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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33 views

Conversion process of lanolin to 7-Dehydrocholestrol [closed]

What is the Chemical process to convert lanolin to 7-Dehydrocholestrol? I don't know about the chemcial reaction, if I get the process I can try in lab scale.
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1answer
48 views

Stability of pyridine derivatives

Arrange the following pyridine derivatives in the order of increasing stability of adduct formed with $\ce{BBr3}.$ Explain briefly. I'm pretty confused about which structure is the most stable. I'd ...
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1answer
198 views

Can Anyone Explain the Mechanism of the Birnbaum-Simonini reaction?

When silver acetate reacts with iodine and $\ce{CCl4}$, it gives esters and 2 moles of $\ce{AgI}$ but when it reacts with iodine and lead acetate, why it gives alkyl halide, $\ce{AgI}$ and $\ce{CO2}$....
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1answer
106 views

Is a Methoxy group meta directing in this problem?

The following question was given in chemistry today , August 2020 edition , page 47 , problem 9. The answer to this problem is (a). My Attempt In the third step , the carbon electrophile can attack ...
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0answers
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Migratory Aptitude [duplicate]

I never understand how or why one group migrates better than the other in case of rearrangement reactions. Is it experimentally determined or is there some logic to it? Please explain in the case of ...
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4answers
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Why is '-ethane' in 'methane'?

Is there a chemical or historical significance in the fact that 'ethane' is just 'methane' without the 'm'?
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1answer
108 views

Vital force theory [closed]

The vital force theory of organic compounds was disproved by a scientist Friedrich Wöhler is 1828 as follows: Urea is a organic compound which was thought to be made only inside the bodies of living ...
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1answer
46 views

Are all 'dextrorotatory' sugars in biology actually 'd' or '+' in chirality?

When papers or articles say that all proteinogenic amino acids are 'levorotatory' or 'L', they often make a point of saying that only half of them are truly, optically levorotatory. All of them (...
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44 views

For a flat, planar molecule, how do you determine which side is up? Or down?

I was just reading about alpha and beta linkages in certain cyclic molecules, and it said that the alpha configuration was the one in which a hydrogen was sticking out above the plane, and an OH ...
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0answers
25 views

Acyl chlorides addition-elimination reactions bond forming and bond breaking

I've recently read up on Acyl chlorides and the addition-elimination reactions that they can react with. However many questions popped up in my head from reading up on this. During the elimination ...
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2answers
129 views

IUPAC name of aldehyde with two functional groups

I am confused as to what suffix to use for the following compound: Should it be carbaldehyde or just -al, like should it be propane-1,2-dicarbaldehyde or should it be propan-1,2-dial? Or maybe it's 1-...
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0answers
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Electrophilic Aromatic substitution reactions of aromatic compounds [closed]

Benzene and substituted benzene (phenols, aromatic ethers, benzaldehyde, aromatic ketones like acetophenone, benzoic acid, aniline and nitrobenzene) generally can undergo electrophilic Aromatic ...
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28 views

Name of proton directly bonded to a functional group e.g. carbonyl

For example, a carbon bonded to a carbonyl group is the alpha carbon, and has alpha protons. Following that there are beta and gamma carbons and protons. Is there a specific name for the proton in an ...
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0answers
29 views

Does imine formation occur for esters before ketones?

I understand that ketones are more reactive than esters but when I take a look at the reaction on the image, it seems to me that the imine is formed on the ester before the ketone to create the ...
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0answers
23 views

Reduction of Benzamide in acidic conditions?

I am going through a mannich type reaction and ended up with my product show in the image. I compared my answer to the answer key but I noticed that the benzamide was reduced completely. I was ...
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0answers
28 views

Use of TsN3, toluene at high temperature

My reasoning: My understanding is in first step the alcohol’s O- does an Sn2 attack on the OTs containing carbon. In the second step I am confused where does the reaction happen in the triple bond or ...
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0answers
43 views

One-piece short distillation glassware - worth it?

Does anyone have any experience using one-piece short distillation setups similar to this: https://www.hornik.eu.com/en/3-985_distillation-bridges/8216-distilling-link-for-short-path-distillation-...
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0answers
46 views

What happens when unsaturated primary alcohol is reacted with acidic potassium dichromate? [closed]

It is clear that the hydroxy group in the substrate gets oxidised to carboxylic acid. But what happens to the double/triple bond in the unsaturated primary alcohol when it reacts with acidic potassium ...
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2answers
54 views

“Bromobenzene” vs “bromophenyl” [duplicate]

What is the difference between the keywords Bromophenyl and Bromobenzene used in organic chemistry.
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Easy to perform enantioselective derivatization of cyclohexenone-like structures

I'm looking for easy-to-use derivatizations of cyclohexenone-like structures. In fact, I'm working with 3-ketosteroids having the same double bond in the A ring as cyclohex‐2‐en‐1‐one has. The only ...
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2answers
102 views

Stereoselectivity of ring closure in intramolecular iodolactonisation

What is the product of the reaction above? I am mainly confused between the following two options: How do we decide the resulting stereochemistry of the $\ce{CH_2I}$ group? The answer given is the ...
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2answers
152 views

Why are alkenes considered nonpolar?

Alkenes have C–C sigma bonds, C=C pi bonds, and also C–H sigma bonds. I know that C–C and C=C bonds will not give any polarity, but what about the C–H bond? I think it should give some polarity ...
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1answer
37 views

Compound Polarity Lookup

I know from the literature that the following compounds have decreasing polarity: Rosmarinic Acid -> TMF -> Sinensetin and I guess comparing compounds of ...
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1answer
49 views

How can one determine if all reagents will react in the reaction? [closed]

Is it correct that all the reagents above the arrow will participate to form an intermediate product, to which the reagents below the arrow are then added, and they react to form the final product? ...
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0answers
43 views

Acidity of butyric acid vs. thiophenol

I am being asked to compare the acidities of various compounds for an assignment, but I am confused about why butyric acid is a stronger acid than thiophenol/benzenethiol. From what I was taught, I ...
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0answers
29 views

Does the Henry reaction (nitroaldol reaction) work on carboxylic-acid-derived carbonyls?

In reading about the Henry reaction in textbooks and online, I can't find any treatment of the reaction with the carbonyls of esters or acyl halides. I am imagining the reaction would be similar to ...
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1answer
80 views

Does the benzene ring in styrene show a negative inductive effect on the ethenyl group?

I know that a group exerts an inductive effect on another one if there is a difference in electronegativity. In the case of styrene (1) all the atoms are sp2-hybridized. So, how could the phenyl ring ...
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0answers
101 views

The best way to designate unsaturation (double bond)

Although it has already been explained here that the use of the "Δ" (Greek capital delta) character is not recommended to designate unsaturation in individual names, IUPAC 1989 Nomenclature ...
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0answers
19 views

Ion Mass Spectrometry of Polymorphs

Can ion mass spectrometry differentiate between 2 distinct polymorphs? Why? In my opinion, the spectrum would be the same as only the crystal lattice differs.
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0answers
34 views

1,5-Pentanediol MS

I'm having troubles assigning the signals m/z = 41 and 56 of the compound 1,5 pentanediol. I tried the basic fragmentations (McLafferty, loss of OH radical, etc.) but I can't figure the structure of ...
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0answers
63 views

Sodamide vs alcoholic KOH

My textbook says In the presence of strong base such as KOH and at high temperatures, triple bond at terminal C-atom of higher alkynes migrates to give disubstituted alkyne.Therefore alcoholic KOH is ...
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0answers
38 views

What is the significance of using cold conc H2S04 followed by boiling water for hydration of alkenes?

I tried searching the internet but I failed to find a answer satisfactory to my understanding. I know if I react the alkene with cold conc. H2SO4 I get an alkyl hydrogensulfate which upon reaction ...
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1answer
123 views

What are the products of alkene oxymercuration with diols?

I was wondering what would be the product of the reaction of alkene with a diol (such as glycol) in alkoxymerucuration/demercuration, i.e. $\ce{(CF3CO2)2Hg/NaBH4}$? I tried to look online but I couldn'...
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1answer
38 views

Reaction of unsaturated lactone and alcohol

Image source I found this equation to turn this compound into an ketoester but I am unsure of the reaction mechanism. I postulate that the alcohol attacks the carboxyl carbon, the O becomes formally ...
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1answer
67 views

Chiral centres with stereoisomeric substituents

The structure of one particular isomer of 4-chlorohepta-2,5-diene is shown here. I am confused about how two of the propenyl groups attached to the central carbon have the same atoms with different ...
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1answer
41 views

Need something that is dishwasher safe that breaks down paraffin

I work for a company that has a lab where there work leaves a lot of dishes coated in paraffin. Today I learned that they wash these in a non commercial dishwasher to remove the stuff.... one issue ...
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2answers
85 views

How can we define optical isomerism?What is the example of non enatiomeric optical isomers? [closed]

My book has very vaguely explained these concepts,I can't understand anything from there. Through a little bit of research on the internet I came to following conclusion: that optical isomers are ...
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1answer
21 views

How come the C1 is above the ring in fructose-6-phosphate and C1 is below the ring in fructose-1,6-bisphosphate?

Does the phosphofructokinase-1 flip the position of the covalent bonds? If I've understood correctly, C2 is a chiral atom, so it would make a difference if C1 goes from above the C2 to below the C2.
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0answers
38 views

How many alternative chemical ways to transport oxygen in living creatures are known?

Mammals and many other groups of animals usually transport oxygen using haemoglobin and other complex proteins, the core of which is based on an iron coordinated to a porphyrin. There are plenty of ...
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1answer
134 views

The desirable property of plastics [closed]

My teacher once asked me that "one desirable property of plastics is that they can be made into very complicated shapes, Explain how this is done as a reaction" I never know how to answer ...
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1answer
35 views

Carboxyllic acid Test

I'm currently in high school doing a project in chemistry. So I had to make a project where concepts from physical chemistry will be used alongside organic chemistry. After going through my book I ...
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0answers
30 views

Reaction of Glucose + NaOH + PVP

I'm trying to synthesize of silver particles by using glucose as reducing agent, PVP as dispersant, and NaOH as pH control. Before adding silver nitrate solution, I've produced a solution which is ...
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0answers
21 views

Reaction of Methyl Cyanide with nitroethane

I want to know the products of reaction of Methyl Cyanide with nitroethane in presence of (Sodium ethoxide + ethanol) and then hydrolysed in concentrated Acidic medium. According to me ,reaction ...
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0answers
28 views

In which of the these structures C-3 carbon is not a chiral centre?

In which of the these structures C-3 carbon is not a chiral centre? I think that the answer to the above question should be both (b) and (c) as C-3 is attached to same groups and also they have a ...
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1answer
34 views

Carbocation rearrangement

I am dealing with some basic reactions in organic chemistry. One of these is the acid reflux of alcohols. Something I came across was hydride shifts. I know how and why they occur, but I don't ...
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0answers
21 views

Halogenation by Phosphorous tribromide vs using HBr

My textbook introduced PBr3 by stating that it leads to an inversion in stereochemistry since it always goes through an SN2 pathway, unlike using HBr. My question is that since Br- is a reasonably ...
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0answers
28 views

Are these molecular structures enantiomers or diastereomers?

What relationship exists between the two structures shown? I think that since the configuration at the bridge head carbons remains the same and only there is an inversion at the carbon bearing $\ce{...
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1answer
46 views

Why do Fullerenes have even number of carbon atoms? [closed]

My teacher started a chapter called "Carbon and its compounds", Which is just an intro to organic chemistry . In which she taught about fullerenes structure and examples and also told that ...
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1answer
53 views

What happens when FeF3 is reacted with benzene? [closed]

My text book says that halobenzenes can be prepared by aromatic substitution on benzene ring by using Fe or FeX3 as Lewis acid but this method isn't useful for preparation of fluoro benzene because of ...
3
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1answer
103 views

Nitration vs Nitrolysis

I am interested in nitrating an aromatic ester in a solution of dichloromethane. I found the following paper that describes creating a nitric acid solution in dichloromethane using KNO3 and sulfuric ...

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