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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Nomenclature irregularities

Why do we say "octadiene" and at the same time name another compound "octanediol"? We also say for instance "pentanedione", but on the other hand we say "butadiyne&...
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Explanation and terminology of a phenomenon [closed]

Please observe the picture given- I want to know what exactly is this phenomenon and what exactly is causing it. Context - an organic solution (WD40) is spilt on a wet surface outside, light bouncing ...
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What is the degree of dissociation of Et3N [closed]

What should be the degree of unsaturation of Et3N. I'm trying to calculate and it comes out 0, but my text book tells me the answer is 3. I'm taking the number of C atoms to be 6 and H atoms to be 15 ...
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N-C Condensation reaction

I am trying to synthesize C-N bond in a cyclic structure by eliminating Cl in a classic Nucleophilic substitution reaction. Reaction with a primary amine for the cyclization. Only reaction literature ...
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Acidity/basicity of N-benzylalanine methyl ester?

I recently conducted a reductive amination between methyl pyruvate and benzylamine using sodium triacetoxyborohydride to yield N-benzylalanine methyl ester (IUPAC: (S)-methyl 2-(benzylamino)propanoate)...
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How to calculate the amount of free and total formaldehyde in a product [closed]

Above is the Certificate of Analysis (COA) of DMDM hydantoin. Free formaldehyde is at 1.0% max Total formaldehyde is ~18% Active matter is 55% minimum Water content w/w is 43-46% Please help me ...
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Comparing melting point of neopentane and butanol

Why does something like 2,2-dimethylpropane have a much higher melting point than butan-1-ol? I know that butan-1-ol has a hydroxyl group, and is capable of hydrogen bonding, and I know that 2,2-...
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What will be the reaction of diospyrol with air? What compound will be formed when diospyrol reacts with air? [closed]

Diospyrol is present in Diospyros mollis which is used to make black dye. What is the chemistry and structure of this black dye? Diospyrol image from here
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Why is it not possible for water to directly attach itself to the alkene to form an alcohol in oxymercuration? What is the need for mercuric acetate?

When going through the preparation of alcohols, I came across the method of Oxymercuration-Demercuration. Now, after going over the reaction, I didn't understand the purpose of the mercuric acetate ...
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Reaction of hydrogen peroxide with acetic acid and potassium permanganate

I conducted an experiment where I mixed hydrogen peroxide $\ce{H2O2}$, acetic acid $\ce{CH3COOH}$ and potassium permanganate $\ce{KMnO4}$ under vigorous stirring. The reaction hasn't stopped after 15 ...
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DNA Base Pair Bonding? [closed]

The following GC base pair is a bonding of two aminos. How does the C and G form a covalent bond shown in the dashed line? If I apply the octet rule to the oxygen to the left of the dashed line its ...
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What matters for ion exchange: net or local charge?

I am interested in separating two small organic molecules by ion exchange chromatography. Following the example set by several old papers for these molecules, I want to use a cation exchanger. Both ...
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Alternative configurations of Purine Nucleobases

I’m not a chemist, but just for fun I was playing around with other possible ways to put together purine nucleobases by changing where the double bonds go on the pyrimidine ring and where amino groups,...
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2 answers
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Is eta hexachloro cyclohexane optically active compound?

Quoting from Wikipedia, Hexachlorocyclohexane (HCH), $\ce{C6H6Cl6}$, is any of several polyhalogenated organic compounds consisting of a six-carbon ring with one chlorine and one hydrogen attached to ...
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Conditions for Pd/C reduction of alkene

I am trying to do a $\ce{H2}$ reduction of cyclic alkene (otherwise simple hydrocarbon with 1 methyl group along with the chain about the weakly-strained cycle) using $\ce{Pd/C}$, the cycloalkene ...
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Universal product contamination method? Cheap? [closed]

Hi so I purchase my substances. And try new ones all the time. Ive seen the worst things too best. And was wondering if I wanted too get geek. How can I check my products for either basic or in depth ...
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Why does DIBAL-H not reduce esters to alcohols directly?

This source says that DIBAL-H reduces esters to aldehydes. Further, it says that, like NaBH4, it reduces aldehydes too. Why in reduction of ester, the aldehyde so formed is not converted to alcohol, ...
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1 answer
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Help with chemical bond associated with 1500cm-1 and 1600cm-1 [closed]

I have IR spectra of polystyrene with characteristic peaks at 1450cm-1. 1500cm-1 and 1600cm-1. What chemical bond is associated with 1600cm-1 and 1500cm-1?
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Is this compound aromatic? (Huckel's Rule) [duplicate]

Hello, Is this compound aromatic? I've learnt that for aromaticity these conditions are necessary and sufficient: $1.$ Compound should be planar (Carbon should be $sp$ or $sp^2$ hybridised) $2.$ All $\...
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Why schiff base reaction between 8-aminoquinoline & 2-carbaldehyepyridine doesn't precipitate

-I Have 2 problems I followed a method but one of them a low yield and the other didn't precipitate(give red liquid) -I used ethanol instead of methanol but it worked with one and the other didn't ...
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1 answer
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Is it possible to physically stretch US paper currency? [closed]

This is not a facetious question. I am curious how one can physically stretch US paper currency, which is allegedly 75% cotton and 25% linen. Unlike cotton or linen fabric, paper currency does not ...
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1 answer
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Shouldn't the negative charge be on carbon in this scenario according to molecular orbital theory [closed]

I am sorry in advance for posting an image in this question. I know it makes searchability difficult, but I don't see any other way The above screenshot is from Claydens organic chemistry. We can see ...
2 votes
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Which 1,2-methylene shift is more favourable in ring expansions where ring has substituents

In the above reaction, first the -OH group is protonated after which it leaves creating a carbocation intermediate as shown Now, ring expansion is a more favourable rearrangement, however there is a ...
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4 votes
1 answer
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Can heterocyclic molecules form sandwich-like complexes?

As unsaturated heterocycles have the same planar structure as cyclopentadiene ion/benzene "sandwich" compounds, I was wondering if a similar coordination between metals can be achieved. When ...
-3 votes
0 answers
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p-nitrophenol synthesis reaction frorm phenol [duplicate]

I have found that in order to synthesize p-nitrophenol from phenol, it should be treated with sodium nitrite (NaNO3) and sulfuric acid (H2SO4) as seen in 1. However I'm interested in knowing the other ...
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2 answers
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Synthesis and retrosynthetic analysis of dicyclohexylamine

I need to consider the retrosynthetic analysis and synthesis of dicyclohexylamine. For the retrosynthetic analysis, I have relied on the method of disconnections, which consists in splitting the ...
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Why can't RX add to alkenes / alkynes like HX?

With an analogous mechanism: C bonded to X has a δ+ charge and attacks the pi electrons to form a carbocation intermediate, with X- as a leaving group. X- then adds to the carbocation to neutralize it....
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Does the ace- or acet- prefix denote simplest forms of functional groups? [duplicate]

For example Acetone has the shortest carbon chain in which a ketone functional group can be added. Other examples include Acetaldehyde, Acetylene. Was this some sort of older naming system in which ...
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1 answer
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Favoured reaction product in acid catalysed addition of methanol to alkene [closed]

I would like to add methanol to an alkene RCH=CH2, catalysed by conc. sulphuric acid. I would like to know which of these endproducts will be preferentially produced: RCH(OMe)-CH3 RCH2-CH2OMe Many ...
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1 answer
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What is resonance in actuality? (How does electron sharing, bond formation, and overlapping of orbitals take place in resonance hybrids?) [duplicate]

In this post I got an answer to the question "what is resonance". What I understand overall is that "resonance is not something really happening physically, it is just an idea to make ...
5 votes
1 answer
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Is resonance possible in a structure with consecutive double bonds? Like in carbon dioxide (CO2)

With all the knowledge that I have secured reading about resonance, I know that delocalisation of pi electrons is possible only with the p orbitals being in the same plane. So for two consecutive ...
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How do I calculate q/m? [closed]

My chemistry book (Mortimer in German) has the following question: Calculate the value q/m for the following Ions: ("mit Masse" meaning "with mass") How do I calculate q/m? Thanks ...
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Dissolving corn in different acids

Corn is mostly starch, which a lot of acids can hydrolize to glucose, but to get to it the acid would need to work through the outer layer which can be digested only with specific enzymes. What I'm ...
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Does the metal complexing of crown ether influence its reactivity?

I am conducting a SN2 reaction experiment with 1-aza-18-crown-6 and bromide compound. I used 1 equivalent of bromide compound and 1.1 equivalent of aza crown, but in the TLC plate the aza crown spot ...
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Why can water act as a base under acidic conditions in organic chemistry mechanisms?

In Organic Chemistry mechanisms, I've commonly seen water getting protonated to complete a mechanism, and I'm getting a bit confused on how water can easily get protonated. From the autoionization of ...
3 votes
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Regioselectivity in oxo-Diels-Alder reaction

I have one doubt about the dimerization of methacryloyl chloride into the product 3: The dimerized product was observerd around 10-15mol% in different commercial samples of methacryloyl chloride, as ...
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Regioselectivity of the Hydroboration and Epoxidation of Limonene

Could someone help me out with the most likely major products for each reaction? 1 eq. of reagent is used for both reactions, so my initial thought was that both processes would only occur at the C=C ...
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Database of Resonance Structures

I am preparing to study organic chemistry in the coming year, and I had hoped to compile a list of practice questions for examining resonance structures. Is there an online database that holds the ...
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Overheated Teflon plumbing tape and pipe dope

I had to solder connection in a water tank, near a fitting that had Teflon tape applied and Kevlar pipe dope. My understanding is that Teflon brakes down above 500F Once the fumes are gone the any ...
3 votes
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Tetra-tert-butylmethane

Does this molecule exist? I've been wondering about extreme steric hindrance and trying to find the limit of what can exist and what not. It appears to exist some basic data about it in PubChem, but ...
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Can glycerine be degraded by UV light?

I would like to know, if UV degradation of glycerine is possible and what is the reaction mechanism? It is explicitly about glycerine and I could not find anything useful in the literature.
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Formation of ester during preparation of Fluorescein

I was going through PYQ of JEE where, I encountered the following question: Q) Phthalic acid reacts with resorcinol in the presence of concentrated $H_2SO_4 $ to give : In the solution provided I ...
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2 votes
1 answer
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Is NH2 electron donating or electron withdrawing? [closed]

Can anyone explain why NH2 shows -I in inductive effect and +R in resonance effect? I mean NH2 is ready to take electrons in inductive effect (with its electronegativity) but in the resonance effect, ...
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1 answer
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What is the reaction priority when methyl 2-(chloromethyl)benzoate reacts with potassium cyanide?

I was going through some PYQ'S of JEE Advanced where I encountered this question. I was not able to decide whether I should go for an SN2 reaction to substitute $\ce{-Cl}$ or a nucleophilic attack on ...
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1 answer
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How does aromaticity play out in carbon nanohoops?

Within the family of carbon phanes,one that has caught my attention is cycloparaphenylene. Considering that in practice it is just a segmented piece of a carbon nanotube, is must be aromatic in nature....
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Mechanism for synthesis of benzofuran

Would someone be able to help me with the mechanism for the synthesis of benzofuran from salicyladehyde (taken from https://en.wikipedia.org/wiki/Benzofuran)? I have got as far as the decarboxylation ...
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Should I use DMA or tensile and compressive testing?

I have some polymer based samples (the exact composition is proprietary) that were additively manufactured, however the sample amount is severely limited so I'm limited on the amount of material ...
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Position or functional isomerism: primary vs. secondary alcohols?

I have a small problem with the "definitions" of functional vs. position isomers. You have a few quite simple examples (pentan-2-one vs pentan-3-one vs pentanal), but there are also a few ...
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Method for monitoring pyridine activation by chloroformate

I am supposed to activate a pyridine using a chloroformate, and then reduce it with hydride to form a dihydropyridine, in a similar way to the paper: Heusler, A.; Fliege, J.; Wagener, T.; Glorius, F. ...
1 vote
1 answer
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How to convert phenylacetic acid to 3-phenylpropionitrile?

I understand that phenylacetic acid reacts with $\ce{KSCN}$ can form phenylacetonitrile plus the side product ($\ce{CO2}$ and $\ce{KSH}$). This is Letts nitrile synthesis However, the problem is to ...

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