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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Definition of Molecularity of a reaction? [closed]

If nucleophilic attack occurs simultaneously at two seperate electrophilic sites of the molecule following SN2 at each site, will the moleculularity still be 2? Does molecularity depend on the total ...
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Is this formula for number of optical isomers correct?

For a symmetric molecule with an even number of chiral centres (for acyclic molecules with chiral centres only, not considering $\pi$ bonds or rings), the formulae (also mentioned in this question) ...
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What is the most stable cycloalkene? [closed]

I'm looking specifically at cyclopentene and cyclohexene. Supposedly, greater instability would lead to a more exothermic enthalpy of combustion. However, based on my data, cyclopentene is more ...
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If there are two possible reactions, will the one with a more negative Gibbs Free Energy be favored?

I was thinking of the reaction between methanol (CH3OH) and sodium amide (NaNH2) and wondering if I could get methylamine (CH3NH2) from it. One reaction forms methylamine and sodium hydroxide, while ...
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2 answers
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why is benzene ring ubiquitous in almost all the organic compounds [closed]

Could you please give me a reasonable cause why benzene ring is found in every organic compound in food, pharmaceuticals, dyes . In addition, benzene is a known canceriogen, why shouldn't it be toxic ...
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1 vote
1 answer
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How does a freeze-thaw cycle separate a mixture?

Imagine that I defrost a tube of serum (only the yellow stuff, with blood cells removed) standing still and upright in ambient air. I have seen that as it defrosts the sample separates into different ...
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3 votes
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%s character distribution of phosphorus hybrid orbitals

The following question was asked in the Indian Olympiad Qualifier Chemistry Part I (IOQC) today: For the given compound, %s character of phosphorus hybrid orbitals which contribute to various bonds ...
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1 answer
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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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What is the major product in the following reaction?

Reaction: My thought-process: According to me, this reaction is like the bromination of alkene but here instead of $\ce{CCl4}$ solvent, we have $\ce{H2O}$ as a solvent. For the first step a $3$-...
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Would magnesium react with acyl halides to form a variant of grignard reagent just like alkyl and aryl halides?

We were having a chemistry class in our school and we were discussing the answer to some question related to acyl halides when this popped up. Our teacher mused that it may be possible but he hadn't ...
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How do I understand the IUPAC naming of 9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1H-carbazol-4-one? [closed]

I'm having trouble understanding the IUPAC naming convention of 9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1H-carbazol-4-one. It would be great if you can help to breakdown the naming ...
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Fractional Composition of Acid Question

I present to you a fractional composition question that my professor refuses to answer because he encourages me to use equations without understanding them. Any help you can provide would be very, ...
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1 vote
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What is the resulting solution after leaching hardwood ash with water?

After doing online research, I've noticed there are differing interpretations on what happens when ash is mixed with water, so I've come here seeking clarification on what indeed happens, and also ...
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Origin of oxygen content among the products of burned carbohydrates

For simplicity, I am only considering complete combustion. I am ignoring variants such as deoxyribose, just pure carbohydrates. Balancing the equation is easy due to the definition of carbohydrate: we ...
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Cannizzaro reaction via electrolysis

As cannizzaro reaction reaction is a redox reaction carried by adding base to an aldehyde, is it possible to carry out the reaction using electrolysis where graphite anode and copper cathode is used. ...
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Why would 1,2,3,4-tetramethyl-1,2-dihydro-1,2-diazete be aromatic?

If the lone pair of the nitrogen on the bottom were to make the double bond with the nitrogen at the top, then the nitrogen on the top would have 10 electrons, meaning that the lone pair on the top ...
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Is N-bromosuccinamide more selective than N-Chlorosuccinamide or TCCA when conducting radical halogenations?

Radical bromination in UV light for instance, is known to strongly favor bromination at the most substituted positions compared to chlorination if elemental bromine and chlorine are the halogenating ...
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1 answer
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Mechanism of terpene alcohol rearrangement [closed]

I thought about all kinds of hydride shifts that could be possible here, but I still could not figure out how the mechanism would work.
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Reaction Workup and Quenching

In the supporting information of synthetic paper by Buchwald's group, They use 2-MeTHF as solvent (See B. General Procedures for Amination part, page 8). After the reaction ends and cools the mixture ...
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How to measure organics in liquid solution

We have a solution that has been put through a filter, it has gotten down to 20ppm. We want to know what the remaining organics are so we can try to filter those out. Is there any machine we can buy ...
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Titration point and half titration point

I am given that $100$ ml of $0.05$ M propanoic acid is titrated with $0.1$ M NaOH and want to calculate the pH at the half titration point and titration point. When I use the equation $$c_1 V_1 = c_2 ...
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Why can I extract all metabolites from blood plasma with one solvent, but to extract only fatty acids I must use many solvents?

I want to do a metabolite study using GC- without derivatization and UPLC-MS (RP and NP) on samples of plasma and urine. My hypothesis is agnostic about which metabolite will correlate with the ...
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1 answer
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Between compounds having same functional groups, why does the one with greater -I effect have higher acidic strength

Consider the two compounds $\ce{FCH2COOH}$ and $\ce{ClCH2COOH}$. Since fluorine is more electronegative than $\ce{Cl}$ it will show a greater –I effect. It will pull the the electrons closer towards ...
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1 vote
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What is the mechanism of the reaction between 1(3H)-Isobenzofuranone and benzaldehyde?

I have been trying to deduce a reaction mechanism for the reaction between the two compounds to give the compound labeled 2 in the diagram but I do not think I have a satisfactory answer. My thinking ...
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2 votes
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Various pathways of an alpha diketone reaction

This is a question from JEE Advanced 1997. I have found two possible products of the reaction: By intramolecular aldol condensation: By benzil-benzilic acid type rearrangement: Which reaction takes ...
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Difference between SN' and elimination reactions

My professor has recently taught us about SN' reaction example in which 3-bromo-3-methyl-but-1-ene was reacted with with KCN to yield 4-methyl-pent-3-ene-nitrile as the major product.When I asked him ...
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Lobry de Bruyn-Van Ekenstein reaction

I've recently read about this reaction called Lobry de Bruyn-Van Ekenstein reaction, where simple glucose is converted to fructose and mannose by adding a base or acid, as I've read this is supposedly ...
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3 votes
1 answer
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Interpretation of permanganate-stained TLC spots

When I stain TLC spots with $\ce{KMnO4}$, I found that some spots appear differently as time goes by. Here is the example: The leftmost one is the plate right after staining, and the others are ...
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4 votes
2 answers
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Hypothetical symmetric carbon peroxide

Could a hypothetical carbon peroxide $\ce{C5O12}$ with the following structure (MolView — 3D model) exist, and I what its properties would be (other than decomposing, of course)? I tried looking it ...
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Addition of HOCl to ethyne [duplicate]

What is the product formed in addition of HOCl to ethyne? Is it dichloroacetaldehyde, or perhaps the enol form of dichloroacetaldehyde could react further with HOCl to form chloral hydrate / chloral?
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1 vote
1 answer
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Can organocuprates do SN2 reactions with tosylates?

In the presence of isolated ketones, can organocuprates add to secondary tosylates in an SN2 fashion without adding to the ketones?
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1 vote
1 answer
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Isopropyl Alcohol Resistant Paint

Which paint binders are most resilient to IPA? Background: I'm looking for an IPA-resistant spray paint to coat a 3D printed model composed of a high-performance stereolithography resin MSDS. "...
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How can the multiplicative number (n) of a chemical series like polyethylene glycol (PEG) be a non-integer?

https://en.m.wikipedia.org/wiki/PEG_400 Down at chemical or molecular formula, it says: C_2n H_4n+2 O_n+1, like for all polyethylene glycols (PEG)s, but then says n=8.2 to 9.1.... Huh?
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Are alkynes weakly polar?

I was reading about physical properties of alkynes in my Chemistry textbook. One of the sentence states Alkynes are weakly polar in nature. I didn't understand how alkynes are weakly polar, so I ...
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Resonance structure with allylic lone pair

Draw the appropriate resonance structure for 5-aminolevulinic acid: As there is an allylic lone pair, my first arrow goes from the lone pair to form a π-bond, and the second goes from the π-bond to ...
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1 vote
1 answer
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Does hot potassium permanganate break benzene rings?

Benzene rings are broken during ozonolysis, and alkenes treated with hot $\ce{KMnO4}$ undergo oxidative ozonolysis. So does that mean that the double bonds of benzene also are broken by hot $\ce{...
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Chloro functional group is given number 4 in phenol but number 1 in nitrobenzene

In the IUPAC name 4-chlorophenol, we see that, the C atom where OH group is attached, is given number 1. But in the IUPAC name 1-chloro-4-nitrobenzene, we see that, the C atom where $NO_2$ group is ...
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1 vote
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Mass spectra interpretation for monitoring Buchwald–Hartwig coupling

I am conducting a synthesis involving Buchwald-Hartwig coupling. The starting materials are 2,3,5-tribromothiophene (MW=320.83) and 1-aza-18-crown-6 (MW=263.33). I used $\ce{Pd_2(dba)_3}$ (MW=915.7) ...
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Oxidation of amino acids with N-bromosuccinimide

I've recently come across the reaction where an amino acid is oxidised to form an imine by using N-bromosuccinimide as reagent and then in hydrolysis it formed an aldehyde moiety. The second step is ...
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How to tell if Neu5Ac is in D/L form and alpha/beta form?

As shown in the figure below, I want to make sure if the last Neu5Ac sugar on the left-hand side is in the D-form or L-form. My understanding is that if the sixth carbon is pointing upward, then the ...
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5 votes
1 answer
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E and Z nomeclature when we have a ring instead of double bond

I am confused as to whether the E/Z nomenclature can be extended to compounds of general structure like in the image. Clearly they are some sort of cis and trans but I cannot see a non-aromatic double ...
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2 votes
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Sodium dithionite reduction of nitro group to amine

I've recently come across the synthesis of 3-aminopthalhydrazine from 3-nitropthalhydrazine where the reducing agent used was sodium dithionite ($\ce{Na2S2O4}$). I wanted to know what the mechanism of ...
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1 vote
1 answer
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Water vapor permeation to the reaction flask

I am conducting a synthesis involving Buchwald-Hartwig coupling. The scale is $\approx10^{-4}$ mols of reagents. After running the reaction at 80 ℃ during 24 hours I found that sealing between the 3-...
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Most appropriate representation of 3,4,4,5-tetramethylheptane [closed]

Is there a specific correct way to draw the structure of 3,4,4,5-tetramethylheptane?
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Why adding sodium bicarbonate quenches a reductive amination using sodium triacetoxyborohydride?

I'm planning to do a reductive amination reaction between methyl pyruvate and benzylamine using sodium triacetoxyborohydride, $\ce{NaBH(OAc)3}.$ Acetic acid is used as a catalyst for protonating the ...
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Molecular orbital theory and Lewis structure for dioxygen

I am a bit confused about how molecular bond theory predicts pairings of unbounded electrons. For example, in $\ce{O2}$ there are two pairs of electrons on each oxygen along with the double bond. ...
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Adequate emulsifier for dimethoate

Dimethoate is a broad-spectrum systemic insecticide and miticide. It is sold for example as Drexel in the US or as Danadim in Australia (there are many others, Rogor, etc). The formulation from Sico ...
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0 votes
1 answer
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What will be the structure of cysteine at pH=4? [closed]

As per my understanding since pKa of RSH and the amino group is >4 hence they would be in cationic form while the acid should be in anionic form. So charge on cysteine would be +1. But while ...
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nomenclature of propane-1,2,3-tricarboxylic acid [duplicate]

The iupac name of this compound is given book as "Propane-1,2,3-tricarboxylic acid" My doubt is, why the carbon of the first carboxylic acid is not included in the main parent chain while ...
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