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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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Dissolving soil particle [closed]

I have dirty samples of soil that have seeds in them. the soil particles in these samples make the detection of the seeds harder for two reasons. the soil particles are the same shape and size as ...
Shahbaz's user avatar
0 votes
1 answer
46 views

Question about regioselectivity depending on the base used [closed]

In one of my organic chemistry lessons, it is possible to produce 2-methylbut-2-ene and 2-methylbut-1-ene from 2-bromo-2-methylbutane using a base, using the mechanism E2. The percentage of the two ...
AT N's user avatar
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0 votes
1 answer
83 views

Why do we use cis/trans for 1,4-dichlorocyclohexane, but R/S nomenclature for its 1,3 isomers?

1,4-dichlorocyclohexane has two isomers, and 1,3-dichlorocyclohexane has three: Looking at the substituted carbon, the reason for the isomers is the same: either the chlorine points up or it points ...
Karsten's user avatar
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-2 votes
1 answer
38 views

Can NaBH4 reduce acid chlorides to alcohols? [closed]

My professor says it reduces only aldehydes and ketones, but acid chlorides are generally more reactive than both of them.
user144848's user avatar
2 votes
0 answers
41 views

Does DIBAL-H reduce acid chlorides?

It's only really mentioned with esters, but acid chlorides are more reactive than esters, so following that logic is this a feasible reaction to convert acid chlorides into aldehydes?
user144848's user avatar
0 votes
0 answers
30 views

Why should higher energy empty orbitals be chosen over lower energy empty orbitals during hybridisation?

Organic chemistry by jonathan clayden states during his explanation of hybridisation using trigonal boron structure (sp2) and tetrahedral boron structure (sp3): You want to populate the lowest energy ...
Richard Xun's user avatar
2 votes
0 answers
34 views

Synthesize pivaloyloxymethyl ester, but with a substrate that is a terrible nucleophile

I want to synthesize an pivaloyloxymethyl ester from a fluorophosphonic acid. The idea is, to make a compound cell permeable that than be cleaved in the cell by enzymes. Apparently, the acid is a very ...
raptorlane's user avatar
-1 votes
2 answers
127 views

Which one has a greater dipole moment: benzamide or benzoic acid?

My guess is that, since the relative electronegativities are similar, therefore the difference would arise only due to magnitudes of difference in electronegativities. And hence the strength should be ...
Gajraj Singh's user avatar
5 votes
0 answers
43 views

Why cool a reaction down when adding reagents if you're only going to reflux subsequently?

I've seen several procedures using thionyl chloride (SOCl2) to make an ester, where the first step is to add the thionyl chloride to the reagent/solvent on ice or subzero temperature, followed ...
sat0ri's user avatar
  • 171
-2 votes
2 answers
73 views

Azo dyes with different colours than Yellow, Orange and Red [closed]

Why are there just Azo dyes with colours of Yellow Orange and Red. Do the molecules become to be unstable with a greater pi-electron System? Every dye or indicator with other colours are'nt Azo dyes.
Jonah's user avatar
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1 vote
0 answers
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Why does hydrogen peroxide decompose during the oxidation of an aryl amine to and nitroarene (rt) and what are the possible overoxidation products?

Small scale: I attempted the oxidation of an aryl amine (2-amino-6-bromonaphtalene) to the nitroarene using hydrogen peroxide (ArNH2, H2O2, MeCN (15 mL as solvent). After trying it on small scale (0.1 ...
The Red Man Jolan Bonelli's user avatar
3 votes
0 answers
33 views

What is the difference in reactivity between the various borates (trimethyl, triethyl, triisopropyl borate) to form boronic acids?

For the transformation of 1,3-dibromobenzene to bromobenzene boronic acid, different groups use different boration reagents namely trimethylborate, triethyborate and triisopropylborate). The reaction ...
The Red Man Jolan Bonelli's user avatar
5 votes
1 answer
86 views

Optical activity in tritiated cyclobutane

How would we determine the optical activity in a compound as such: The biggest difficulty I'm having is determining the R-S configuration as that will determine whether the pair are enantiomers or ...
Bongo Man's user avatar
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7 votes
0 answers
196 views

Difference in 13C NMR spectrum

The tasks proposed in Spectroscopy challenge, I found two structures that are mostly similar in allylic moiety, the contradiction is presented below: Considering two carbons of the alkene bond, it ...
Shira's user avatar
  • 553
0 votes
0 answers
32 views

Need Suggestion for Picking the Right Solvent for Column Chromatography

I've completed my reactions, and based on the stoichiometry and TLC analysis, I think my mixture should contain 3-4 compounds: Ethyl gallate (my product) Gallic acid (the reagent/starting material) ...
Jonathan's user avatar
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5 votes
2 answers
564 views

Geometrical isomerism in 1-(chloromethylidene)-3,5-dimethylcyclohexane

Will this compound exhibit geometrical isomerism? This question was asked in JEE (Mains) 2020, which is an entrance exam held in India annually. The official answer given for this question was "...
Haider's user avatar
  • 93
1 vote
1 answer
138 views

Product of Monochlorination of 2-methylbutane [closed]

Question: Find out the number of products of monochlorination of 2-methylbutane including stereoisomers. The given answer is 6, but why can't it be 7? I am getting 7 products, the one which I am ...
Rudresh's user avatar
  • 45
2 votes
1 answer
55 views

Norbornadiene + hexachloro-1,3-cyclopentadiene, does norbornadiene react with 1 or 2 molecules of the hexachloro-1,3-cyclopentadiene?

So I was doing an exercise from the book and i saw this question: Norbornadiene + hexachloro-1,3-cyclopentadiene gives aldrin and I had to determine the structure of aldrin. The reagents of course ...
Roxtron's user avatar
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4 votes
0 answers
235 views

Exchange of Fluorine to Oxygen for Fluorophosphonic acid by silylating agents or other methods?

[Warning, long post!] Dear all, I am confronted with a seemingly easy transformation. I want to remove a fluorine atom at a fluor phosphonic acid salt. The usual method to achieve this is the basic ...
raptorlane's user avatar
1 vote
1 answer
119 views

How does the following cyclization reaction work?

The following is a reaction from a school provided lab manual. However, I am unable to find anything similar to the cyclization reaction taking place. All of the reactions I have found online make use ...
Marethyu's user avatar
-1 votes
1 answer
92 views

Does styrene really react with KMnO4? [closed]

A benzene derivative $ \ce{C_8H_x} $ did not produce white precipitate with the ammonical silver nitrate solution but decolorised the cold dilute alkaline $\ce{KMnO4}$ solution. The compound is ...
Akilan SS's user avatar
3 votes
6 answers
353 views

Removing carbon matter from molten beeswax

In my candle manufacturing process, I melt down used candle stubs, filter the molten wax (heated to ~ $\pu{75^\circ C}$) and use this to create new candles (in addition to fresh beeswax). I'm ...
Peter's user avatar
  • 47
0 votes
1 answer
79 views

What is the full mechanism for the controlled reduction of an alkyne using LiAlH₄?

Was going through my notes and realised I didn't completely fill them in. The first few steps I think are quite self-explanatory but I'm really confused about the last step where I go from the five-...
ajk's user avatar
  • 49
0 votes
1 answer
75 views

Hydrogen–deuterium exchange in 1,4-benzoquinone

Problem Find number of deuterium exchanges in the following compound. Solution Question I have been taught that hydrogen attached to the carbon which is directly or indirectly in conjugation with ...
Haider's user avatar
  • 93
-1 votes
1 answer
57 views

How exactly are mirror images of molecules rotated to determine enantiomeric pair?

I know there are many similar questions to this but none could clear my confusion over how exactly the mirrored molecules is rotated i.e on which axis it is rotated to superpose with the original ...
ADITYA DAS's user avatar
1 vote
0 answers
32 views

Why do protons in same chemical environment do not exhibit spin-spin coupling?

Reading introductory tutorials on proton NMR for the determination of chemical structure, I was told that protons can exhibit spin-spin coupling, thus creating multiplets on an NMR graph. The coupling ...
ScientiaNatura's user avatar
3 votes
1 answer
71 views

Is Breslow's intermediate aromatic?

When looking at Stetter's reaction (umgepolter aldehyde + michael akzeptor -> 1,4-dicarbonyle), I was wondering wether the occuring intermediate, after the umpolung step, is aromatic. I can imagine ...
Rivinius's user avatar
1 vote
2 answers
166 views

Is it really that simple to make dimethylmercury?

I was reading about methyl iodide and I saw a warning to not let it come into contact with sodium amalgam or it will create dimethylmercury. I'm wondering if that's really all that it takes to create ...
long4d99's user avatar
-2 votes
1 answer
36 views

Is HCl in salt form reactive with metallized aluminium plastic film? [closed]

I’m in the process of packaging an amino acid that contains HCl in salt form. The mixture is 60% base and 40% HCl salt. Will this react to metallized aluminium plastic?
user144358's user avatar
0 votes
0 answers
25 views

Is this fused ring molecule aromatic? [duplicate]

In my notes, I can see that it is listed as anti-aromatic because of the 16 electron ring current that would be formed on the periphery of the entire molecule were the right benzene ring drawn in the ...
Bytes Per Second's user avatar
0 votes
0 answers
23 views

The mechanism for the addition of HCl to propylene

Problem: The mechanism for the addition of HCl to propylene is described below. Complete the mechanism in step 1 with one curved arrow showing the electron movement that occurs when the double bond ...
Nora's user avatar
  • 123
0 votes
0 answers
22 views

Why can't the fructose monomer in sucrose be α-fructose?

In all academic sources, sucrose is identified as α−glucose (1-->2) β−fructose. However, I cannot find any explanation anywhere as to why the fructose monomer has to be in the β configuration. ...
MD P's user avatar
  • 11
2 votes
0 answers
71 views

Product of 4-chlorobutan-1-ol treated with KOH in alcohol

I am looking at this problem: I thought the KOH in alcohol would support a nucleophilic attack of hydroxide on the haloalkane, so the product I would get is B (elimination of HCl). However, this ...
DUDE_WITH_J's user avatar
1 vote
1 answer
28 views

Nomenclature for 5-Methylhepta-1,3,6-triene

I was practicing writing nomenclatures for several organic compounds with the help of Blue Book Essentials and I have some queries regarding the following structure: According to the blue book, the ...
Akilan SS's user avatar
0 votes
0 answers
21 views

-I effect vs +M effect of Chlorine on acidity of benzoic acid

The -I power of Halogens like Chlorine is stronger than their +M power. Therefore, we consider -I effect for comparing acidity of benzoic acid [Ka-> ortho > meta > para]. But shouldn't -I ...
EagerToLearn's user avatar
-4 votes
2 answers
139 views

Why can't elements and atoms be separated by physical and chemical means?

Our textbook tells us ''that elements and atoms cannot be separated by chemical and physical methods. He says only atoms can be separated by nuclear methods.'' First of all, I would like to start my ...
Bilgehan Yılmaz's user avatar
1 vote
0 answers
45 views

Define a rate-determining step and an energy barrier for a multi-step reaction profile

I am currently making reaction profile by means of DFT calculations. I am able to correctly draw a whole reaction profile. However, I am struggling to find what exactly is the energy barrier of a ...
thchem's user avatar
  • 398
0 votes
1 answer
84 views

Are these stereoisomers considered geometrical isomers?

I came across this compound in the Black Book of Organic Chemistry by Ashish Mishra. The question asked whether this compound could show geometrical isomers. Now, I know the compound has the ...
Man's user avatar
  • 199
0 votes
1 answer
33 views

Which of these monomers can polymerize by chain addition reaction?

Problem: Which of these monomers can polymerize by chain addition reaction? Solution: The monomers with red crosses underneath them can polymerize by chain addition reaction. Question: So, how I am ...
Nora's user avatar
  • 123
0 votes
1 answer
44 views

Calculating the Barrier Between Rotamers

There are two stable conformations of a medium-sized organic molecule roughly 5 kcal/mol apart in ground state energies. One is probably the global minimum conformer identified through a conformer ...
quantchem's user avatar
1 vote
2 answers
66 views

How do you identify an organic base?

Problem: Solution: The molecules with red crosses underneath them are considered organic bases. Question: From my understanding an organic base has an atom with a lone pair of electrons. Doesn't ...
Nora's user avatar
  • 123
3 votes
0 answers
55 views

1,3-butadiene conformation difference [duplicate]

I am aware that there are 2 well-known conformations of 1,3-butadiene which is s-cis and s-trans conformation. The s-trans conformation is clearly more stable than the s-cis conformation whose ...
Seiji's user avatar
  • 183
0 votes
1 answer
60 views

Which of these molecules have stereoisomers?

Problem: Which of these molecules have stereoisomers? Solution: (The molecules with a red X beside them are the ones with stereoisomers.) Question: What is the method used to identify which molecules ...
Nora's user avatar
  • 123
3 votes
0 answers
44 views

UV-Vis spectrum of alkane

My reference books stated: Methane's maximum absorption wavelength is 125 nm, ethane's is 135 nm. The longer the carbon chain, the larger the absorption wavelength, it is 165 nm for n-octane. Well, ...
Shira's user avatar
  • 553
3 votes
1 answer
109 views

If a compound has a strong and weak minus I group, will the stronger group always have a δ- charge?

In a compound like acrolein (prop-2-enal or $\ce{CH2=CH-CHO}$, will the oxygen in the $\ce{-CHO}$ group always have a $\delta$- charge? Acrolein does have three resonance structures as shown below, ...
Bongo Man's user avatar
  • 369
1 vote
1 answer
103 views

How do I number the atoms in strychnine?

I know the basics of naming organic molecules, but this one is a bit more complex than I'm capable of. How can I number the atoms in strychnine? Systematic IUPAC name: ($4$bR,$4$b$^1$S,$7$aS,$8$aR,$8$...
imrobert's user avatar
  • 163
0 votes
0 answers
27 views

Why is 1-ethylcyclohexene more stable than ethylidene cyclohexane?

Both compounds yield the same product, ethylcyclohexane, when hydrogenated. However, 1-ethylcyclohexene has lesser heat of hydrogenation than ethylidenecyclohexane, hence more stable. I want to know ...
Anu Vanguri's user avatar
-5 votes
1 answer
79 views

Why can't the diene in a diels-alder also be a dienophile [closed]

why can't the diene react with itself like this
OZWizard X's user avatar
-2 votes
1 answer
55 views

Is this a allyl bromide? If not what is it?

This molecule should be a allyl bromide: but what about this one: What is it?
Antonio Azevedo's user avatar
1 vote
0 answers
37 views

What is this gel byproduct of acetylsalicylic acid recrystallization?

I did a very simple acetylsalicylic acid synthesis from salicylic acid and acetic anhydride (with phosphoric acid as a catalyst). After rinsing, filtering and drying the product I dissolved it in ...
Thomas's user avatar
  • 21