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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Treatment of alkyl borane with AgNO3 and NaOH
I found the following reaction in a book but no mechanism mentioned to it. I searched the internet but could not find anything relevant to the mechanism. I am just stuck and I do not know whether I am ...
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Why August Wilhelm von Hofmann used "ne" in ane ene yne of alkane-alkene-alkyne [duplicate]
Numerous sources point to August Wilhelm von Hofmann introducing the ‘ane’, ‘ene’ and ‘yne’ endings based on the vowel letter.
By the way i saw question like i asked above and some answer have source ...
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why does OH group have more priority than a double bond?
I learnt that a double bond has the most priority in a compound while naming it. but in this case, apparently, the functional group has more priority than the double bond and I don't get why.
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Is there a quantitative definition of inductive effect?
Usually, Inductive effects are compared using the electronegativities and distances. However, this only works in compounds with similar structures. For example, we can predict the following orders of ...
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What is the final product of the reaction? (Where does the 3 membered ring opens)? [closed]
What is the final product of the reaction? (Where does the 3 membered ring opens)?
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Caustic pumps are filling up with grease/gel like substance? [closed]
I am using a caustic pump to pull caustic from a caustic tank that sits outside. The caustic is used to treat a demineralizing unit. The pumps are filling up with a grease/gel like substance. Is this ...
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Does the Oxy or Alkoxy Claisen Rearrangement Exist?
@Waylander's cogent Comment to the query of @Random Guy inspired me to post a problem in synthesis to test a question I have pondered for some time. The activation energy (AE) for the Cope ...
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Why can't alkyl groups show -I effect or can they?
Inductive effect is the partial shifting of the bonded electrons towards more EN (take as electronegativity or electronegative in this text) atom so why we will say that alkyl groups will always ...
CommunityBot
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Easy way to derivatize silsesquioxanes
I have a polymer end-capped with a polysilsesquioxane (POSS) like this one $(\ce{R} = \ce{i-Bu})$:
I haven't found much info on what type or reactions these POSS groups can undergo. Are there any ...
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Ethanol vs IPA for drying electronics [closed]
Ethanol and IPA are both effective for cleaning electronics, but ethanol leaves oil traces on the surface it evaporates from and has a slower evaporation rate compared to IPA. Can anyone explain why ...
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What are the best conditions for EDC coupling of 2 small molecules?
I want to couple 2 small molecules, one is a DNA oligo with an amine group and the other one a small molecule with with a carboxyl group.
I found protocols for EDC coupling of amines and carboxylic ...
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Effect of Solvent - Nucleophilicity of RS- and RO-
While reading on order of nucleophilicity of $\ce{RS-}$ and $\ce{RO-}$, I came across this:
Source: Page 355, Organic Chemistry by Jonathan Clayden, Nick Greeves, and Stuart Warren
However, my teacher ...
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How long would it take to break down the peptide bond between Aspartic acid and lysine in pure water? [closed]
How long would it take to break down the peptide bond between Aspartic acid and lysine in pure water at 25 degrees C with a pH of 7 without any enzymes or other catalysts?
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Cleavage of an enol-ether via methanolic KOH? [closed]
Not very experienced in organic Chemistry and can't find the answer anywhere. Very confused as to how addition of methanolic KOH could cleave the enol-ether to generate the methoxy chloro quinoxaline.
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Need a fictional chemical name for a triple halogen compound nicknamed "TriX" [closed]
I am writing a fictional piece and want a realistic sounding chemical name for a compound that is nicknamed "TriX". I imagine it being something with a triple halogen base (It doesn't matter ...
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Glutaraldehyde or Glutardialdehyde
Recently I was searching for a chemical compound to meet my research needs, i.e. glutaraldehyde, and later I found that Merck has been released different name of compound: (1) glutaraldehyde and (2) ...
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How to calculate molecular emission spectra?
Is there free software that can calculate the fluorescence emission spectra of organic molecules?
Let's say, for example, rubrene
There is a bunch of quantum free quantum chemistry software:
https://...
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Why does Alcohol-Dehydrogenase prefer ethanol over methanol?
So I've had this experiment at university, where we tried using (yeast) ADH on different alcohols and measuring which one gets turned over the fastest. We also learned that ADH prefers shorter ...
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evaporating DMSO/Ethanol
I'm preparing to do a thiolclick reaction and to get a homogenous phase I found it's best to use DMSO/ethanol as solvent for the -ene and thiol reagents. I need the ethanol specifically for hole-...
CommunityBot
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Reaction of cinnamic acid with Br2/Na2CO3
The first reaction produces benzaldehyde, and the next one (perkin's condensation)produces Cinnamic acid.(X)
Now the treatment of X with $\ce{Br2/Na2CO3}$ is whats troubling me. $\ce{Na2CO3}$ being a ...
CommunityBot
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What is Y-aromaticity? Is the trinitromethanide anion aromatic?
The wikipedia article on trinitromethane claims that:
There is some evidence that the anion (which obeys the $4n+2$ Hückel rule) is aromatic.
Unfortunately the citation is behind a paywall so I ...
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why does -CHO hold higher priority over -CH2OH according to CIP rule [closed]
i am unable to find proper resources to learn CIP rule at a high school level withut delving deeper into terms i cant understand and hence the basic confusion.if i am correct one has to first compare ...
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What is the pH of acetone in water?
Reaction of Acetone with Water
Acetone in water can react in three ways:
The different reactions change the concentrations of $\ce{H+}$ and, consequently the pH, differently. My question is what is ...
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How to calculate dielectric constant of molecules using gaussian software in DFT studies? How to make input for these calculations? [closed]
I am trying to find the dielectric constant of my organic solar cell molecules, but I don't know how to make input files for these calculations. Can anybody please tell that which parameters should be ...
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What is the best way to draw chemical structures in LaTeX? [closed]
I was just wondering what the best option is for getting chemical structures/reactions in LaTeX. Should I just draw the molecule in ChemDraw/ChemSketch then export it to LaTeX or is there a particular ...
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How many compounds of 4 atoms (with C,N,O) are there? [closed]
Involving only C, N and O, how many different, stable compounds can be formed with exactly 4 ...
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In ozone, are the electrons in the bonds shared equally between the central oxygen and the terminal oxygens? [duplicate]
I know ozone is polar because of its shape, but I still don't understand how the dipole moment of each bond in ozone is not equal to zero, even though they're non-polar bonds since they're between the ...
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Neighbouring Group Participation of Aldehyde group
Does the aldehyde group -CHO give neighbouring group participation? For example in the following compound:
Why or why not will the formyl group show neighboring group participation? Although I have ...
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Have I named this compound correctly using IUPAC naming conventions?
I think it is 3-[3-[2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethylamino]-R-phenyl]-4-Ar. But I'm not sure and would really appreciate some help
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Electrophilic Aromatic Substitution: Are protonated OH-groups ortho-/para- or meta-directing?
In Electrophilic Aromatic Substitution ($\text{S}_{\text{E}}\text{Ar}$) reactions groups that can donate an electron pair into the aromatic ring, e.g. $\ce{-OH}$ or $\ce{-NH2}$, are ortho-/para-...
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What is the total number of isomers, considering both structural and stereoisomers of cyclic ethers with the molecular formula C4H8O?
According to me, it should be 11 and this is how I have worked out as shown in the attached diagram.
However, I am not sure whether all these 11 isomers can be considered as those belonging to ...
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Comparing basicity of imidazole and 2-imidazoline
I recently sat for an exam in which I was asked to compare the basicity of the above compounds. I thought imidazole would be more basic because it is aromatic but according to the answer key 2-...
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1
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Can cyclopropane be synthesized from propan-1-ol?
I know the dehydration of propan-1-ol derives in prop-2-ene by removal of the hydroxyl group and a hydrogen atom from the second carbon, but could the hydrogen come from the ones bonded to the third ...
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If there are multiple double bonds in a compund which one undergoes ozonolysis first [closed]
In the given question we have been asked about the stereoisomers but I can't figure out where would the ozonolysis take place as in the mechanism molozonide and ozonide are formed but I am not able to ...
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Why does N,N-dimethylethanamide have a higher boiling point than butanoic acid?
According to Wikipedia, N,N-dimethylethanamide has a boiling point of $\pu{165.1 °C},$ while butanoic acid has a boiling point of $\pu{163.75 °C}.$
From what I learned, butanoic acid should have a ...
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Which group has higher priority according to Cahn-Ingold-Prelog rule? [closed]
I cannot confirm which group has higher priority according Cahn-Ingold-Prelog rule in the above groups?
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Why does this show E1CB mechanism?
The following is a solution to a "match the following" question from IITJEE 2006.
I'm confused why does it show E1CB mechanism? Isn't the mechanism exclusively for highly acidic Hydrogen ...
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Why does hybridization significantly matter for organic chemistry?
I just recalled, and still see that almost every organic chemistry book starts with bonds, empahsizing hybridization. One thing is straight forward but the rest doesn't seem to connect well.
The thing ...
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How can a methyl cation exist without 8 valence electrons?
So far I have been taught that everything wants to achieve noble gas configuration - 8 electrons in the outer shell.
I came across a methyl cation. Which contains a positive carbon, no lone pairs and ...
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Will alcoholic acid solution with organic acids break down Bakuchiol and reduce it's biological effect?
I wish to use Bakuchiol in a solution of isoproply alcohol and water in the presence of glycolic acid (7%), citric acid (0.5%) and salicylic acid (1.4%) at a pH of 4 to 5, adjusted with TEA. Wu et ...
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Does the first step in electrophilic aromatic substitution follow equilibrium? If so, can equilibrium constant be calculated?
Using chlorine (a Lewis base) and ferric chloride (a Lewis base) as an example, the first step I saw in the textbook looks like this:
The picture above depicts the Step 1 in the EAS mechanism using ...
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Why salicylic acid is insoluble in water if it has a carboxylic function with a pKa of +3?
My question is the following:
Why salicylic acid is insoluble in water if it has a carboxylic acid function with a $\mathrm{p}K_a = 3$?
The acid function upon deprotonation goes into resonance without ...
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What does unactivated, activated and deactivated aryl chloride mean in cross-coupling reaction?
Hartwig et al. [1] used unactivated aryl chloride for Buchwald–Hartwig amination. What does unactivated, activated and deactivated aryl chloride mean in a cross-coupling reaction?
Reference
Hartwig, ...
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Oxidation Mechanism of A Peroxide reacting with a sulfide to form Anthracene
I have the following reaction: A peroxide reacting with a sulfide to form anthracene, sulfoxide and water or sulfoxide and water depending on the reactant. The reaction is from a paper discussing the ...
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Difference between ketone rings in wavelength using an IR device [closed]
It is said that the smaller the ring size, the greater the wavelength of the carbonyl group, but why does cyclobutanone have a higher wavelength than cyclopropanone?
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Enamine formation mechanism. Can't there be alternatives?
I'm studying organic chemistry, more specifically the imines and enamines. I've read about the mechanism of formation of enamine from a generic ketone and a question popped up in my mind. The ...
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(stereochemistry)epoxide from alkene
picture above describes two ways of forming epoxides from alkene.
(a) peroxy acid
(b) Br2 and H2O / NaOH
it says R groups stay in the same position.
and I want to ask some about (b).
is it possible ...
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What is the mechanism of azulene synthesis?
In the Organic Syntheses preparation of azulene (http://www.orgsyn.org/demo.aspx?prep=CV7P0015) there are two reactions. First is a clevage of the C-N bond in pyridine and the second one is the ...
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How much can we extend the Finkelstein reaction?
Finkelstein reaction explicitely entails on the conversion of an alkyl chloride or an alkyl bromide to an alkyl iodide by treatment with a solution of sodium iodide in acetone.
$$\ce{R−X + NaI→[...
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If hybridised states don't exist, how to explain the shapes of molecules?
In the book Concise Inorganic Chemistry by JD Lee (4th ed.) (pg 73) the author states the following...
It is a common misconception that hybridization is the cause of a particular molecular shape. ...
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