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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Cyclopentadiene planar
Cyclopentadiene has a sp3 carbon yet it is said to be planar. I am not able to understand and haven't been able to find a credible source. Some sources say it to be non-planar
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Why does a hydroxyl group decrease the acidity of an Aromatic ring?
We are currently learning about resonance and induction, but I am confused why the addition of the hydroxyl group increases the pKa. As oxygen is more electronegative, should it not increase the ...
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Why does alpha-carbon substituents increase the rate of E2 reactions?
The reason for more reactivity of more substituted alkyl halides for E2 Reaction is said to be due to the more stability of its more substituted alkene character having transition state but here (...
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How does a pyrrole react with its C2?
First of all, thank you for reading my question. There is a mechanism I read where the pyrrole reacts with its C2 but I can't draw the arrows so I don't know if I am correct to think that :
the ester:...
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Does a slippery liquid leak through pipe fittings?
We use a 6% potassium hydroxide (KOH) solution for electrolysis. This solution is known to be "slippery". Does this mean that it will leak/seep through NPT pipe threads more than plain ...
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Lithium aluminium hydride
Lithium aluminium hydride is an important reducing agent in organic chemistry.
Since I cannot find the half-equations telling how this reducing agent performs its action, I am wondering, is lithium a ...
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Standard electrode potentials
I know that many substances have their own standard electrode potential and they can be arranged in he electrochemical series. For example, the standard electrode potential of iron is -0.440V.
Since ...
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Alcohols and bromine
As far as I know, bromine can act as an oxidising agent. But when propan-1-ol is mixed with bromine water, there is no reaction.
Why bromine cannot oxidise alcohols? Is the reaction available if a ...
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Solubility of esters
In my chemistry test, I was asked whether methyl ethanoate, CH₃COOCH₃, is a soluble compound.
The result turned out that methyl ethanoate is actually insoluble. Based on my research, the solubility of ...
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Hydroxyl-Terminated Polybutadiene Structural Formula
Anyone know why there are parentheses and brackets in this skeletal formula? Also wondering if this representation gives a full chemical formula, or just the structure of a repeating hydrocarbon chain?...
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<CNH Bond Angle in Acetamide [duplicate]
For context, I'm a student who is new to organic chemistry. I recently came across a question which asked me to determine the C-N-H bond angle in acetamide:
My answer was <109.5°, since the ...
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Clear polystyrene bottle holder repaired with butyl acetate glue. Is it safe to use in the fridge?
I've successfully repaired my fridge's bottle holder, which is made of clear polystyrene, using butyl acetate glue.
While the glue smelled at the time I was gluing, the repaired bottle holder no ...
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Can Acyl halides react with PCl5, if not, why?
I was searching for reaction of $\ce{PCl5}$ with carboxylic acids and found this mechanism:
Here a corresponding acyl chloride is formed from a carboxylic acid.
Now I doubt if this is the final ...
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Does lime juice "alkanize" in the body?
My brothers and I have a dispute. They claim lime juice alkanizes in the body. I contest as an acid it remains acidic in the body. My guess is they are confusing "lime water" with "...
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Steric inhibition in resonance (Ortho Effect)
Does Steric inhibition of resonance occur in case of Benzene sulphonic acid (Ph-SO3H)? If not , then why? As So3H itself is bulky group then on attaching group like methyl on its ortho must cause ...
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The exchangeable NH proton in H NMR [closed]
Can the exchangeable proton NH in H NMR appears but not as singlet peak when DMSO is the solvent
And if yes, is that related to the hydrogen bonding that may occur with my compund that contains NH and ...
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Reaction of eugenol with concentrated hydrobromic acid in the presence of gaseous hydrogen bromide [closed]
DISCLAIMER: I am not using any of this information to commit a crime, my university has a license from the relevant authorities to investigate clandestine chemical procedures.
We are investigating an ...
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NH exchangeable proton in 1H NMR [closed]
I need an explanation please in my 1H NMR, my compunds' scaffold is quinazoline ring with 2 substituents that have sometimes 1 or 2NH exchangeable protons and they are both aliphatic, they should ...
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Why having a carbonyl group is not contributing to binding energy
I am carrying out a virtual screening project for a protein receptor to identify possible ligands (small molecules). After the virtual screening, molecular dynamics, and MMGBSA calculation, I ...
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What mechanism do reaction of PCl5 follows, SNi or SN2?
I was taught that $\ce{PCl5}$ reacts with alcohols by $S_Ni$ mechanism as shown below:
Here it can be seen that $\ce{PCl5}$ exists as $\ce{[PCl4]+[PCl6]-}$ and so lone pair of the alcohol is donated ...
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Avoid triethylphosphate as a side product during P-C-P coupling reaction with diethylchlorophosphate with LDA
I have a reaction in which I perform a deprotonation of an acidic proton at a phosphate and later do a P-C-P coupling. The coupling partner is diethylchlorophosphate. Deprotonation is performed with ...
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Stereoselectivity in catalytic hydrogenation
Why is cis stereo selectivity is observed in this case? See image below.
I can't think of any reason why cis addition is major.
In my opinion, the ratios should be opposite because of easier ...
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how can a chemist detect the element boron in a sample of ordinary dust?
After the world trade center attack 22 years ago, the USGS sampled dust from the world trade center site and from lower Manhattan. They tested for every solid element except boron. I'm curious about ...
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Would having a greater H-bond donor count make a substance more readily enter a twig?
Yes, weird plant scientist asking weird plant questions...
Background:
I am looking at how the twigs of trees absorb water, a poorly understood means by which trees alleviate water stress. Of 4 ...
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Why is m-fluorophenol less acidic than m-chlorophenol?
Why is m-Fluorophenol less acidic than all the other m-Halophenols, even though it has the most inductive effect
The data is from :
A guidebook to Mechanism in organic chemistry for the JEE, 6th ...
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Formalin as a hydrogenating agent
According to an article from 1917, formaldehyde and water (presumably in the form of methylene glycol CH2(OH)2) react with methylene imine, reducing the imine to an amine as formaldehyde is oxidized ...
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Comparision of Lucas reagent test for neopentyl alcohol and ethanol
Why is it that neopentyl alcohol reacts faster to give turbidity in Lucas reagent test (HCl + anhydrous ZnCl2) as compared to ethanol?
Even though ethanol is a primary alcohol with 3 alpha hydrogens ...
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How does tBu2Si(OTf)2 react in uridine in DMF at 0°C
I have to write the mechanism of a four steps reaction that aims to transform uridine into a deoxythymidine by following these steps :
(tBu)2Si(OTf)2, DMF, 0°C
ClCSOPh, DMAP, 20°C
AIBN, Bu3SnH, 80°C, ...
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IUPAC nomenclature of a molecule contain polyene and polyyne [closed]
I'm thinking a complicated hydrocarbon containing many double bond and triple. What if the longest chain does not contain double bond and triple bond, how to name this? Alkene and alkyne which one ...
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How does polarity increase when electron density in oxygen decreases when comparing acidity
My book says the following statement:
Due to the higher electronegativity of $sp^{2}$ hybridized carbon of phenol , the electron density in oxygen decreases. This increases polarity of O-H bond and ...
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How many number of major contributing resonance structures are there of 1,3-butadiene-1-ol?
I am confused if there are 4 or 3 majorly contributing resonance structures of 1,3-butadiene-1-ol .If there are three then I wanna ask that wouldn't the terminal pi bond also do resonance with middle ...
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Why is it okay for the central carbon to lose a bond when forming a resonance structure for acetone?
As the title reads, I'm confused as to why it's okay for the central carbon in acetone to have a +1 formal charge when we push the electrons from one of the bonds with oxygen to form a lone pair and ...
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Glycerol's reaction with excess HI
In this scheme, why allyl iodide reacts with HI to get iodine on central carbon atom?
In my opinion it should be on 3rd carbon as in its mechanism carbocation is formed and CH3I is electron ...
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What will be the product if ethane reacts with SO2?
At first I thought it was Reed's reaction but then I looked up the reaction and the reactant was actually $\ce{SO2Cl2}$ (sulfuryl chloride).
I couldn't find the product which would be produced when ...
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Formation of cocrystals troubleshootin
In cocrystal formation what would the possible reason be for the precipitation of an amorphus oily precipitate not suitable for PXRD? Solvent was DMF and the reagent were L-thyroxine and ...
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What is the major product on mono chlorination of 2-methypentane?
I understand that mono chlorination of 2-methylpentane are :
My Question is : How can you determine the major product from those results ?
The probability of monochlorination of :
Amount of 1-chloro-...
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Make ethanol with sourdough [closed]
I have seen a lot of videos on internet and to make ethanol they ferment sugar with yeast but is it possible to ferment sugar using sourdough ?
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Conformational analysis [closed]
In organic chemistry, much emphasis is given to the study of the conformers of alkanes and the broader topic of conformational analysis. Can you elucidate why the spatial arrangements and rotations ...
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Neopentane melting point [duplicate]
Given that neopentane and n-pentane are both hydrocarbons derived from pentane with five carbon atoms each, but differ in their structural arrangements — with neopentane being more branched and n-...
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Ring Expansion in dimethylcyclopropane carbocation
I was taught in my class that ring expansion occurs in dimethylcyclopropane carbocation which forms methylbutane carbocation. The reason the teacher gave to us was that the ring expansion + the 3 ...
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1,2,4,5-tetrasubstituted cyclohexane stereoisomers
What is the best way to teach the number of stereoisomers in highly substitued cyclohexanes? For example, a 1,2,4,5-tetrasubstitued cyclohexane?
If I take for example 1,2,4,5-tetrachlorocycohexane, we ...
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How are conformational isomers different form optical isomers? [duplicate]
Optical isomers seem to be a result of rotation about one or more than one combination of single bonds (represented in fischer form).
Are they then a special case of conformational isomerism?
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Acidic Strength comparison
I wanted to compare the acidic strength of aniline and water.
Water on losing hydrogen gives $OH^-$ and aniline on releasing H gives $\ce{Ph-NH-}$ and this -ve charge goes into resonance so the -ve ...
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Why is there difference in reactions in alcoholic and aqueous medium while both are polar protic solvents?
We use an alcoholic medium for reactions in which we want to prevent the characteristics of the anionic species and an aqueous medium for the reactions in which we want to control the activity of the ...
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Retinal 11-cis-retinal to all-trans induced by photons
In the reaction involving conversion of 11-cis-retinal to all-transform, why does the isomerization specifically occur at the 11th carbon in the molecule? When reforming the broken pi-bond, why wouldn'...
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Are Starch, Amylose and, Amylopectin reducing sugars?
Amylose and Amylopectin;
As per the information I've learnt, Amylose is considered a reducing sugar but Amylopectin is not because Amylose has a free "reducing end" which Amylopectin lacks, ...
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2
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Calculation of the retained mass after hydrolysis of an oligopeptide
I would like to ask about a problem that I am stuck on:
An oligopeptide is made up of glycine, alanine, and valine. Hydrolysis of X in $\pu{500 mL}$ of $\pu{1 M}$ $\ce{H2SO4}$ solution yields ...
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Integration of Artificial Intelligence in Chemistry [closed]
How is Artificial Intelligence impacting the design and discovery of new compounds and medications?
Given the rapid advancements in artificial intelligence and machine learning methodologies over the ...
user137106
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Study of superconductivity from organic compounds
What advancements have been made in understanding and applying organic superconductor materials?
Although traditionally superconductivity has been studied in inorganic materials, are there any organic ...
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Knoevenagel reaction in acidic condition
I read the supporting information of an article today. And it says that ketone can react with malononitrile in acidic conditions (acetate acid and ammonium acetate). Can anyone provide me with the ...
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