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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Creating 100mg/L aspirin solution

I plan on creating 100 mL of 100mg/L aspirin solution by dissolving 10 mg of pure aspirin powder in 100 mL of buffer solution (of different pHs). Problematically, aspirin doesn’t tend towards ...
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77 views

Acid catalysed dehydration of 5-methylidenecyclopent-2-en-1-ol [closed]

I think the following reaction is NOT possible. I could not find a mechanism for ring expansion. Is ring expansion possible in any way? Is the following mechanism correct?
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Why don't phenol behave like aniline in electrophilic substitutions?

As far as I know, many electrophilic aromatic substitution reactions fail to undergo the usual way in aniline. This is due to $\ce{-H2N}$ group being basic (pKa of $\ce{NH3}$ = 38), even it is ...
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1answer
52 views

Acids used in Friedel-Crafts alkylation

I am learning adding alkyl groups to benzene using Fridel-Crafts alkylation: I know that it is very common to use $\ce{AlCl3/AlBr3}$ as Lewis acid catalyst in this reaction. But I am just wondering ...
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1answer
40 views

Phenol vs 4-hydroxypyridine - Enol Content [duplicate]

Which has a higher enol content; phenol or 4-hydroxypyridine? The solution to this question in my book says that phenol has a higher enol content due to aromaticity. But 4-hydroxypyridine is also ...
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27 views

Resonance hybrid and octet

I am a student of grade 11. I am learning about resonance phenomena. I am a beginner with this and I am a bit confused about this. I wished to know whether atoms in resonance hybrid (not resonating ...
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1answer
131 views

activating and deactivating groups and directing effect

In electrophilic aromatic substitution: I have just learnt a 'rule' about benzene with more than 1 substituents attached (excluding the effect on steric hindrance): if a strong activating group (EDG) ...
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2answers
60 views

Dehydration of primary alcohol with a cyclobutadiene substituent [closed]

Note: Primary alcohol will follow E2 mechanism, therefore, removal of protonated water and proton (RDS) shall proceed in a single step in the above mechanism. My questions are: 1- According to ...
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1answer
57 views

Ozonolysis of alkene

(from Wikipedia) I am having trouble in the last step where the alkene ozonide is reduced to ketones / aldehydes specifically in the presence of water. My teacher is telling me that water will be ...
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25 views

Dipole moments of cis and gem alkenes [duplicate]

The procedure for comparing dipole moments for cis- and trans-alkenes is quite easy, but how to compare dipole moments of 1,1 dichloroethene (1); and cis-dichloroethene (2)? My teacher told me that ...
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2answers
56 views

Choise of solvent for extraction

In the synthesis of (S)-Diphenyl(pyrrolidine-2yl)methanol, I need to extract the product using an organic solvent and water. Which organic solvent is the most suitable in this case? Ethyl acetate: I ...
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146 views

Yield of possible products from acid catalysed hydration of an alkene with a phenyl group

Here, (d) may be the major product due to high temperature. My questions are: Will a kinetically favoured (minor) product (c) form? What shall be the order of yield of products?
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114 views

Huckel's rule and aromaticity [closed]

I am learning to determine whether a monocyclic conjugated alkene is aromatic or anti-aromatic or not. question 1: cyclobutadiene: according to Huckel's rule, 4 * 1 = 4, it should be antiaromatic, ...
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1answer
183 views

Electrophilic substitution on Borazole

As Borazole ($\ce{B3N3H6}$) is aromatic, it shows electrophilic aromatic substitution. Now, my question is when borazole undergoes electrophilic aromatic substitution reaction, on which atom does the ...
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1answer
69 views

How to get or understand a sample in chemistry without knowing its chemical name or compound or formula [closed]

How to get or understand a sample in chemistry without knowing its chemical name or compound or formula? I was thinking about whether there is a way to understand what the chemical compound sample ...
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2answers
69 views

Can I use calcium chloride instead of sodium sulfate as drying agent?

In the synthesis of N-ethoxycarbonyl L-proline methyl ester from L-proline and ethyl chloroformate, I dry the organic phase over sodium sulfate. Can I use calcium chloride instead of sodium sulfate? I ...
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108 views

Can I use potassium acetate instead of potassium carbonate?

In the synthesis of N-ethoxycarbonyl L-proline methyl ester from L-proline and ethyl chloroformate, I use $\ce{K2CO3}$ to neutralize $\ce{HCl}$. Can I use $\ce{CH3CO2K}$ instead of $\ce{K2CO3}$? I ...
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45 views

Poisoned catalysts

CaCO3 in rosenmund reduction, lead in Lindlar's catalyst, or steel in Raney nickel all act as poisins but the carbon in Pd/C is just for support. How do the others affect the catalytic activity but ...
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1answer
156 views

Pyridine synthesis by tin(II) chloride reduction of 5-nitronorbornene

What is the reaction mechanism here? I guess the $\ce{SnCl2}$ reduces $\ce{NO2}$ to $\ce{NH2}$ but then what happens?
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48 views

Acid dehydration to ether

Can anyone please help me come up for a curved arrow mechanism for the reaction pictured? I'm familiar with the mechanism for the general acid catalyzed dehydration of butanol, where the arrow comes ...
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23 views

What is the meaning of pi selectivity?

I came across this term while going through a research paper for the first time of organic chemistry on diastereoselectivity of tricyclo[2.1.0.02,5]pentan-3-ones. I am not familiar with the term and ...
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2answers
61 views

Order of rate of acid catalysed dehydration of alcohols

The relative rate of acid catalysed dehydration of following alcohols would be: According to me, we have to arrange them in order of their carbocation stability. Q will be the most stable as it is ...
6
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1answer
127 views

Name of this bond-line formula? [closed]

I don’t know much about chemistry but I recently found the below bond-line structural formula painted on a wall near my place. I really can’t let go of trying to find the name of the compound. If ...
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2answers
42 views

Aspartic acid conjugate base acidity

Question Which hydrogen among the four in the conjugate base of aspartic acid is most acidic? Answer My attempt I am confused between Hb and Hc I know Hd has $\mathrm pK_\mathrm a \approx 9$, so ...
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46 views

Why does the solubility of haloalkanes in water decreases as the length of the carbon chain increases?

Due to the polar halogen-carbon bond in haloalkanes, they are more soluble than hydrocarbon in water. But the solubility is still very low because the overall influence of the dipole-dipole ...
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2answers
106 views

What is the mechanism for this intramolecular SN1 reaction?

What is the mechanism for the following intramolecular $\mathrm{S_N1}$ reaction? For this question, my professor hinted at an intramolecular reaction, and he asked us to recall the bromonium ion as ...
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3answers
359 views

Synthesing tetrahydropyran from ethylene oxide

I thought that the first step must be using a Grignard reagent to add carbons, but I need a hydroxyl group on the carbon on the other side to make it a diol and produce the product given, but nothing ...
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1answer
241 views

Why do electron-rich aryl groups have greater migratory aptitudes?

In the following reaction there are three possible aryl groups that can migrate: an unsubstituted phenyl group, a p-methoxyphenyl group, and a p-nitrophenyl group: Why does the electron-rich p-...
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1answer
198 views

Is hybridization of the cyclopropyl anion sp5?

I have read some answers about the $\mathrm{sp^5}$ hybridisation of carbon atoms in the $\ce{C-C}$ bond in cyclopropane as well as the $\sigma$-bond resonance in methylcyclopropyl cation. Overall, the ...
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1answer
122 views

Reaction of carboxylic acid with phosphorus trichloride

The reaction of carboxylic acid $\ce{RCOOH}$ with $\ce{PCl5}$/ $\ce{SOCl2}$ / $\ce{PCl3}$ yields an acyl chloride $\ce{RCOCl}$. With $\ce{PCl5}$ and $\ce{SOCl2}$ the reaction is quite simple utilizing ...
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1answer
106 views

Regioselectivity in coupling reactions of α-naphthol

I have seen in the following reaction of azo coupling where coupling takes place at position 4 of $\alpha$-naphthol. Now the electron density accumulation is similar at both position $4$ as well as $...
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53 views

Mechanism of addition of H-X to alkynes

Vinylic carbocation is unstable as the carbocation is bonded to a $\mathrm{sp^2}$ carbon that has high electron density, and pulls the electrons from the carbocation, which is already electron-...
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36 views

Synthesis question: Using reductive amination to form pyrrolidine

What molecule results from treating 4-oxopentanal with $\ce{NH4Cl}$ and $\ce{NaCNBH3}$? Why? Is this a good, high yield reaction? I believe that pyrrolidine is formed because amination will convert ...
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1answer
46 views

Comparison of basicity of o-phenanthroline and ammonia

I was trying to compare the basicity of o-phenanthroline and ammonia. According to me, the factors that are seen in o-phenanthroline are: o-Phenanthroline has two nitrogen atoms at the 1,10 positions....
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52 views

SN1 products for (1S,2R,4R)-1-chloro-2,4-dimethylcyclohexane [closed]

Question Total number of SN1 products of given compound are A) $3$ B) $4$ C) $5$ D) $6$ Answer My attempt I can find only $4$ products. The two stereoisomers formed from the carbocation, when ...
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2answers
255 views

Formation of toluene from (cyclobutane-1,2,3-triyl)trimethanol using conc. sulphuric acid

In my book this reaction is given without any mechanism: I thought that simple dehydration reaction is going to take place with rearrangement of the carbocation but I have no idea as to how toluene ...
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0answers
63 views

Alternate pathway of Gabriel synthesis to prepare secondary amine

Can modifying the Gabriel synthesis, which is generally restricted to synthesis of primary amines, be used to synthesise secondary amines? I have attached my idea regarding the synthesis (the final ...
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1answer
87 views

What is the molecular weight of bilirubin?

There is a discrepancy among different sources on the molecular weight of bilirubin, $\ce{C33H36N4O6}$: 584.673 (Fisher Scientific); 584.66 (Sigma Aldrich). What is the correct value and why?
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75 views

Why aren't the hydrogen bonds in carboxyllic acids like this?

Why don't carboxylic acids form H-bonds in this formation with the red dots (diagonal) instead of the black dots (horizontal)? I was always taught that H-bonds formed between partially negative and ...
2
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1answer
53 views

The best chromatographic technique to analyse a solution of benzene, toluene, and ethylbenzene in n-hexane

What is the best chromatographic technique to analyse a solution containing benzene, toluene, and ethylbenzene in n-hexane? Is gas chromatography (GC) the best way to analyse this solution? Or is ...
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1answer
102 views

Reaction of styrene oxide with hydrogen iodide

The question is to find the product of the reaction of Styrene Oxide with Hydrogen Iodide. According to me, this should be the mechanism- As the benzylic carbocation will be more stable, therefore ...
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41 views

What drives the 'internal return' in SNi?

I just learnt that alcohols can undergo $\mathrm{S_N}i$ with $\ce{SOCl2}$ (without pyridine) to achieve retention: However, what I really do not understand is the 'internal return' step (forming '...
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61 views

Clar's rule of polycyclic aromatic hydrocarbons

Clar's rule states that the Kekulé resonance structure with the largest number of disjoint aromatic π-sextets, i.e., benzene-like moieties, is the most important for characterization of properties of ...
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16 views

Acidity of cyclopentadiene [duplicate]

Why is cyclopentadiene more acidic than dibenzocyclopentadiene although in the latter, the negative charge will be more distributed and consumed in resonance stabilization.?
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39 views

Questions on formation of cyclic ethers using Williamson Ether synthesis

question 1: In the synthesis, both intra- and intermolecular SN2 can undergo, in which only intramolecular reaction gives the cyclic ethers. However, both reactions happen in the reaction mixture. ...
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1answer
44 views

Water solubility comparison of stereoisomers of bicyclo [4.4.0] decane-3,4-diol

I think, (I) must be more soluble in water. It is due to trans configuration and thus, forming more effectively inter-molecular hydrogen bonds with water molecules.
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22 views

Reasons for antiperiplanar arrangement in E2 reactions

From what I have learnt, there are 2 reasons that synperiplanar arrangement cannot give E2 reactions: In Newman projection, synperiplanar arrangements is in a eclipsed form (very high in energy), so ...
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36 views

Is nitrogen with 3 different substituents and lone pair a chiral center? Does it make the whole compound chiral too? [duplicate]

Is nitrogen considered a chiral centre or stereocenter when it has three different substituents attached to it along with a lone pair. By definition LG Wade says An asymmetric carbon atom is the ...
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29 views

Definition of throughput

I wonder what's the exact meaning of throughput in chemistry synthesis, eg. in organic synthesis or production of pharmaceutical products. For instance, what are their units? How are they measured? I'...
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0answers
34 views

What specific toxins are formed during deep frying? And how (chemically) do they attack the body cells? [closed]

From what I understand, deep frying causes the oxidation of lipids into advanced lipid oxidation products. When these are consumed and metabolized by the body, they release ROS or free radicals which ...

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