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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Can primary amine be produced using Grignard reagent?

I found a way to produce Secondary Alkyl Amines using Grignard Reagent. Ref: Z. Huang, J. Lv, Y. Jia, Chemistry Select 2016, 1, 5892. DOI: 10.1002/slct.201601464 But I want to know if I can use $\ce{...
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-2 votes
0 answers
40 views

Does Cannizzaro reaction occur simultaneously during benzoin condensation?

Does Cannizzaro reaction occur simultaneously during benzoin condensation of benzaldehyde catalyzed by $\ce{NaOH}$ and thiamine? I assume that benzaldehyde break down to benzoic acid and benzyl ...
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2 votes
0 answers
75 views

Red P+HI with some specific functional groups

I've seen the related question (Does RedP+HI reduce all carbon functional groups to alkane?). Although the question is admittedly similar, neither the answer provided nor the document linked in it ...
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-1 votes
1 answer
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Why is the carbocation on the left more stable? [closed]

I assume resonance is coming into play here due to the hydroxy group on the carbon adjacent to the positive charge. What about the electron donating effect of the alkoxy groups?
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1 vote
0 answers
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How to get the total number of numbered positions in a molecule/compound

I'm working on a metabolite database where "labeled" compounds can contain isotopically labeled atoms in specific positions. When a new labeled compound is entered into the database, we'd ...
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3 votes
0 answers
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Troubleshooting synthesis of halazone from dichloramine-T

I was trying to oxidize some dichloramine-T to halazone. It should be easy enough since dichloramine-T has a free methyl group para to the para-sulfomyldichloro group. I followed a published procedure ...
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-2 votes
1 answer
49 views

How to draw the structural formula for 3-ethyl-5-methyl-3-heptene? [closed]

This is the kind of structural formula we need to draw: I took help from Reddit. Here is the attempt: I have done one more attempt: Though the 4th carbon of the left condensed version needs to have ...
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2 votes
0 answers
56 views

Evaporation of sample solvent and redissolving

When I conduct a synthesis, after some workups, I usually evaporate large amount of solvent using rotovap, recover compounds sticked to the wall of the flask to the glass vial using small amount of ...
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2 votes
0 answers
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How much analyte should I use for paper chromatography?

I am looking into using paper chromatography to distinguish between standard drugs and counterfeit drugs for my high school research project. I have decided on using aspirin as the "standard"...
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3 votes
3 answers
125 views

Comparing reactivity of 3-bromocyclohexa-1,4-diene and 5-bromocyclohexa-1,3-diene towards SN1 reaction

Compare reactivity of 3-bromocyclohexa-1,4-diene (P) and 5-bromocyclohexa-1,3-diene (Q) towards $\mathrm{S_N1}$ reaction. My teacher claims that the reactivity of P is more than that of Q. He ...
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3 votes
0 answers
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Are fluorine atoms less polarizable than the table predicted?

According to this table, per-fluorocarbons like CF4 are slightly more polarizable than analogous hydrocarbons like CH4 (2.824 vs 2.448). However, polarizability is measured under uniform electric ...
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Why don't secondary alcohols react with HBr/HI via SN2?

In polar protic solvents, $\ce{Br-}$ and $\ce{I-}$ are considered to be very good nucleophiles. Now, here the solvent is alcohol which is polar protic. So, why don't secondary alcohols react with $\ce{...
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0 votes
0 answers
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How do I determine if a nucleophile attacks the electrophilic atom directly or indirectly?

How do I determine if a nucleophile attacks the electrophilic atom directly or indirectly? For instance a nucleophile could attack the carbon in a molecule with a carbonyl directly, but in another ...
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8 votes
2 answers
200 views

Stereochemistry of nitrosyl chloride addition to an alkene

My book states addition of $\ce{NOCl}$ to propylene results in 2‐chloro‐1‐nitrosopropane: Would it follow syn or anti addition? According to Mallya and Nagendrappa [1], the reaction would follow syn ...
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0 votes
0 answers
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Would a 0.3 micron filter be effective in blocking formaldehyde fumes produced by curing cyanoacrylate?

I’m looking into purchasing a mask that blocks particles larger than or equal to 0.3 μm in size. I’m hoping it blocks the formaldehyde fumes produced by curing cyanoacrylate. How effective such mask ...
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1 vote
0 answers
77 views

Monochlorination of (R)-2-chlorohexane: Number of possible chiral dichloro products

How many possible chiral dichloro products can be formed when (R)-2-chlorohexane reacted with one equivelent of $\ce{Cl2}$ in the presence of UV radiation (monochlorination only)? $$\ce{C6H11Cl + Cl2 -...
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2 votes
0 answers
28 views

Transforming hydroxyl group to carboxylic acid in an aqueous environment

I am looking for a way of converting a hydroxyl group into a carboxyl group in an aqueous environment for eventual coupling to an amine. There seem to be plenty of ways of achieving this in various ...
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1 vote
1 answer
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Do azaindoles primarily exist in anionic form at physiological pH and act as bases?

I am reading an article where they describe azaindoles (bicyclic pyridine/pyrrole rings) as being basic with $\mathrm{p}K_\mathrm{a} \approx 4.6.$ I suppose at physiological $\mathrm{pH}$ and after ...
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4 votes
1 answer
51 views

Amino Acid Derivative Naming Conventions

Is there a trivial name for compounds based on glutamic acid, or other amino acids, where it is not the α-amino acid group that is functionalised? (I.e. that shown on the right) Glutamylsulfonic acid, ...
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2 votes
1 answer
85 views

Reaction of chloroform with DBU

There's a certain reaction I've been doing that involves DBU (I've drawn the structure out below). The reaction is done in a flow machine (ie. high temperature and high pressure). I've read that ...
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2 votes
1 answer
54 views

Comparison of the acidic nature between substituted benzoic acids and acetic acid

p-Methoxybenzoic acid $(\mathrm{p}K_\mathrm{a} = 4.47)$ is a stronger acid than acetic acid $(\mathrm{p}K_\mathrm{a} = 4.76)$ despite the presence of an electron donating group. I understand this is ...
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1 vote
0 answers
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Rearrangement vs. Ring Strain in Cyclobutanecarboxaldehyde Nucleophilic Reaction

Predict the major product of the following reaction: Note: Product A is incorrectly marked as secondary halide, it should have been primary halide This question appeared in an national level ...
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1 vote
0 answers
76 views

What are the compounds that this article refers to?

The linked article studies the effects of a set of organophosphorus compounds on the bioelectrical activity in the digestive system. The OP compounds studied are referred to in the abstract as IMFF, ...
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2 votes
0 answers
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Buchwald-Hartwig coupling troubleshooting

I am conducting a synthesis using below scheme. And Below is some information about my reaction history. The basic condition is 1 eq of 1-aza-18-crown-6, 1.4 eq of 3-bromothiophene, 1 mol% of ...
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2 votes
0 answers
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Creating custom spectra graphs

I wanted to make a few custom spectra graphs for some homework questions I'm assigning. The issue is that the Education Board issued datasheets do not reflect online images. They often say that bonds ...
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3 votes
0 answers
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How to explain mesylate structural homologues (e.g., "esylate") being weaker leaving groups than mesylate itself?

I came across a piece of scientific literature (https://patents.google.com/patent/US20080045602A1/en) that would seem to imply leaving groups formed by reacting hydroxy groups with, e.g., ...
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0 votes
0 answers
48 views

Orbitals in benzene and other delocalised structures

I've read that molecular orbital theory demands that if there are $n$ orbitals prior to some event like bond formation, there should be $n$ orbitals after this event. Does this hold even in structures ...
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2 votes
0 answers
45 views

How does iodic(VII) acid oxidise amines? [closed]

What happens when 3‐aminobutan‐2‐one undergoes oxidative cleavage with $\ce{HIO4}?$ I'm particularly interested in the amine part. Would the hydroxy and amino groups on the same carbon be stable? Or ...
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-1 votes
1 answer
57 views

How to synthesize 1,1,1-trichloro-2,4-dimethylpentan-2-ol from methyl isobutyl ketone?

Chlorobutanol can be made with chloroform and acetone in the presence of potassium or sodium hydroxide. Would it work with other ketones such as methyl isobutyl ketone to yield 1,1,1-trichloro-2,4-...
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4 votes
0 answers
51 views

How should the reactivity of 1-propanesulfonyl chloride be expected to compare to tosyl chloride for sulfonylation?

I've come across some scientific literature (e.g., https://doi.org/10.1021/jm400751p) that notably feature 1-propanesulfonyl chloride (PsCl) in the selective activation of hydroxy groups, such as a ...
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4 votes
0 answers
52 views

Rate of polymerization for copolymers with two monomers

I've found in textbooks that for a chain growth homopolymerization the rate of polymerization $r_\mathrm{p}$ is $$r_\mathrm{p} = k_\mathrm{p}\sqrt{\frac{f_\mathrm{kd}}{k_\mathrm{t}}}c_\ce{A}^ac_\ce{B}^...
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3 votes
1 answer
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How does coenzyme A produce proton from pyruvate ions?

Coenzyme A (CoA) is a complex molecule consisting of mercaptamine, β-alanine, pantoic acid, diphosphate, pentose, phosphate and adenine moieties: Which part of it actually plays role in the formation ...
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3 votes
0 answers
72 views

Acidification of a vicinal diol [duplicate]

The following is a question from Advanced problems in organic chemistry by MS Chouhan: The options given are: My initial thought was that this could be a pinacol–pinacolone rearrangement. However ...
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1 vote
0 answers
51 views

Comparison of boiling points between 2‐butanol and isobutanol

Which has higher boiling points among butan‐2‐ol (1) and 2‐methylpropan‐1‐ol (2)? I know that branching decreases the boiling points, but I want to know how position of substituents affects the ...
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-2 votes
2 answers
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Information about liquefied carbon factories from carbon dioxide

I am looking for some information about the factories that turn CO2 gas into the liquid CO2. I want to know the methods that they are using. Can anyone help me? Thanks
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0 votes
0 answers
33 views

How does the second hydrolysis of phthalimide work (hydrolysis of amide)?

In the hydrolysis of Phthalimides we can see two successive hydrolysis of "amides" see ChemLibre for a nice mechanism This is interesting because normally (also according to ChemLibre) ...
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4 votes
0 answers
73 views

Is There a Problem with the Assignment of Stereochemical Descriptors by ChemDraw in Select Examples?

While using ChemDraw Professional 21.0.0.28 to construct some cyclic allenes and rotationally restricted biphenyls, I came across anomalous assignments of stereochemistry. [For the latest version of ...
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6 votes
1 answer
374 views

The major product of radical halogenation: Why is it a halogen attached to a primary carbon and not a tertiary carbon in the given example?

There's this problem that I saw in my Organic Chemistry book: The reaction between $\ce{(CH3)3CH}$ and $\ce{Cl2}$ forms two products: $\ce{(CH3)2CHCH2Cl}$ (63%) and $\ce{(CH3)3CCl}$ (37%). Why is the ...
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If they both form hydrogen bonds, Why does borax make polyvinyl alcohol slimy/elastic but water doesn't?

When dissolved borax (borate ions) and polyvinyl alcohol are mixed, an elastic slime is formed. To my understanding, this is because the borate ions form hydrogen bonds with the OH groups on the PVA, ...
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0 votes
0 answers
26 views

Table of viscosity of water vs temperature

Above is the table for water physical properties table with temperature related with a,v,b,Pr,Ra factor. This table has temperature only from 0 to 100. May I ask if there is a full table for this with ...
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0 votes
1 answer
51 views

Substitution v/s elimination

For SN2 pathway we use an strong nucleophile (OH-,CN-) so they can easily substitute X(halogen) group from rear side. While for elimination bimolecular reactions we use a strong conjugated base (RCH2O-...
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2 votes
1 answer
72 views

Reaction of 2-carboxybenzaldehyde with $\ce{NaCN/HCl}$ - does carboxylic acid interfere?

In the reaction of 2-carboxybenzaldehyde with $\ce{NaCN/HCl}$, the aldehyde will form cyanohydrin. But my question is, will the carboxylic acid remain intact? Will it react separately or with the ...
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4 votes
1 answer
601 views

Converting benzaldehyde to benzophenone in no more than two steps

This is a question from my book, as stated in the title: How will you convert benzaldehyde to benzophenone in no more than two steps? I can do it in three steps - first using $\ce{PhMgBr}$ on ...
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0 votes
0 answers
18 views

Descriptive explanation of different Carbon Nanotubes Conductivity

I'm soon having a talk about Carbon Nanotube FETs and wanted to give a short introduction into CNTs in general. Of course for device operation it's important that some types of single-walled CNTs are ...
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1 vote
0 answers
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What is the inherent mechanism in carbocatalysis?

When checking non-metallic catalysis materials, one mentioned example is that of carbocatalysis; using heterogeneous carbon structure to catalyze a reaction (Not to be confused as a support surface ...
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7 votes
1 answer
250 views

Stable conformer of protonated ethane-1,2-diamine

I had been studying on the stable conformers of ethylene glycol and ethane-1,2-diamine. Due to hydrogen bonding in the vicinal $\ce{-OH}$ groups, ethylene glycol prefers to show gauche conformer. The ...
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0 answers
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General conditions for aryl migration of 2-bromo-1,1-diphenylethylene with sodium amide [duplicate]

In this reaction, I am quite unsure whether a phenyl shift would be involved or not because I was managed to solve the phenyl shift mechanism before in pinacol-pinacolone rearrangement. What are the ...
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1 vote
0 answers
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Does 3-hydroxy-penta-2-one give positive Tollen's test? [duplicate]

I know that alpha hydroxy ketones that can tautomerise to an aldehyde give positive Tollen's test because an aldehyde gives a positive Tollen's test. This molecule however doesn't tautomerise (or ...
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1 vote
1 answer
53 views

Can I synthesize 4-aminophenol and/or acetic anhydride at home? [closed]

I am going to try to synthesize acetaminophen as a possible science fair project, or just for fun, but doing it with precursors to the precursors of it might be more fun for myself then just using the ...
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Does formal charge impact electron donation and withdrawal?

Does an atom with a positive formal charge withdraw more electrons than that atom without formal charge, due to the extra positive charge on the atom? For example, I know the carbonyl group becomes ...
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