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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Is polycyanoethene unsaturated or saturated? [closed]

Is polycyanoethene unsaturated or saturated?
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1answer
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Why does stable compounds have less heat of combustion?

My brain somehow doesn't accept that more stable compounds require have less enthalpy. Isn't it like, if a compound is stable, it requires more energy to break the bonds because the compound doesn't ...
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Reaction of alkenes with AlCl3/HCl

I stumbled upon an interesting organic chemistry problem: Previously I thought $\ce{AlCl3}$ would only be used with benzene in acylation and alkylation, but apparently it can also be used in ...
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Predict compound structure from NMR spectra and formula?

Can anyone predict the compound structures from these NMR spectra and formulas? 1: Formula: C14H14 1H NMR: 13C NMR: 2: Formula: C10H10O2 1H NMR: 13C NMR:
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What software was used to create these organic reaction scheme figures?

I am aware that software such as ChemDraw, ChemDoodle or MarvinSketch can be used to draw skeletal formulas and the like. But what can I use to draw (in a similarly professional way) reaction schemes, ...
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pKA versus amount of base Question

so I am stuck on a problem, which basically asks what the concentration of the base will be given the high pKa. The answer is that the higher the pKa, the lower the concentration of the base, since ...
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Is the first step of most the accepted mechanism of Perkin's reaction correct?

If I am not wrong this is the most accepted mechanism of perkin's reaction: In the first step, is the acetate ion basic enough to abstract proton from acetic anhydride? If yes, I have a counter ...
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Question involving a ring contraction

The only reagent used is $\ce{NaOH}$ so i suppose it abstracts the acidic Hydrogen from the $\ce{-OH}$ group. A nucleophilic attack at the carbonyl is also possible, as it could form a Tropylium like ...
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Effect of hydrogen bonding on acidity of compounds

Does intramolecular hydrogen bonding increase the acidity of compounds or decrease it? For instance, ortho nitro phenol is less acidic than its para isomer whereas that of ortho nitro/hydroxy benzoic ...
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Mechanism of electron delocalisation from the other end of alicyclic chain

When one adds $\ce{Br2}$ and $\ce{CH2Cl2}$ to 5-Methylhex-5-enol, this mechanism follows; Also,in adding $\ce{Br2}$ to 2,2-Dimethylhexa-3,4-dienol, this follows; What is the mechanism here, in which ...
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H NMR Chemical Shifts [closed]

How does changing the magnetic field strength from 60 to 400 MHz change the appearance of chemical shifts and splitting patterns?
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Why/how is 2-hexanone also called butyl methyl ketone?

I was given: butyl methyl ketone. How do I figure out how to draw this to determine that it's also 2-hexanone? Thank you!
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Acidity of carboxylic and

Some background details of the question Recently came across this statement in my textbook Statement 1 "Direct attachment of groups such as phenyl or vinyl to the carboxylic acid, increases the ...
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Why is Silver Oxide Used in the Hofmann Elimination?

The Hofmann elimination involves the conversion of an amine into a quaternary ammonium salt via exhaustive alkylation. This is because the quaternary ammonium salt is a much better leaving group than ...
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Predict the hybridisation state of each carbon atom in the following compounds [closed]

Predict the hybridisation state of each carbon atom in the following compounds: CH3 CH2 C CH CH2=CH-C-O-O-CH3 CO2
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What are the factors contributing to ring strain?

what are the factors affecting ring strain (ring size is obvious) couldn't think of any other apparently there are more,so can you list them all and also answer the question in image.So according to ...
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Converting Chlorine Dioxide to Free Residual Chlorine

Our water treatment facility used Chlorine Dioxide to disinfect the produced drinking water. The analysis results indicate concentrations of 0.2 mg/l of chlorine dioxide at the source. Can we analys ...
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1answer
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What is the solubility of d-Glucose in water as a function of temperature? [closed]

I can't find solubility of d-Glucose in water as a function of temperature. I.e. a function that can tell me that at 35 Celsius the maximum amount of d-Glucose that can be dissolved in 100g water is ...
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In “Organic Chemistry” We often see the reagent aqueous NaOH .What is the approximate range we can say of this so called aqueous NaOH? [closed]

For example, in coupling reaction we often see that we write aq. NaOH, but since it depends upon pH scale, so what's the approximate range of aq. NaOH.
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How many non-cyclic isomers exist for C4H7Br? [closed]

The compound Q has the formula $\ce{C4H7Br}$ and contains a double bond. How many non-cyclic isomers exist for Q? Should include cis-trans and any other form of isomers as well.
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Reaction of 1,2-diketones with periodic acid [closed]

$\ce{HIO4}$ can oxidise alcohols. But does $\ce{HIO4}$ undergo any reaction/act as oxidant with 1,2-diketones?
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1answer
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Writing a organic reaction in different form

Can I write this reaction $$\ce{A + B ->[\ce{X}] C + D ->[\ce{Y}] E + F}$$ as $$\ce{A + B ->[\ce{(1) X}][\ce{(2) Y}] E + F}$$ Can I write any organic reaction in this way or are there any ...
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Can ferrocene type sandwich compounds be made with fluorene?

Ferrocene will be well known to made members of this site. It consists of two cyclopentadienyl anions sandwiching an iron-II ion. During my first year organic chemistry course (about 40 years ago) I ...
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1answer
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Why is it that when I add yolk to vinegar and olive oil, it doesn't create a stratification?

Why is it that when I add yolk (which mostly consists of minerals, vitamins, lipids and proteins) to vinegar and olive oil, it doesn't create a stratification? I'm really confused about this because ...
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In free radical substitution of propane with halogens, how do you know which carbon ends up with an unpaired electron after fission of C-H bond? [duplicate]

In free radical substitution of propane with a halogen (eg- chlorine), how do you know which carbon out of the three ends up with an unpaired electron after fission of C-H bond? This image shows ...
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What would be the aldol condensation products in B

In this question (13) I figured out A,C were wrong and D would be correct choice but I am stuck at finding out products formed in B and also why it would be wrong? Please help.
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Mechanism of Possible Acid Catalysed Ring Opening

Here's a problem I'm stuck with - The first step looks like the usual addition of hydroxylamine to the ketone, resulting in two diastereomeric oximes (this is probably what (A) is). Further, in the ...
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1answer
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Help with molecular dynamics and computational modelling to check validity of hypothesis regarding SN2 reaction mechanisms [closed]

Polar aprotic solvents have a less hindered electronegative atom pointing out, namely oxygen, fluorine, and nitrogen, all of which have lone pairs besides having a partial negative charge. Now, all ...
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1answer
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Chirality and number of sterioisomers

I have recently read that the number of sterioisomers in a compound having n chiral centres is 2^n. (That is, if no meso form is present) The below question asks for the number of sterioisomers in ...
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why -I groups are meta director? [closed]

in benzene if a EWG is placed then why it is meta directive not para directive since -I effect will be minimum at para position
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Is it possible to synthesize a benzene ring with every carbon on the ring substituted?

We recently began covering aromatic electrophillic substitution in my first year organic chemistry course, and we've been discussing the nature of certain functional groups being activating $(\ce{-OH},...
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Why does cyclopropane have a higher melting point than propane? [closed]

Ok so I've read that cyclopropane has a higher melting point ~-128°C than propane ~-188°C (Courtesy: Wikipedia). Now I know that cyclopropane is more compact and therefore it's lattice is more stable ...
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1answer
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How to compare the rate of decarboxylation?

For the following acids compare the rate of decarboxylation on heating I $\ce{Ph-CO-CH2COOH}$ II $\ce{Ph-CO-COOH}$ III $\ce{CH3-CH2-COOH}$ IV $\ce{HOOC-CH2-COOH}$ I tried this ...
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Why do the splittings in mirrored COSY crosspeaks differ?

I have a COSY spectrum of a mixture of butanal and butyl bromide and I don't understand why the cross-peaks have various/different splitting on the other sides of the diagonal. I think it may have ...
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How to determine which molecule is planar? [duplicate]

I've been having difficulty in this particular question for some time, primarily because I have no idea how the correct option was arrived at: Which of the following is not a planar molecule? (...
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Can grignard reagent be with CN group? [closed]

is CN--Mg--Br possible?? and can it be used to attach CN- group to alkanes with O= group attched to them already?
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Carbon compounds with no covalent bonds [duplicate]

The first line of the Wikipedia article on Organic Chemistry says: "Organic chemistry is a subdiscipline of chemistry that studies the structure, properties and reactions of organic compounds, which ...
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1answer
54 views

Benzyl Carbocation Stability: Would electron-withdrawing group on the ring destabilize the carbocation?

In the following question I need to decide whether the reaction would undergo SN1 reaction or SN2 reaction. I initially thought it would be SN1 since the resulting benzyl carbocation can be ...
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Do aprotic solvents “slow down” SN1 reactions?

SOLVENT EFFECTS. Predict if using the polar, non-protic, solvent N,N-dimethylformamide (DMF, $\ce{Me2NC(=O)H})$ will speed up or slow down the following reactions and BRIEFLY justify your answers. ...
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Conjugation and Lithium aluminium hydride

When does lithium aluminium hydride reduce double bond in conjugation with carbonyl group? I found that it reduces benylic alcohol to alkane. Does it have anything to do with congjugation of phenyl (...
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Naming Functional Isomers

For naming the isomers of this compound, (1-chloropropane and 2-chloropropane), is 3-chloropropane a valid isomer? Since 3-chloropropane is the same as 1-chloropropane, is it customary to just mention ...
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Synthesis of ester [closed]

I have a question about synthesis of ester from carboxylic acid and alcohol. When an alcohol is still left in the product after ester synthesis, what does that indicate in terms of experiment process? ...
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Regioselectivity of Epoxide Opening: How do you compare the steric hindrance of Phenyl group and -CH2OH?

The following is one of synthetic steps for reboxetine, a drug developed by Pfizer. The following step was carried out in the presence of NaOH: I was taught that a nucleophile attacks at less ...
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3answers
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Which compound will have the most stable enol form?

Which compound will have the most stable enol form, Phloroglucinol or 4-Pyridone? My Thoughts: Both in their enol form are aromatic. I am not sure how do I compare their stabilities. The answer ...
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What is the effect of pH on tautomerism ( general and wrt imine - enamine tautomerism) [closed]

I presume it's interplay of thermodynamic and kinetic factors where only thermodynamic considerations would suffice. The yield may depend on pH as tautomerism involves abstraction of H. Note: I am ...
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Metalation of thiophene

So lately I've been studying the concerted metalation-deprotonation of thiophene and I came to the conclusion that the alpha positions of thiophene are the most reactive, which is why one of those ...
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1answer
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Elimination reaction with bad leaving groups [closed]

If a halogen is present, as in case of 2-fluorobutane, which is reacted upon by alc. KOH then, shouldn't the product be according to Zaitsev's rule. Then, why does the removal of hydrogen takes ...

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