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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37 views

Do Esters have a mesomeric effect? [closed]

currently I am working on a presentation in which I am supposed to explain Bohr's orbital model applied to esters. As an example, I chose methyl ethanoate. I have assigned the $\ce{C}$ of the alcohol ...
4
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1answer
104 views

Why does dimethyl sulfoxide have higher boiling point than acetone?

They have very similar structure except for a central atom, but the difference in boiling points is very large $(\pu{186 ^\circ C}$ for DMSO and $\pu{56 ^\circ C}$ for acetone). How is central atom ...
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1answer
57 views

formation of a compound due to photo-isomerisation [closed]

I was reading through a topic called photoisomerism, where I read that when a molecule is hit by a photon it changes its structure to a more stable one. Is this a one-way reaction, or is it reversible ...
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34 views

Find the major products when these cyclohexenone bromides react with caustic potash in alcoholic medium:

Question: Also find the order of the rates of the given reactions. Answer: The answer of this question is given as option 'D' ie. all products are identical, however I am getting the answer as ...
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Why does more s-character stabilise Carbanions?

Since carbanions carry a negative charge, more the distribution of electron density, more is the stability. What does this have to do with more s character? Does the distribution of electron density ...
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45 views

The main difference between using AlCl3 and FeCl3 in Friedel-Crafts alkylation

What is the main difference between using $\ce{AlCl3}$ and $\ce{FeCl3}$ in Friedel-Crafts alkylation? Is that $\ce{FeCl3}$ disfavors carbocation rearrangement in Friedel-Crafts alkylation?
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36 views

Resonance forms of diazomethane [duplicate]

Most references show resonance structures of diazomethane as a dipolar molecule with positive charge on first nitrogen atom and negative charge at carbon or second nitrogen atom. why isn't there a ...
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1answer
56 views

Anthracycline nomenclature - doxorubicin [closed]

Why $\ce{-OCH3}$ is Number 3? I think that $\ce{-OCH3}$ Appropriates Number one.
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1answer
53 views

Lucas test in the presence of EWG like -CN

Does the given compound give Lucas test? My teacher says due to the presence of a strong electron withdrawing group the carbocation formed is unstable. But I say if it undergoes $\mathrm{S_N2}$ ...
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1answer
46 views

Is a tautomer's stability compared with refernce to its initial compund [closed]

Considering the following example while comparing the enolic content in the product, am I supposed to compare its stability with reference to its initial state or am I supposed to compare it between ...
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1answer
353 views

How are organic compounds with radioactive atoms synthesized? [closed]

We often see reactions such as these in textbooks to highlight how reaction mechanisms work: How are the radioactive substrates required for these mechanisms synthesized in the first place? There ...
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34 views

Aldol Condensation Product selection

It is known that the enol form double bond tends to attack the electrophilic carbon centre in an aldol reaction. But what will be the majour product in this reaction. The latter one may be enol attack ...
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1answer
234 views

Assigning R/S configuration

Question: Assign the R/S configurations to the carbons which are attached to different rings of this molecule (carbons 1 and 3 according to IUPAC numbering): My Solution I first started out by ...
5
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1answer
48 views

Why the formation of a fog is observed when triethylamine is added?

In the procedure for the synthesis of N-anisoyl-2-pyrrolidinone that was given to me, it is written that when triethylamine is added, a "fog" is observed inside the flask. Triethylamine is ...
5
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2answers
77 views

How is nomenclature decided in this case (formyl vs oxy)?

I was asked the IUPAC Name of the following compound in JEE Mains (2nd September, Shift 1) 2020. There were two names occuring to me: 5-formyl-2-methyl-hex-2-enoic acid (2,5)-dimethyl-6-oxo-hex-2-...
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0answers
28 views

Stability of EDAC in solution

I diluted ethyl-carbodiimide hydrochloride (EDAC) powder in water to 1 M and stored it at -20 °C. I am using a 10 mM solution as working solution and I keep it at room temperature. Would the EDCA be ...
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1answer
48 views

How to Choose if a reaction will go elimination of substitution? [closed]

I want to know how to choose if a given reaction will prefer going substitution mechanism or elimination mechanism.Both elimination and substitution reactions have types like Sn1 ,Sn2 ,SnNGP,Sni and ...
5
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1answer
102 views

Aromatisation of a ring which includes nitrogen

Question Complete the following reaction sequence: Answer My solution I was able to complete all the steps except for the last one. This is what I ended up with: What I'm not getting is how the $\...
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0answers
31 views

Formation of methane using Kolbe's electrolysis reaction

I have read in my book that methane cannot be formed using Kolbe's reaction (mechanism — Organic Chemistry Portal). And honestly, I kinda think I get where they are coming from: that two radicals are ...
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0answers
28 views

Why can't methyl glycosides mutarotate?

I found this link trying to explain it: Why pyranosides do not mutarotate? however, I don't understand a step of the reasoning. Why is it that acetalisation needs a stronger acid than for hemi-...
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3answers
110 views

How to identify cis and trans forms of cyclohexane [closed]

How can identify which one is cis and which one is trans . If I consider it as a planar molecule (though it is not) I understand that if the substituents are in same side it is cis else trans but this ...
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0answers
18 views

Why do 6 member rings have lower strain than 5 member rings? [duplicate]

I was having a look at this graph here graphing the ring strains for various chain lengths: Evidently, 6 member rings have lower strain energy than 5 member rings. However, looking at the bond angles ...
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1answer
31 views

Compare the boiling points of isobutane and 1-butyne

Question: Compare between the boiling points of isobutane and 1-butyne The answer to this question is given as 1-butyne has higher boiling point than isobutane. My approach: I have been taught a few ...
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0answers
16 views

Rubber/Silicon Decomposition?

I'm very curious about this situation that's a little bit off-topic but bear with me. So today I found that back cover of my old cell phone (that was stored in a box along with some car LCD, tablets ...
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1answer
61 views

What mechanism is this? [closed]

I was solving problems in Organic Chemistry related to Substitution and Elimination. This was a question asked in JEE 2019 This was the solution for above. At last of solution, It has been mentioned ...
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108 views

What are acid/base sensitive groups?

My textbook says that Clemmensen Reduction cannot take place in the presence of an acid-sensitive group and the Wolf Kishner reaction won't happen in the presence of a base sensitive group, citing $\...
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1answer
57 views

Pyridine: Protic or Aprotic

I know pyridine is a polar aprotic solvent (owing to a permamnent dipole generated), but if acidified it forms pyridinium cation. So, does it then function as polar protic solvent?
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1answer
62 views

How are diazonium salts prepared without self coupling

While preparing diazonium salts, what prevents the freshly formed diazonium salt from reacting with the still unreacted amines left in the solution and perform diazo coupling? If this happened then ...
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1answer
55 views

For IUPAC nomenclature, does the number of multiple bonds take precedence over the chain length?

I've received a few mixed answers to this question. Some sources say when determining the parent chain for unsaturated hydrocarbons, the longest chain should be considered before the chain with the ...
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1answer
48 views

What is cn axis of symmetry [closed]

While reading about axis of symmentry and I'm not able to comprehend what does C infinite or rather n signify in a molecule I know axis of symmetry is the axis along which rotation of molecule ...
3
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1answer
42 views

Tautomerism in 3,5‐dimethyl‐4H‐pyrazole

How would tautomerism take place in 3,5‐dimethyl‐4H‐pyrazole? I am aware of nitro–aci nitro and keto–enol, but I haven't seen such a compound before. I recognize that a hydrazone formation was done ...
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1answer
294 views

Comparing reactivity of 1-chloroethane and 1-chloropropane in an SN1 reaction

Beginning with a reference to a well known question. Order by reactivity towards SN1 reaction. According to some facts about SN1 reactions, rate depends on: Stability of carbocations Better leaving ...
3
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0answers
32 views

Comparing nucleophilicity of oxygen and nitrogen in acetylation of 4-aminophenol

Here, the answer has $\ce{N}$ acting as a nucleophile making the answer (C). I thought that $\ce{O}$ would be more nucleophilic, considering the fact that $\ce{O}$ has two lone pairs, one in ...
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0answers
32 views

Oxidation of ethanol upon heating in a test tube

The diagram shows an experimental set-up which can be used in several different experiments. Which processes could be demonstrate by using the above apparatus? 1. Oxidation of ethanol (liquid X) 2. ...
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0answers
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Why can't Grignard reagents react like Organolithium does (with acids)?

I'd read yesterday that Grignard reagents can't give ketones on reaction with carboxylic acids. It is because of the fact that Grignard reagent is a "super-base", and it will deprotonate the ...
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1answer
73 views

Terminologies used in isomerism [closed]

What is the difference between the terms constitutional isomers, stereoisomers, geometric isomers? I know cis and trans-1,2-dichloroethane shows cis trans isomerism and 1,1 dichloroethene, 1,1,2 ...
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1answer
52 views

What compounds are produced when you heat CuO and sugar?

I'm wondering on what compounds are produced when you heat CuO and sugar?
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38 views

Product of Grignard and carboxylic acid [duplicate]

What is the product formed when grignard reagent reacts with a carboxylic acid? At one instance my book says alkane and at another it say alcohol. Since it is a reducing agent I inferred that both ...
0
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1answer
133 views

How to identify whether a molecule is planar [closed]

While solving for plane of symmetry of molecules I came across 1,3-dichlorocyclobutane (1) and I realized it does not have any plane of symmetry because we don't know whether hydrogen and chlorine are ...
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1answer
9k views

Oxidation of Unsymmetrical Ketones using Selenium Dioxide

I have searched the whole internet but I could only see examples where the authors of the article took $\ce{R1}$ and $\ce{R2}$ as the alkyl groups around the carbon. This is regarding the oxidation of ...
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0answers
29 views

Does HI-6 form a covalent adduct with acetylcholinesterase?

According to sources provided below, the oxime HI-6, or Asoxime Dichloride, as it is also called, besides being a reactivator of acetylcholinesterase that has been inhibited by organophosphorus ...
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2answers
118 views

Why is sodium bicarbonate added to lower the pH? [closed]

I use salicylaldehyde, chloroacetic acid and sodium hydroxide for the synthesis of o-formylphenoxyacetic acid. In the procedure it is written that after the reaction I need to add sodium bicarbonate ...
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1answer
54 views

Why is aniline more basic than pyrrole?

In a question asking to compare the basicity of pyrrole and aniline, the explanation given for aniline being more basic than pyrrole was as follows: Basicity depends on the availability of lone pair ...
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2answers
560 views

Why is borole not considered aromatic

I came across a problem which stated that borole isn't aromatic. I thought that borole is similar to pyrrole so it should be aromatic, but that isn't the case. Can I know why isn't it aromatic? I was ...
3
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1answer
55 views

Electrophilic Substitution with Ceric Ammonium Nitrate and Lithium Bromide as reagents

The 2020 IChO Preparatory Problem List (source here) had the following reaction as part of the solution to the first question: (CAN = Ceric Ammonium Nitrate). What is the mechanism for this '...
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0answers
34 views

Reaction of a cyclic tertiary alcohol with chromic acid

We know that $\ce{H2CrO4}$ cannot oxidize tertiary alcohols. The mechanism is: Now the ${\alpha}$ carbon does not have any hydrogen to proceed to next step. Therefore, this reaction would not occur. ...
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Can a reaction have more than one rate determining step?

There are many organic reactions in which two steps have comparable rates. Can we say they are both RDS? For example, the rate of iodination of benzene and deuterated benzene is different even though ...
3
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1answer
82 views

Laboratory and commercial preparations of aniline other than reduction of nitroarenes [closed]

Till now I could only find one laboratory preparation of aniline, i.e. reducing nitrobenzene with $\ce{Sn}$ and concentrated $\ce{HCl}$. I'm confused if Hofmann degradation is only commercial. I'd ...
2
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1answer
41 views

Hydrogen bonding in sugar acids

I recently learnt that the reason for low solubility of mucic acid as compared to glucaric acid was more hydrogen bonding in the crystal state of mucic acid as compared to glucaric acid. I would ...
4
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2answers
170 views

Oxidation of hydroxyl groups of glucose

In all oxidation reactions of glucose, it seems that the aldehyde group alone gets oxidised and none of the hydroxyl groups. In one reaction with nitric acid, the aldehyde group and the terminal ...