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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17 views

HOBt and DCC in the synthesis of peptides

DCC is a well known reagent used for the synthesis of peptides, aiding the formation of the amide bond by forming an intermediate with the carboxylic acid that contains a leaving group. During my ...
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182 views

Finding order of acidic strength for given compounds

The decreasing order of acid strength of the following compounds: The given compounds are Water ($\ce{H2O}$) Ammonia ($\ce{NH3}$) Acetylene ($\ce{C2H2}$) Triphenyl system ($\ce{Ph3CH}$) a) $\ce{NH3}$ &...
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According to Markovnikov rule and stability of carbocation which is most likely to form if HI “excess” is not given?

Problem Answer > I thought "I" can stabilizes carbocation formed intially by resonance so there can be a shift of (+) to the carbon close to "I" and ...
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1answer
22 views

Thermodynamic properties of enantiomers

Pairs of enantiomers have the same chemical and physical properties (except rotation of plane polarized light) within an achiral environment. However, I am curious about the thermodynamic properties ...
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1answer
16 views

Do phosphoryl thiocholines, their uncharged analogs, and other organophosphates, interact differently with Acetylcholinesterase?

As asked in the title, would the various salts -such as hydrochloride or methyl iodide- of V-Agents interact any differently with acetylcholinesterase compared to the neutral compound? For instance, ...
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Are there any increment systems for guessing the heat of formation for organic compounds that have C, H, O in them?

In the link, you can find two methods of approximation which can help one calculate the heat of formation for Alkanes. I do realize that with the addition of O, the position of the functional group ...
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What substance, material can adhere to plastics but not to paper and the other way around [closed]

What can stick to plastic but not paper and what can stick to paper but not plastic. The paper and plastic I mean are just pure paper and pure plastic without any other added materials. So they can be ...
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1answer
59 views

Can the guanidinium ion give stable N-nitrosamines under mild metalworking conditions?

Can the guanidinium ion react with inorganic nitrite under mild basic metalworking conditions ($\mathrm{pH\ 8 - 10}$ and temperature $\lt \pu{70^\circ C}$) to give stable N-nitrosamines? Usually, the ...
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How to check type of R, S, E and Z geometrical isomerism [closed]

Like I get confused when the question comes up to identify configurations of achiral centers. With options like 2R, 3R, 2S... Please help!!
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1answer
77 views

Is there a way to convert aniline to phenol without diazotizing it?

I am a high school student and while reading about reactions on amines, I was trying to figure out a way to convert aniline $(\ce{C6H5NH2})$ to phenol $(\ce{C6H5OH})$ without diazotizing it with ...
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What kinetic model does the hydrogenation reaction of dibenzyltoluene follow?

So during the course of my research, I've read countless papers related to the hydrogenation of dibenzyltoluenen and the dehydrogenation of perhydro-dibenzyltoluene. Now what I've noticed, is the fact ...
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35 views

Trans junctions in fused cyclopentane rings

Is it possible for the ring junction to be trans in a molecule containing 2 fused cyclopentane rings? I am aware it is not possible for fused cyclobutane rings but am not sure about the 5-membered ...
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1answer
79 views

Does the position of a functional group in an organic compound have any effect on the compound's heat of combustion?

Is there a link between where the functional group is located in an organic compound and the compound's heat of combustion? It has been mentioned before that it is difficult to accurately get the ...
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1answer
70 views

Are acid anhydride and anhydride the same thing?

In my organic chemistry course, I have been made familiar with the term acid anhydride and anhydride. I know that anhydride denotes the structure : But I am confused about whether acid anhydride ...
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26 views

Reliance of migratory aptitude on steric hindrance and its effect on rate of reaction

I've learnt that the migratory aptitude of phenyl is greater than that for methyl, for example. But how do I find the order of the same for any given 2 groups, like $\ce{Cl-}$ and $\ce{PhCH2CH2CH3-}$, ...
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34 views

Hybridisation of free radicals and carbonium ions

What hybridisation do the following carbonium ions and free radicals exist in: $\ce{CH#C+}$ $\ce{CH2=CH+}$ $\ce{CH#C^\circ}$ $\ce{CH₂=CH^\circ}$ According to me all are $\mathrm {sp}$ hybridised. ...
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What computational software is available to simulate drug receptor activity?

Is there any programming software/simulation software that can allow us to see whether a drug/molecule can form interactions with a receptor/enzyme pocket. Does it have anything to do with molecular ...
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48 views

What will this compound be named [closed]

I found this structure on the cover page of my chemistry module and am very curious regarding what it will be named
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43 views

What is a cinammyl system?

I came across this term while searching for reference in March's Advanced Organic Chemistry. It said: LAH gives significant double reduction only in cinammyl systems, for example, with PhCH=CHCOOH. ...
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1answer
37 views

How does temperature and other factors affect sigmatropic rearrangements?

The image below shows a [3,3] sigmatropic rearrangement. My question is why does the increased temperature favour the right side? The arrangement is technically the same except for the methyl groups ...
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34 views

How do you know whether a molecule or drug can fit within a receptor/enzyme pocket? [closed]

Suppose biological studies have revealed a specific receptor to being responsible for a specific disease. Suppose we also stumble across a lead molecule that has the potential to display therapeutic ...
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1answer
82 views

Can sodium borohydride reduce hemiacetals?

In the synthesis of Panacene by Canesi et al. [1], a step involves the installation of an $\ce{-OH}$ group on a double bond, using the oxymercuration-demercuration procedure. However, the product ...
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3answers
61 views

What exactly is a 'chiral centre' in a carbon compound? [duplicate]

The typical progression (in books, YouTube videos) of explanation of chiral carbons in a compound is as follows: Chiral compounds are non-superimposable by their mirror-image; It is easily seen that ...
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Are there any tests which distinguish between triglycerides and polar lipids/impurities that can be conducted in a high school setting?

I am currently writing a research essay about using a mixed polar (methanol) and non-polar (heptane) solvent system to extract oil from mango seed kernels. One of the difficulties of using polar ...
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Mechanism for Ce(IV) Oxidation of Naphthalene

S. Cotton's Lanthanide and Actinide Chemistry reports that naphthalene can be oxidized to naphthalene-1,4-dione using cerric ammonium sulfate (CAS), $\ce{MeCN, H2SO4},$ and $\ce{H2O}$.1 No mechanism ...
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32 views

What is a better laboratory set up for dehydration of ethanol to form ethene?

as shown in the question, I will have to design a lab on dehydrating ethanol to form ethene. The current method I am using is by heating up ethanol and sulfuric acid with a hot plate under a water ...
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1answer
35 views

Usually petroleum ether solvent can be separated from the extract via water bath. Can i use water bath for hexane too?

Usually petroleum ether solvent can be separated from the extract via water bath. Also usually hexane as a solvent is separated from the extract via rotary evaporator. I don't have rotary evaporator ...
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Saponification - Oil and Alcohol?

I've been reading that a saponification reaction typically involves NaOH or KOH. I was wondering - could anything that contains an OH group cause a saponification reaction? For instance, coconut oil + ...
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1answer
19 views

Acidity of Alcohol, Ketone, Alkane [closed]

Why is alcohol so much more acidic than a ketone compound, but ketones are more acidic when compared to alkanes (with the same number of C atoms)?
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The things you wish you would have done before doing a PhD in Organic Chemistry? [closed]

Hello there fellow chemists. I am really interested in doing a PhD in Organic chemistry. I haven't really thought which field I would like to specialize in, but it's definitely on my mind ever since ...
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48 views

Wurtz reaction for secondary alkyl halide [closed]

I have found Wurtz reaction for primary alkyl halide in my textbook. My textbook also says that only primary and secondary alkyl halide shows Wurtz reaction and tertiary alkyl halides doesn't show ...
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Why can't the following product be formed in the given Intramolecular Aldol Condensation? [closed]

In the final step I have extracted the hydrogen from the alpha carbon, please tell me where I am wrong. Thanks
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1answer
36 views

Compare reactivity of carbocations and stability of carbanions, radicals, and carbocations

For ranking the carbocations in the image above, I thought of taking the approach that the 1st molecule, the secondary carbocation was the most reactive because it has no electron donating group, then ...
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17 views

An example of non-covalent Polymer-Particle interactions

When doing research for shear-thinning. I come across to many interpreations. Shear-thinning is the non-Newtonian behavior of fluids whose viscosity decreases under shear strain. In other terms, the ...
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Why while writing resonating structures of CH2=CH-CH=CH2, the middle structure(as photo) is not considered or not counted as resonating structure? [closed]

Why the middle structure is not considered as resonating structure (or is it considered?) No rule is broken here, still I haven't seen the middle structure?
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Can secondary alkyl halides be used in the Corey–House synthesis?

I've been told by my teacher that the Corey–House synthesis cannot proceed with secondary alkyl halides; they will prefer to undergo elimination over $\mathrm{S_N2}$ substitution. [used as the pseudo ...
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0answers
23 views

Photochemical Bromination of Cyclohexenes

I am still very confused with the bromination of alkenes. Can I ask help in finding the structure of the main product when each of these 3 are subjected to photochemical bromination? I know for a fact ...
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What are the limitations of the D, L system and the (+), (-) system for naming organic compounds

In organic chemistry, both the D, L system and the (+), (-) system are widely used, in conjunction with the modern (R, S) system. The D, L system names an organic molecule based on the direction that ...
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38 views

Ring Expansion in a bicylic compound

The following compound undergoes ring expansion and contraction simultaneously. I am not able to figure out a clear mechanism for the same, and stuck for a lot of time to get this clear. Kindly help ...
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30 views

In a pair of diastereomers, which of the following is true?

While going through my book, I came across this question and got really confused. Here's what the problem was: In a pair of diastereomers, Both can be laevo-rotatory or both can be dextro-rotatory ...
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1answer
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What would be the product (B) in the following sequence of reaction?

Here is how I approached this: As we know, alc. KOH results in dehydrohalogenation of the compound which takes place as an anti elimination. And then, we're simply conducting halogenation of the ...
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How carbon nanotube sensors works?

How carbon nanotube sensors works? Is the protein (or chemical compound used as part of the sensor) placed inside the tube or where is it placed? and how is the technology used to place the protein ...
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Comparison of resonance structues of unsaturated radical [closed]

Which of these two structures is more stable? I think the second one is more stable because it's 3rd degree allylic.
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1answer
36 views

What is the double bond equivalence of the following compound?

What is the double bond equivalence of the given compound? The given answer is 14 (8 pi electrons and 6 rings = 14 DBE). But why isn't the lone pair on nitrogen considered?? The lone pair on nitrogen ...
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3answers
59 views

Doubt regarding steam distillation

According to my textbook, in steam distillation the liquid boils when the sum of vapor pressure due to the organic liquid and that due to water becomes equal to the atmospheric pressure. Why? I did ...
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How to find normal boiling temperature if vapor pressure is known in any temperature?

I can calculate the vapor pressure of the Acetone at any given temperature using the Antoine equation. Is it possible to find the normal boiling temperature of the Acetone? (It has to be done by just ...
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What is the product of reaction between 2‐cyclobutyl‐2‐isopropyl‐1,3‐dioxane and hydrogen with Raney nickel?

I have 2‐cyclobutyl‐2‐isopropyl‐1,3‐dioxane (alcohol protection) and I have to react it with $\ce{H2}$ and Raney nickel, but I don't know what the product would be. I have seen a similar reaction ...
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Examples to show how useful or not useful of dimerization, trimerization, tetramerization and their likes in synthesizing alkenes and other compounds?

this answer shows that dimerization is a synthetic method On wikipedia, 1-octene is showed to made from numerous dimerizations or a tetramerization. When I read that piperazine $\ce{C4H10N2}$ is made ...
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1answer
38 views

Mechanism for condensation reactions of amino acids

It is well known that peptides are synthesized by a so called "condensation" reaction between an amine and a carboxylic acid group to form the final amide moiety (because it releases water). ...
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49 views

Possibility of removing two water molecules from glycerol

Not a chemist, but from a chemical formula perspective, how hard would it be to create acetone by acidifying glycerol? $$\ce{C3H8O3 + 2 H+ <=> C3H6O + 2 H2O}$$ Has anyone ever heard of this ...