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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Hydrogen Bonding in case of nitro group

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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What is the name of category when hydroxyl group is attached to a unsaturated carbon of triple bond {do not consider keto form}

When OH group is connected to benzene ring it’s called phenol and when it is connected to unsaturated carbon of double bond it’s called Enol similarly what it will be called when it is connected ...
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Acidic strength of ortho, meta, para amino benzoic acid

The ortho, meta and para amino benzoic acids are all weaker acids than benzoic acid. However, according to what I have learnt so far, the ortho isomer should be a stronger acid, due to steric ...
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Stability of a carbocation

In 1-ethyl 2-methyl cyclopentane, why would a carbocation at 1(ethyl) be more stable than the carbocation at 2(methyl). The carbocation at 2 will have more alpha-hydrogens right?
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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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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 ...
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1answer
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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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Does Phenol + FeBr3 +Br2 forms para bromo phenol or not Please Help as it's gonna decide my future [closed]

According To me it wouldn't form para bromo benzene as FeBr3 is a lewis acid and form dative bond with oxygen atom and it will form -HO-Fe(Br)3+ and its meta director as well as deactivating group so ...
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1answer
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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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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
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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
271 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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Are butane, hexane, octane, and the remaining “even” alkanes considered polyethylene? [duplicate]

If a polyethylene chain contains hydrogen at its ends, isn't it just an alkane with an even number of carbons? Is there any distinction between polyethylene and even alkanes that I'm missing?
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What is N2O4 used for in organic synthesis? [closed]

Hi I came across N2O4 in my organic chemistry class and before I could ask, my teacher went ahead, so can someone please help me out and tell me what N2O4 is used for?
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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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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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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 ...
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uv-vis same spectra [closed]

Hi there I am doing an experiment of uv assay of Dextromethorphan hydrobromide where its run under uv in two solutions an acitic acid and sodium hydroxide the uv results showed that both solutions had ...
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1answer
178 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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Conversion of a compound to a racemic mixture of enantiomers [closed]

I am studying for the GRE Chemistry and came across this question. I was not sure how to proceed with it. The answer is A but I do not know why. It has been a little bit since Organic chemistry, but I ...
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experiment of UV assay of Dextromethorphan hydrobromide in a cough medicine [closed]

Hi there so I have the experiment in the title above and the first step was to make up two flasks of a 10 times dilution of the stock solution ( dextromethorphan hydrobromide) in 0.1m of sodium ...
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Can glacial acetic acid be stored in sub zero temperatures? [closed]

Can glacial acetic acid be stored in sub zero temperatures without the loss of function?
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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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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
46 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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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
56 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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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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Would para-aminobenzoic acid exist as a zwitterion or non-ionized at pH 4?

The two $\mathrm{p}K_\mathrm{a}$ values for p-aminobenzoic acid (PABA) are: $\mathrm{p}K_\mathrm{a1} = 2.50$ and $\mathrm{p}K_\mathrm{a2} = 4.8$. My thought was that at a $\mathrm{pH}$ of 4, the ...
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2answers
66 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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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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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
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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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Synthetic resins that are as stable as amber? [closed]

It looks like all man made resins degrade quickly, but natural amber lasts millions of years. Are there any synthetic resins or epoxies that are as stable as amber and will not degrade? EDIT: More ...
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2-Iodoxybenzoic acid oxidation reaction

I was thinking about using 2-Iodoxybenzoic acid to selectively oxidize primary alcohols to aldehydes. I've found papers using various solvents like acetone/water mixture1, 2-methyl-2-propanol2, DMSO ...
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2answers
630 views

IUPAC naming for a ring system containing different ring structures

Regarding the IUPAC naming convention for compounds in which one ring is more highly $\pi$-conjugated than the other ring but contains fewer carbon atoms: I can name this compound as either: (a) 1-[...
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2answers
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If rate of SN1 is more does that automatically mean rate of SN2 is less, and vice versa?

If I have a list of compounds and I compare their SN1 reactivity, for SN2 reactivity, is it correct to use the same list but order inverted? Are there any exceptions?
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Is it possible to run column chromatography in reversed phase?

I'm conducting a synthesis involving aza-crown-ether. Whether aza-crown-ether acts as a base or not is unclear, but when I do TLC using dichloromethane/methanol, it is hardly drawn up with the mobile ...
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Can molecular systems display negative magnetic susceptibility of a higher magnitude than bismuth?

Bismuth has the biggest value when it comes to a negative magnetic susceptibility than all other elements, ignoring superconductors, as they would have a value of -1. Yet, when tables displaying ...
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Are syn-anti the same as cis-trans? [closed]

In my textbook cis trans and syn anti have been used interchangeably are they the same thing?
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How come the methyl group (-CH3) is electron donating?

If the inductive effect operates purely through electronegativity differences, how come the methyl group is considered to donate electrons through the inductive effect? My textbook says that there is ...
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38 views

Why is the carbanion stability order the way it is? (3*<2*<1*)

According to the lecture notes I made, a 1* carbanion is more stable than a 3* carbanion. I can't grasp exactly why. (I had a look at the similar questions, the answers didn't help) With my very ...
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101 views

comparing acidity of oxonium cations ( conjugate acid of ketone, ether and alcohol)

I read that alcohol is the most basic among alcohol, ether, aldehyde and ketone. I am curious about the reason and I found the pKa of their conjugate acids: It makes me wonder: why is the ethanol ...
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42 views

Does borax contain pi bonds?

Are all B-O bonds in borax ($\ce{Na2[B4O5(OH)4].8H2O}$) purely sigma and single bonds or is there any presence of pi bond or partial double bond character due to back bonding between the oxygen atom ...
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1answer
81 views

Major product formed in Reimer-Tiemann reaction when Potassium Hydroxide is used as a base

Reimer-Tiemann reaction is known to give ortho major product when NaOH is used as a base. However there seems to be some confusion regarding the major product in case KOH is used as the base. It is ...
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25 views

Is the correct parent chain the longer one or the one including two double bonds?

I want to know which is the correct parent chain in this compound: Is it the one inside the loop, or the longer one that includes the part to the left of the allyl group? I know that once a ...
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32 views

Which is the correct parent chain in this compound?

In this compound: Will the parent chain be the one inside the loop, or the longer one including the single bonds to the left of the vinyl group? I know that carboxylic acid is the highest-priority ...
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1answer
72 views

Can dimethyl sulphide be used for ozonolysis of benzene?

There is literature that suggests that ozonolysis of benzene occurs with ozone and $\ce{Zn/H2O}$. Can it take place with ozone and dimethyl sulphide?
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38 views

Number of products formed in radical chlorination on a chiral center

If an organic compound with a chiral center of a specific (R) or (S) configuration, is chlorinated on that carbon center through a radical mechanism, will one product be formed or two? Basically will ...
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1answer
153 views

Reaction of cyclooctatetraene with sulfuric acid

Problem The correct statement is (A) P & Q are aromatic compound and Q has $\mathrm{sp^3}$-hybridized carbon atom. (B) P is aromatic with 10 π electrons and Q is aromatic with 2 π electrons. (C) ...

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