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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How can the oxidation of TEMPO be selective?

According to the article "TEMPO oxidizes alcohols to aldehydes and ketones", the oxidation of TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl, 2564-83-2) can be highly selective. I assume it ...
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1answer
64 views

Grignard-type reaction of 3-bromocyclohexene, or rather recombination?

I have a question regarding a proposed Grignard-type reaction which involves the conversion of 3-bromocyclohexene to 1-(cyclohex-2-en-1-yl)propan-1-ol, in diethylether. As the bromine atom lies in ...
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2answers
105 views

Action of EtONa/EtOH on compound containing -CN group

In the above question, I know compound A will be prepared by just replacing -Cl with -CN group in the starting compound. I wanted to know what work would be C$_2$H$_5$ONa/EtOH doing in order to make ...
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1answer
55 views

Mechanism of cyclisation with tin(IV) chloride

I have taken this photo from synarchive: https://synarchive.com/syn/325 I tried reading the research paper this synthesis was found in (Couladouros, E. A.; Vidali, V. P. Chem. Eur. J. 2004, 10 (15), ...
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1answer
84 views

Mechanism of acid-catalyzed ring opening of a cyclopropane ring

I have a question regarding following synthesis which apparently only needs a sour medium to occur: What exactly happens as a mechanism? What I thought was: The alcohol group gets protonated and ...
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32 views

Reason for adding TFAA in this synthesis pathway?

I have included a short part from a synthetic pathway from: https://synarchive.com/syn/112 $\ce{Mg3N2}$ reacts with $\ce{MeOH}$ to liberate $\ce{NH3}$ which I believe is used in nucleophilic ...
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(How) can a reaction be both stereoselective and stereospecific?

From what I have learnt, stereospecific and stereoselective reactions are defined as follows - Stereospecific - The stereochemistry of the reactant dictates the stereochemistry of the product. Thus, ...
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1answer
109 views

What does one mean by saying "in conjugation"

In my chemistry class in high school we just started with resonance and my teacher said that its the phenomenon of moving around of negative charges, lone pairs or pi electrons with no change in ...
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36 views

Reasons for scratching the wall of a flask when precipitate crystals [closed]

I heard that scratching the wall of the flask helps precipitate crystals when obtaining crystals. By scratching the wall of the flask, the crystals from it fall in the center and act as seeds to help ...
2
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1answer
61 views

Product of reaction between cyclohexene and bromine in methanol at 273 K

What product could we expect when we let cyclohexene react with an equivalent of bromine in methanol at 0 °C? Is it just the trans-addition of bromine (rac.) or also the SN1-susbtitution on a carbon ...
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1answer
31 views

Where do the chloride ions go during saponification precipitation?

During saponification hydroxide ions from the lye join to the triglyceride to form glycerol, and the sodium bonds with the fatty acids making the soap molecules. However, it is sometimes the case that ...
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1answer
48 views

What is the role of magnesium nitride in ammosamide B synthesis?

The following is a snapshot of the synthesis of ammosamide B from Synarchive: In the final step $\ce{Mg3N2}$ is used to convert esters to amides or amides to amines. What is the mechanism of this ...
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1answer
44 views

How come bromine adds meta to phenol in this reaction, which is catalysed by HSbF6 [duplicate]

This is a rxn in the synthesis of Tramadol. I found in in IChO prep problem 2001, Q19... Edit: I have seen in clayden a rxn with HSbF6 whereby the benzene ring gets protonated so I followed that path ...
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1answer
43 views

Separation of Racemic Mixture

In the racemic mixture below, if it is reacted with Mosher's Acid Chloride, it would form X and Y. Can I ask why my book state that X and Y are not enantiomers and thus can based on differences in ...
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1answer
115 views

Why is carbon tetrachloride more stable than methane?

When a mixture of methane and chlorine is exposed to ultraviolet light – typically sunlight – a substitution reaction occurs and the organic product is chloromethane. However, the reaction doesn't ...
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39 views

Reaction of 3-chloro-2,2-dimethylbutane with sodium ethanolate in EtOH, which mechanism?

When we let 3-chloro-2,2-dimethylbutane react with sodium ethanolate in EtOH, which reaction do we expect? SN2, E2, E1 or SN1? I would say it's an SN2 reaction because ethanolate is not that strong of ...
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suffix in IUPAC nomenclature [duplicate]

The name of the following of compound is given as propane-1,2,3-triol. HO-CH2-CH(OH)-CH2-OH The structure and nomenclature is very simple for this compound (C3H8O3) but my doubt is why propane does ...
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1answer
49 views

Stereochemical relationship between the given compounds

Are the given compounds enantiomers or diastereomers? Or are they identical? The compound is trans-1,2-dimethylcyclobutane: My reasoning is that they are identical. They are not mirror images, and on ...
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55 views

How can we synthesize 1,1-dichloro-2,2,3,3-tetramethylcyclopropane from pivaldehyde?

How to synthesize 1,1-dichloro-2,2,3,3-tetramethylcyclopropane from pivaldehyde? I don't know how to close the ring structure: Should we synthesize an epoxide first? I'd appreciate any tips regarding ...
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Why are sulfoxides usually stable as ylides (S charged positively and O negatively)? What's the BDE for S-O?

I can't find any info on BDE for singularly bonded S to oxygen. Moreover, I'd like to understand, why is it quite usual to find sulfoxides structure written with charge separation?
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1answer
58 views

Aromaticity in cyclic ketones

I have read that, cycloprop-2-ene-1-one is aromatic and cyclopent-2,4-dien-1-one is antiaromatic. Basically this is visualized by visualizing the resonance structures of this. Similarly if I apply ...
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1answer
60 views

nBuLi and tBuLi can take part in halogen metal exchange OR deprotonate. Is there any way to predict which it favours?

I have included a synarchive pathway: https://synarchive.com/syn/144 where BuLi favours deprotonation over halogen metal exchange
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Does benzene sulphonic acids show steric inhibition of resonance / ortho effect?

I have read about ortho effects in aniline (steric inhibition of protonation) and benzoic acids but have not seen anything about Sulphonic Acids ($\ce{-SO3H}$) do they also show considerable ortho ...
5
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1answer
214 views

Does C8H2N4 (in pentagon shape) exist and what is it called?

My primary school released a folder which contains some sketches. As you can see, they included two molecules. One of them is isopropanol. What's the name of the other molecule (bottom)? Does it exist?...
5
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1answer
70 views

Symbol to denote a group which is either an oxygen atom or NH group

I'm drawing the generic structure of several different organic molecules in my thesis. They share some features, one of which is a carbonyl carbon attached to either an oxygen atom (i.e. ester) or an $...
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1answer
106 views

Which amines show N−N coupling reaction?

We add 1 equivalent of $\ce{KCN}$ followed by catalytic reduction via Lindlar's reagent $(\ce{H2}/\ce{Pt})$ to 4-chlorobenzyl chloride (1). Verify whether the product (P) obtained will undergo an N−N ...
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42 views

Major product in the reaction of alcohol with unsymmetrical acid anhydride

When alcohol reacts with symmetrical acid anhydride to form ester. We have the following reaction, But if the acid anhydride used is unsymmetrical how can we identify the major product? For example ...
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27 views

Side-chain Oxidation vs Oxidative Cleavage

When the above compound is subjected to acidified $\ce{KMnO4}$, can both side chain oxidation and oxidative cleavage of $\ce{C=C}$ bond occur? Or will one have priority over the other?
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2answers
683 views

Materials for McBride's Freshman Organic Chemistry at Yale University

I have been looking over the online Organic Chemistry course taught by McBride at Yale and named "Freshman Organic Chemistry", 125A, which is on Itunes University. Only the lectures are ...
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What is the mechanism when 1-chloro-4-nitrobenzene reacts with NaOH?

The reaction mechanism in my textbook when 1-chloro-4-nitrobenzene reacts with NaOH is given as follows, When chlorobenzene reacts with NaOH the product formed is phenol with benzyne as the reaction ...
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1answer
35 views

How to convert benzyl alcohol to 2-phenylethanoic acid?

How can we convert benzyl alcohol to 2-phenylethanoic acid? This is what I have tried. Can someone tell me whether this is correct because I am not sure about the second reaction. In my textbook it ...
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19 views

Oxidative cleavage of alkenes by Chromic Oxide

Does CrO3 (hot concentrated or acidified like Jones Reagent) cleave alkenes and alkynes like hot conc KMnO4 would, like this reaction? If not, why not? And do any other reagents other than Ozone ...
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1answer
61 views

Method to remove impurities from acetaminophen synthesis experiment

I'd like to know about impurities from acetaminophen synthesis experiment. Are there any impurities produced by oxidation of p-aminophenol? If there is any impurity produced by oxidation of p-...
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1answer
76 views

Why is "Carbon can form many compounds with long carbon chains" not correctly explained by "Carbon atoms can share electrons with one another"?

Why is "Carbon can form many compounds with long carbon chains" not correctly explained by "Carbon atoms can share electrons with one another"? I am a high school student just ...
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0answers
19 views

Mechanism of Action of Carbachol

Carbachol (carbamylcholine chloride) is known to be a cholinergic agent. Does it work as an indirect agonist by inhibiting acetylcholinesterase, as a direct agonist of acetylcholine receptors, or is ...
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1answer
43 views

confusion regarding meta-cresol and phenol

when I googled the answer, i found out that m-cresol has a PKa value of 10.1 whereas phenol has 10.0. I am simply unable to use any logic to compare their strengths. We have been taught only the ...
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1answer
43 views

Reaction Mechanism for a radical ring opening

I have a radical reaction which I got from an organic chemistry lecture and was drawing the possible mechanism for it. Fig 2. shows my thought process. The I is removed making a radical and ISnBu$_3$. ...
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1answer
29 views

Reducing sugars and redox potential

I am wondering if reducing sugars are those that can act as reducing agents, and they act as such with Tollens and Fehling reaction, then what's the redox potential here? And is it a reversible ...
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0answers
48 views

How to remove starch from silicone ("Oogoo")?

Oogoo is an easy and cheap way of creating silicone rubber objects from a hand-formable putty. Basically: just mix silicone caulk with starch (I'm using acetate moisture absorbing silicone caulking ...
3
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0answers
35 views

Why ketoses undergoes dehydration more rapdily than aldoses?

I was reading about Seliwanoff's test and Wikipedia mentions the principle behind this test This test relies on the principle that, when heated, ketoses are more rapidly dehydrated than aldoses. ...
3
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2answers
122 views

What are skew positions in the conformation of cyclohexane?

I encountered a question which mentioned the skew position during discussion of the conformers of cyclohexane (chair/boat). Here is the question (grammatical errors have been emended): Which of the ...
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2answers
73 views

Why are acidic solutions often neutralised with carbonates rather than hydroxides?

In many syntheses stuff like calcium carbonate is used to neutralise acids, but this seems annoying, as you have to add it very slowly to avoid too much fizzing. Could someone explain why anyone would ...
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16 views

Reed Reaction Alkyl free radical attack

During the Reed reaction the alkyl free radical attacks the sulphur atom in SO$_2$. But why doesn't it attack the oxygen atom?
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2answers
209 views

What is the error in the number of aromatic isomers of C7H8O?

I am a student studying basic organic chemistry (isomerism) and was asked a question to find the number of aromatic isomers of $\ce{C7H8O}$.In fact this was a question in IITJEE exam. So I tried to ...
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77 views

How is this Clemmensen Reduction taking place? [closed]

How did that isotopically labelled Carbon migrate? I know that an carbanion is formed, but I am not able to conclude the final product. Please Help
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2answers
65 views

Why is this compound more basic than the other?

So, the original question was which compound is more basic. Compound A and Compound B respectively. My reasoning is that on protonation, Compound B would be more stable than Compound A as well, ...
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1answer
61 views

Dextrose equivalent values (DE) of the most common sugars

What are the dextrose equivalent values (DE) of lactose, and other common sugars? Some data like the values for sucrose (0), maltodextrin (x<20), maltose (52), and glucose (100) can be found at ...
5
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1answer
178 views

The total number of stereoisomers of 1,2-dibromo-3,4-dichlorocyclobutane

I tried writing all the geometrical isomers for 1,2-dibromo-3,4-dichlorocyclobutane, and then saw if they were optical or not. And I am getting the answer as 10: However, the given answer is 8. I can'...
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0answers
37 views

How to compare the stability of 3,4-Dimethylcyclopentene and Cyclopentane, 1-methyl-2-methylene

Two alkenes are given as follows: , How do I compare their stability? Denoting the first compound as (A) and the second as (B). Both the alkenes have same number of $\alpha$ hydrogens, which is $3$. ...
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2answers
73 views

what does the prefix tetrahydro actually means?

After encountering a few compounds which their name includes the prefix "TETRA HYDRO" I'm wondering what that prefix actually means? For example THC (tetrahydrocannabinol) and also THF folic ...