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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Does triethylamine affect all materials in TLC?

In TLC, I heard that if I treat acid-sensitive materials such as amines, then I can add some triethylamine. The principle of TLC is interaction between materials and polar silanol group of silica. ...
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183 views

Nucleophilicity of sterically hindered enolates

Problem Answer Question Here $\ce{KH}$ obviously acts as a base, and forms the enolate from the ketone, which subsequently act as nucleophiles causing an SN2 reaction on the $\ce{CH3I}$. When this ...
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1answer
100 views

Reduction of conjugated ketone with lithium aluminium hydride

I came across a question about reduction of a conjugated ketone with $\ce{LiAlH4}$. Although it seemed quite easy at first sight, everything became cloudy as I dug deeper. My doubts regarding the ...
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Do CHF3 and acetone form a hydrogen bond?

I haven't been able to find a reference confirming that fluoroform forms hydrogen bonds with acetone. Do they?
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1answer
117 views

Why doesn't hydrolysis of isocyanides take place in basic medium?

Acidic hydrolysis of alkyl isocyanide gives rise to primary amines and formic acid. But alkyl isocyanides do not undergo hydrolysis in basic medium. Why?
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1answer
71 views

Can sodium metal deprotonate terminal hydrogen atom from propyne to form propynide?

I've read that sodium metal is used to form ethynides but for forming propynide, they have used $\ce{NaNH2}$. Is there some reason for not using sodium metal for propynides as well? Source: Chemistry ...
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63 views

Planarity at the Junction between multiple Rings

My Approach: As cyclohexane should be in the chair form and cyclopentane should be in the envelope form, more the number of five-membered rings more should be its planarity, as envelope form is more ...
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Acidity of alcohols

So everywhere that I've read, there's the reasoning that the acidity of a compound is determined by how stable the conjugate base is, this should be the same for alcohols too, but on Chemistry ...
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48 views

A problem on Intramolecular Cannizzaro's Reaction

My textbook has the following reaction given as a special case of Intramolecular Cannizzaro reaction: As far as I understand, here one Phenyl group migrates (instead of hydride ion) from the carbonyl ...
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Analysis of reaction mixture by TLC and finding column chromatography condition

I am conducting an organic synthesis. Below is the TLC image. I used dichloromethane:methanol:triethylamine=10:1:0.15 as eluent, but I stored it during 3 days, so it may be a little bit concentrated. ...
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508 views

Does Phenylacetylene undergo side chain oxidation with hot alkaline Potassium permanganate?

This question was asked in my book: To my knowledge, side chain oxidation with KMnO4 occurs only when a benzylic hydrogen is present. However this doesn't contain a benzylic hydrogen and hence ...
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138 views

Can resonance structures account for NMR spectroscopy chemical shifts?

I am unable to understand why the alpha carbon to the carbonyl group is of lower chemical shift compared to the beta carbon based on the effects of electronegativity and hybridisation. Since if ...
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59 views

C=C and C=O bonds in molecular orbitals

For both $\sigma$ and $\pi$ bonds: A. In terms of electronegativity: Since effective nuclear charge of $\ce{O}$ is higher than $\ce{C}$, so the E.N. of $\ce{O}$ is higher than $\ce{C}$. Therefore, ...
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95 views

Can a Lindlar catalyst reduce aldehydes, nitriles, and carbonitriles?

The major product obtained in the following reaction is: Question source: JEE Main 2019 The molecule shown as product is the official answer given by JEE from the given options. I have written the ...
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Priority among Halogens in Organic Nomenclature

I have been trying to learn IUPAC nomenclature during the past few days. I have been using the MarvinSketch software to play around with random structures and its generated names and comparing them to ...
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1answer
112 views

What is the reason for the boiling point of benzene-1,4-diol being higher than that of benzene-1,3-diol?

What is the reason for the boiling point of benzene-1,4-diol being higher than that of benzene-1,3-diol? Both have hydrogen bonds. I think it is due to quinol's symmetry but can't point out exactly ...
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Name and Mechanism of this Reaction

Problem Find the product X in this reaction - Answer Question After seeing the solution, I came up with the following mechanism for the reaction - I am not sure if my mechanism is correct, nor do ...
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Conversion of allyl alcohol to 2-chloro propanediol with HOCl [duplicate]

going through the preparation of tri hydric alcohol(glycerol), i came across this reaction i.e. preparation of glycerol from propene. In the first step of this reaction, we did allyl substitution with ...
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1answer
110 views

Of 2-bromobutan-2-ol and trans-1,2-dimethylcyclobutane which is chiral as well as dissymmetric?

In an examination I was asked to determine the molecules which are chiral as well as dissymmetric. There were four options, and among them, two were achiral, as they had an improper axis of symmetry. ...
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46 views

Which oxygen in ester group is more nucleophilic?

According to my understanding, the filled orbital (lone pair electron for this) is more nucleophilic (higher energy) if: it has more $\mathrm p$ character (since p orbital is the furthest from the ...
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34 views

Difference between nucleophilicity of phenoxide ion and acetate anion in protic/aprotic solvent

As far as I could think, the phenoxide ion is comparatively larger as compared to acetate ion, so it should undergo less solvation in presence of a protic solvent and thus its nucleophilicty should be ...
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1answer
90 views

What is the mechanism of temporary bleaching of flowers by SO2 ? Can H2S be used?

There are many claims on the web, explaining that the bleach action of Chlorine gas in discoloring of flower proceeds as follow and require moisture for it : $$\ce{ Cl2 + H2O <=> HOCl + HCl <=...
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1answer
79 views

Friedel–Crafts acylation of substituted anisole

I am attempting to form a synthetic route to a tetrasubstituted benzene compound. In the scheme, there is a step that requires the formation of a carbon–carbon bond in the C-6 position of a methoxy ...
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35 views

Different products with varying aluminium chloride concentration in a reaction of propiophenone

How does the product change with varying $\ce{AlCl3}$ concentration? Answer: In excess, meta bromination is observed and if not, then alpha hydrogen is substituted by ketone halogenation mechanism I ...
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3answers
431 views

Choosing reaction stoichiometry in organic synthesis

Reading papers about organic synthesis, I see many cases like setting one material as 1.2 eq. I presume that reagents used more than 1 equiv are relatively inexpensive or less reactive than other ...
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1answer
48 views

Does rearrangement occur in schmidt reaction? [closed]

I recently read about schmidt reaction in which a carboxylic acid is converted to an amine. While forming this, acyl carbocation $(\ce{RCO+})$ is formed, so does rearrangement takes place or reaction ...
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How to proceed a reaction between piperidine and cyclopropyl methyl carbocation!

Since cyclopropyl methyl cation is highly stable, I proceeded through SN1 as elimination is not possible because of strain in the ring. Need help now in approaching the question. Actually the given ...
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1answer
54 views

Hydrogen Bonding in case of nitro group [closed]

In many different cases of Nitro group I have seen that only one oxygen atom is particularly used for hydrogen bonding but not the other one.But I guess both the bonds should be polar and hence show ...
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31 views

Problem about TLC solvent and staining

I am conducting an organic synthesis involving 1-aza-18-crown-6-ether. I tried TLC, but they didn't work well. I have tried: (1) hexane+ethyl acetate in various ratio, (2) dichloromethane:methanol=3:1,...
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36 views

Friedel-Crafts acylation with withdrawing group?

Will a Friedel- Crafts acylation take place on ortho-bromotoluene? I do understand that Friedel Crafts reaction does not occur when there is an electron withdrawing group on the ring but is there any ...
4
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1answer
88 views

Acid catalyzed bromine substitution in an alcoholic ester. What is the major product and why?

This was in a paper I gave. I want to know the mechanism by which both of these products will be formed and why is the 1st one the major product. My thinking is that the -OH group will be converted ...
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1answer
54 views

How Bread is made with yeast, sugar and luke warm milk? [closed]

Materials and Apparatus: wheat flour sugar dry yeast glass bowl covering plate milk Procedure: Lukewarm milk is taken in the glass bowl and sugar is added to it. Then, yeast is added to the same. ...
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73 views

Etard's reaction

My textbook says the following on Etard's reaction: Now, if the alkyl group attached to benzene is an unsymmetrical or branched alkyl group, such as this: What will be the reaction product(s)? Which ...
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1answer
55 views

Setting up reactor in inert atmosphere

I am searching for reactor set-up that can maintain inert atmosphere, and found that many organic synthesis labs use Schlenk line. But organic synthesis is not main thing of my lab, so there is some ...
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1answer
359 views

Reaction of phenol with phosphorus tribromide

I know that aliphatic alcohols react with reagents like $\ce{PBr3},$ $\ce{PBr5},$ $\ce{SOCl2}$ etc. to give alkyl halides as a product. But what will happen if we put aromatic alcohols like phenols ...
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74 views

Tautomerism between cyclohex-2-en-1-one and cyclohex-3-en-1-one

I think cyclohex-2-en-1-one and cyclohex-3-en-1-one should undergo tautomerism as shown below: I'm calling it tautomerism because of it's similarity with the tautomerism mechanism in basic medium. I ...
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1answer
205 views

Mechanism of reaction of ketones with isoalkanes under conc. sulfuric acid and heat

Taken from the book of GOC by Dr. O.P Tandon, Himanshu Pandey, Dr. A.K. Virmani, Can anyone elaborate on the mechanism?
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1answer
131 views

Why does LiAlH4 reduce the double bond of cinnamaldehyde, whereas it does not reduce the double bond in crotonaldehyde?

$\ce{LiAlH4}$ is a strong reducing agent capable of breaking the double bonds. It does break the double bonds in cinnamaldehyde. Shouldn't $\ce{LiAlH4}$ be able to break the double bond in ...
3
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1answer
304 views

Reaction of naphthalene with sodium dichromate/sulfuric acid

I recently came across a question where naphthalene undergoes oxidation with sodium dichromate in presence of sulfuric acid. The given options were benzoic acid, phthalic acid, decalin, and tetralin. ...
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0answers
17 views

Ortho effect and the relative acidity in aromatic acids [duplicate]

What is the order of the acidity of 2-methyl benzoic acid and 2-isopropyl benzoic acid? I know about ortho effect which states that the acidity of ortho- substituted aromatic carboxylic acids is ...
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0answers
36 views

Comparing geometries and substrates calculated with DFT for different pathways

As DFT calculation is an excellent tool for confirming and understanding experimental results, I got deep into this field as organic chemist. I successfully isolated interesting transition states (TS) ...
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1answer
60 views

Fields of Study in Chemistry [closed]

Is there a standard classification scheme for different areas of study and research for chemistry like mathematics has Mathematics Classification Scheme (MSC)?
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44 views

Can phosphoric acid be used to substitute sulfuric acid in the synthesis of thymolphthalein?

I am planning to synthesize thymolphthalein, a pH indicator. I am wondering if phosphoric acid can be used to substitute sulfuric acid in the preparation. I know it can catalyze Friedel-Crafts ...
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1answer
76 views

Ethyne reaction with HCN (red hot Fe) and CH2N2 (cold ether solution)

I have tried this and according to me $\ce{C2H2 + HCN -> C5H5N (pyridine)}$ and $\ce{C2H2 + CH2N2 -> C3H3N2H (pyrazole)}$ But according to my teacher the case should be vice versa, i.e. $\ce{...
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53 views

Purification of Buchwald-Hartwig amination

I am conducting a synthesis involving Buchwald-Hartwig amination. I use $\ce{Pd2(dba)3}$, $\ce{P(o-tol)3}$, and $\ce{Et3N}$ as base. In many proposed mechanisms, they often omit the precatalyst. I ...
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2answers
98 views

Synthesis of active chemical manganese dioxide (CMD) for primary alcohol oxidation

This paper1 uses chemical manganese dioxide (CMD) instead of activated manganese dioxide for mild alcohol oxidation. I'm looking for a route on how to synthesize active CMD. Could this work? $$\ce{...
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35 views

Does HIO4 cleave hemiacetals? [duplicate]

I had written in my notes that it does. But I can't find any credible source for it. A simple Google search only brings up this old and unanswered question. The questioner failed to specify the source ...
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37 views

Effect of trifluoromethyl substituent on electrophilic substitution [duplicate]

Problem - Find which carbon is most susceptible to electrophilic attack (among carbons numbered $1$ to $6$): Answer given (may not be the correct one) - My question - $1.$ I know that $\ce{-CCl3}$ ...
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2answers
86 views

Should I do solvent extraction for Buchwald–Hartwig amination?

I am conducting a synthesis involving Buchwald–Hartwig amination. Catalyst is $\ce{Pd2(dba)3},$ ligand is $\ce{P(o-tol)3},$ base is $\ce{Et3N},$ and solvent is toluene. Image below is the proposed ...

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