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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Reactivity of meta and para xylene towards nitration

Is meta xylene more reactive towards nitration or is it para xylene? I would say it is meta xylene as it has two methyl groups meta to each other. Since both are activating groups, there would be a ...
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[3+1]-Cycloadditions of Sulfur Ylides and 1,3-Dipoles(?)

My question is basically regarding the stereoselectivity of the situation. I am not being able to decide on the positioning of the sulfur ylide with proper justification. In the attached hand-drawn ...
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On baker nathan hyperconjugation

Recently I have been reading about the history of the Baker Nathan reaction. In addition to the large rate increase for Me vs H, all the other alkyl groups showed decreases with respect to Me ...
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How does Lindlar's catalyst work?

I can not find a mechanism online. I understand that some poisoning effect causes the catalyst to be unable to reduce an alkene to alkane; however, if the catalyst is poisoned, how does it continue to ...
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Hammett plot shape: dependent on substituent or mechanism?

So, we were shown a Hammett plot that, on the left was linear, but on the right was concave up. How would I explain the shape of the Hammett plot? Does it depend on whether the substituent is an EDG ...
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Oxidation of dihydropyridine

This is a step in a experiment I have carried out. Usually DDQ (dichlorodicyanoquinone) would be used here to oxidise the dihydropyridine. However in this case Nitric Acid is being used as the ...
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520 views

Sodium Naphthalenide

The sodium fusion test done in the lab for the systematic identification of a given organic compound is basically fusing sodium metal in a fusion tube, and then adding the compound in a small quantity,...
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640 views

Experimentally proving the mechanism and rate laws of SN1 & SN2 reactions

I have been given the task of experimentally proving the rate laws and mechanisms of $\mathrm{S_N1}$ and $\mathrm{S_N2}$ reactions. Unfortunately, the only equipment I can use is limited to analytical ...
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Why doesn't beta hydride elimination happen in alkenyl/aryl halides?

Beta hydride elimination is an important reaction in organometallic chemistry: This reaction prohibits the use of saturated alkyl halides in coupling reactions, because it can take place after ...
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Stability of unsaturated syn/anti 3-ladderane

In an oral exam for physical organic chemistry, one student was asked to explain the differences in the ionization potential ($IP$) of syn and anti tricyclo[$4.2.0.0^{2,5}$]octa-3,7-diene (unsaturated ...
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Regioselectivity of the Beckmann rearrangement

It seems to be that the Beckmann rearrangement is a nice way to prepare secondary amines. This can be achieved by removal of oxygen via the use of $\ce{HI}$/$\ce{P}$. However, if ketones are used, ...
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Molecule analog similar and commercially available

I wanted to carry out some experiments on the following molecule: Unfortunately this molecule (santalene; either isomer will do) seems neither commercially available nor easily synthesizable. Hence ...
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Benzyl (3,4-difluorophenyl)carbamate reaction with epoxide in basic conditions

I attempted this mechanism, however I am uncertain if I am correct.
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IR spectra and melting point range comparison

I did a Diels-Alder experiment in lab, and the desired product was 9,10-dihydroanthracene-9,10-α,β-succinic anhydride. According to my IR spectra, I believe I isolated the product. However, my ...
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An alternate purification process for sugar separation form bee honey?

Bee honey contains 75% sugars (Fructose, Glucose, Maltose, Sucrose and others), some water and low amount of different compounds (up to 5%) Wiki. Basic purification is done by addition of phosphoric ...
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Why doesn't 1-cyclopropylethyne give a positive reaction in the bromine-water unsaturation test?

1-cyclopropylethyne has a triple bond: Hence it seems like it should yield a positive unsaturation test with bromine water. But, my book states that the opposite is true. I guess this may be due to ...
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Oxidation of alkenes by selenium dioxide to diketones

I know that $\ce{SeO2}$ readily affects the allylic position. The reaction mechanism of this reaction goes like this: (Source: Wikipedia; License: Public Domain) But, in my book, there's another ...
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288 views

Why don't we have hyperconjugation with C-C bonds?

C-C bonds are weaker than C-H bonds.So why is hyperconjugation with C-C bonds not possible?
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What causes the yellowing of the linear alkylbenzene (LAB) cocktail?

In our lab, we use the liquid linear alkylbenzene (LAB) cocktail mixed with 2g/L 2,5 diphe-nyloxazole (PPO) as the organic scintillator for radiation detection. The new LAB cocktails are stored in the ...
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260 views

Does alcohol hydrogen in the enol tautomer of a β-dicarbonyl have sp² character?

My reasoning for the somewhat implausible "$\mathrm{sp^2}$" character of the hydrogen between these two oxygens on the enol structure of the right comes from recognizing that if it were, then we would ...
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343 views

Why does RCN attack the benzene ring in Hoesch Reaction?

In the Hoesch reaction, an alkyl cyanide reacts with a polyhydric benzene ring, and forms an imine salt by attacking the activated benzene ring. Most acid derivatives (and even alkyl cyanide itself ...
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780 views

Is the para-position of anisoles more reactive than ortho in electrophilic substitutions?

In my group’s seminar last Friday, we discussed the total synthesis of 6-demethyl-6-deoxytetracycline 1 by Woodward et al.[1] One intermediate of their synthesis is meta-substituted anisole 2 that ...
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109 views

Ene-yne metathesis product

In the ene-yne metathesis how to know which product will form predominately, as the mechanisms to both are plausible?
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178 views

Phosphorus and Boron groups

I know some sulfur groups such as sulfones and disulfides and sulfonic acids. I also know of 1 phosphorus group. That is the phosphate ion. I don't know of any boron groups. What is the phosphorus ...
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573 views

degradation of sertraline

The picture above is a drug called Setraline. Suggest a likely mode of degradation of sertraline hydrochloride alone in aqueous solution, giving likely structures of the degradation products. From my ...
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How do popular reducing agents react on compounds that have ester, carbonyl, and unsaturated functionalities?

Suppose we have a chemical compound like ethyl 4-oxo-2-cyclopentene-1-carboxylate It is $\ce{-COOC2H5}$ bonded to a five-membered carbon ring with one double bond and the ring has another carbonyl ...
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Identifying the structure of an amino acid from NMR spectra

I have the 1H, 13C, and DEPT spectra of an unknown compound, listed in text form below, but I have also attached original images of the spectra. I know that it is an amino acid that has a cyclic ...
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145 views

Auto ignition of tert-butyl mercaptan mixed with mineral oil

I am designing an experiment that involves immersing pieces of pipe lining in a mixture of tert-butyl mercaptan (2 %) and white mineral oil (98 %) at 230 °C (the standard temperature for the test). If ...
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274 views

What is the average chain length of a glutaraldehyde crosslink between primary amines?

Imagine I'm performing a primary amine to primary amine (i.e. PA to PA) crosslinking reaction at $37~^{\circ}\mathrm{C}$ in phosphate-buffered saline (pH $\approx 7.4$) with glutaraldehyde drawn from ...
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190 views

Does presence of alkyl groups on alpha carbon increase yield of alkane in Kolbe's Decarboxylation?

We know that, during the synthesis of alkanes by Kolbe's Decarboxylation reaction, the reaction proceeds via a free radical $\ce{R.}$ at the anode. So, an alkyl group, say methyl, when substituted at ...
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89 views

Terminology for “proton stripping”?

This is going to probably be an easy question for an organic chemist, but I am looking for the proper terminology to describe the following reaction mechanism. In particular, what is a more precise ...
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2answers
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Nucleophilic nature of ions

Consider the following species: $$ \underset{(\text{A})}{\ce{\overset{⊖}{O}H}} \quad \underset{(\text{B})}{\ce{CH3-\overset{⊖}{O}}} \quad \underset{(\text{C})}{\ce{\overset{⊖}{C}H3}} \quad \...
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Determining the stereochemistry of the product(s) when an alkyl shift in a carbocation generates a chiral carbon

Consider this carbocation: We know that this carbocation would immediately rearrange - by a methyl shift - to form the more stable carbocation. Now, notice that the migration will produce a chiral ...
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What are the parameters of protonation of a molecule?

Adding an acid replaces the $\ce{-MgBr+}$ with an $\ce{H+}$. Why does this happen? Is $\ce{H+}$ a better electrophile than $\ce{MgBr+}$? Or, to put it another way, why doesn't $\ce{MgBr}$ stays ...
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Why are acid catalysed reactions of carbonyl compounds reversible?

I am currently studying aldehydes and ketones and their reactions. I've noticed that acid catalysed reactions are represented with reversible arrows, while base catalysed reactions are shown with ...
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Reaction of alkyne with sodium in ethanol

What is the product obtained on the reaction of but-2-yne with $\ce{Na}$ in ethanol? I know that $\ce{Na}$ in liquid $\ce{NH3}$ converts an alkyne to an alkene by anti addition, and $\ce{Na}$ in ...
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Staggered Conformation Classification

I was working on an assignment I had a question about conformations of a molecule about a single bond. Given a random molecule like this with multiple large substituents on one side of the $\ce{C-C}$ ...
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Does optical isomerism fall under the category of stereoisomerism?

I have been asked to find the total number of dichlorination products (including stereoisomers) for the following reaction: I have figured out nine possible structures out of which two are optically ...
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What is the structural formula of a monomer of hydroxypropyl methylcellulose?

I'm studying the properties of the polymer hydroxypropyl methylcellulose (HPMC) with the static scattering technique. I'm trying to interpret the molar mass obtained with a Zimm plot, that is $\pu{(3....
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Does β-hydride elimination in main group metals occur?

As a side reaction of Grignard reagents, the following reaction is introduced on the Internet. I think this is β-hydride elimination reaction, but magnesium is a main group metal, not a transition ...
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What happens when tran-2-butene reacts with aqueous bromine in the presence of chloride?

$\ce{Br2-H2O}$, containing some $\ce{NaCl,AlCl3}$ ? I initially though that there would be anti addition of Br and OH to give 3-Bromobutan-2-ol but then I also got the intuition that NaCl might ...
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Stability of a carbanion that is attached to three phenyl groups

I had come across a question - which asked me to predict the stability of a carbanion attached to 3 phenyl rings, in opposed to one in which the same 3 phenyl rings that are attached to the carbanion ...
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Adsorbable Organic Halides (AOXs) in bleach residue

I have a question regarding using household bleach, and wonder if someone knowledgeable can help, please? I have used household bleach (sodium hypochlorite, sodium hydroxide, coco alkyldimethyl, ...
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Differences in AChE inhibition kinetics between VX and VR

According to the referenced paper, VR has an AChE inhibition reaction rate constant almost 4 times that of VX. Interestingly, its reaction rate constant for aging of the enzyme is less than that of VX,...
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Stereochemistry of the product of crotonic acid with bromine

Is there a a simple rule for determining the stereochemistry for the product of a reaction between an unsymmetrical alkene like (2E)-but-2-enoic acid and bromine (anti reaction)? If it's an anti ...
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Comparing of melting point of dibromo p-xylenes

How to compare the melting points of the above isomers? I know that melting point depends upon the packing of the molecule, more efficient the packing, higher is the melting point. Symmetry in a ...
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Why do nitrogen-containing organic compounds give N2 as the combustion product?

My teacher gave the explanation stating that consider that first the nitrogen in lower state is oxidised to $\ce{N2}$ and then the further oxidation would stop as the $\ce{N-N}$ bond energy of $\ce{N2}...
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What's the chemical reaction between NaOCl and Brilliant Blue dye?

Based on my research NaOCl dissociates into Na+ and OCl-. Looking at the photo, how does the OCl- ion and the brilliant blue dye structure end up as the product? How does the OH attach itself to the ...
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In aldehydes with an alkene substituent, what conditions favor Wolff–Kishner reduction over Clemmensen reduction?

This module I am answering asked me to provide a reason why Wolff–Kishner reduction is favored over Clemmensen reduction in reducing (3Z)-pent-3-enal to (2Z)-pent-2-ene but either Wolff–Kishner or ...
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What are the compounds in oxygen and carbon dioxide indicator solutions that gives their color?

My brother had some leftover oxygen and carbon dioxide indicator solution for one of his take-home experiments from school, so he let me have them. I want to use them for an experiment and write out ...

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