our teacher isn't sure either: (each has a free valency through which it is attached to a benzene ring): ...
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132 views

Why is dimethylmercury more toxic (to animal life) than methylmercury or ethylmercury?

It's obviously a two step process to reduce dimethylmercury to the less harmful inorganic form. Is neuronal uptake also enhanced due to lipophilicity? Is there some other mechanism of toxicity I'm ...
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How can I test fruits and vegetables for certain insecticides?

I live in Turkey and I don't feel safe eating the fruits and vegetables that I enjoy that are plentiful here. After reading this article, I have been washing all fruits and vegetables with water and ...
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Nucleophilic substitution of 2-chloropropanoyl chloride

Upon heating 2-chloropropanoyl chloride with concentrated ammonia in a sealed vessel, a primary amide is formed but the chlorine atom at the beta carbon does not get substituted with an amino group, ...
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Should I add more of a trihydrate chemical to a solution if recipe calls for hemihydrate?

I am running phosphate by the ascorbic acid method (SM 4500-PE, PDF), and making the antimony potassium tartrate reagent. Standard methods uses $\pu{1.3715 g}$ of $\ce{K(SbO)C4H4O6 * 1/2 H2O}$ per $\...
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Why does viscosity decrease when divalent cations are dissolved into aqueous solutions of sodium carboxymethylcellulose?

Sodium Carboxymethylcellulose (CMC/NaCMC/Aqualon) is a common product used in many instances for its unique properties, especially its ability to make solutions viscous. It is well known that the ...
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Thyroid peroxidase - can atomic iodine serve as iodinating agent?

McMurry's Organic Chemistry (7th Ed.) states, that Tyrosine is iodinated by mechanism of electrophilic aromatic substitution and the iodinating agent is $\ce{I+}$ or $\ce{HIO}$ formed by thyroid ...
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246 views

Oxidation of alkenes and alkynes by Chromic Oxide?

As far as I know, $\ce{CrO3}$ doesn't effect the $\mathrm{\pi}$ bonds in an inert medium like pyridine. Would $\ce{CrO3}$ in acidic medium reduce alkynes to have the same products as acidified, warm $\...
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156 views

Expedient phosponium synthesis (for Wittig)

I have been making ethyltriphenylphosphonium bromide (somewhat of a time crunch, would have used iodoethane instead of bromoethane if we didn't have to wait for it). All the syntheses I see of Wittig ...
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47 views

Is optical activity of a given compound a statistical picture?

When optical activity is taught it is done in terms of single molecules. But when it is actually measured it is done on a large collection of such molecules. So, how does the asymmetry manifest itself ...

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