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.
10,354
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How to determine if all carbon atoms in a cyclic compound lie on the same plane?
I'm currently doing a-levels chemistry and came across a question asking if all 17 carbon atoms in cyclic rings of a cholesterol molecule lie on the same plane. I've done some googling and it turns ...
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1
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311
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Order of basicity for arylamines and ammonia in gas phase
In aqueous solution, the basicity order is: $\ce{NH3 > Ph-NH2 > Ph-NH-Ph > (Ph)3N}$
What will be the order in gas phase?
Following are some considerations:
1- In $\ce{NH3}$, $\ce{N}$ is $\ce{...
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1
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207
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Mechanism for hydrolysis of cyanohydrin [closed]
I know that acetals can be hydrolyzed with H2SO4 but I am not sure how benzaldehyde would be formed following hydrolysis of the cyanohydrin. When I searched online it I found answers suggesting that a ...
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Boiling and melting points of hydrocarbons [closed]
What happens while boiling and melting hydrocarbons? Which bonds are broken?
When we compare the boiling point (b.p.) and melting point (m.p.) of certain hydrocarbons the order is inverted. For ...
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Would TFA be a strong enough acid to perform an SN1 reaction on alcohols?
The pKa of sulfuric acid, which is usually used to do this reaction is -3, but would TFA be sufficient even though it has a pKa of 0.5?
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374
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Acidity and structure of EDTA at different pH
I was conducting complexometric titrations to measure the concentration of magnesium ions in my solution.
But of course, as EDTA is a chelating agent, knowing it’s structure and ionization form at ...
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1
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195
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Reaction of primary amine with mixed acid anhydride
Is this reaction $\ce{S_N2}$ (because attack of nucleophile and removal of leaving group are not taking place in a single step)?
Which part of anhydride should form the substituted amide? If it is an ...
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1
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131
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Why are alpha hydroxy acids stable? [closed]
We were told by our teacher that 4 hydroxyl groups on same carbon atom results in formation of carbon dioxide by removal of 2 water molecules and he also told that 3 hydroxyl groups on the same Carbon ...
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Is the azo group basic?
I know that amino groups (nitrogen with single bonds with hydrogen and/or carbon) are basic.
I wanted to know if azo groups ($\ce{R-N=N-R}$) are similarly basic.
I searched online but couldn't find ...
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How do ketone react with a peroxy acid to yield an ester? [duplicate]
This may be a really dumb question but I can't find any mechanism plot or reasoning how ketone reacts with carboxylic acid and form an ester. I thought R-OH react with RC(O)OOH to form ester..
I tried ...
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2
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710
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addition of HBr to a conjugated alkene
here we shift double bond and change the carbocation from 3 degree to 2 degree, by doing so we are saying that hindrance matters more than carbocation stability, is this always the case in such ...
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BTX nitration work-up
I'm trying to understand washing step in a btx nitration process. In all these processes the work-up streams are very similar. The reaction mixture passes from the nitrator to a separator or ...
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0
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803
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Does inductive effect operate through pi bonds?
I have been told that the inductive effect is only present in sigma bonds by my teacher, and the book I've referenced also says the same thing.
However, I can't think of why this is. Answers to this ...
7
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Fluorine detection in organic compounds
Many of you will know why I am asking this question. There is a lot of attention recently to the dangers of the so called Perfluoroalkyl and Polyfluoroalkyl Substances (PFAS). In essence organic ...
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Where does Aluminum Hydroxide come from in a reduction of a ketone by LAH? [closed]
The experiment was done in a Laboratory. A ketone was reduced with LAH in THF under reflux.
At the end of the reaction, the protocol stated to add water until there is no more H2 released. The H2 ...
2
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What dodecahedral molecule is Linus Pauling likely holding in this photograph? Does it have 40 carbon atoms? [closed]
The video Quasicrystals ; Prof. Daniel Shechtman ; Nobel Prize in Chemistry focuses on Professor Dan Shechtman but happens to include some photos of Linus Pauling who never believed in quasicrystals. ...
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Selective secondary amide/lactam hydrolysis
I am working on a synthesis for a compound (4-aminophenol with alkyl chain and lactam at carbon 2). The final step of the synthesis involves hydroylsis of the secondary amide at carbon 4. My problem ...
2
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Stereochemical outcomes for hydrohalogenation when there is a carbocation rearrangement
The following reaction is given:
I want to be able to tell which of the following stereochemical outcomes are possible.
I am aware that there are other possible products than the ones shown here ...
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345
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Selective reduction of aromatic nitro group
In the following compound, is it possible to selectively reduce the aromatic nitro group to an amine, as shown in the reaction?
I fear that the methods usually used to reduce aromatic nitro compounds,...
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1
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294
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What is the "frequency of occurrence" referring to in this paper?
In Zhou et al.(2018) 22. 10.1016/j.geoderma.2018.02.015, table 1 of the different microplastics refer to a "frequency of occurence".
Why does the % frequency of occurrence add up to >100%...
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239
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Numbering of carbon chain in 3-bromo-2-methylpropene
I have a specific confusion in numbering the carbon chain for 3-bromo-2-methylpropene.
I found two carbon chains of equivalent length (three atoms) and equivalent side chains (one atom).
For both ...
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45
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Why do hydrocarbons give out a blue flame on complete combustion? [duplicate]
In complete combustion of hydrocarbons the colour of the flame is blue. But what is the reason behind the flame being blue and not green or black or any other colour?
Edit: I've searched the web for ...
5
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1
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113
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Regioselectivity in the opening of 3-membered heterocycles
(a) Consider the following reactions :
For these two reactions, the nucleophile attacks the less substituted carbon as it is less sterically hindered.
(b) Now consider the following reactions :
For ...
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2
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249
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Substitution in aryl halides
I need to propose a route for the synthesis of 2-(bromomethyl)benzonitrile from 1-bromo-2-(bromomethyl)benzene. In the attached figure, the structure of the starting compound and the species to be ...
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51
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Calculating the electric potential of a fruit battery
In a fruit battery, if I am using a reactive metal electrode for the cathode but the cathode reaction is the reduction of the hydrogen ions (in the acid of the fruit), how can the type of the cathode ...
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1
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103
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Natural Sources for S-(-)-Limonene?
I'm interested in developing an undergrad organic lab that delves deeper into distillation/extraction, optical rotation and enantiomers. Our lab currently does a steam distillation extracting R-(+)-...
5
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1
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Nitro as a leaving group in an aromatic ring
I came across a chemistry problem posted on Discord. The objective is to propose a reagent that will enable the following reaction to occur:
One proposed answer for the mysterious Reagent D is sodium ...
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1
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244
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Reaction of Grignard reagents with phosphoric acid derivatives
The use of Grignard reagents that people are most familiar with is the production of tertiary alcohols by reaction with a suitable carbonyl compound, whether it be an ester, ketone, or aldehyde. As I ...
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225
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Formation of α,β-unsaturated ketone from tertiary propargyl halide
My attempt: I went ahead with an $\mathrm{S_N1}$ type reaction followed by the attack of $\ce{OH-}$ on the 3 degree carbocation formed.
This does not match with the answer given (see image below), in ...
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Blue Tinge for White Paint [closed]
I am trying to make an aqueous white paint with Mica and TiO2 as mainstay that gives a slight tinge of blue when it dries but should remain white while in solution.
So far I have tried optical ...
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Preference for most acidic hydrogen
I understand that deprotonation from the carbon circled in red is feasible because deprotonation results in a resonance-stabilised structure. But according to it, deprotonation is also feasible in ...
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Why is acidic strength of A>B? [closed]
a) H-(C=O)-OH
b) H-(C=O)-O-OH
The acidic strength of the two structures given below was a>b .
I think the explanation to that is in structure A, the O atom of carboxyllic acid is in resonance with ...
2
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1
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How can Phthalocyanine be aromatic when it is not planar? [closed]
Even as Hückel's rule is not applicable in every scenario, especially in metallic clusters, it seems that organic structure need to be planar to show aromaticity. That being the case, Pubchem's ...
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1
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Do the phosphoester and glycosidic bonds of dNTPs increase thermal stability?
A while ago, I provided an answer to a question on Biology.SE concerning the half-life of dNTPs under PCR conditions. At the beginning of my answer, I give a qualification:
Caveat: ignoring the ...
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1
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(IUPAC) How do you number an alkane that has two equally small starting points?
For example, do you number this from left to right or right to left? How do you know?
Would you get 2,4-dibromo-6,6-dichloro-5-methylheptane or 4,6-dibromo-2,2-dichloro-3-methylheptane?
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How does double bond placement, in an alkene, affect the boiling point of the alkene? [closed]
Will having the double bond be closer to the middle of the molecule result in a higher or lower boiling point than that of an isomer with the double bond closer to one of the ends? Also, does the same ...
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Which form does Casein take in milk (before and after extraction)? [closed]
In this video, NileRed said
casein is exists in milk as a salt Calcium caseinate. And that structure of the salt is composed of ...
2
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Why do the splitting pattern on my NMR differ from those stated in literature?
I attempt the synthesis of p-toluic acid using the Grignard reagent (prepared from 4-bromotoluene and Mg) and dry ice. The NMR of the raw product was recorded using $\ce{CDCl3}$ and a peak showing ...
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How are these two enantiomers? [duplicate]
I was wondering how these two chair conformations are enantiomers, because they do not seem to be mirror images of each other. The molecule on the left undergoes a ring flip to achieve the ...
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1
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What would the mechanism be for intermediate B to Supinidine, and what would by product C be? [closed]
I have managed to do the mechanism for the first step, but have no clue how 4 equivalents of MeLi are used for the second step of the reaction.
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Isomerization of tertiary carbocations in cholesterol synthesis
The following reaction mechanism happens in cholesterol synthesis inside human body. I am unable to understand why on earth the hydride shift happens here. I mean its already a tertiary carbocation, ...
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Accidental hydrolysis of tert-butyl chloride
Yesterday, I performed the synthesis of tert-butyl chloride from tert-butyl alcohole in my practical organic chemistry class. However, I only obtained a relatively low yield of about 30 %. Since I ...
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0
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Reaction of propanoic acid with chlorine used in wastewater treatment
I'm asked in a problem to write down the equation of the reaction of propanoic acid with chlorine used in wastewater treatment: $\ce{CH3-CH2-COOH +Cl2}$. The problem also states that, in this reaction,...
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is this compound meso? trans-1,4 dimethylcyclohexane [duplicate]
I had a question on a quiz that asked if the compound below was meso or not. I thought that it would be meso because there is a plane of symmetry going through the two methyls, but the answer was that ...
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Reactivity with rubbing alcohol and PVC
Rubbing alcohol seems to make polyvinyl plastic more sticky; i.e. if I clean a tube connector with rubbing alcohol first and then insert it into the plastic tube, it supposedly secures the seal ...
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Why is the NMR result for my p-toluic acid product so odd?
I just started learning about NMR and did a lab session where we conducted Grignard rxn with CO2 to form p-toluic acid and my NMR result is:
1H NMR (400 MHz, CDCl3) δ 9.63 (s, 4H), 8.07 – 8.00 (m, 5H),...
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Hazards of eating non-stick coating, particularly considering the coating primer [closed]
How unhealthy are teflon / non-stick coating chips that end up eaten? What role does the primer coating play?
Existing similar threads that don't go into enough detail: 1, 2
I understand that there is ...
2
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0
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885
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TCP and KCP product [closed]
Q:
According to me, the kinetic controlled product(KCP) should be
While the Temperature controlled product(TCP) is:
What should be the answer to this question because no temperature has been ...
2
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2
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Efficacy of Intramolecular Friedel-Crafts reaction on =o, c=o bonds of ring structures? [closed]
Updated Q:
Inquiring to understand the efficacy of intramolecular Friedel-Craft like reaction on stability on the ring structures with =o, c=o bonds.
Keen to know if ring structures are challenged
...
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Organic solvent that won’t attack either PET or butyl rubber?
I am looking for a suitable organic solvent for dissolving dried-on polyurethane adhesive on a substrate of nylon/butyl/polyester. Acetone is ruled out because it attacks polyester (PET) and Toluene ...