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.
10,127
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How do polyurethane varnishes cure after only the solvent evaporates
How do polyurethane varnishes cure after only the solvent evaporates?
I believe that polyurethane varnishes have as components isocyanates & polyols that react to form the polyurethane portion of ...
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1
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Hydration of alkenes [closed]
In the image I've provided, I offer two alkenes. The first is in conjugation while the second isn't. Additionally, both of the C=C groups are symmetrical, in the sense that they both have one hydrogen ...
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What nucleophilic reaction takes place in case of bad leaving group as well as 1* alpha carbon?
If we add HI to a substrate Ph-C-C-OH what will be the major product and what reaction mechn. will be followed?
My attempt: as -OH is bad Leaving Group, we cannot just simply proceed with Sn2 and ...
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Reaction Order from Percent Yield?
Referencing this paper, I am trying to approximate the order of reaction for cyclohexane (4a). Trials 1-3 provide the relevant information of mmol changes and corresponding percent yield but I'm ...
5
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2
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563
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Does Grignard reagent on reaction with PbCl2 give PbR4 and not PbR2?
I was told by my teacher that $\ce{RMgX}$ forms $\ce{PbR4}$ when it reacts with either $\ce{PbCl2/PbCl4}$ the later case is clear to me but why does $\ce{PbCl2}$ forms a compound of the form $\ce{PbR4}...
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Does heating 3-phenylpropionic acid decarboxylate it?
Here, when P is reacted with $\ce{SOCl2}$ and then NaCN to give 3-phenylpropionitrile and then hydrolysed to give 3-phenylpropionic acid. Why shouldn't it further decarboxylate and dehydrogenate to ...
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206
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Different types of bond representations [duplicate]
What do the following different kind of bonds mean?
Although this answer to the question "What are the meanings of dotted and wavy lines in structural formulas?" does describes some of the ...
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150
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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 (1-Ethyl-3-(3-dimethylaminopropyl)...
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1
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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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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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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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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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2
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270
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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 ...
- 2,205
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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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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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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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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 ...
0
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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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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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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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How much can we extend the Finkelstein reaction?
Finkelstein reaction explicitly entails the conversion of an alkyl chloride or alkyl bromide to alkyl iodide by treatment with sodium iodide in acetone.
$$\ce{R−X + NaI→[acetone] R−I + NaX↓ }\\
\ce{(X$...
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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?
0
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Why the common name of 1,2-dichloro-ethane is ethylene dichloride if it has no double bonds in it? [duplicate]
Why the common name of 1,2-dichloro-ethane is ethylene dichloride if it has no double bonds in it? The -ene in the common name suggests that it should have a double bond. I believe this is due to the ...
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polymerized Dimethylbutadiene or "methyl rubber"
"Methyl rubber", polymerized Dimethylbutadiene, is the first synthetic rubber, but it falls behind polyisoprene having inferior shear strength & oxidizes more easily.
I'm looking into ...
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1
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111
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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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For radical polymerization reactions, azobis(isobutyronitrile) (AIBN) can also be used as a radical initiator
Draw the mechanism of radical formation if you know that N2 is formed as a by-product.
The solution they give us is
I know what radical polymerization is. The free electron of a molecule binds with ...
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How to proceed with iodometric titration to determine caffeine concentration in liquid coffee?
Context
I'm a high school student who decided to investigate the relationship between caffeine concentration and brewing temperature of coffee out of their love for the substance. For my method, I ...
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Valence, Variable Valence, and Valency
As per the latest IUPAC Compendium of Chemical Terminology, informally known as the "Gold Book", the terms valency or variable valence are not defined; however, valence is defined as:
The ...
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Are the anomeric hydroxy groups of α-maltose and β-maltose, axial or equatorial, respectively?
This Q&A is a continuation from the following Q&A;
What do we get when we joint two α- glucoses via an α1,4 bond?
More straightforwardly, the question may focus on whether the bond represented ...
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Does resonance stablization of carbocation increase ease of $\ce{S_N1}$ reaction or decrease it due to delocalization?
(A)
(B)
In both of the cases when a nucleophile approaches for $\ce{S_N1}$ reaction a carbocation is formed in place of $\ce{Cl}$ atom. I know that the rate of $\ce{S_N1}$ increases with increase in ...
3
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What do we get when we joint two α- glucoses via an α1,4 bond?
What do we get when we joint two α- glucoses via an α1,4 bond?
Is it alpha maltose or beta maltose?
In other words, if we cleave amylopectin with amylase (α-amylase or β-amylase), which form of ...
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Which group takes CIP priority CH2OH or CH2OCH3?
I am confused why this structure is (2R, 3R) when CH2COMe takes priority over CH2OH which takes priority over CH3, surely it should be (2S, 2R)?
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Does nitration of phenol with nitric acid yields 2,6-dinitrophenol?
I've learnt that the $\ce{OH}$ group is 2- and 4-directing, but this has caused some confusion. If $\ce{HNO3}$ reacts with phenol, would there be any 2,6-dinitrophenol produced?
I know that the first ...
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Why does silver have more affinity for chlorine and bromine rather than fluorine in Swarts reaction?
Why do silver and other metals used in Swarts reaction $(\ce{AgF},$ $\ce{HgF2},$ $\ce{CoF2},$ $\ce{SbF3})$ have more affinity for chlorine and bromine even though fluorine is more electronegative?
$$\...
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1
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Doubt in chirality and pseudo chirality
So a carbon atom is chiral if it has 4 different group attached to it, and it is pseudo chiral if it has 3 different groups of atoms attached to it, where the 2 similar groups have different ...
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Possibility of carbocation rearrangements in SNi reactions
According to several sources, the $S_{N}i$ reactions follow a mechanism allowing carbocation formation while others disagree. Precisely, for example, according to A Guidebook to Mechanism in Organic ...
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NMR and dienes to isolate certain isotopes?
I am looking to achieve isotope separation using transition states.
In the rxn of dienes with halogens, based on the temperature, the dienes can create a thermodynamic product or a kinetic product. ...
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Can alkyl groups show -I effect?
Inductive effect is the partial shifting of the sigma-bonding electrons towards more EN (take as electronegativity or electronegative in this text) atom so why we will say that alkyl groups will ...
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Is dimethyl amine a sigma-donor or acceptor or pi-donor or acceptor? [closed]
I would argue that the $\ce{-NMe2}$ is a $\pi$-donor because the nitrogen atom has an unbound pair of electrons. At the same time it is a sigma-donor as the two methyl groups are good sigma donors. Is ...
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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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Why is the phrase "abstraction" used in radical reactions? [closed]
Often, I see the phrase "abstraction" used to describe certain radical reactions. Why is this specific term "abstraction" used in the case of radicals? This may be more of a ...
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By what mechanism does amylase catalyze hydrolysis?
I've recently been learning bits and pieces of starch metabolism, and am wondering if anyone could explain exactly what is going on when alpha or beta amylase "cleaves" the 1-4 glycosidic ...
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How do I make this terminal alkyne into a methyl alkene on the third carbon?
How do I get from but-3-yn-1-ylbenzene to (3-methylbut-3-en-1-yl)benzene? I have tried $\ce{NaNH2}$ in $\ce{CH3Br}$ and then $\ce{H2}$ with a Lindlar catalyst, but that adds the methyl group at the ...
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How do I reduce this ketone to two double bonds on the carbo chain?
What reactants should I use to get from 1,5-diphenylpentan-3-one to ((1E,3E)-penta-1,3-diene-1,5-diyl)dibenzene (picture for reference)? Either in 1 step or in multiple steps. I have tried $\ce{NaBH4}$...
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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-...
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Is neo-octane possible and if yes, what is its structure? [closed]
I know iso-octane is an exception and is 2,2,4-Trimethylpentane which intuitively contains both iso and Neo groups. But then what is the structure of neo-octane or even is it possible?
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What could be the origin of a persisting distorted water NMR signal?
I am currently running some solvent suppression experiment on water samples. I first run a one scan 1H experiment to get the ''O1P'' and then implement it in the solvent suppression experiment (''...
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HPLC Solubility vs polarity
According to this data collected from PubChem, polarity of nitrobenzene and benzonitrile should be similar since solubility is dependent on the polarity:
Nitrobenzene: Solubility in water, 0.2 g/100ml
...
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Mechanism of Denigés' test?
According to Wikipedia, Denigés' test detects tertiary alcohols through their dehydration, marked with a colored precipitate. The reagent itself is some form of aqueous mercury(II) sulfate. My ...
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How do we synthetis a peptoid from beta-Alanine?
I did a reaction that contains 4 steps described in this picture :
I understood that this 3 steps helped me to synthetis the NGlu part but I don't know why did we do alkylation ? It can't be a ...
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