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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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 ...
Rory McGuire's user avatar
-2 votes
1 answer
34 views

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 ...
Isteak Ahamed Imon's user avatar
-4 votes
1 answer
63 views

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 ...
Arnav Tyagi's user avatar
-1 votes
2 answers
147 views

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 ...
Shubhayu Basak's user avatar
1 vote
1 answer
130 views

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 ...
CHEMUMAN's user avatar
-1 votes
1 answer
70 views

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 ...
SUBHAN's user avatar
  • 11
-1 votes
2 answers
91 views

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 ...
Āñé's user avatar
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-4 votes
1 answer
108 views

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?
BlueInfinite1729's user avatar
4 votes
0 answers
81 views

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 ...
HasturQ's user avatar
  • 49
4 votes
1 answer
85 views

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 ...
hemant kumar's user avatar
1 vote
0 answers
24 views

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 ...
user73910's user avatar
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0 answers
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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&...
Avani's user avatar
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-2 votes
1 answer
41 views

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 ...
Sudarshan Kulkarni's user avatar
16 votes
4 answers
6k views

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 ...
Jakob Lovern's user avatar
1 vote
0 answers
135 views

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 ...
AG_Coder's user avatar
-1 votes
1 answer
106 views

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?
user132308's user avatar
2 votes
1 answer
74 views

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 ...
Spencer's user avatar
  • 187
6 votes
1 answer
87 views

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 ...
RTChou's user avatar
  • 128
-4 votes
2 answers
90 views

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 ...
Solus's user avatar
  • 35
-1 votes
1 answer
52 views

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 ...
Avani's user avatar
  • 11
-3 votes
1 answer
64 views

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 ...
user132245's user avatar
1 vote
0 answers
34 views

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 ...
Mattias Weiland's user avatar
2 votes
1 answer
151 views

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 ...
Satya's user avatar
  • 434
1 vote
0 answers
55 views

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 ...
Jim's user avatar
  • 29
-1 votes
1 answer
70 views

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 ...
keenenvy's user avatar
2 votes
0 answers
29 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 ...
toodles's user avatar
  • 109
-3 votes
1 answer
74 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 ...
Kevin's user avatar
  • 1
5 votes
0 answers
58 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. ...
toodles's user avatar
  • 109
-5 votes
1 answer
75 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 ...
TheBorcanu's user avatar
-2 votes
2 answers
98 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 ...
Kavin Ishwaran's user avatar
5 votes
2 answers
318 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.
Julio César's user avatar
-1 votes
1 answer
46 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 ...
Grimm's user avatar
  • 29
-3 votes
1 answer
91 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 ...
Shubhayu Basak's user avatar
6 votes
5 answers
639 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 ...
mral's user avatar
  • 71
0 votes
0 answers
42 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 ...
Audrix's user avatar
  • 107
-2 votes
1 answer
56 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
ASHISH's user avatar
  • 99
-3 votes
1 answer
58 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
Maanik Khurana's user avatar
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) ...
ASHISH's user avatar
  • 99
10 votes
1 answer
459 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 ...
Edward Harvey-Latham's user avatar
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 ...
DuckHoly's user avatar
3 votes
1 answer
143 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 $\ce{O^.}$ ...
Q the Platypus's user avatar
4 votes
2 answers
351 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 ...
vamsi's user avatar
  • 144
-3 votes
1 answer
91 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 ...
riemannium's user avatar
1 vote
1 answer
88 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 ...
Chuck's user avatar
  • 23
2 votes
0 answers
25 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 ...
Blob's user avatar
  • 21
-2 votes
1 answer
69 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?
Shubhayu Basak's user avatar
5 votes
3 answers
695 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 ...
Richie12138's user avatar
-2 votes
1 answer
51 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?
user131501's user avatar
4 votes
0 answers
51 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: ...
Zack Eichenbaum's user avatar
2 votes
0 answers
28 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 ...
rawmeat21's user avatar