Organic chemistry is a branch of chemistry that deals with organic molecules. Organic molecules generally have C-H or C-C bonds.

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Limiting Reagents [duplicate]

in this example why LiC4H9 is the excess reagent
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Concerted hydride and alkyl shifts

I noticed while looking through a couple of books (specifically, Wade, Carey, and Vollhardt/Schore) that the mechanism of concerted hydride and alkyl shifts is always shown with alcohol leaving ...
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How to find the molecular formula for a hydrocarbon compound from known combustion products?

What is the molecular formula of a compound containing only carbon and hydrogen if combustion of $1.05~\mathrm{g}$ of the compound produces $3.30~\mathrm{g}$ $\ce{CO2}$ and $1.35~\mathrm{g}$ ...
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Method of allylic and benzylic oxidation

I am told that $\ce{MnO_2}$ oxidizes allylic and benzylic alcohols. However, what is the mechanism of this oxidation? All the professor had to offer me was that the metal ion, manganese 2+, chelates ...
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How does Temperature influences the rate of protein turnover?

A very similar question I asked can be found here. It seems that this other question as I formulated it has a hard time attracting answer, so I'm giving another try with a slightly different question. ...
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How to interpret the MSDS warning?

Just a quick question; I was looking up the MSDS for o-Toluic Acid for an experiment when I came across this in the "Hazards Identification" section. ...
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Simple experiments involving enantiomer synthesis

I want to do an experiment to investigate factors affecting the synthesis of chiral molecules. The only problem is, my institution doesn't have much money, and it seems like the chemicals required for ...
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How could the pH of this solution rise instead of fall when exposed to the atmosphere?

I have a couple of big barrels with a 50L demi-water solution of the following nutrients: $$ \begin{array}{rl} 200~\mathrm{\mu M} & \ce{NH4NO3} & +\\ 30~\mathrm{\mu M} & \ce{KCl} & ...
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Does the iodoform reaction form hydrogen iodide or water?

I am currently learning about the iodoform reaction, i.e. when CH3COR compounds react with iodine and sodium hydroxide to form iodoform. My course book and Chemguide both says that the reaction is as ...
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Proton affinities in machine readable format?

Short: How to get proton affinities for a large list of chemicals? A database? A programming API? Longer: I have ca. 2000 chemicals (downloaded from MCM, mostly organics that occur in the atmosphere ...
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Carboxylate “cage” concept

My professor emphasizes the concept of the carboxylate "cage" or the idea that electrons participate in resonance within a carboxylate group such as in the benzoate anion but the electrons in the ...
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1answer
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Carbonyl carbon electropositivity?

Is the carbon in a carbonyl functional group electropositive? I had a professor tell me so, but I immediately refuted him, because he defined electronegativity earlier as the ability to stabilize ...
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1answer
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Free rotation of sigma bonds; diastereomer formation; thermodynamic and kinetic products

For the reaction of 1,3-butadiene with DBr (D = heavy hydrogen), I found that several possible products could be formed. Kinetic products A pair of enantiomers is formed. One of the pi bonds ...
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Does Carbon dioxide smells “cold” [on hold]

It may be a strange question. But, whenever I smell my roasted coffee,the air in the alloy smells "colder" than the air in the kitchen. Is it due to $\ce{CO2}$ degassing in the first days after ...
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Dipole moment of cis-2-butene

I need someone to back me up on this before I go confront my teacher: I was doing some analysis of the dipole moment of cis-2-butene. Let's say that the alkyl groups are both on top. Would the dipole ...
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1answer
142 views

Difference between polyethene and polyethane

The monomer in polyethene seems to drop the C=C bond and end up with a C-C bond. The polymer chain then looks like [CH2-CH2]n. If I were to look at that polymer chain I would probably call it ...
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Sodium metal reduction of chloroform

In discussing how best to deuterate chloroform, it occurred to me that we could use sodium metal to reduce hydrogen into hydrogen gas. If this could actually happen, this would be a great thing - we ...
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can't predict IUPAC name of this compound, seems i am missing some concept of nomenclature here

I am talking by keeping the below diagram in my vision. This compound on elaborate elongation would result in this structure. But is the below given numbering correct? I am just dubious that ...
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Steric effects of a lone pair and piperidine

I know that in piperidine, the lone pair on the nitrogen can occupy either an axial or a equatorial position in the two chair forms. I also read that the axial position for the lone pair is preferred ...
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Is Sodium metal more reactive towards an alkyl halide or an alcohol in a protic polar solvent?

Will Sodium metal donate its electrons to bromine in 1,3-dibromopropane or to the hydroxyl group in ethanol in a polar protic solvent? This question comes from a problem: 'What is the major product ...
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Finding rf value of methyl benzoate

What is the $R_f$ value of methyl benzoate and 3 nitro methyl benzoate in hexane and ethyl acetate?
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Conversion of Propane to Methane

I have a problem with this conversion. It was asked in a text book. The basic idea was chlorination in presence of Sunlight however two products are obtained in this case namely 2-chloro-propane and ...
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2answers
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Formation of 2,4-Dichlorophenol by free chlorine mediated oxidation of Triclosan

I cannot find much guidance in the literature. This is the reaction between free chlorine in water and triclosan. I understand ether cleavage and electrophilic aromatic substitution (maybe) involved. ...
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Is there any replacement for ethyl mercaptan in LPG?

Ethanethiol,commonly known as ethyl mercaptan,is a colorless gas added to LPG inorder to detect its leakage. My question is: Apart from "ethyl mercaptan",is there any gas or liquid, which may be ...
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How to determine number of structural isomers?

I have come through many questions in which they ask to give number of possible structural isomers. For example number structural isomers of hexane is 5, while number structural isomers of decane is ...
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Influence of Temperature on Biochemical Reactions

Short question How (quantitatively speaking) does temperature influences rate of decay of proteins? I am looking for some general number/function, the influence of temperature on an average protein. ...
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Acidities of amines and carboxylic acids

I have been told that the first of the two acids is the stronger acid. According to this person,deprotonation for both occur at the nitrogen.The resulting conjugate bases include,respectively a ...
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Basicities of meta-nitrophenoxide and para-nitrophenoxide

The negative oxygen is the site of protonation. Size and EN are the same for both oxygens. We are mainly looking at resonance (and possibly inductive) effects here. We want the least resonance ...
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What has stronger antioxidant potential: BHT or BHA?

Butyl Hydroxy Toluene (BHT) has two tert-butyl groups that can stabilize a free radical. Butyl Hydroxy Anisol (BHA) doesn't, though it has the 4-substituted methoxy group (I'm not sure what that ...
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Index of Hydrogen Deficiency for para-Toluenesulfonylchloride

In para-Toluenesulfonylchloride, there are 5 pi bonds and 1 ring. This suggests a IHD of 6. However, the actual IHD is 4. How come? Is it because the formula IHD = rings + pi bonds does not apply to ...
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Is trans-2-butene IR active with regard to its C=C bond?

To be IR active, the vibration of a bond must result in a substantial change in dipole moment. Since trans-2-butene is symmetrical, will the C=C stretch show up on IR? Something tells me no because ...
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Synthesis of 1-hexene from 1-octyne

This is my synthetic pathway. For one, is it plausible? For another, is it efficient? 1) Reduction of 1-octyne with hydrogen gas and Lindlar's catalyst to 1-octene. 2) Oxymercuration to install a ...
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Chemical structure of water-soluble polysaccharide

I don't know much about analytical chemistry, but I need to determine the chemical structure of a water soluble polysaccharide which is not pure and may have D-glucose, mannose and fructose. How do I ...
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Equivalents of chromic acid in oxidations

How many equivalents of chromic acid are needed to oxidized a primary alcohol to a carboxylic acid? A secondary alcohol to a ketone? I understand that the chromium starts with a +6 oxidation state. ...
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Ionic Character

Can ionic character also be construed as a poor sharing of electrons rather than simply as the taking of electrons? For example, NaCl is ionic, and that's because the chlorine takes sodium's one ...
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Triple Bond Character in Acyl Chlorides

I am told that because of the poor overlap between a chlorine atom and a carbon atom and chlorine's relatively high electronegativity, there is a strong partial positive character on the central ...
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2-methylpropene to tert-butyl alcohol Reaction Mechanism

Can someone explain what reaction is going on here? I looked in my list of mechanisms learnt: I find nothing related!
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Regioselectivity of Birch reduction (electron donating groups)

Why does Birch reduction on benzene derivatives with an electron donating group happen at ortho and meta positions? When the substitute is electron withdrawing, ipso and para reduction take place ...
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Can in any case the faster step of the reaction be rate determining?

I found a sentence in book which states the reverse step of this reaction ( I forgot what was it!) has the faster step as rate determining . Even Rate determining step-Wikipedia states: In ...
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Are phenylboranes susceptible to ipso or meta substitution?

Are phenylboranes susceptible to ipso or meta electrophilic aromatic substitution, i.e. what's the regioselectivity?
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Ammonia to tri substituted nitrogen

I am told that an intramolecular proton abstraction can occur. For some reason this seems at least sterically unlikely. Is it possible sterically? Or is the proton abstraction best described as a ...
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Resonance contributors and IR stretching frequency

I am told that a carboxylic ester would have a higher carbonyl stretching wave number than a carboxylic amide due to there being more double bond character in the carbonyl group of the ester. This ...
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Carbon decrease from 1-octyne to 1-hexene

I am to turn 1-octyne to 1-hexene. Method 1 1) Reduction using sodium metal in pure ammonia to an alkene. 2) Halohydrin formation; the -OH installs at the more substituted carbon due to its ...
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What are the correct resonance structures of bromoethene?

Can anyone explain why my textbook only gives the following resonance structures? I also put two resonance case where the double bond electrons are moved on the individual carbon atoms.
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Resonance stabilization and size of ligand atoms

I am told that for these two molecules, one of them is not as resonance stabilized as the other. Apparently it's the chlorine one, and it's because of the mismatch in the size of chlorine and carbon. ...
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Dehydration of alcohol with Lewis acid aluminum trichloride

I am told that this method yields ONE equivalent of water, but I seem to get two equivalents of water. Also does this mechanism actually work? I ave never seen anything like it, but it seems to make ...
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Amine group - electron donating or withdrawing group?

Is the amine group a donating or withdrawing group? I think it depends on resonance. If the amine group can participate in resonance, the amine group is inductively donating. Resonance depictions ...
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Is 4-nitrobenzaldehyde or 4-aminobenzaldehyde more likely to be hydrated?

Of 4-nitrobenzaldehyde and 4-aminobenzaldehyde, which has the higher $\ce{K_{eq}}$ of hydration? $\qquad \qquad$ Steric factors can likely be ignored in this problem since we are dealing with ...
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Donation by inductive effect and withdrawal by conjugation

Is there a group that would attached to a benzene ring, donate electrons by inductive effect and withdraw them by conjugation?
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Separating citric acid from sugar

I'm trying to get as pure citric acid as possible from a mandarin. It's not because I desperately need citric acid, but because I want to achieve this. I started by grating the mandarine and ...