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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7 views

Why is potassium tertbutoxide not used to deprotonate the tertiary alcohol?

The question is asking which reagents can be used to carry out this reaction. I get the L (PCC) is used to turn the primary alcohol into an aldehyde. However, I believe that is not the only reagent ...
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5 views

What Is The Heat Of Combustion Of Diesel And How Do I Find It?

I need help in finding the heat of combustion of diesel, no where online can i find it, and my chemistry teacher does not know how to find it....
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1answer
18 views

Why do Ketones Have Lower Wavenumbers than Esters?

The average wavenumber for a ketone is about $\pu{1720 cm-1}$ and the average wavenumber for an ester is about $\pu{1740 cm-1}$. This, however, does not make sense, as the carbonyl group of an ester ...
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Which is more basic: oxaziridine or diaziridine?

Which is more basic: oxaziridine or diaziridine? Oxaziridine's got one nitrogen and one oxygen as heteroatoms, while in diaziridine there are both nitrogens.
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17 views

How would you order alkyl groups of this compound numerically?

If akyl groups are ordered alphabetically and ethyl comes before methyl, would this compound be called 2-ethyl-3,4 dimethyl pentane? Since that would be less than 4-ethyl-2,3 dimethyl pentane, correct?...
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38 views

Number of stereoisomers of polysubstituted cubane

The molecule given below is a substituted cubane. a) How many stereoisomers exist for this molecule? b) How many pairs of enantiomers are possible? How do I calculate the number of ...
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25 views

Finding out more stable conformer via molecular orbital interaction

Out of these two, which one is more stable? I'm unable to imagine the orientation of the lone pairs of O and ABMO of C and Cl bond. Any tips to tackle these kind of problems?
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33 views

How does cross-conjugation destabilizes a molecule?

Wikipedia article on ortho effect suggests that o-toulic acid is more acidic than benzoic acid. This fact is rationalized by suggesting that steric effect causes COOH group to "twist" out of the plane ...
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1answer
28 views

Partial dissolution of non-polar solutes in polar solvents

I have learnt that in order for dissolution to occur, the solute-solvent intermolecular forces must be strong enough to overcome the solute-solute and solvent-solvent forces. However if this is the ...
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1answer
519 views

Why does this image of cyclocarbon look like a nonagon?

The $C_{18}$ allotrope cyclocarbon has been synthesized and imaged. Science has most details behind a paywall, but this discussion includes an image: In this octakaidecagonal molecule, each $\color{...
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Product of electrophilic substitution reaction [on hold]

In the following Electrophilic (probably substitution) reaction of the compound with chlorine in the presence of Aluminium chloride what should be the product and why? I am not sure about its name ( ...
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20 views

Is the black carbon powder useful for preparing printers black ink(water-inks)?

I need to prepare black water ink for printers. Is The carbon black powder is the right pigment to create black water ink for printers. What are the specifications of the perfect black carbon powder ...
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22 views

Do any decent thermochemical databases exist? [duplicate]

The more thermochemical properties the better, but specific heat/ specific heat capacity is what I am looking for.
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Ethyl acetate produces red colour on ceric ammonium nitrate test

When I did CAN test on ethyl acetate red colour was seen. I thought water may get added with Ethyl acetate to produce this compound which in turn gave red coloration but carbon should not make three ...
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1answer
26 views

Which of these reactants will not generate this racemic amine?

I understand that in E there is no electrophile the amine can attack, however, I do not understand why A is an answer as well. The amine in A can perform an intramolecular attack on the aldehyde and ...
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25 views

Ease of formation of 3 membered heteroatomic rings [on hold]

A three membered ring is easier to form than a four membered one, although the former has a larger ring strain.. Why???
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18 views

Is the 1,4-adduct of carbonyl compounds ever a major product over the 1,2-adduct?

If, say, propenal undergoes nucleophilic addition of hydrazine, will the 1,2- adduct or the 1,4-adduct be preferred? Why? There is an obvious reasonace structure with an electrophilic beta carbon so ...
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31 views

What would the transition state look like for the following reaction? And a question on Gibbs free energy of the Transition State [on hold]

The alkaline hydrolysis of ethyl acetate. Also wanted to know whether the addition of solvent would have an impact on the Gibbs free energy value of the Transition State since the transition state ...
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1answer
20 views

Role of THF in oxymercuration of alkenes

I am trying to self learn solomon's organic chemistry book, but there is no explanation over why we should use THF in oxymercuration. After a quick search I found out that THF help stabilize in ...
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Cleaning of chlorbutyl plungers

This is my first post, so please bear with me. At work I have some chlorobutyl plungers that I need to clean from any residual material that might be left after production. A colleague of mine told ...
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2answers
33 views

Acidic Cleavage of ether with a 2° alkyl group

I know that an ether with a 3° alkyl group and a 1° alkyl group is cleaved by Sn1 mechanism to give a tertiary alkyl halide and a 1° alcohol. And an ether with a two 1° alkyl groups is cleaved by Sn2 ...
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Increasing concentration of acetylcholine via SPE

I am trying to increase the final yield of acetylcholine (ACh) in my biofluid samples. I need to get the yield high enough for high confidence annotation of ACh (currently all I can really say is that ...
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2answers
630 views

Why is tert-butoxide often used in elimination reactions when it is not necessary?

I understand that tert-butoxide is used to favor the Hofmann product in elimination reactions due to its steric bulk (and thus inability to abstract a proton in a more substituted position); however, ...
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50 views

Preparation of 3-ethylpentan-3-ol

Is it possible to use CI3TMS (a carbon with three iodo groups and a trimethylsilyl protecting group) and three equivalents of an ethyl grignard reagent to prepare 3-ethylpentan-3-ol? By deprotecting ...
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42 views

Calculating ionic strength and pH of a buffer solution [on hold]

Im trying to calculate ion strength and pH of solution. Components of the solution: 47 ul of 1000 pmol DNA in Elution Buffer (10 mM Tris-HCl pH 8.5) was bound to 3 ul of 10 µM YoYo1 (flourescent dye) ...
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1answer
35 views

How to avoid cannizaro reaction during aldol reaction? [on hold]

I am doing some Aldol reaction in lab,problem is **basically one of my Aldehyde is converting largely in cannizzaro products.**Please suggest me which base I can use so that I will not get cannizzaro ...
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2answers
278 views

Why is the Lucas test not recommended to differentiate higher alcohols?

I read about the Lucas test for alcohols in which a cloudy precipitate is produced with a tertiary or secondary alcohol. However, on a side note it was mentioned that this test is useful only for ...
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1answer
27 views

Doubts Regarding Ceric Ammonium Nitrate Test for Alcohols

I read about Ceric Ammonium Nitrate Test for Alcohols and a red colour is produced if the solution has an alcohol functional group however as a side note it was mentioned that this test is only useful ...
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15 views

Doubts Regarding Compounds Which Can Give Aniline Dye Test

I read that to test for the presence of Phenol Groups in an Organic Compound Aniline Dye Test can be performed. If the solution has phenol present it gives a red or orange precipitate to confirm the ...
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20 views

How to remove the foggy discoloration in polycarbonate tubes caused by acetone?

Unknowing that the tubes used in the centrifuge are made of polycarbonate, I cleaned them with acetone. Following, a white smoky discolouration appeared and the tubes turned opaque. Is there any way ...
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25 views

Reaction of carbonyls with alcohol

Why dont ketones react with mono alcohols to give acetals unlike aldehyde? They are very similar and almost share all general reactions. However, there was no reaction of ketones with mono alcohol but ...
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1answer
23 views

Can five membered ring form through Friedel-Crafts alkylation?

Our teacher told us that five membered ring can’t be formed through Friedel-Crafts alkylation but acylation is OK. Why is that? Is it because alkylation is an unfavored 5-endo-trig reaction but ...
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3answers
56 views

Identify the type of structural isomerism

Question: My Approach: Since both the compounds have the same principal functional group, they can't be functional isomers. Obviously they are different compounds. Now options A and C are ruled out. ...
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Does an electronegative atom which carries a negative formal charge withdraw electrons by induction?

Electronegative atoms withdraw electrons by their inductuve effect. Does this fact remain true even when they are heavily loaded with electrons through negative formal charge? Are these two ideas ...
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2answers
89 views

Number of sterioisomers of 2,3,5,6-tetrachloroheptane [closed]

The answer given by Himanshu Pandey in the book Advanced Problems in Organic Chemistry, Chapter Isomerism, Page 76 is 10. But by calculating using the fundamental principle of counting and by viewing ...
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2answers
52 views

Resonance and mesomeric effect [closed]

Can you please explain to me why are A and E not relevant resonance structures of the molecule F? And is B aromatic?
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21 views

Inductive effect on benzene ring [on hold]

I have read that : "Any charge on benzene ring gets stabilized or destabilized by Inductive effect only " If it is true then what is the reason behind this? Why don't we use Mesmeric and other ...
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1answer
30 views

Negative hyperconjugation

Compare the acidity of the following compounds: $\ce{CF3OH}$ and $\ce{CCl3OH}$. My attempt: according to me $\ce{CCl3}$ group will show a stronger Negative hyperconjugation effect than $\ce{CF3}$, ...
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1answer
59 views

Why does the addition of tetraethyl ammonium bromide reduce solution pH? [closed]

I am looking at a system that adds tetraethyl ammonium bromide to water. Over time, the concentration of tetraethyl ammonium bromide gradually increases, leading to a fall in the pH. I am trying to ...
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2answers
54 views

does table salt dissolve in glycerin [closed]

Tell me, does table salt dissolve in glycerin? And is it possible to increase its solubility? I have vegetable glycerin with nicotine that I use for vape. So that nicotine would not be bitter, on ...
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1answer
54 views

How to convert 1,4 pentadiene to 1,3 pentadiene? [closed]

Are there any 'conjugating agents' to accomplish the above transformation? If not, then how to proceed?
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35 views

Ionic vs covalent behavior of sodium [closed]

The given chemical reaction: $$\ce{R-OH + NaBr + H_2 SO_4 \bond{->} R-Br + NaHSO_4 + H_2O}$$ I wanted to write the chemical mechanism of the chemical reaction, given above, but I'm facing a bit ...
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1answer
36 views

Comparison of stability of aromatic compounds [closed]

What is the basis of comparison between two aromatic compounds having different ring structures Like in propyl and heptyl rings
3
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1answer
61 views

Lactone acylation

Can anyone propose/draw a mechanism for Method A, below, from this paper? Almost all other literature use method B and reagents such as SOCl2.
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1answer
39 views

Does 1,3-butadiene in bromine/water do addition twice?

Considering 1,3-butadiene (below) added to bromine water (considering it as $\ce{Br2(aq)}$): I've seen online that the products are 1,2-dibromobutene and 1,4 but what I don't understand is why ...
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1answer
40 views

Finding structural isomers of an alkene

I am doing problems on finding structural isomers. I am asked to find the structural isomers of $\ce{C5H10}$. The answer to problem states there are 10 structural isomers possible. I was able to find ...
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2answers
49 views

Energetic stability in relation to α-hydrogens

I am new to organic chemistry and was asked to rank the following materials according to energetic stability. I think I have understood that the way to do this is to count the amount of α-hydrogens: ...
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0answers
40 views

What does a simple or a complex substituent mean? [duplicate]

I am reading rules for IUPAC Nomenclature. The following statement is from my book. Prefixes di, tri, tetra, etc., are not considered in deciding alphabetical order for simple substituents but ...
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0answers
46 views

Parameters by which to distinguish SN1 from E1

I am new to organic chemistry and am struggling with the following very basic question: Given is the following reaction: $$\ce{(CH3)3CCl + NH3(aq) →}$$ I am supposed to analyse the end-product (the ...