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.
10,002
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Methods for immobilization of DNA on gold surfaces?
I've been looking for methods for immobilizing 5'-Thiol modified dsDNA on gold slides. Most of what I've come across suggests using DTT followed by a desalting step or using TCEP. However, I haven't ...
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votes
1
answer
34
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Stability of benzyl free radical hyperconjugated with a methyl group
In this picture, which one is more stable?
My teacher says the second one as it has 4 alpha-Hydrogen whereas in the first picture the free-radical carbon has only 1 alpha-Hydrogen. That's why second ...
-4
votes
1
answer
63
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Preparation of alkane through decarboxylation by soda lime
Can we still prepare alkane through decarboxylation (using soda lime) if instead of using sodium salt of carboxylic acid, we use the carboxylic acid directly.
Because I have always seen the ...
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2
answers
147
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Why is Carbon marked as 1 acting like a pseudo chiral centre?
Since there is a plane of symmetry passing through the middle of the compound, the C (chiral centres) at 2 and 3 will rotate the light through angles opposite in magnitude, say, +A and -A respectively ...
1
vote
1
answer
130
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Is CD4 an alkane?
Can $\ce{CD4}$ or $\ce{CT4}$ be considered an alkane?
I know that an alkane is $\ce{C_nH_p}$ where $p = 2n + 2$. An alkane is considered a "hydro"carbon, i.e., a compound containing purely ...
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1
answer
70
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How can I protect the ester group from reduction? [closed]
If I process this reaction the NaBH4 will also reduced the ester group to alcohol. I want to convert the Nitro (-NO2) functional group to Amine (-NH2) without disturbing the Ester group. So, my ...
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votes
2
answers
91
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Which is more acidic, alcohol or phenol?
My teacher taught yesterday that though resonance happens in phenoxide ion, it is less stable because the negative charge gets distributed over the carbons in the ring. And hence, alcohols are more ...
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1
answer
108
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Degree of Unsaturation or Index of Hydrogen Deficiency [closed]
I know the formula for the DOU, but don't really understand why the formula works. Could someone elaborate that to me?
4
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0
answers
81
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What is the driving force of Bartoli indole synthesis?
The Bartoli indole synthesis mechanism begins with a series of attacks on the nitroarene regent by the Grignard reagents. But the atom $\ce{O}$ in $\ce{-NO2}$ should be negative, and Grignard reagent ...
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4
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1
answer
85
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Comparison of acidic strength in organic compounds by assigning charges to rings
Generally we compare acidic strengths by comparing relative stability of negative charge formed by removal of acidic hydrogen. However I can't understand the following comparison
The solution given ...
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1
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0
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24
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Why is AChE inhibited by triflates not susceptible to reactivation?
According to a report, certain esters of trifluoromethanesulfonic acid are capable of acting as irreversible inhibitors of acetylcholinesterase. Also, 3-PAM, while capable of reactivating AChE ...
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0
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45
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Why the IUPAC naming of this compound is 6-hydroxycyclohex-2-en-1-one?
Should it not be 2hydroxycylohex-5-en-1-one?
Functional groups are usually given more priority than double/triple bonds, except in cases of Nitro, halides, etc.
Shouldn't the priority order be Ketone&...
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votes
1
answer
41
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Stability comparision between cyclopropylmethyl and other stabilised cations?
So I had a test recently where this following question came
I don't have any concern with (1), there is no doubt in it. But, how do we tell the stability between (2), (3) and (4). Our sir said that ...
16
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4
answers
6k
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Why is a C4 ring impossible?
I am admittedly not a chemist. I was playing with a molecule set recently and I created a ring molecule where I double-bonded four carbon molecules to each other in a ring.
I was in my university's ...
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1
vote
0
answers
135
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Why do diastereomers have different physical and chemical properties?
While going through my book (Organic Chemistry, Paula Bruice) I came across the following line:
We have seen that enantiomers have identical physical properties. They
also have identical chemical ...
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1
answer
106
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Why is the melting point of 4-bromoacetanilide so high? Does it have any reason to do with the chemical structure, or the para aspect?
We used melting point to determine the type of bromoacetanilide, and it was closest to 4-bromoacetanilide. How can I explain why the melting point was what it is?
2
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1
answer
74
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Confusion in carbocation rearrangement
In the above dehydration reaction (asked in a competitive examination) I have shown two paths, obviously only one of them is correct.
According to test correct answer is product formed through A but I ...
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votes
1
answer
87
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How to explain the acidity difference between these β-diketones?
In DMSO, pentane‐2,4‐dione (1) and 1,3‐diphenylpropane‐1,3‐dione (2) possess nearly identical $\mathrm{p}K_\mathrm{a},$ whereas 1‐phenylbutane‐1,3‐dione (3) is almost 1 $\mathrm{p}K_\mathrm{a}$ unit ...
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2
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90
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Why is the dipole moment of Anisole less than that of Phenol? [closed]
According to Wikidata, anisole has a dipole moment of 1.38D and according to this page on Researchgate, phenol has a dipole moment of 1.70D.
Resonance in anisole:
Resonance in phenol:
According to my ...
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1
answer
52
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How to find the percentage of chloroderivatives after monochlorination of a compound
There are series of examples in my textbook to decipher the chlorination selectivity.
The example was to find percentage of monohlorderviatives of n-pentane after free radical halogenation giving ...
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-3
votes
1
answer
64
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Methanol Evaporation/Degradation From Surfaces [closed]
I've seen resources indicate how quickly methanol in small amounts evaporates from a dry surface in open air. Does this apply to methanol mixed with other substances, such as that in wiper fluid? I'm ...
1
vote
0
answers
34
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Will this reaction apparatus work (refluxing under inert atmosphere)
The nitrogen flow comes from the right side, directly into the flask. Then will go up the condenser and through the bubbler to release pressure. I am worried that my solvent that evaporates when ...
2
votes
1
answer
151
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Which hydrogen in 3-ethynyltoluene is the most acidic?
Arrange the three types of hydrogens in 1‐ethynyl‐3‐methylbenzene in the order from the most acidic to the least.
From my understanding, the hydrogen on methyl would be the most acidic as the ...
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0
answers
55
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Could there be any reaction between piperine and Pink curing salt #2 [closed]
EDIT: I originally (incorrectly) asked this question re: capsaicin; but found that the actual compound of concern in black pepper is "piperine".
This question originates on a forum dedicated ...
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votes
1
answer
70
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Carbon monoxide question [closed]
When reading lots of articles about carbon monoxide poisoning cases I came across to it being referred as "silent killer" many times. Now, I know that carbon monoxide is a byproduct of an ...
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2
votes
0
answers
29
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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 ...
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votes
1
answer
74
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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 ...
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5
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0
answers
58
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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. ...
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1
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75
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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 ...
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votes
2
answers
98
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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 ...
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5
votes
2
answers
318
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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.
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1
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46
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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 ...
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votes
1
answer
91
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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
639
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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 ...
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0
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42
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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 ...
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1
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56
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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
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votes
1
answer
58
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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
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0
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16
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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) ...
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10
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1
answer
459
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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
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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 ...
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3
votes
1
answer
143
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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 $\ce{O^.}$ ...
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4
votes
2
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351
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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 ...
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votes
1
answer
91
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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 ...
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1
vote
1
answer
88
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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 ...
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2
votes
0
answers
25
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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 ...
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votes
1
answer
69
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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
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3
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695
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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 ...
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1
answer
51
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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?
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4
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0
answers
51
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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
28
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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 ...
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