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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38 views

Isolable activated esters: Other than N-Hydroxysuccinimidyl ester and Pentafluorophenyl ester?

Are there activated esters that undergo amide bond formation with an amino group in a mild and selective fashion, other than NHS ester and Pentafluorophenyl ester? I am aware that there are many ...
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36 views

Degradation of Pd catalyst in Buchwald-Hartwig amination

I am conducting Buchwald-Hartwig amination. I use $\ce{Pd_2(dba)3}$ and $\ce{P(o-tol)_3}$ as catalyst and toluene as solvent. Temperature is 100 ℃ and reaction time is 24 hours. During the reaction, ...
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31 views

What are the major products formed by reaction of methylidene cyclopropane with HBr in CCl4 solvent?

I am confused between two products: bromomethyl cyclopropane Allyl bromide Reason for my confusion: We know CPM cation will be formed which is stabilized by dancing resonating structures why can't ...
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1answer
61 views

Name of a beehive like organic structure, is it aromatic? [duplicate]

I was just studying organic chemistry and came across a weird, yet beautiful, structure, don't know its name but its structure is given below:                                                 I wanted ...
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41 views

Are these two molecules enantiomers or diastereomers?

I had a long discussion with my professor about these two molecules, and we both agreed to do some of our own research and reconvene. These two molecules appear to be non-superimposable mirror images ...
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0answers
46 views

When do the Wolff-Kishner Reduction and Clemmensen Reduction not take place for carbonyl compounds?

I came across some examples of organic compounds with acidic groups that didn't undergo the Clemmensen reduction. So, I was wondering which types of compounds the two reagents cannot reduce. Also, why?...
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1answer
55 views

Number of enol forms of acetylacetone

Here is what I tried: These are the two enolic forms that I could make. So according to me, the total number of distinct enol forms of acetylacetone is $2$. But the answer is 3, what am I missing?
5
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1answer
98 views

Does the Oxy or Alkoxy Claisen Rearrangement Exist?

@Waylander's cogent Comment to the query of @Random Guy inspired me to post a problem in synthesis to test a question I have pondered for some time. The activation energy (AE) for the Cope ...
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41 views

During of Formation of aldol why Enolate ion react from carbon double bond end even though carbonyl group is a hard electrophile

When we are reacting 2 moles of an aldehyde /ketone ( with alpha H ) with OH- as base to form aldol first step is formation of Enolate ion by reaction of OH- with acidic alpha H, second step is ...
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38 views

Converting Newman projection to dash and wedge structure

I want to convert the following Newman projection to a dash and wedge structure but the examples I've seen online are with simple molecules with methyl groups on the side. I wanted to show the long ...
2
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0answers
20 views

DEG monobutyl ether pH change

We are using DEG monobutyl ether (CAS 112-34-5) in our production. Normally it is pH neutral, however suddenly we noticed that it has shifted to being acidic (pH=3.4). What has changed in the material?...
3
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1answer
119 views

What are the major products when naphthalene reacts with ethyl chloride in the presence of AlCl₃?

From Arihant Test Drive, JEE Advanced 2020; Ramchaya builiding, Daryanganj, New Delhi, India; January 2019, p. 342: Napthalene gives 1-ethylnapthalene on reaction with ethyl choride in the presence ...
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23 views

Sigma resonance vs ring expansion [duplicate]

I was solving some problems on carbocation rearrangement and I happen to come across a situation in which there's a carbocation on the methyl group attached to cyclopropane such that it can show ...
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40 views

Alcohol to Ketone by CrO3 in cyclohexane

I have encountered an exercise question on conformation of cyclohexane and there is a statement saying, 'converting alcohol to ketone by CrO3 is much faster when R-OH is in axial position'. I would ...
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33 views

Waste management of hazardous solvents

How should one safely dispose of chemicals like dichloromethane, toluene or acetone that were mixed with water? Is the water contaminated to a degree that it needs also treatment? For example ...
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0answers
53 views

Comparing stability of two carbocations [duplicate]

Which of the following ions(A and B respectively) is more stable? How can we explain this on the basis of resonance? Here's what the solution said: Structure (A) is a primary carbocation and has no ...
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44 views

Separation of cyclopentanol from cyclopentanone

I've been having an issue in a hydride reduction of . I would fractionally distill it had I not broken my column a few days earlier. I don't have access to NMR or IR or frankly any method that is used ...
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47 views

Is the reaction stated below a SN1 or SN2 when ethanol is a solvent?

According to me, ethanol has an acidic H (attached to O) so it should support SN1 as a protic solvent. But in case of the following example, it is taken as an aprotic solvent, and thusly the reaction ...
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0answers
43 views

Can amide form Schiff base?

Can amide ($\ce{RCONH2}$) form Schiff base? When I searched for it, most papers deal with aliphatic amines. Some paper conducted synthesis with amide-containing compound, but iminization occured at β-...
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24 views

When does chain termination occur exactly?

In the reaction of substitution of alkane. There are chain initiation, chain propagation and chain termination. However, when does the chain termination reaction occur? Does it occur simultaneously ...
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2answers
87 views

Why is the chirality center in (1R, 2S)-2-fluorocyclopentane-1-carboxylic acid 1R and not 1S?

I'm confused why the chirality center in (1R, 2S)-2-fluorocyclopentane-1-carboxylic acid, is 1R and not 1S. I'm personally think that the carboxyl carbon at C1 should have a higher priority than the ...
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16 views

Stability of nucleophilic acyl substitution intermediates

If I have an acid chloride and I want to substitute it with ammonia to get an amide, I have a two step reaction. First the ammonia attacks at the electrophilic carbon giving me a tetrahedral ...
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1answer
52 views

Mesylation of cyanohydrins [closed]

Is it possible to add methane sulfonyl chloride to benzaldehyde cyanohydrin, or add toluene sulfonyl chloride to form the tosylate group on the alcohol and then perfom a grignard reaction on the ...
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1answer
63 views

SN1 mechanism on 3,5-dimethylbenzyl bromide [closed]

I wanted to see how to make the product on the right so my thought was to have an SN1 reaction to remove water and have the bromine ion attack making the product on the right hand side. Is this ...
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1answer
153 views

Mechanism for alcohol synthesis via terminal acetylene reaction with sodium amide followed with epoxide and protonation

If anyone can give me some guidance here, it'd be much appreciated. I know the NaNH2 would dissociate and the NH2- base would deprotonate the terminal acetylene. I'm assuming the resultant product ...
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38 views

Michael Addition- which hydrogen atom is removed

I have the following Michael addition reaction and wanted to know which H atom would be removed. I know that the more acidic H atom is removed and the more stable intermediate is formed which then ...
2
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2answers
110 views

Elucidating an unknown compound using 1H- and 13C-NMR spectral data [closed]

I am currently struggling with the following NMR spectrum for this compound: I know for sure that we should multiply the integrals of the hydrogen atoms by four, and that the compound contains at ...
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1answer
34 views

How does addition of side chains affect solubility and processibility of polyphenylene vinylene?

I am studying electrical engineering and physics. In a recent lecture I was told the $\ce{OC1C10}\text{-PPV}$ molecule has the chains added to the oxygen atom down below because it allows for ...
2
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0answers
88 views

Is syn addition possible with Br2? [closed]

How is this reaction correct? I have studied until now that with $\ce{Br2}$ only anti-addition takes place.
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1answer
122 views

What is the mechanism of paracetamol synthesis from N‐acetylsulfanilic acid? [closed]

C can be converted to D with NaOH and heating at 300 °C. What is the mechanism of the reaction?
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51 views

Will all aldehydes and ketones give 2,4-DNP test?

I've recently gone through 2,4-DNP test for aldheydes and ketones on Byjus: An aqueous solution of 2,4-dinitrophenyl hydrazine (DNP) is known as Brady’s reagent. It reacts with carbonyl compounds (...
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0answers
14 views

Name of type of bond where configuration at the carbon and geometry of double bond is not fixed [duplicate]

For the given compound X, the total number of optically active stereoisomers is ____. I'm having difficulty understanding what the squiggly bond line means. Is there a name given for it organic ...
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0answers
29 views

Can methoxide ion be used as a base in an E1 elimination reaction?

This one problem given in my textbook is confusing because all I know is we can use a weak base for an E1 Reaction. But the reagent given is a methoxide ion. I thought the answer would B but it is C. ...
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2answers
51 views

Just looking for some help with finding relative ratios of components in a mixture using proton NMR

G'day, I am used to identifying molecular structure in isolation using proton and carbon NMR, but have never worked with a mixture before. The mixture relates to the following spectrum: The spectra ...
0
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1answer
39 views

Why do some biofuels have a maximal blending ratio?

ICAO has several conversion processes for sustainable aviation fuel (SAF) with various maximal blending ratios. What would happen if we tried to increase the blending ratio with these processes?
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1answer
52 views

What antimicrobial can be readily synthesized in a school laboratory for a project on antimicrobial resistance? [closed]

I am currently a student studying at a high school hoping to do a project on antimicrobial compound synthesis to use in investigating antimicrobial resistance in E. coli strains. I am hoping to ...
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0answers
46 views

Lewis acid catalysis with BF3

I am a beginner of Lewis acids/bases reactions and found Lewis acid catalysis. There is an example, which is the opening of epoxide by an alkyne anion activated by $\ce{BF3OEt2}$: According to ...
2
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1answer
123 views

What molecule is pictured on the cover of Dead Sara's album "Ain't It Tragic?"

An album released today by Dead Sara, titled Ain't It Tragic, has a chemical structure on the album cover. Here's a close-up of that structure: As the structure is partially obscured, it's difficult ...
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1answer
36 views

How to do work up of reactions (Problem of Emulsion) where NO2 group is reduced using SnCl2.2H2O?

I did a reaction where I have reduced Nitro group to -NH2 group. I have added solid NaHCO3 and shifted pH to 10 as reported in procedure. While extraction emulsion is forming so how to overcome the ...
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0answers
34 views

How could we synthesize tert-butyl-alcohol, starting with just methane as only carbon source?

would it be possible to synthesize tert-butyl-alcohol with methane as the only carbon source? I mean, I almost figured it out, so basically methane is radically substituted by bromine under UV, then ...
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0answers
84 views

Why doesn't the protonated propyne rearrange? [closed]

In the reaction of propyne with $\ce{HBr}$ this cation (prop-1-en-2-ylium) was mentioned by my teacher: $$\ce{H3C-\overset{+}{C}=CH2}$$ He told me that the carbocation will not rearrange as it will ...
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0answers
42 views

Acidity of triphenylmethane

The question is : Why does triphenylmethane have such a high pKa value (going up to $33$) My reasoning suggests that the conjugate base is highly stabilized and hence triphenylmethane should be a ...
2
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0answers
21 views

Reaction of 1-Bromo-1-phenylethene with two equivalents of LDA

I was confronted with the reaction of 1-bromo-1-phenylethene with two equivalents of LDA, then the product is hydrolyzed. As it is a bulky base, it will surely deprotonate and form the phenylacetylene,...
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2answers
109 views

What is the major product of the reaction between 1‐methylcyclohex‐1‐ene and BrCl? [closed]

Would the bromine add to the more substituted carbon due to selectivity?
5
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2answers
297 views

How can we synthesize this cycloester, starting with methyl 4-phenylbutanoate?

I was wondering how to realize following synthesis: I am struggling with this one; for sure, this has something to do with the benzyl position which is particularly reactive, and something ...
2
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0answers
47 views

Synthesis of allylic ether, starting with phenalene

I stumbled across a retro-synthesis question, for which I don't know the exact answer; I prepared two synthesis ways, but I don't know if they could be realized in a lab. The question is the following:...
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0answers
15 views

By what chemical process does shellac in alcohol degrade over time?

It is well established that shellac dissolved in alcohol ('liquid shellac') has a limited shelf life. The actual shelf life is highly variable, depending on the source, manufacture, storage. But after ...
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0answers
32 views

Simmons-Smith reaction, example reaction

Does this reaction work in theory? It's based on the Simmons–Smith reaction but with ZnCCl$_4$ instead of ZnCH$_2$Cl$_2$.
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1answer
67 views

What is the reason behind the stereoselectivity of the conversion of vinyl silanes to alkenes?

I have included some snapshots from clayden organic chemistry: The photos show a discussion of the addition of an electrophile to the bottom of the vinyl silane. However, what if the electrophile ...
4
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1answer
117 views

Comparing Rate of Hydrolysis of Acyl halides

In this particular question, my answer is (D) as steric hinderance is minimum there, but answer (B) was given due to the electron withdrawing (-M) effect of the nitro group. Isn't steric hinderance ...