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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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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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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2 answers
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Hybridisation of the O atom in the hydroxyl group of ethanoic acid

Currently studying high school organic reaction mechanisms and encountered a question. It goes like this: The C=O bond and the C–O bond of an ethanoate ion is equal at 127 pm, while the C=O bond of ...
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Mechanism of alkyl benzene reaction with KMnO4/KOH to form carboxylic acids

I came across this reaction regarding formation of carboxylic acid by treating alkylbenzenes with KMnO4/KOH. I know that alpha-(C-H) bond in this compound is easily broken down into radicals. Then it ...
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1 answer
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Paracetamol infrared spectrum issues

I was studying Infrared Spectroscopy and i analyze different polymers. When i prepared paracetamol making a pill mixing 2mg of it with 200mg of $\ce{KBr}$ on a vacuum-connected press when i put it in ...
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Chemical Equilibrium of the Esterification Reaction Between Propanol and Ethanoic Acid

I am trying to investigate the relationship between temperature and equilibrium constant of the esterification reaction between propanol and ethanoic acid in reflux system, with conc. sulphuric acid ...
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How is propene more reactive as well as more stable than ethene?

I know that hyperconjugation stabilises a double bond. But in propene an electron-donating group $(\ce{-CH3})$ is increasing the electron density at the double bond, so its nucleophilicity should be ...
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How does Hyperconjugation stabilize a Carbon Free Radical? [closed]

I tried drawing the resonance structures but just cannot see how donating two electrons to a carbon that only needs one electron make it more stable? I stumbled upon this question asked years ago ...
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What is the mechanism of aldol condensation between two diketo-compounds with sodium bicarbonate?

In particular, what is the mechanism of aldol condensation of dimethyl-1,3-acetonedicarboxylate and 2,3-butanedione with sodium bicarbonate? I'm trying to work out the mechanism of this aldol ...
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What is the mechanism for the reaction of (Ph)2CO and succinic acid with NaH and quenching with acid?

I'm guessing the C=O will be attacked first on the PhCOPh, but how do you get rid of the O? Just out of interest, how else could you convert C=O to C=C?
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Which is more acidic alcohol or ketone? [closed]

I have read about it and i found that the alcohol is more acidic, but isn't the conjugate base produced from losing the alpha hydrogen of the ketone more stable ?! The negative charge in this ...
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Should the principal carbon chain contain maximum number of functional groups or just the principal functional group?

My answer was the 6 carbon chain, i.e. the name would be 2-(2-hydroxyethyl)-4-methylhexanoic acid. But the given answer is the 4 carbon chain, i.e. the name would be 4-hydroxy-2-(2-methylbutyl)...
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Is the graphene sheet in graphite considered molecule? What is considered molecule? [duplicate]

molecule, a group of two or more atoms that form the smallest identifiable unit into which a pure substance can be divided and still retain the composition and chemical properties of that substance. -...
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Chlorinated hydrocarbon destruction

What's a convenient method for lab-scale destruction of chlorinated hydrocarbons? Reductive dechlorination, total oxidation are fine as well as other routes you want to point out. If specific ...
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1 answer
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Does the same name represents all resonance and hybrid structure of a molecule?

The name chlorobenzene represents the following molecule. But the molecule shows resonance and its resonating structures are So does the same name represents all the resonance structures? Does it ...
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Comparing acidic strength of acetic and p-anisic acids

In p-anisic acid the phenyl ring with methoxy group acts as strong electron donating group by mesomeric effect (+M), whereas in acetic acid there is only an electron donating nature by inductive ...
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A Multistep Reaction Provided with IR Spectra (Guessing Started with Esterification)

Below, IR spectra for this sequence are provided: For compound E, I suggest the formation of a conjugated ester with the elimination of $\ce{-OH}$ group. The IR peak at $\pu{1732 cm-1}$ is a ...
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When does the Mukaiyama-Addition follow which transition state and how does it affect the stereochemistry?

in the course on enantioselective organocatalysis, we discussed the route to hexoses via organocatalytic aldol addition and subsequent Mukaiyama addition. The use of either TiCl4 or MgBr2 leads to ...
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Making C14 or C13 chlorobenzene site specific label

Imagine that you want to make chlorobenzene with a carbon-14 label in one site only, the only site you want it to be in is on the carbon bearing the chlorine. Can you think of a better and shorter ...
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2 votes
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171 views

Does 'aromaticity' apply to individual resonance structures or the hybrid?

When we define the aromaticity of a compound, is it meant to describe the resonance hybrid of the compound, or for individual resonance structures of the compound? I think the latter is wrong because ...
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Comparing stability of 1,3-dioxolan-2-ide and 1,3-dithiolan-2-ide carbanions

I'd like to compare stability of 1,3-dioxolan-2-ide and 1,3-dithiolan-2-ide carbanions: I think there is no mesomeric or hyperconjugation effect and we should consider inductive effect. Oxygen is ...
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6 votes
2 answers
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How does molecular structure contribute in the property of fluorescence?

Fluorescence is the property which is exhibited when electrons emit wavelength of light lower than the one they absorbed so does that mean we can make every molecule to become fluorescent? I wanted to ...
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3 votes
1 answer
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Safe disposal of pyrolysis side products in production of wood gas

I am in the process of building a pyrolysis chamber producing wood gas for use in a generator. The process involves heating a batch of biomass (wood) in absence of oxygen (air) in a closed vessel, and ...
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Will the rate of the reaction of discoloration of crystal violet change if I vary the concentration of crystal violet?

I'm trying to find a relationship between the concentration of crystal violet (limiting reagent) and the rate of reaction in the hydroxide medium. I've only seen examples of experiments varying the ...
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5 votes
1 answer
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Comparing acidic strength of crotonic and isocrotonic acids

Compare acidic strength of crotonic acid (1) and isocrotonic acid (2): On comparing $\mathrm{p}K_\mathrm{a}$ values, cis-form $(4.44)$ turns out to be more acidic than the trans-form $(4.69)$. Most ...
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Selectivity in dehydration of isopropyl alcohol to diisopropyl ether

Can isopropyl alcohol be dehydrated by sulfuric acid to diisopropyl ether in a similar way as to how ethanol can? Is there a way to avoid or at least minimize the inevitable dehydration to propylene?
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Comparing acidic strength of phthalic acid isomers

I'd like to compare the acidic strengths of phthalic, isophthalic and terephthalic acids. As I understand, phthalic acid is the most acidic due to steric inhibition of resonance (SIR), but as ...
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Hoffmann elimination of an amine [duplicate]

The Hoffmann elimination is a reaction that allows an alkene to be obtained from an amine. Mechanistically, it is a three-step reaction. In the first stage, the compound undergoes exhaustive ...
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Planning regio selective protection of functional groups in glycochemisty

Lately I was trying to get a thorough understanding of some questions, I have delved into many research resources such as Scifinder, Google Scholar, and Organic Chemistry Portal. but I'm not satisfied ...
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When oxygen is connected only to carbon, are then the oxygen and carbon connected with a double bond?

My teacher showed us three molecules: a carbohydrate molecule, a protein molecule, and a lauric acid molecule. I noticed that, when an oxygen atom is connected to one carbon atom and isn't connected ...
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Experimental setup

I would like to know your opinion regarding the setup of a system for oxygen purging with nitrogen. Before ordering the necessary materials, I'd like to be sure if this setup is feasible or if it can ...
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1 vote
1 answer
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Determination of geometrical isomers for chains with rings and double bonds

How can we determine the geometrical isomers for this compound . It contains a ring and 3 double bonds . I am confused because i was told to consider 1 ring = 1 double bond. When i tried it i got it ...
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Organic chemistry aromatic compounds

How can we determine which of the above conpounds are aromatic . My teacher taught me to remove a hydrogen and shift the electrons but I did not understand it . Could someone help me so that i can ...
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Why 1-methylethanol is not preferred IUPAC name for isopropyl alcohol?

For the compound $\ce{CH3-CH(OH)-CH3}$ I propose two names: propan-2-ol and 1-methylethanol. Which is the correct name as per the IUPAC guidelines? According to Organic Chemistry by Morrison and Boyd, ...
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Diels-Alder and Synthesis Problem: Confused about how to add carbon chain and double bonded oxygen

I am working on this synthesis problem. My first step was converting the dienophile given into a diene via E2 elimination. From the product given, I concluded that the dienophile will carry the double ...
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3 votes
1 answer
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Why does BH3/THF reduce the carbonyl group to a methylene rather than an alcohol?

This reaction is taken from: Pintér, Á.; Sud, A.; Sureshkumar, D.; Klussmann, M. Autoxidative Carbon-Carbon Bond Formation from Carbon-Hydrogen Bonds. Angew. Chem., Int. Ed. 2010, 49 (29), 5004–5007. ...
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5 votes
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Aren't electrophilic addition reactions of alkenes also nucleophilic addition reactions?

And if they are nucleophilic substitution reactions as well, then why do we not call them "electrophilic and nucleophilic addition reactions of alkenes"? Consider the reaction between ethene ...
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Does Markovnikov's Rule apply to reactions like Dehydration of Alcohols?

I understand Markovnikov's rule essentially tells us the major product in addition reactions when a smaller polar molecule is added onto an unsymmetrical larger compound, however does it also apply to ...
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2 votes
1 answer
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Criteria for establishing an order of basicity among several organic compounds

In an exercise from an exam several years ago, they ask to order the following three compounds from highest to lowest basicity: I would not know how to start the exercise without going to a database, ...
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What is the reaction mechanism for formation of alkene from vicinal dihalide in presence of zinc and alcohol?

I have proposed the mechanism that zinc gives its two valence electrons to the halogen so it leaves the electrons of carbon which get shifted to form π-bond and the other halogen is pushed out. Then ...
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The effect of hyperconjugation on the stability of alkenes without MO theory

Hyperconjugation is used to stabilize carbocation by "alpha" hydrogens providing sigma electrons to C+ and forming pi bond. But what exactly is happening in the case of alkenes. How is ...
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4 votes
3 answers
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IUPAC nomenclature of extremely long alkanes

What would be the name of a linear alkane containing 10000 carbon atoms, i.e. $\ce{C10000H20002}$? I have searched for it, but the longest alkane I could find had 9000 carbon atoms (and was apparently ...
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2 votes
1 answer
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Why does cyclopentadiene react faster than cyclohexadiene in Diels Alder reactions?

How does the length of the bridge of the resulting bicycle change the rate of the Diels Alder reaction (examples below)? I can't seem to think of how one would be more electron donating than the other ...
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2 votes
1 answer
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What organic molecule, if any, does this diagram represent in Louis CK's "Louie" Season Four, Episode Eleven, just before the six minute mark?

I'm wondering what molecule this is, if any, and whether this molecule is even physically likely or possible. Here is a screenshot of the scene from "Louie" (a hilarious and fascinating ...
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1 vote
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CIP Rule and giving priority to phenyl or alkene phenyl

The problem is to provide absolute configuration to Sulphur atom. I know that Oxygen atom will get the highest priority by Cahn Ingold Prelog rule but what about the next priority? I believe it should ...
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Aldol Cyclization Cascade Reaction between Two Ketones in Basic Alcoholic Solution

My professor gave a hint that the reaction scheme is a multiple carbonyl reaction which involves cyclization. He emphasizes that the reactivity of carbonyl compound in terms of C-H acidity and ...
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