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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Bleaching of chlorophyll stains using hydrogen peroxide

I have been doing some experiments concerning bleaching of chlorophyll stains from cotton clothing. Currently I have found that $\ce{H2O2}$ is fairly effective, but still leaves visible stains. Would ...
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Product of Diels-Alder reaction + Consecutive Reaction with base and heat

there is a problem regarding a Diels-Alder reaction that I do not understand (see image). The Diels-Alder reaction of the diene and the dienophile should lead to the product A. I hope I did it ...
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1answer
55 views

Doubt in isomerism

Question Give isomeric relations between these compounds. My answer A and B show metamerism and positional isomerism. A and C show chain isomerism and metamerism. B and C show chain ...
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1answer
51 views

Which is the correct definition for metamers (or metamerism)?

I have heard two definitions of metamers. Compounds having the same molecular formula but different number of carbon atoms on either side of the functional group. Compounds having the same molecular ...
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Cyclic polyynes

Cyclic polyynes have been proposed as theoretical compounds to illustrate the “particle on a ring” model discussed in many quantum chemistry courses. I've looked it up on Wikipedia but there it's not ...
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1answer
41 views

Decomposition of alkene in acidified potassium permanganate

A low boiling point liquid A, molecular formula $\ce{C5H10},$ reacts with chlorine to form B, molecular formula $\ce{C5H10Cl2},$ and with $\ce{HCl}$ (gaseous) to form substance C, molecular formula $\...
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Investigating the effect of solvents (protic vs aprotic) on the alkaline hydrolysis of ethyl acetate using a conductivity meter

What different areas about solvents can be explored with the conductivities collected of the alkaline hydrolysis of ethyl acetate in propanone and ethanol? $$\ce{CH3COOC2H5 + NaOH -> CH3COONa + ...
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25 views

Difference in major product of sulphonation of phenols

When phenol is sulphonated by fuming sulfuric acid at a lower temperature, the ortho product is the major whereas at higher temperature the para product is formed as the major. Why does this happen, ...
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42 views

What is the major product of the reaction of 2-methyl-but-1,3-diene with HBr?

What is the product of the reaction of 2-methyl-but-1,3-diene with HBr? What I understand is that carbon (2) will get a positive charge after protonation. But after this, which should be the major ...
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36 views

Will cyclopenta-2,4-dienecarbaldehyde undergo aldol condensation or cannizzaro reaction?

The following question was given in an exam.Which of the following undergo aldol condensation ? Given answer : a,b,c My answer: b,c My Logic : Cyclopenta-2,4-dienecarbaldehyde(1) on reaction with ...
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Why are carbonyl groups so important [closed]

The most important are π orbitals as they are lower in energy than σ orbitals and the carbonyl group (C=O) is the most important of these—indeed it is the most important functional group of all. ~...
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1answer
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What chemical could dissolve low-density polyethylene?

What chemical could dissolve plastic aside from acetone? Preferably, low-cost and environmentally friendly. Any suggestions would be helpful. I'm targeting for thin plastic (low-density polyethylene)....
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Can you use a photon's torque to change a molecule?

Can you use the torque of a photon to change bond angles, etc.? 11-Cis-Retinal to the all trans version, in the eye, is a good illustration [1]. Note: This phenomenon can be observed by closing ...
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26 views

Where does the protons and electrons go in this redox reaction?

In the above oxidation reaction, does the 2 protons and electrons released get accepted by oxygen molecules? If not, where do they go? Appreciate all answers :)
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1answer
107 views

Synthesis of an epoxide from 1,2-diol

Why is there no formation of epoxide when the two OH-groups are on different planes? I do understand the epoxidation mechanism. However, I would be grateful if someone cleared the specific ...
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1answer
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Would the mixture of Latex Rubber and the Squid's chitin make a biodegradable plastic?

I don't know much of Chemistry but I put the chemical structures of each. Thank you!
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How do you purify phosphoric acid from cheap commercial (hardware-store) products?

I am looking for idea's on how to purify phosphoric acid for lab use, as the the price for reagent grade V's home-use ended with me buying a product designed as a rust-killer for steel... The ...
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3answers
181 views

Reaction mechanism of rearrangement

I am currently studying for my organic chemistry exam, but there is one problem I do not understand. Unfortunately, I do not have any solutions. See image for the problem. My first thought was the ...
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54 views

Products of the oxidation of 1,4-dimethylcyclohexane

I am having difficulty identifying the second product. Is it an ether, or a kind of epoxide? I am out of ideas on how to reach it. However, I do have a general idea how to receive the first product, ...
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2answers
2k views

What is this fluorinated organic substance?

The corresponding author of the paper where this formula was published as appendix passed away. Can someone help me with identifying what is the name of this compound and why have strange zig-zag ...
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1answer
47 views

What is the major product of the reaction between 4-chlorobut-1-ene?

When acetic acid looses hydrogen, an acetate ion is formed which attacks 4-chlorobut-1-ene, forming methyl butenoate. How does the cyclic structure form? Does the lone pair of oxygen attack the butene ...
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1answer
184 views

Does benzene react with steam to create an alcohol?

Benzene has a molecular formula of $\ce{C6H6},$ right? Surely it has some alkene-like properties because of the double bonds, so can it undergo a hydration reaction to create alcohol?
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1answer
131 views

Is chlorophenylmethane the correct IUPAC name rather than chloromethylbenzene?

I thought that the correct IUPAC name for the molecule below (benzyl chloride) would be chloromethylbenzene because the ring always gets priority over the chain unless a primary functional group is ...
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1answer
47 views

Reaction between 1-methylcyclopentanol and potassium permanganate

In my basic organic chemistry class, I learned that only primary and secondary alcohols undergo oxidation (using $\ce{KMnO4}$). However, what is the outcome of reacting tertiary alcohol (1-...
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1answer
52 views

Can someone explain 3‐(propan‐2‐yl)cyclohex‐1‐ene forming a carbocation?

Can someone explain this one, especially the formation of the secondary carbocation (in the solution)? Solution: After the electrophilic attack by $\ce{H+}$ on the π bond, I had expected the ...
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2answers
73 views

Product of this Michael addition

I'm having problems when trying to know the outcome of this reaction. The first step must be a Michael addition of the 1,3-dicarbonyl compound to the α,β-unsaturated carbonyl compound, followed by a ...
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2answers
231 views

Prime in substituted benzene

I was sent data for a molecule referred to as 1,2'-bis(4-aminophenoxy)benzene. I haven't been able to figure out if that is a real molecule. If I drop the prime, I know 1,2-bis(4-aminophenoxy)benzene ...
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2answers
135 views

Is cyclic ether oxidised by periodic acid?

Is the three member ring of cyclic ether oxidised by periodic acid? As this also has oxygen attached to adjacent carbon so I think that cyclic ether of three members should be oxidised by periodic ...
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0answers
30 views

What makes determining entropy changes theoretically so hard compared to enthalpy?

It is really hard to determine the entropy change of a reaction accurately because of subtle solvent effects and a lack of standard entropies. On the other hand, enthalpy is relatively easy and ...
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2answers
57 views

The Trend Between Boiling Point and Solubility in Organic Chemistry

Is it true in assuming that a higher boiling/melting point means that an organic compound will be more soluble in water? I'm trying to distinguish between the solubility of aldehydes vs. ketones ...
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0answers
99 views

Is there a reliable chemical theory that predicts pKa based on structure?

Obviously, there are general stability arguments that can be made to estimate relative pKas, such as evaluating the stability of the conjugate base of an acid, or thinking about how polarized the bond ...
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36 views

Reaction rate of Mg with aryl halides

I have been thinking of the rate of reaction of aryl bromide and aryl chloride with $\ce{Mg}$ to form Grignard. When considering the electronegativities the carbon in aryl chloride is more ...
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1answer
27 views

Reduction of conjugated double bond by sodium borohydride

Some of my teachers were debating about whether a double bond in conjugation with a ketone is reduced or not by $\ce{NaBH4}.$ One of my teachers presented the evidence from Clayden which had an ...
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13 views

Comparing rates of HBr addition to propene and propyne

I was asked to compare the rates of electrophylic addition of HBr (no organic peroxide) to propene and propyne. I thought that the rate of addition to propyne is faster than addition to propene, my ...
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1answer
39 views

What will be the product ratio if I do chlorination of p-toluic acid?

If I do chlorination of p-toluic acid using Lewis catalyst, e.g. $\ce{FeCl3},$ what will be the ratio of major product to side product? Main product shall be 3-chloro-p-toluic acid and other product ...
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0answers
31 views

How do blue shifts in Raman spectra indicate a co-crystalline compound?

The short conference paper The Acetylene-Butane Co-Crystal: A Potentially Abundant Molecular Mineral on Titan (mentioned in EurekaAlert's 'Bathtub rings' around Titan's lakes might be made of alien ...
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1answer
39 views

How is chlorocarbene synthetised?

The wikipedia page on cyclononatetraene says that the aromatic cyclononatetraenyl anion can be synthetised by a rearangement of 9-chlorobicyclo[6.1.0]nona-2,4,6-triene. My first idea on how to ...
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0answers
33 views

What was the process that created a plastic-looking material from the jam leftovers? [closed]

I was making apricot jam using fresh apricots and gelling sugar. All went well except I burnt it. Some of the solid parts sank to the bottom and stuck there. After putting the good stuff in jars, I ...
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0answers
20 views

Why isn't the base reformed in base-catalyzed hydrolysis of esters?

In acid-catalyzed hydrolysis, the hydronium ion is clearly reformed; however, in the base-catalyzed hydrolysis, an alcohol is formed as a by-product, but the strong base isn't reformed. Is it a ...
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2answers
57 views

Reduction of ester in presence of ketone group

As there is no ring expansion I'm assuming that a carbocation should not form at ester carbon as it leads to ring expansion. But is there any an exception to it? Also the hint provided along with this ...
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1answer
59 views

How many dipeptides are possible by the reaction of glycine and alanine?

How many dipeptides are possible by the reaction of glycine and alanine? Glycine has no chiral centre. Alanine has one chiral centre. The products are alanylglycine and glycinylalanine (I not sure ...
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1answer
73 views

What is the mechanism of this pyrylium synthesis?

In this preparation, http://www.orgsyn.org/Content/pdfs/procedures/CV5P1106.pdf, 2,4,6-trimethylpyrylium perchlorate is prepared from 4 molecules of acetic anhydride and 1 molecule of t-butanol. ...
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0answers
30 views

Oxidation of Aromatic Methyl to Aldehyde by CAN

I read in my text that Ceric Ammonium Nitrate is used for oxidation of primary alcohols. But the surprising part was that, according to the book, it could oxidise aromatic methyl group to a -CHO group....
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2answers
119 views

Potassium carbonate vs. Potassium hydroxide in Wood Ash

I'm trying to get more concrete information about the chemical process of creating soap from wood ash. What I’m confused about: Many soap-making materials say that you create potassium hydroxide ...
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0answers
30 views

Formation of isocyanide on reaction with silver cyanide whereas sodium cyanide forms a regular cyanide

Organic halide react with silver cyanide and an isocyanide is formed, whereas on reaction of sodium cyanide, normal cyanide is found. What is the reason behind the difference in the products?? In a ...
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1answer
27 views

Why does benzoyl peroxide homolytically cleave to give phenyl radical

Benzoyl Peroxide cleavese rapidly to give out $\ce{CO2}$ and phenyl radical. What I could not understand was why phenyl radical is formed because it is not at all resonance stabilized and nor any ...
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19 views

Procedure for determining the levels of Acrylamide from a cup of coffee

For experimental purposes, I want to determine the level of Acrylamide in cups of coffee. Is there a method that doesn't use spectrometric analysis to determine it as I do not have access to it in the ...
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1answer
133 views

Difference between oxo and formyl

What is the difference between oxo and formyl? both represent aldehyde when used as a substituent(correct me if I am wrong). But when should I use formyl and when oxo? This answers my problem and ...
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27 views

Stability of carbanion in elimination reactions

Let's start with the reaction of 2-chlorobutane with ethanolic KOH. Now, as per the stability of carbanions, 1-butene should be formed (due to higher stability of primary carbanion in its ...
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1answer
75 views

How to improve efficiency of the diamine synthesis from fluorescein?

In this work, fluorescein was incorporated with an equal molar of 1-chloro-4-nitrobenzene and double potassium carbonate (molar ratio), the solvent of this reaction is dimethylacetamide (50 ml for 5 g ...