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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26 views

Chemical equation for the reaction of Allura Red AC with NaClO

I am trying to figure out the chemical formula for the reaction between Allura Red AC and $\ce{NaClO}$ (bleach). I have never met such reactions before in my study, and I was unable or maybe looked in ...
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24 views

method of separating product and conserving the catalyst

I'm looking for a way to separate reaction product of iodobenzene with ethyl 2-methyl-3-oxopentanoate in 1,4-dioxane (toluene is an alternative as a solvent). The catalyst being used is Pd2(dba)3 with ...
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41 views

What is the function of toluene in this reaction?

I'm trying to find the mechanism for this reaction: My (tentative) thought for a possible mechanism is: EDIT: New thought for mechanism: But this leaves some loose ends that I haven't been able to ...
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1answer
34 views

Can NaCN or HCN be used as sources of cyanide ion in substitutions? [duplicate]

When cyanide ions act as nucleophiles in substitution reactions, why is KCN the reagent of choice? Would some other source of cyanide such as NaCN or HCN work equally well in the reaction, since they ...
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2answers
533 views

Which biphenyl is optically active?

Which biphenyl is optically active? I know that it can never be 1. I don't think it will be 4 either as I read that it should be ortho-substituted biphenyl. So, when I look at 2 and 3, I can't ...
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27 views

What apparatus is needed to get a balloon full of anhydrous carbon dioxide from solid carbon dioxide? [closed]

I'm currently planning a research project (new to this) and we need to bubble CO2 through our reaction mixture, however we are not able to use compressed gas so have been advised to pass CO2 from dry ...
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2answers
93 views

Is (2R,3S)-3,4-dimethylpentan-2-ol feasible to be dehydrated with POCl3 and pyridine?

I was given a problem of reaction between (2R,3S)-3,4-dimethylpentan-2-ol and $\ce{POCl3}$ and pyridine. I know that $\ce{POCl3}$ will be attacked with hydroxyl group and the hydrogen on hydroxyl will ...
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1answer
50 views

What is the white powder that I have extracted from cinnamon?

In Advanced higher chemistry, I am extracting cinnamaldehyde using this procedure- https://www.flinnsci.ca/api/library/Download/ba6ab218508047ea843bb0d9e580be16 . After evaporating the hexane, instead ...
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0answers
25 views

How to prevent feasibility of intermolecular attack of 1,2-diol?

I was given a problem that requires me to synthesize (1R,2R)-2-methoxycyclohexanol from cyclohexene. I tried it with syn-hydroxylation of alkene $\pi$ bond with $\ce{OsO4}$ and NMO then directly ...
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1answer
66 views

Organic Chemistry - Effect of methyl substituent in Aromatic Substitution via Benzyne

The following reaction has been taken from my study material. This shows that the benzene ring is undergoing a nucleophilic aromatic substitution via benzyne mechanism (presence of a strong base like $...
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1answer
48 views

What should be the name of the given compound?

Following compound is named as (1) 6-Mercaptocyclohex-4-ene-1,3-diol (2) 1-Mercaptocyclohex-2-ene-4,6-diol (3) 1-Mercaptocyclohex-5-ene-2,4-diol (4) 4-Mercaptocyclohex-2-ene-1,5-diol ...
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1answer
75 views

What is the IUPAC name of the given compound?

IUPAC name of the given compound is (1) 3-Hydroxycyclohex-4-en-1-one (2) 5-Hydroxycyclohex-3-enone (3) 5-Ketocyclohex-2-enol (4) 3-Ketocyclohex-5-enol By what I understand by ...
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31 views

How do I separate a graphene/graphite oxide and NaOH solution without centrifugation? (filtration didn't work)

The graphene oxide solution was made from electrolytic exfoliation of graphite electrodes in a 10M NaOH solution. Some graphene powder deposited on the bottom of the recipient but a brownish solution ...
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2answers
117 views

Why acidity of p-methoxybenzoic acid is more acidic than p-hydroxybenzoic acid?

I know +M effect of $\ce{OCH3}$ is more than $\ce{OH}$, but in my book (ALLEN General organic chemistry), it is given that $\mathrm{p}K_\mathrm{a}$ of para-substituted benzoic acid containing $\ce{...
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0answers
43 views

How does electrophilic bromination with 1,2-dibromoethane work?

Hi I am trying to figure out the mechanism of a reaction containing a lithium carbanion and 1,2-dibromoethane in THF. The lithium carbanion is generated by deprotonating using LDA. Then 1,2-...
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1answer
55 views

Intrahydrogen bonding [duplicate]

Is it okay to conclude that in 2-nitrophenol where intra hydogen bonding is experienced, two similar molecules are only held by the weak van der waal's forces and is the reason for it to have a ...
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0answers
53 views

Last step of proposed cubane synthesis

I was watching an online lecture on decarboxylation by soda lime and the first few examples were straight forward but after a while a felt that the questions couldn't simply have one effect and maybe ...
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0answers
29 views

Enol percentage comparison between 1,3 diketones and 1,2 cyclopentadione [closed]

To what extent does 1,2-cyclopentadione exist in enol form? Will it be more than for 1,3 diketones? 1,3-Diketone with active methylene groups can form hydrogen bonds with a 6-membered ring structure. ...
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1answer
905 views

How is taste of chemical compounds determined?

How do we know the taste of compounds, and their smell too, when some of them are poisonous. My textbook had that Lead is sweet in taste, but it's poisonous. So, how exactly do we determine their ...
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0answers
60 views

What should be IUPAC name of given compound (see image)? [closed]

I think the name should be 1-carbamoylpentane-3-sulphonic acid, but the answer sheet mentions it as 2-carbamoylpentane-3-sulphonic acid: Can anyone please explain why the chain starting with methyl ...
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0answers
102 views

Oxidation of certain acids by potassium permanganate

Why does potassium permanganate oxidize formic acid and oxalic acid, but has no reaction with benzoic acid and acetic acid? The reactions were heated in a water bath (~70-80 °C). Oxalic acid had ...
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45 views

Can a per-acetylated sugar anomerize?

So I have a question concerning a reaction mechanism for the reaction below. I know for certain that I get the alfa anomer, but I can't explain it. When I draw out the mechanism it doesn't make sense ...
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27 views

How many times should I run a solvent extration experiment through?

For advanced higher chemistry project, I am extracting cinnamaldehyde from cinnamon via first steam distillation and then solvent extraction using hexane. I'll be adding sodium chloride to the water/...
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0answers
23 views

How to convert pepsin into powder form?

I have pepsin powder which is now hydrated due to humidity. I want to convert it back to the powder form. How to do it? I don't have access to a freeze-dryer . I prefer any cheap procedure other than ...
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0answers
41 views

Charactaristics of Certain Hydroxyl Protecting Groups

I have been reading through Philip J. Kocienski's book Protecting Groups to try to better understand some of the characteristics of hydroxy protecting groups. I am looking to understand the ...
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1answer
38 views

Reduction of amides with lithium aluminium hydride [closed]

Since $\mathrm{p}K_\mathrm{a}$ of primary amides are close to alcohols, will there be an acid-base reaction between amides and $\ce{LiAlH4}$ besides reduction?
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38 views

Why London force dominates in Alkyl Halides

Why London Force is greater than dipole-dipole interactions in Alkyl Halides? As we know that most of the time London force is weaker than other forces. Then why in this case it's not so? ...
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1answer
49 views

Why is 1,2-diiodoethane unstable? [duplicate]

Diiodoethane is a product of the reaction between glycol and $\ce{PI3}$. Why is 1,2-diiodoethane unstable?
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32 views

Is the reaction of anhydrous aluminium(III) chloride and anhydrous ethanol reversible?

I'm planning an experiment that I'll do in silico in the near future, and one of the steps involves the extraction of the $\ce{AlCl3 · C2H5OH}$ adduct without any water in it. Can the ethanol be ...
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0answers
34 views

Reaction with ethyl chloroacetate and potassium carbonate

I am carrying out a reaction using ethyl chloroacetate, potassium carbonate in acetone for a compound containing $\ce{-NH}$ group. So, the substitution will be at $\ce{-NH}$ position. I have tried ...
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2answers
101 views

What are the chemical Tests and/or reactions to distinguish propanone from butanone? [closed]

Is there any series of chemical reactions that will help in distinguishing propanone and butanone? A simpler series of reactions or tests would be optimal. I know it's easy to distinguish and possibly ...
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0answers
35 views

What is the name of the glyoxal radical after removing two hydrogen atoms?

What is the name of the radical that results from removing two hydrogen atoms from glyoxal ($\ce{CHO-CHO}$)? It has a roughly this structure: $$\ce{O=C^.-C^.=O}$$ It is an important intermediate in ...
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1answer
75 views

Do secondary alcohols react faster than primary alcohols or is it the other around? [closed]

My questions is that do secondary alcohols react faster than primary alcohols or is it the other around? This for the oxidation of the alcohol to a ketone or an aldehyde. This reaction is with KMnO4 ...
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1answer
19 views

What compressible rubber like gasket material is the least permeable to CO2?

I am trying to can a carbonated solution at 120 PSI. I am trying to figure out the best material to use for the gasket on the valve cap. I am carbonating my fluid with $\ce{CO2}$ and it is loosing ...
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1answer
84 views

How can methane absorb infrared light within wide range of frequency but CO2 can't?

Methane is one of the most potent greenhouse gases in Earth's atmosphere.I saw a lot of answers related to it but lacks de facto exegesis to it.
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30 views

Racemic mixture vs enantiomers in drugs [duplicate]

a racemic mixture has 50-50% of the 2 different enantiomers. There are racemate drugs out there in the world. The misunderstanding I have is that usually 1 out of the 2 enantiomers molecules have a ...
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0answers
47 views

Hydroxy Protecting Groups that are not Cleaved Under Acidic Conditions

I am currently designing a synthesis requiring the use of hydroxy protecting groups. The problem I am having is that the protecting group must be able to survive highly acidic conditions. I would have ...
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0answers
39 views

Why is an alkyne substituent on benzene is electron withdrawing, but alkane and alkene are electron donating?

Hammett constants for alkyls/vinyls/etc. are all negative (i.e. toluene), and my understanding is that they donate electrons through inductive/resonance effects. However, ethynylbenzene has a ...
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0answers
29 views

Home test for the presence of sugar in erythritol

Is there a test to distinguish erythritol from sugar at home without expensive lab equipment or exotic reagents? Sometimes I purchase erythritol online and wonder if it's been diluted with sugar.
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18 views

Alkylation before ring closure?

So, another question from my side. I have been thinking about the folowing reaction: The reaction above exists and was already done on two occasions and reportedly works really well and it seems to ...
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1answer
62 views

Polystyrene properties after dissolved by acetone

Polystyrene plastic can be dissolved in acetone. I would like to understand: If the dissolved polystyrene will take-out of the acetone and becomes solid again (after all the acetone evaporates), will ...
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0answers
59 views

Why does Pubchem show cis-1,3-cyclohexanediol with the hydroxyls in the equatorial position?

I am a beginning organic chemistry student and trying to reason about something based on information in my book, but seeing that Pubchem gives a different structure than I'd expect. In considering a ...
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1answer
116 views

Energy cost of C−N rotation in hydroxamate group

I am looking for a literature reference on the energetic cost of C−N rotation in hydroxamate group such in LC5 in water. I have been googling for a while.
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1answer
54 views

Conformers of a meso-compound [duplicate]

In a particular question in one of my reference book, I was asked if the given compound (meso-butane-2,3-diol) was a meso compound or not. In it’s solution part, to show that the compound was ...
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1answer
75 views

Why doesn't this reaction happen? [closed]

In the synthesis of DMAD, we eliminate two bromides from dibromosuccinic acid in basic environment to get acetylenedicarboxlyic acid (Step 2). However, this reaction could also happen: The reaction ...
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2answers
61 views

Alkene reaction with acid via SN1 reaction

I want to ask a question about alkenes and their reactivity with acids. From high school studies, I recall that if you had an acid $\ce{H3O+}$ i.e. $H^+$ that it would react with an alkene as shown ...
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1answer
71 views

Is m-cresol or p-cresol more reactive towards electrophilic substitution?

Which is more reactive towards electrophilic substitution, meta-cresol or para-cresol? Both oxygen and methyl are activating groups. I don't know on what basis do I compare their reactivity. There's ...
3
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2answers
66 views

H-NMR with 10H integration?

I have the following two spectra (IR and 1H-NMR) see below. The chemical formula is: C16H16O2 Thus DBE = 9 My approach: From the IR, I can see that there's no broad peak around 2500-3300, thus I ...
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1answer
70 views

What is the mechanism for trans-stilbene to stilbene dibromide?

What is the mechanism for trans-stilbene to stilbene dibromide? This is what I know: The bond between the hydrogen and bromine is broken and the bromine is given a negative charge, while the $\ce{H}$...
4
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0answers
56 views

Reaction mechanism of thiol to disulfide oxidation under basic conditions?

I have been looking everywhere for an explanation to a reaction mechanism concerning the oxidation of DTT (or just thiols to disulfides in general) using oxygen as the oxidant. I'm aware that ...