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.
9,937
questions
2
votes
0
answers
22
views
Glycation of peptides (Maillard reaction) by reductive amination
I would like to link glucose to the primary amines in a peptide containing lysine. Can I just mix glucose and the peptide and add some cyanoborohydride to perform a reductive amination? As long as my ...
- 109
-2
votes
0
answers
47
views
Dehydrohalogenation of Alkyl Halides
Is the dehydrohalogenation of alkyl halides (containing only 1 halogen atom) always β-elimination, excluding carbocation rearrangements?
- 1
-3
votes
0
answers
14
views
Choline alphoscerate polyhydrate synthesis
After reading through various sites in order to understand polyhydration or what is done to form a polyhydrate substance, I haven't been able to comprehend whether it just means water infused or if it'...
- 1
-3
votes
1
answer
47
views
How is SO3H added to a benzene ring with two substituents present
If a benzene ring with an isopropyl group in the first position and bromine in the 3rd position was mixed with SO3 and H2SO4, where would the SO3H attach? Since Br is a deactivating agent that directs ...
- 1
5
votes
0
answers
52
views
Oxygen tolerant RAFT polymerization using AIBN?
I want to do some RAFT polymerizations but don't have a nitrogen line at the moment. It seems that people have recently implemented oxygen scavenging strategies to enable open-air RAFT polymerization. ...
- 109
-5
votes
1
answer
53
views
Does KMnO4 Oxidize Alpha-Beta Unsaturated Aldehydes? [closed]
I suspect that since $\ce{KMnO4}$ is a strong oxidizing agent it will react with the $\alpha,\beta$-unsaturated part of the carbonyl forming an epoxide. Are there any secondary reactions that one ...
-2
votes
2
answers
85
views
Why this preparation of Alkyne by dehydrohalogenation is done in two steps? [closed]
My teacher was explaining preparation of alkyne by dehydrohalogenation of Alkane dihalide. Actually the preparation is carried out in two steps. In the first step an alkane dihalide is ...
- 107
-3
votes
0
answers
46
views
Is my understanding of resonance correct? [duplicate]
I'm new to organic chemistry and needed some conceptual clarity on some points like...
Resonance hybrid has maximum similarity with most stable resonating structure
And the resonance hybrid is real
...
5
votes
2
answers
293
views
Can carbocations exist in a nonpolar solvent?
I have seen in organic chemistry books that the solvents they used in reactions are either protic or aprotic, both polar, but can carbocation exist in a non polar solvent? I believe it cannot exist.
- 59
-1
votes
1
answer
41
views
Question about ozonolysis of alkene/alkyne [closed]
I'm having trouble with this problem. I do not see how any of the options could produce the given products on ozonolysis.
We're performing reductive ozonolysis, so products should be either ...
- 29
-3
votes
1
answer
86
views
Planarity of rings [closed]
Can a 7 or less than 7 membered homocyclic ring with unsaturated C atoms and fully conjugated system, loose planarity ? the smallest homocyclic non planar ring that I know is Cyclo-Octatetra-ene which ...
6
votes
5
answers
622
views
Acidity of alcohols and basicity of amines
I've been studying acids and bases in organic chemistry. My textbook says that alcohols are very weak acids, therefore they cannot react with strong bases. the conclusion i formed from this was: very ...
- 71
0
votes
0
answers
41
views
What two processes occur that dictate the microstructure of a polymer?
Firstly, I'm not 100% sure on what a microstructure is as our lecturer didn't explain it all too well. From what I've gathered, its the backbone structure of the polymer chain - but I may be wrong.
In ...
- 107
-2
votes
1
answer
39
views
3-Bromo-2-propylbutanal vs 2-(1-Bromoethyl)pentanal, which one is correct name according to IUPAC nomenclature standards and why?
In above example, What should should be the main chain. According to the IUPAC nomenclature standards whether it's name should be - (a) 3-Bromo-2-propylbutanal (b) 2-(1-Bromoethyl)pentanal
- 99
-3
votes
0
answers
39
views
Why is Carbonyl carbon in benzaldehyde less electrophilic than in formaldehyde
Shouldn’t the sp2 hybridised benzene carbon be more Electronegative compared to the hydrogen and therefore make the carbonyl carbon have a more partial positive charge
-3
votes
1
answer
50
views
Can acyl chloride give Wurtz reaction? [closed]
Since the mechanism involves formation of free radical so is it possible to yield a ketone from wurtz reaction of acyl chloride
Such as CH3COCl reacts with Na in dry ether so can it yield CH3COCH3
0
votes
0
answers
16
views
Rules for numbering in unsaturated cyclic compounds according to IUPAC? [duplicate]
Below is a cyclic compound. What should be the numbering scheme for this compound while naming it according to IUPAC rules?
As per the lowest set of locants option one (3-Ethyl-2-methylcyclohexene) ...
- 99
10
votes
1
answer
438
views
What is the best way to deprotonate a methyl group?
I am attempting to deprotonate the methyl group on 2-methylbenzo[d]thiazol-6-ol (hydroxyl group is protected with a silyl group) in order to attach a phosphate group in the form of diethyl ...
1
vote
0
answers
28
views
Why does the chlorine radical attack the carbon-hydrogen bond in methane as apposed to the chlorine - carbon bond in a molecule of chloromethane? [duplicate]
During the propagation step in a free radical substitution for the production of haloalkanes, a chlorine radical attacks the carbon-hydrogen bond in chloromethane. Even though this feels right, and I ...
- 19
3
votes
1
answer
105
views
How does tetraethyl lead prevent knocking?
My understanding of knocking is that in a spark ignition engine as the fuel is being compressed it heats up. The heat causes some of the oxygen to break up into oxygen radicals the $\ce{O^.}$ ...
- 133
4
votes
2
answers
320
views
Acidic strength of nitrophenols
I've seen the pKa values of Nitrophenol as follows:-
pKa of o-nitrophenol= 7.23
pKa of p-nitrohenol= 7.14
so p-nitrophenol is more acidic than p-nitrophenol
But both phenoxide ions are stabilized ...
- 144
-3
votes
1
answer
83
views
Polycyclic or heterocyclic compound naming [closed]
What is the order and name of the following polycyclic compound?
I am studying heterocyclic chemistry to teach some notions to my high school students even if it is outside curriculum (to give them ...
- 482
1
vote
1
answer
64
views
How to name ether with ketone and carboxyl groups?
Carboxylic acid is the main functional group due to higher priority, but since it's an ether, what's the proper way to name the following compound?
My attempt: 2-(1-methyl oxo propyl ether) ethanoic ...
- 23
2
votes
0
answers
21
views
Why does hydrogen bonding cause a broad stretch in IR spectroscopy?
So hydrogen bonding is an intermolecular forces. I'm assuming that the hydrogen bonding strength varies between molecules and some molecules won't undergo hydrogen bonding causing different bond ...
- 21
-1
votes
0
answers
20
views
Can the Pinacol coupling reaction be regio/stereoselective?
Question is straightforward as it is. Are modifications in aldehyde/ketone reagents or catalysts that result in the resulting Diol's hydroxyl group having an orientation that is specific in the ...
- 204
-2
votes
1
answer
64
views
Acidic strength order among hydroxytetralones [closed]
I can understand in 1 the conjugate base has more stability for better resonance but in 2 and 3 the effect of resonance cannot be considered. How can we compare the inductive effect in such case?
5
votes
3
answers
570
views
Why will changing the solvent crack the column for column chromatography?
When we perform column chromatography with silica to purify the reaction crude product, we sometimes need to change the solvent system to better extract our target product.
For example, changing from ...
- 401
-2
votes
1
answer
40
views
Stereochemistry of reaction of thionyl chloride and phosphorous pentachloride with alcohol [closed]
When a secondary alcohol reacts with SOCl2 (or even PCl5), does the reaction proceed via SN2 or SNi?
- 33
4
votes
0
answers
49
views
Retrosynthesis of 1-(3-chloro-5-nitrophenyl)-2,2-dimethylpropan-1-one
I was tasked with figuring out the order of attaching the functional groups to a benzene ring for the synthesis of 1-(3-chloro-5-nitrophenyl)-2,2-dimethylpropan-1-one:
I propose the following order:
...
2
votes
0
answers
27
views
Can benzene diazonium chloride always participate in a coupling reaction with any compound that contains a phenyl group?
I know that benzene diazonium chloride couples with phenol and aniline. One N atom of the diazonium ion forms a bond with the carbon at the para postion of the ring. That made me think, can a coupling ...
- 21
-1
votes
1
answer
71
views
Potassium permanganate changes from pink to clear on reacting with urine
KMnO4 was used by the cleaners to clean the water tank in our building. For a day or two all the water in our and taps cisterns was pink. On using the toilet before flushing I noticed that the colour ...
- 19
2
votes
1
answer
52
views
Nomenclature of monocyclic molecule with multiple insaturation
The PIN (Preferred IUPAC Name) of this molecule
is (Z)-cycloocta-3-en-1,5-diyne, but at first I thought it was (Z)-cycloocta-1-en-3,7-diyne, following the rules of the Blue Book, P.31.1.3
Can someone ...
- 411
-1
votes
1
answer
79
views
reaction of PCl5 with alcohol [closed]
I am able to think of two possible mechanisms for alcohol+PCl5 here, SN1 and SN2. In SN1, Inversion won't occur whereas, in SN2 inversion will occur. Which of the two is correct?
- 1
0
votes
0
answers
36
views
Why are carbon atoms of glucose considered chiral?
A chiral carbon atom is defined as
"a carbon atom with four different groups attached to it."
I am aware that the open-chain form of glucose has four chiral carbon atoms.
However, I do ...
- 79
-1
votes
1
answer
32
views
Why can i not use glue (which contains cyklohexane, petrol and ethyl acetate) for gluing PVC materials? [closed]
The manufacturer do not recommend using glue to gluing PVC. But Why? Thank you for your help.
- 1
1
vote
1
answer
51
views
Does decreasing pH decrease solubility of adipic acid?
I added 3 grams of adipic acid to 150ml deionized water with heating + mixing until it was completely dissolved. This was then boiled and cooled to allow crystals to form. The maximum amount of adipic ...
- 21
-4
votes
1
answer
63
views
Acidity of Benzenepropanenitrile [closed]
Which is the more acidic hydrogen in the parent chain of this compound?
I am confused while considering the various electronic effects.
- 1
0
votes
0
answers
27
views
How can I make a polyurethane formulae more adhesive?
For a project I'm working on, how can I make polyurethane more adhesive and able to stick to surfaces more effectively, not necessarily super-glue like but just stickier properties. What other ...
- 1
6
votes
1
answer
155
views
Why does the FTIR-ATR spectrum for hexamethylenediammonium adipate not have a peak for the N-H bond?
I have synthesized pure hexamethylenediammonium adipate by reacting equimolar quantities of adipic acid and hexamethylenediamine in ethanol. The diammonium salt, being insoluble in ethanol, was ...
- 77
0
votes
0
answers
34
views
If Ethyne has the lowest C-H bond length (highest C-H bond energy) compared to Ethane and Ethene, why is it the most acidic? [duplicate]
I am not an expert in chemistry, but these are the few facts I know from Standard XII chemistry books (these facts could be wrong or incomplete or modified by now).
Facts I know -
Ethane has 'sp$^3$' ...
- 109
5
votes
1
answer
245
views
Aromaticity of [14]annulene
Our teacher had taught us that cis-trans-[10]annulene is non-aromatic. The reason he gave is due to repulsions between hydrogens, the structure is no longer planar
But later he told us that [14]...
- 144
0
votes
0
answers
41
views
Is there any literature regarding the neutral hydrolysis of nylon 66?
I am working on a project for my thesis regarding the neutral hydrolysis of nylon 66 at high temperatures and pressures (265C,40 bar) however the only literature I could find relates to alkaline and ...
- 21
-1
votes
1
answer
38
views
Why is Quinone used, while oxidising primary alcohols by Oppenauer Oxidation, instead of Acetone? [closed]
Usually, during Oppenauer Oxidation, while oxidising secondary alcohols, acetone solution is used with Aluminium Tertiary Butoxide.
This results into the oxidation of secondary alcohol into a ketone, ...
- 1
0
votes
1
answer
37
views
Process of Arecoline Extraction
What would be the proper procedure to extract and isolate arecoline, an alkaloid ester, from the seed of the Areca nut, and is it possible to mass produce arecoline using that method?
0
votes
2
answers
122
views
Is there a reaction involving alkene formation from diazomethane?
I need help regarding the following question:
I identified some of the compounds as follows:
I think (G) should be Me₂C=CHMe because on reaction of (E) with HCl/Peroxide (Kharash effect doesn'...
- 39
3
votes
1
answer
51
views
Will ethyl 2-amino-1H-imidazole-5-carboxylate undergo ester aminlysos with the primary amines of bPEI efficiently in methanol?
I was about to set up the following reaction, but before I do, I wanted to see if anyone has some suggestions or thinks this will not work:
24mmol Nboc protected ethyl 2-amino-1H-imidazole-5-...
- 109
2
votes
1
answer
26
views
Thiol vs carboxylic acid reactivity to acyl chlorides?
I want to form a thioester between some acyl chlorides and NBoc-cysteine. Is the free thiol so much more reactive than the carboxylic acid in cysteine that the side product formation of carboxylic ...
- 109
1
vote
0
answers
41
views
Would the mechanism for the reaction be polar or radical?
I've disregarded the fact that the reaction could proceed via a concerted mechanism but am unsure how else it would go.
My thoughts are that it either goes via a polar mechanism or a radical mechanism....
- 107
0
votes
0
answers
45
views
Are meso compounds also included in optical isomers or are they just stereoisomers
Our teacher has taught us today about optical isomers . And at the end given a formula for finding number of optical isomers of a symmetrical molecule( n is number of chiral atoms and the n is odd for ...
6
votes
2
answers
2k
views
Colour changing Lipstick
I have bought a colour changing lipstick with the colour Phloxine B.(Other ingredients, see below...)
Normally this colour changes to pink at pH 5.
So this means on skin it changes its colour because ...
