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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Negative Frequency for a Starting material

I am currently beginning a project in computational chemistry, from what I understand a negative frequency occurs only in a TS due to the presence of a saddle point from another previous post. I am ...
nking1390's user avatar
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Overlapping powers and bond strengths of hybrid orbitals of carbon

A similar question has been asked before, but there is no satisfactory answer. Another question without any answers has been asked here. Therefore, I am posting this question with more details. ...
ananta's user avatar
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Can an HCl salt solution of an API crystallize to API base in a slightly acidic medium?

Is it possible for a HCl salt of an active pharmaceutical ingredient (API) solution crystallize to the same API base, in a slightly acidic medium of around pH 4-5
Dqrko's user avatar
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Difference between KCN and CuCN [closed]

Can there be a general difference on the function/working mechanism between KCN and CuCN, particularly with their reactions in Aliphatic and Aromatic compounds?
Jo Nga's user avatar
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1 answer
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Which of these molecules have stereoisomers?

Problem: Which of these molecules have stereoisomers? Solution: (The molecules with a red X beside them are the ones with stereoisomers.) Question: What is the method used to identify which molecules ...
Nora's user avatar
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0 answers
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R/S configuration of 2-methyl-3-oxo-3-phenylpropanoic acid

I keep getting S configuration even though it should be R. I thought the OH would have higher priority than the phenyl group. Can someone explain this please?
Alexa's user avatar
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3 votes
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UV-Vis spectrum of alkane

My reference books stated: Methane's maximum absorption wavelength is 125 nm, ethane's is 135 nm. The longer the carbon chain, the larger the absorption wavelength, it is 165 nm for n-octane. Well, ...
Shira's user avatar
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2 votes
1 answer
93 views

If a compound has a strong and weak minus I group, will the stronger group always have a δ- charge?

In a compound like acrolein (prop-2-enal or $\ce{CH2=CH-CHO}$, will the oxygen in the $\ce{-CHO}$ group always have a $\delta$- charge? Acrolein does have three resonance structures as shown below, ...
Bongo Man's user avatar
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1 answer
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How do I number the atoms in strychnine?

I know the basics of naming organic molecules, but this one is a bit more complex than I'm capable of. How can I number the atoms in strychnine? Systematic IUPAC name: ($4$bR,$4$b$^1$S,$7$aS,$8$aR,$8$...
imrobert's user avatar
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Why is 1-ethylcyclohexene more stable than ethylidene cyclohexane?

Both compounds yield the same product, ethylcyclohexane, when hydrogenated. However, 1-ethylcyclohexene has lesser heat of hydrogenation than ethylidenecyclohexane, hence more stable. I want to know ...
Anu Vanguri's user avatar
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1 answer
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What is the relationship between 3-Ethylpentane and 3,3-Dimethylpentane?

these are structural isomers but which type of structural isomerism do they show? my guess is functional isomerism . IS this correct?
waterbottle's user avatar
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1 answer
72 views

Why can't the diene in a diels-alder also be a dienophile [closed]

why can't the diene react with itself like this
OZWizard X's user avatar
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1 answer
53 views

Is this a allyl bromide? If not what is it?

This molecule should be a allyl bromide: but what about this one: What is it?
Antonio Azevedo's user avatar
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0 answers
20 views

Why OH has more +Inductive effect than OCH3?

In OCH3 O is surrounded by CH3 which gives +inductive effect but in OH ,O is more electronegative than H so electron cloud will be displaced towards O increasing its tendency to donate electron. ...
Phami's user avatar
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23 views

what is the role of extra amine in my system at room temperature?

I have methoxysilane, silanol, epoxy resin, and aminosilane in one system, and amine groups are more than the required amount to react with epoxy groups, what is the role of extra amine in this ...
Ghasedak's user avatar
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0 answers
27 views

My question is about hyperconjugation [closed]

If we have a free radical on a double bonded carbon carbon,can the free radical show hyperconjugation?
Madhav Mittal's user avatar
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What is this gel byproduct of acetylsalicylic acid recrystallization?

I did a very simple acetylsalicylic acid synthesis from salicylic acid and acetic anhydride (with phosphoric acid as a catalyst). After rinsing, filtering and drying the product I dissolved it in ...
Thomas's user avatar
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0 answers
30 views

The reaction of PEG and epichlorohydrin [closed]

I am trying to synthesis Functionalized PEG. So reacted Epichlorohydrin and Poly ethylene glycol methyl ether using Tetrabutyl ammonium hydrogen Fluoro phosphate (TAHFP) as the base to remove the ...
Riswat's user avatar
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-3 votes
0 answers
30 views

How many resonating structure are possible in it? [closed]

How many resonating structure are possible in it?
Fhami's user avatar
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0 answers
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Mechanism of oxidation reaction with periodate

What is the mechanism of reaction of periodate with β-hydroxy amine? I tried the to write the mechanism similar to that of reaction with 1,2-diol but I am not able to obtain 2 carbonyl compound and ...
WIZARD GAMER's user avatar
2 votes
0 answers
20 views

Reason for differences in AChE aging/reactivation kinetics between neutral and charged organophosphorus inhibitors

According to the referenced papers, acetylcholinesterase that has been inhibited by an organophosphate possessing thiocholine as its leaving group is more susceptible to reactivation by oxime ...
user73910's user avatar
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2 votes
1 answer
135 views

Reaction Mechanism for tert-butyl alcohol and an aldehyde

Consider the reaction between tert-butyl alcohol and acetadelhyde in the presence of $\ce{HBr}$ in aqueous solution: $$\ce {(CH_3)_3COH(aq) + (CH_3)CHO(aq)} \longrightarrow ?$$ Here is my assumed ...
user1117233's user avatar
-1 votes
1 answer
35 views

What is the correct way to write sodium tetraphenylborate formula? [duplicate]

In wikipedia, it is written in two different ways. (C6H5)4BNa and NaB(C6H5)4 Is there not a unique criterion? Or is it chemistry-brach-dependant?
Martín Montoto Fernández's user avatar
4 votes
1 answer
110 views

How to draw endo-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride on ChemDraw?

I'm struggling to draw endo-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride on ChemDraw. I currently have this: How can I draw it in the chair conformation side on view? I know what it is ...
avogadros_pupil's user avatar
2 votes
0 answers
73 views

Removing DCC and its by-product from Steglich Esterfication

In my small research, I want to synthesize 3 alkyl gallates (ethyl gallate, butyl gallate, and hexyl gallate), and here's my overall reaction using Steglich esterification): However, from reading ...
Jonathan's user avatar
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0 answers
48 views

Why is picric acid not more steam volatile than p-nitrophenol, if intramolecular bonding results in increased steam volatility? [duplicate]

I understand that relative to p-nitrophenol, o-nitrophenol would be more steam volatile (as p-nitrophenol can form intermolecular hydrogen bonds), but my question lies in the fact that its volatile ...
rania h's user avatar
4 votes
2 answers
63 views

Mechanism for elimination in 3-Chloro-1,4-cyclohexadiene

So, I came across this reaction as an example of E2 elimination. Our teacher told us that this is what we call E2' reaction, as in, the $\ce{OH^-}$ takes the terminal $\ce{H^+}$, followed by ...
Laxmi Narayan Bhandari's user avatar
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0 answers
21 views

How to form an Hemi aminal in a cycle

I’m trying to resolve a mechanism of the formation of a bis-adduct with and 2 dG (Guanosine). I don’t know if I missed a step but I am stuck and I don’t know how the cyclization occurs, here is the ...
Mi Riame's user avatar
-3 votes
1 answer
80 views

Can someone help me name this molecule?

I'm having a hard time deciphering it's IUPAC name like I have 4-butanoxy and 3-propanoxy so far, but how do you put it all together with the double-bonded oxygen? Thank you and really sorry for the ...
i dont know how to code's user avatar
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0 answers
64 views

Which of the following observation is shown by 2 -phenyl ethanol with Lucas Reagent?

The answer mentions that there will be no turbidity obtained in the above reaction which is true if you only consider it to be a primary alcohol. I was wondering whether a hydride shift causing the ...
Dabeet's user avatar
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0 answers
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Would there be any short way (under 9 steps) to convert ethanoic acid to benzene? [closed]

all the ones i've seen require conversion into ethyne before converting to benzene, is there anyway you could get it to cyclohexane and then convert directly to benzene without halogenation?
zen's user avatar
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-2 votes
0 answers
25 views

Can someone explain me the 3D structure of sodium alginate? [closed]

I understand the numbering in the 2D structure and the carbon numbering for both the mannuronic and guluronic acid repeating units pretty well, but I can't in the 3D structure. Can someone please ...
snr's user avatar
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0 answers
80 views

Is LiN(CF3SO3)2 is valid, being similar to Lithium Bistriflimide (LiN(CF3SO2)2)?

According to Wikipedia, $\ce{CF3SO3}$ is Triflate (Trifluoromethanesulfonate), $\ce{CF3SO2^{-}}$ is Triflyl and $\ce{N(CF3SO2)2^{-}}$ is Bistriflimide (Bis(Triflyl)amide), or simiply Triflimide. ...
Blacklight MG's user avatar
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0 answers
33 views

Optical Isomerism in Threonine

If around C-C there is free rotation, shouldn't all of these molecules be the same?
A levels Chem student's user avatar
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78 views

How many times does substitution happen here?

(This question is from a dubious source) The reaction taking place here is Friedel-Crafts acylation of benzene with 1-chloro 2,2-dimethyl propanone (pivaloyl chloride?). To me, the options seem most ...
zxen-xi's user avatar
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0 answers
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carbocation stability: any resonance delocalization > substitution?

My organic text (Karty, 3rd) seems to assert without much justification that in general any resonance de-localization trumps a greater degree of substitution for determining CarboCation stability. ...
some bits flipped's user avatar
2 votes
1 answer
145 views

How to name LiN(CF2SO3)2?

I found this compound in the list of inorganic lithium salts from this article on ScienceDirect. It is said to be of the sulfonate group. Let's focus on the anion alone. I'm not sure if it can be bis(...
Blacklight MG's user avatar
-2 votes
1 answer
52 views

What do the arrows mean in the Structural Formula of Oxaliplatin? [duplicate]

What do the arrows mean in the Structural Formula of Oxaliplatin? I haven't seen these and couldn't find anything explaining them.
imrobert's user avatar
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2 votes
1 answer
37 views

How to safely add a lithiated reagent (R-Libenzene) to another flask using the NE-1002X syringe pump?

I would like to do a murahashi coupling (lithium coupling) between 1,4 dibromo benzene and 2,6-dinaphtalene-4-tertbutyl-iodobenzene. I am trying to copy the exact procedure from this article: ...
The Red Man Jolan Bonelli's user avatar
-1 votes
0 answers
25 views

How can Optically inactive isomers even be optical isomers? [duplicate]

Optical isomers are defined as those compounds which rotate PPL in opposite orientations, but if they are optically inactive (hence not rotating the PPL) how can they be considered as optical isomers ?...
dwvansh's user avatar
-1 votes
0 answers
13 views

Why do ethanamide has a higher boiling point than that of propanamide? [duplicate]

It's because of the positive inductive effect that is greater in propanamide than in ethanamide. This cause the -NH2 to be less stable.
UMUHIRE Jean Chance Credo's user avatar
1 vote
0 answers
79 views

Stability comparison between Acetylene/Ethyne (C2H2) and Nitrogen Gas (N2) [closed]

N≡N is more stable than H2N—NH2 (hydrazine) But HC≡CH is less stable than H3C—CH3 Why is it so? Even though the size of the corresponding compounds and hybridization is the same? (Usually ethane is ...
Maddy's user avatar
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0 answers
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Regarding Hinsberg reagent, potassium salt of primary amine soluble in base become insoluble after acidification?

Distinguish between ethylamine, diethylamine and triethylamine by using Hinsberg's reagent? Ans. This reaction is useful for the distinction of primary, secondary and tertiary amines. (i) Primary ...
JUA's user avatar
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0 answers
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What kind of elimination is this?

Considering the series of reactions given below: (pg. 398, Organic Chemistry, 2e., Clayden, Greeves, Warren) The aim is to obtain an alkyne from a halosubstituted alkane. I understood the first two ...
zxen-xi's user avatar
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3 votes
1 answer
142 views

Smell of orange peel travels super fast

Many years ago, my college chemistry teacher squeezed an orange peel in the front of the auditorium asking us to raise our hands when we smelled it. Hands rippled through the auditorium (at least 40 ...
Greg's user avatar
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-1 votes
0 answers
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Synthesis of indoles from 2,4-DNPH (fischer indole synthesis)

I am unable to find any data at all about conversion of 2,4-dinitrophenylhydrazones into their indoles through Fischer method. Can you give me some links for its procedure.
Muhammad Ali's user avatar
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0 answers
17 views

what are factors that affect the reactivity of halogens in palladium catalyzed reactions

What affects the reactivity of a halogen in palladium catalyzed cross coupling? For example if i have different halogens on a molecules (all of them being iodines for simplicity) how to predict which ...
CC.chem's user avatar
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-2 votes
1 answer
40 views

Water is removed by distillation to speed up dehydration. Why would that not work for the dehydration of 4-methyl 2-pentanol?

I understand that due to LeChatelier's principle, the removal water forces the reaction to move forward and make more to get back to equilibrium. However, I'm not sure why this would not work for this ...
user143617's user avatar
0 votes
1 answer
79 views

Testing whether an unknown powder is wheat gluten (at home)?

Last week, I ordered wheat gluten to make seitan. I received some powder and attempted a recipe, which mixes 100g of water with 100g of gluten to form a sticky dough. However in my case, I only got a ...
Alduno's user avatar
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1 vote
0 answers
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Which position do retro aldol reactions occur in (comparing glucose and fructose)?

Regarding glycolysis, my text states: What is the biochemical rationale for the isomerization of glucose 6-phosphate to fructose 6-phosphate and its subsequent phosphorylation to form fructose 1,6-...
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