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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2
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0answers
35 views

Reaction pathway - Extra molecule used in one step only?

I am currently building a reaction mechanism through Gaussian calculations. I successfully found each TS and intermediates through the different jobs (opt, freq, irc) for my 3-step mechanism from ...
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26 views

Comparison of boiling points of para-derivatives of phenol

The boiling points of four para-derivatives of phenol are: How can we compare the boiling points of p-nitrophenol and p-aminophenol? Apart from the hydroxyl group, p-nitrophenol has two oxygen atoms ...
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26 views

steam distillation vs fractional distillation

I am a high school student and I am a little confused in the techniques used to purify organic compounds, for e.g we study in steam distillation we reduce the external pressure on the compound to be ...
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1answer
53 views

iupac name please? [closed]

I am kind of confuse here whether to number $\ce{NO_2}$ or double bond in the ring.
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1answer
68 views

How to carry out cyclization of 1‐(2‐methylbutyl)‐2‐nitrocyclohexane?

How the cyclization can take place as there is no other functional group than $\ce{NO2}?$ One way that I can think of is photochemical bromination which occurs selectively at tertiary center which ...
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1answer
39 views

Calculation of concentration at equilibrium for extraction

The equation for equilibrium of solvent-solvent extraction is: $$\ce{PhOH(toluene) <=> PhOH (aq)}$$ An aqueous solution contain $\pu{1.5 \times 10^{-2} M}$ phenol and is shaken with the same ...
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1answer
78 views

Are phenyl and allyl groups in prop-2-enylbenzene coplanar?

Wouldn't C1 and C2 in prop-2-enylbenzene be on the same plane as that of the phenyl ring, right? If the double bond connected to C2 was between it and C1, they would be, but is it correct that now ...
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0answers
45 views

Why does allyl anion have only two resonance structures?

There are only two resonance structures of allyl anion with negative charge distributed over positions 1 and 3: $$\ce{\overset{-}{C}H2-CH=CH2 <-> CH_2=CH-\overset{-}{C}H2}.$$ What's the criteria ...
3
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1answer
78 views

What is the IUPAC name of this organic compound? [closed]

Variety is the spice of life. I have made an organic compound myself. Can you please tell me the name? I thought that the correct answer is - 3,3-dibromo-2,4-dichloro-1,4-difluoro-2,4-diiodo-1-...
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0answers
28 views

Which electrons are in HOMO in a peptide bond?

We've recently studied the absorption of UV light by polypeptides, and found that the peptide bonds itself absorhs UV light at around 210nm. I'm confused about what feature causes this to happen.
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1answer
165 views

Why is quinone mono oxime more stable than 4-nitrosophenol?

When we do nitrosation of phenols, we get para-nitrosophenol as the major product, which tautomerises to quinone mono oxime. This article states that it largely exists in the quinonoid form. My ...
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1answer
69 views

Why is isopropyl alcohol (isopropanol) used in rubbing alcohol instead of 'regular' propanol?

Is isopropanol (or 2-propanol) a better solvent than ordinary propanol (or n-propanol, or 1-propanol)? This is strongly implied, from what I have read, but I can't seem to find a place that distinctly ...
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1answer
42 views

Reaction of 1,3-dimethyl-2,5-dintrobenzene with NaOMe/MeOH

I have looked through articles and closest I feel is in this question there will be a nucleophilic aromatic substitution. Now, a lot of questions are available where there is a halogen and OMe group ...
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1answer
122 views

Mechanism of ring opening of amine combined with formylation

What is the mechanism for this reaction? The tertiary amine is converted into an amide and the ring gains a double bond. I can't figure out how the C-O double bond would be formed.
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1answer
96 views

Estimating BDE Values

I'm having trouble understanding how to "estimate" the value of the BDE for the compound shown below (I believe it is a secondary benzylic C-Br value) shown below (the 58 kcal/mol). We are ...
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0answers
25 views

How to decide the order of stability of allylic carbocations when comparing to benzylic carbocation?

I was going through my organic notes and found this order of stability of carbocation: 3° benzylic > 2° benzylic > 2° allylic > 3° alkyl I understand that all this is explained on the basis ...
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1answer
35 views

Amides and Alcohol acidity

Are amides more acidic than alcohols? I thought this regarding a secondary amide and a tertiary alcohol functional group since amides have both electronegative oxygen and nitrogen, compared to alcohol ...
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0answers
30 views

Is it possible to do Cobalt catalyzed directing group asisted meta C-H functionalization of arenes

Directing Group assisted Pd catalyzed (sp2)meta-C-H functionalization has a growing attention in recent years. In addition, few examples can be found for meta-C-H functionalization via Rhodium. I am ...
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0answers
34 views

Related to liquid-liquid extraction

I was reading about purification of organic compounds and I came across this. I quote below, a line from the excerpt that caused my confusion. The organic solvent is later removed by distillation or ...
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0answers
23 views

Why do amides have an inconsistent boiling point trend?

For many organic compounds such as alcohols and alkanes, the relationship between molar mass and boiling point is generally linear when graphed. However, amides have a very high boiling point and as ...
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2answers
131 views

Is it correct to look at plane of symmetry in substituted cyclohexane for determining a meso compound?

I read this question and it's answer by @orthocresol. Now, he has written that the compound in question is meso not because there is a plane of symmetry but because of the rapid flipping of the ...
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2answers
90 views

Why IUPAC name this amine is written as 2-methylpropan-2-amine and not as 2,2-dimethylethanamine? [closed]

Why IUPAC Nomenclature of following amine is written as 2-methylpropan-2-amine and not as as 2,2-dimethylethanamine?
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1answer
44 views

Would this be a correct resonance structure?

In the (B) option, second resonance structure is supposed to be valid. But according to my textbook, many adjacent charges would make the resonance structure too unstable and hence it would not be ...
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1answer
31 views

Depicting a mechanism of peptide bond formation with protonated and deprotonated amino group

I've noticed that some textbooks and video lectures use an amino acid wherein the amino group has two hydrogens, and others use an amino acid with three hydrogens in the amino group (in the formation ...
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3answers
355 views

How to assign overlapping multiplets in 1H NMR spectra?

In the above $\ce{^1H}$ NMR spectrum ($\pu{400 MHz}$, $\ce{CDCl3}$) the methyl, alkene, and $\ce{CCl3CH2}$ protons are fairly easy to assign however, the protons in the cyclohexene ring show overlap ...
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0answers
61 views

Draw the enantiomer products of the reaction between 1,3‐butadiene and (3Z)‐pent‐3‐en‐2‐one

From this reactants I need to draw two products with cyclohexene rings that are enantiomers to each other with chemical formula $\ce{C9H14O}.$ And also draw the reaction mechanisms. Why does it form ...
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3answers
71 views

What is non toxic to fish, has a low freezing point, and floats on water?

I am looking for a liquid that floats on water that will prevent the water from freezing (or at least slow it down). The application would be a small area (less than a square foot). It has to be non-...
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1answer
35 views

Entropy of Dissolution of Hydrocarbons

Here is what I think I know: The entropy of dissolution reactions increases as methylene groups are added (i.e. butanol has higher entropy of dissolution than propanol). Also, acyclic saturated ...
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1answer
56 views

Acidity of Carbonyl group

I m a high school chemistry learner. I have learnt that acids are substance that can liberate H+ on hydrolysis. For that they must be connected to an electronegative atom. In carbonyl ( mainly ...
2
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1answer
290 views

Mechanism of retro aldol condensation of hydroxycyclopropylketone

The reactants were treated with $\ce{NaOH} $. How the product here obtained. Can you show me the reaction mechanism for this. I found this is somewhat Retro Aldol Condensation. But how?
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1answer
49 views

How does Combinatorial Chemistry differ from Rational Drug Design?

I stumbled on Vertex Pharmaceuticals - Wikipedia. It was one of the first biotech firms to use an explicit strategy of rational drug design rather than combinatorial chemistry. Then I looked up ...
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1answer
67 views

Succinic anhydride esterification won't go forward

I'm trying to react succinic anhydride with a decyl alcohol to produce mono-decyl succinate. Literature and Google searches suggest that the monoesterification should proceed without catalyst. However ...
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0answers
20 views

Which one out of a keto group or a hydroxyl group would get protonated first if both are present in a compound (attachment)

In the solution provided by my teacher he protonated the ketone, moved the +ve above by resonance did methyl shift and then did dehydration to form a benzene type system. Is this only because for this ...
2
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1answer
30 views

Gaussian calculation - PCM model for IRC compared to gas phase?

Finding a reaction pathway thanks to Gaussian calculations is tricky exercise requiring a lot of resources for each step of this time-consuming process. Thus, man needs to wonder if each calculation ...
5
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1answer
161 views

Is cyclohexane‐1,3‐dicarboxylic acid a correct IUPAC name?

I did the numbering by taking all the functional groups in principal chain (scheme A), but my teacher did it differently and proposed the name cyclohexane‐1,3‐dicarboxylic acid (scheme B): The ...
2
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1answer
52 views

Numbering for the IUPAC name of this benzene derivative [duplicate]

My first guess was 2-chloro-4-nitrotoluene, but this was not among the choices for this question. My teacher says we will begin numbering from Cl, as halogens have higher priority than a nitro-group. ...
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1answer
65 views

Is CH₃CH(CH₂CH₃)₂ the same as CH₃CH(CH₃CH₂)₂

The carbon in front of the parenthesis is bonded to 2 CH2 which then bonded to CH3, it cannot bond directly to CH3. I assume the correct way of writing the formula of this molecule will be CH₃CH(CH₂CH₃...
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0answers
10 views

Acidity order in substituted Phenylboric acid

Here, we are asked to find the acidity order. For the first one, the answer given is ii > i > iii (c) and for the second one, it is iii > ii > i (b). Any logic that I think for one of ...
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3answers
127 views

What is Resonance, exactly? [closed]

I know the that it(Resonance) is the delocalisation of pi electrons but how and why are those electrons delocalised? What is the driving force that causes the effect?
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0answers
29 views

Why is Chlormephos highly toxic despite requiring metabolic activation?

According to the book "The Chemistry of Organophosphorus Pesticides", the insecticide Chlormephos (S-(chloromethyl) O,O-diethyl phosphorodithioate) has an oral LD50 in rats of 7 mg/kg. For ...
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0answers
37 views

Can the energy used required to break a molecular bond of plastic (e.g. - PVC) be used to dissociate plastics into its constituent elements?

Dear Molecular Chemists and Physicists, Pardon my ignorance, but why can not plastic polymers be broken down into their constituent elements? Common bond energies are shown in these two separate ...
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0answers
21 views

How to know which way to calculate an extraction

I have been solving a number of extraction problems and thought I had figured out how to solve each problem depending on if I started in an aqueous solution or in an organic solution. However, I just ...
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0answers
20 views

Is it possible to add R chain that contains a carbonyl (ketone) to the alpha carbon?

I'm trying to synthesize 2‐(3‐oxobutyl)cyclohexan‐1‐one from cyclohexanone: I thought about LDA, then adding an R group that has a ketone. Is that possible? As far as I know, we can add halogen or ...
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2answers
85 views

What hydrocarbons burn in air without a change in volume?

Find all hydrocarbons(alkanes, alkynes, alkenes), which answers given conditions: the sum of volumes of combustion air products equals to the initial sum of volumes of airs. ( volumes are measured in ...
5
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1answer
64 views

Is tautomerism in ketimines possible?

In a reaction between an aliphatic primary amine and a ketone, I could expect a ketimine as a product or intermediate. My question regards tautomerization of this intermediate: has tautomerization ...
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2answers
93 views

CO2 Catalytic Converter

We all know how CO2, as a greenhouse gas affects the climate and causes global warming. I was thinking of a small device, which could be attached to the exhaust pipe of an automobile. It could convert ...
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0answers
40 views

Quantum Internal Efficiency

I'm reviewing a homework problem where we're given a hypothetical organic semiconductor which has a fluorescence efficiency of $40$% and a phosphorescence efficiency of $60$%. From theory, I know that,...
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0answers
27 views

Assigning carbon-13 NMR for ethyl 2-oxo-2H-chromen3-carboxylate

I have a molecule and an NMR spectrum, and I need to assign the NMR peaks to each of the carbons to the molecule: I know that the 14.19 ppm and the 61.94 ppm correspond respectively to the carbon 12 ...
3
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0answers
46 views

Comparing of melting point of dibromo p-xylenes

How to compare the melting points of the above isomers? I know that melting point depends upon the packing of the molecule, more efficient the packing, higher is the melting point. Symmetry in a ...
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1answer
36 views

Priority of the stabilising factors of resonating structures of Organic compounds

When finding the stability order of resonationg structures of certain molecules.. there is some confusion since some structures satisfy certain factors and others satisfy certain other factors. I want ...

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