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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What can I do if a peptide won't go in solution in a biological assay?

I have working on the realisation of on assay, that is intended to examine the activity of a protein. The assay works in a way, in which the product of the target enzyme is transfered by a support ...
raptorlane's user avatar
-2 votes
2 answers
60 views

Liquid-liquid extraction of sorbicillinol in water with ethyl acetate

My solution consisted of sorbicillinol and water, sorbicillinol being a polar substance. I wanted to isolate sorbicillinol from water using liquid-liquid extraction. For my solvent I used ethyl ...
Charlotte's user avatar
4 votes
1 answer
298 views

Nomenclature of C6H5CO-O-NH2

How to name the following compound using IUPAC nomenclature? I found benzyl carbamate to be very close to my structure, but couldn't find an exact compound online which matches mine.
kzmom's user avatar
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2 votes
0 answers
42 views

Which group is more ortho/para-directing?

Currently working on assigning the C NMR and H NMR spectra for this molecule (I believe it's called E-E bis(4-methylbenzylidene)acetone ) but I'm a bit confused as to whether the methyl group is more ...
ajk's user avatar
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-1 votes
1 answer
44 views

Optical rotation and chirality

I had the same question as in Molecular chirality and optical rotation In the answer, it says that there can't be such a mirror position where the effect of one molecule be cancelled by other. But I'm ...
Leon Raj's user avatar
0 votes
0 answers
29 views

Is it possible to create a solid from PVDF solution?

I am working on a project where I am attempting to line an aluminium tube with PVDF. The finished wall thickness is required to be 4mm thick. I have investigated such processes as injection moulding ...
PERRY COOPER's user avatar
0 votes
0 answers
43 views

Why is the reaction between the two free radicals below not observed?

All the below reactions are observed: Why is this one not happening?
Shaktyai's user avatar
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3 votes
1 answer
164 views

Nitronate anion reduction with TiCl3. Nef reaction

We can do the Nef reaction, by treatment of nitronate anion with $\ce{TiCl3}$. Here is the mechanism from article: And I can’t understand what is exactly happening in $35\to38$ or $36\to37$. Can you ...
Wvfnct's user avatar
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2 votes
2 answers
837 views

Why does the measured CO2, TVOC and CH2O increase rapidly when I cook/bake?

I have a device at home that measures $\ce{CO2}$, TVOC (total volatile organic compounds), and $\ce{CH2O}$ (formaldehyde) levels, and I conducted similar observations in my friends' house. I noticed a ...
Suslik's user avatar
  • 131
5 votes
1 answer
351 views

Using Thionyl Chloride with tertiary alcohol

I have a question regarding using $\ce{SOCl2}$ to convert an alcohol into a alkyl halide. The Klein book mentions that $\ce{SOCl2}$ is only used for primary and secondary alcohol; however, in the ...
Jaehyun Ahn's user avatar
4 votes
0 answers
91 views

I can't understand a fragment in the Mass-Spectrum of Benzophenone

Summary: Took multiple Mass spectra of Benzophenone; There always is a peak at $\pu{152.2}$ that I don't understand. I made some Measurements of Benzophenone with a GC-MS. Always using EI (electron ...
Franz Emanuel Rüger's user avatar
-4 votes
1 answer
79 views

Alkynes on ozonolysis [closed]

What are the products formed on ozonolysis of 1-hexyne followed by hydrolysis? I am not getting whether Pentanal is formed or pentanoic acid is formed and sub products
Yash 's user avatar
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0 answers
36 views

Carbon 13 NMR peaks - ketones

Why the shift of acetophenone's carbonyl carbon at C13 NMR spectrum is larger than the equivalent peak at trifluoroacetophenone ? Particularly , the first one is located at 197.94 ppm whereas the ...
user142167's user avatar
6 votes
3 answers
542 views

What part of ascorbic acid is oxidized when it reacts with iodine?

When vitamin C reacts with iodine, it will lose two of its electrons (oxidation) which iodine will accept (reduction). What I do not understand is what part of the vitamin C exactly is losing the ...
user138990's user avatar
1 vote
1 answer
67 views

Rearrangment during dehydration of 2,2,5-trimethylcyclopentanol

Here I thought doing the following mechanisms I thought the product option through the first pathway (left) would be the major product because the intermediate cation is more stabilised due to more ...
Sudarshan Kulkarni's user avatar
1 vote
0 answers
38 views

Will benzyl halides undergo SN1 or SN2 mechanism in a polar aprotic solvent?

If benzyl bromide reacts with KF in the presence of a polar aprotic solvent like DMF, will it undergo SN1 mechanism or SN2 mechanism ? I understand that polar aprotic solvents favour SN2 mechanism but ...
standardsolution's user avatar
1 vote
0 answers
27 views

Nucleophilic strength of Fluorine vs iodine

Fluorine is less nucleophilic than iodine because it has greater electronegativity. However, in an aprotic solution, it is more nucleophilic than iodine. Why? I read that fluorine is less stable under ...
Jacob's user avatar
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0 votes
1 answer
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Basicity of pyridine and 2,6-di-tert-butylpyridine

Among pyridine and 2,6-di-tert-butylpyridine, which one would be more basic? My guess was that since two bulky groups are substituted at ortho position in the latter, it will experience steric ...
Ayanokouji Kiyotaka's user avatar
0 votes
0 answers
75 views

Steglich Esterification in Alkyl Gallates

Based on my research (reading some articles), some alkyl gallate syntheses used Steglich esterification instead of the usual esterification (Fischer esterification). The reason why Steglich ...
Jonathan's user avatar
  • 117
0 votes
1 answer
63 views

Acidity of formic acid and 3-fluoropropanoic acid [duplicate]

I'm getting conflicting answers when I want to find out the acidity of 3-fluoropropanoic acid and formic acid. I argue that 3-fluoropropanoic acid is stronger acid than formic acid as it has a -I ...
Akilan SS's user avatar
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0 answers
41 views

How does the Eschweiler Clarke reaction occur with sodium cyanoborohydride as a reducing agent?

I am specifically confused with 2 concepts. How sodium cyanoborohydride acts as a reducing agent. I read that it acts as a source of hydride but I am not sure how this works. If anything, I assumed ...
glowabit's user avatar
2 votes
1 answer
60 views

Does Sugru (Formerol) decay underwater?

Sugru is described as waterproof and dishwasher-safe, but I still wonder if it will decay quickly (within months) if submerged in room-temperature tap water. Aren't silicone rubbers susceptible to ...
MWB's user avatar
  • 519
1 vote
0 answers
33 views

Regioselectivity for double elimination of dihalides

I came across a question shown below, When predicting the product, I thought the internal alkyne would be preferred over the terminal alkyne as the former would be more substituted. However, the book ...
user141992's user avatar
0 votes
0 answers
80 views

Reagent for conversion of 1-phenylpent-1-en-3-one to 1-phenylpent-1-en-3-ol

This conversion was recently asked in the NSEC, an Indian (preliminary) chemistry olympiad for high schoolers and the official answer key stated LiAlH4 is the correct reagent to be used. However I ...
Gaurav Sai Maddipati's user avatar
0 votes
2 answers
125 views

Reasonable mechanism for conversion of 2-methylbut-3-en-2-ol to 1-Bromo-3-methylbut-2-ene

In the book "Designing Organic Syntheses - A programmed approach to the Synthon Approach" pg 23, the author proposes that one route to 1-bromo-3-methylbut-2-ene would be by reacting 2-...
gregmagdits's user avatar
-4 votes
1 answer
41 views

What do the dots mean in DABCO's IUPAC name? [duplicate]

I came across this molecule with the following IUPAC name: 1,4-Diazabicyclo[2.2.2]octane What do the dots inside the brackets mean, or where can I read about the IUPAC guidelines that require this?
imrobert's user avatar
  • 161
-1 votes
1 answer
62 views

what would be the mechanism for these reactions?

I believe the first one would have an intramolecular attack by the sulfur inverting the stereochem followed by an attack by OH- but I can’t get the second one.
david's user avatar
  • 1
-3 votes
1 answer
90 views

Reason behind benzylamine being a primary amine

Benzylamine is a primary amine. Now a primary amine has the general formula R-NH₂ where R is an alkyl or aryl group. So here R will be equal to $\ce{C6H5CH2}$. But $\ce{C6H5CH2}$ is neither an alkyl ...
Rajesh Paul's user avatar
2 votes
2 answers
203 views

Should I remove inhibitor from methyl acrylate?

I need to run multiple aza-Michael additions of methyl acrylate with various amines (dimethylamine, benzylamine, phenylethylamine, aniline, etc.) in order to get the bis-ester. I was wondering if the ...
Matt's user avatar
  • 21
1 vote
1 answer
81 views

What is the priority of an alkyl substituent containing double or triple bonds, in comparison to the other functional groups?

If we have an alkyl substituent containing a double bond(s) or triple bonds(s), what is it's priority in comparison to other functional groups and substituents? For example, take the compound given ...
Bongo Man's user avatar
  • 361
4 votes
1 answer
57 views

What are the byproducts of ozonolysis?

I understand that ozonolysis of alkenes leads to formation of aldehydes or ketones or carboxylic acids depending on the type of work up, reductive or oxidative. But when I tried searching online I ...
Rassank's user avatar
  • 99
0 votes
0 answers
29 views

Which is more stable, a secondary allylic carbanion or a primary allylic carbanion?

I came across this picture in a polymer chemistry course, specifically on anionic polymerization of conjugated dienes (butadiene). I dont understand why the secondary carbanion is more stable. Based ...
Dannis's user avatar
  • 1
2 votes
0 answers
37 views

Is the amine nitrogen of methylglycinediacetic acid (MGDA) protonated?

MGDA is a tertiary amine with 3 acetic acid groups. I would like to know whether the amine Nitrogen of MGDA is protonated or not for a given pH value. I could not find any literature data which ...
VKM's user avatar
  • 29
0 votes
1 answer
119 views

Products formed upon pyrolysis of alkanes

What sort of products will be formed when we subject a higher alkane (say decane) to pyrolysis by heating at 773-973 K in the presence of $\ce{H2/Ni}$? I know that lower aliphatic alkanes and alkenes ...
calcandquant's user avatar
2 votes
0 answers
55 views

Cyanoacrylate glue and citric acid

I got some cyanoacrylate glue on my fingers yesterday which dried up quickly and would not fall. My daughter (n.b. she's 7th grade, no chemistry education but wants to be a chemist and reads a lot by ...
ivan's user avatar
  • 121
0 votes
0 answers
31 views

Can products of Claisen Condensation undergo the reaction again?

I have a reaction of ethyl acetoacetate with 1-bromopentane in ethanol and sodium ethoxide. I understand that the main product is formed by SN2 mechanism between ethyl acetoacetate and 1-bromopentane, ...
prokop's user avatar
  • 1
-1 votes
1 answer
27 views

How do you perform an ion exchange of a monovalent cation with Br- counterion to a divalent or trivalent anion?

I tried to react an organic compound I have synthesized containing a di-N substituted imidazole bromide salt with Ag3PO4 with water at room temp to try to replace the Bromide with PO4(3-). I dont ...
toodles's user avatar
  • 137
0 votes
0 answers
21 views

What is the product: Ethyne + (conc)KMnO4? [duplicate]

In cold and alkaline medium it gives ethane-1,2-dial. But what happens in conc KMnO4? Does it give CO2? Also, what will happen to other triple bond containing hydrocarbons?
user350536's user avatar
1 vote
0 answers
60 views

How can I isolate products that cannot be cleanly distilled or visualised by TLC for column chromatography?

I am a first year PhD student in the UK, and without giving too many details of my work as it is industrially funded and my sponsors are a bit touchy over IP, I am struggling to isolate the products ...
Matthew's user avatar
  • 11
0 votes
0 answers
36 views

Is this mechanism of reduction using LiAlH4 followed by hydrolysis of an amide correct?

Hello everyone. I had been given a question on reducing an amide group into an amine group using any reagent I saw fit as homework. I had used LiAlH4, which provides H- and does an acid base reaction ...
OrganicGod's user avatar
4 votes
1 answer
109 views

Why is benzene more soluble than chlorobenzene in water?

Wikipedia lists chlorobenzene's solubility in water at 0.5 g/L at 20C, and benzene's at 1.79 g/L in 15C and 1.84g/L at 30C. Chlorobenzene is very slightly polar, shouldn't it be more soluble? What ...
ead1's user avatar
  • 41
-4 votes
1 answer
47 views

R/S designation [closed]

Why is my answer wrong ? (Tutors answer in blue bubble) OH is highest priority, the carbon groups are second highest priority, H is lowest priority
Anna's user avatar
  • 1
2 votes
2 answers
486 views

Changes of colour of sunset yellow in water

I am conducting an experiment on “sunset yellow (FCF)”. Based on my observations, the substance, when in powder form, is bright red in colour (observed with naked eyes). When I dissolve the powder in ...
Freeby Freeby's user avatar
1 vote
1 answer
143 views

Why can't picric acid be made more acidic by adding nitro groups at the meta positions?

I understand that picric acid is acidic because of the $\ce{-NO2}$ electron withdrawing group, but why can't we add more of those on the meta positions to make it more acidic? Is it because that $\ce{-...
User10001010001000's user avatar
2 votes
0 answers
38 views

Comparing reactivity of benzaldehyde and 2-butanone for nucleophilic addition

I was taught that, in general, aldehydes are more reactive than ketones because of two reasons: 1) less steric hindrance, and 2) alkyl groups on both sides of carbonyl group in ketones have a stronger ...
AVS's user avatar
  • 481
-3 votes
1 answer
48 views

Ether has +R effect nd CH3 has +I effect, if R effect is more effective than I effect then why is CH3COOH less acidic than CH3OCH2COOH

The More is the electron donating effect, the more will be the charge on carboxylate ion, the more will it be unstable and the less acidic it will be.
Shreya's user avatar
  • 1
1 vote
0 answers
118 views

Why is sulfur more nucleophilic than nitrogen in thiourea?

In $\ce{S_N2}$ reaction using thiourea and alkyl halide, it is the sulfur atom rather than nitrogen atom that attacks alkyl halide. But nitrogen also has lone pair, so there is a chance that it acts ...
Krang Lee's user avatar
  • 1,081
0 votes
0 answers
103 views

How dangerous is Naphtha?

According to a safety datasheet of Naphtha, it's fairly dangerous stuff (including genetic defects). But, as they say, the dose makes the poison, just how much dose should I be worried about? ...
Rocketmagnet's user avatar
0 votes
2 answers
76 views

When you do dehydrohalogenation of 1° alkyl halides, do you use a strong base or sterically hindered base?

I know when do you dehydrohalogenation of 2° alkyl halides, you can do either a strong base like KOCH2CH3 to get the most substituted product or a sterically hindered base like t-butoxide to get the ...
Jordan's user avatar
  • 11
0 votes
0 answers
52 views

When C2 axis of symmetry is present then is the compound meso?

If suppose a compound has C2 axis of symmetry then is it confirmed that the compound will be meso or it can have an enantiomeric pair? And which of following conditions are sufficient enough to ...
Garv Chaudha's user avatar