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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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What is the reason that resonance do not seem to increase the reactivity of organic compund but actually decrease the reactivity by making it stable? [closed]

In Organic reaction mechanism , resonance seem very important for certain group of reaction for Example:- Due to resonance in benzene ring it will increase the electron density in ortho and para ...
-1 votes
0 answers
28 views

Why do we normally prefere one perspective when doing a chair flip?

The common representation of the chair flip looks like this: But why go through the "trouble" of drawing the skeleton differently if it would work the same way with this representation:
0 votes
0 answers
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Can 2-methylpropanal + 2-methylpropanal undergo an aldol condensation reaction?

After solving the mechanism, I found it to be correct. Can someone please guide me through the reaction and correct any mistakes. If you go step by step through the mechanism, and do it, you have to ...
10 votes
1 answer
515 views

Frontier orbital analysis of zinc-catalysed carbonyl-ene reaction

Q1. Is the $\sigma_\ce{C-H}$ bond a donor in this reaction? If not, then can we take the alternate combination (HOMO of alkene, LUMO of the $\ce{C-H}$ bond and, HOMO of the carbonyl)? Q2. We can also ...
0 votes
0 answers
68 views

Why is the Molar mass of CO2 different than the weight of the sum of its particles?

The Molar mass of CO2 is stated to be 44.009 grams per mol But in a calculation of the weight of each atom's particles((Electrons,Protons,Neutrons) times Avogadro's constant I get 44.36 grams per mol ...
0 votes
1 answer
110 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 ...
2 votes
1 answer
59 views

(Di)chlorination of phosphonic acid ester

What is the best way to do this reaction to form the dichloride as an reactive intermediate when the substituent R is acid sensitive? In the literature the reaction is either performed with PCl5, a ...
1 vote
1 answer
71 views

Does di(n-propyl)ether support Grignard reactions?

It is known that diethyl and dibutyl ethers are good solvents for Grignards, it has been also found that diisopropyl ether does not work. I have never seen dipropyl being discussed. Edit: For clarity, ...
3 votes
1 answer
156 views

Electrolysis of benzyl alcohol in methanol

I am conducting following electrochemical experiment on Au wires in organic medium: I suppose the anodic reaction goes through a benzaldehyde intermediate: The cathodic reaction is hydrogen ...
-2 votes
0 answers
21 views

Doubt related to IUPAC nomenclature and RCOOX functional group [duplicate]

Does this compound exist? If yes, then what will be its IUPAC name? Also, what is the RCOOX functional group called?
8 votes
1 answer
28k views

Color of precipitate formed on reaction of acetylene with Tollen's Reagent

I am asked to find the color of the precipitate formed by the passage of acetylene gas into an aqueous solution of ammoniacal silver nitrate. I thought ammoniacal silver nitrate was Tollen's reagent,...
-2 votes
0 answers
52 views

Number of stable molecules [closed]

Is there are software/freeware (artificial intelligence or whatever) that given some types of atoms and their number how many "stable"/"reliable" molecules we can build involving ...
2 votes
0 answers
54 views

Clean *di* protection of phosphonic acid dichloride with a suitable protection group with clean deprotection

For some time I am struggling with a tricky synthesis problem in my pHD. I think I came closer now, but I still need a link in the chain to make my idea work. The principle goal here is access a free ...
0 votes
1 answer
68 views

Do Electron-Withdrawing-Groups give an hypsochromic shift or a bathochromic one? and why?

I'm not familiar with this topic,but i know that bathochromic shifts occur when the energy gap between energy levels of the substituted molecule, are lower than the unsubstituted one;viceversa ...
-2 votes
0 answers
45 views

No. of Transition States

enter image description here So in this question I had gotten the answer as 5 Transition states, however the official answer key states it to be 6. Upon digging further for resources I found a ...
5 votes
4 answers
3k views

Unexpected reaction during acid hydrolysis of cellulose

Recently I tried to hydrolyze some cellulose: I added some acid to it ($\ce{H2SO4}$) then noticed nothing. Even after a few days there was no visible change and after doing some tests for glucose, ...
0 votes
1 answer
58 views

Phenol reaction with nitration mixture

When phenol is reacted with nitration mixture my teacher said that picric acid as minor product and a major oxidation product. Is that oxidation product benzoquinone or anything else?
1 vote
0 answers
25 views

Xylitol qualitive detection

I'm going to add xylitol into my new dental cream formula. I need cheap and easy test to verify that material I receive is indeed xylitol. Xylitol comes from ISO certified supplier so as per law there ...
6 votes
1 answer
878 views

Treatment of ketones with excess Tebbe reagent

The reaction in black below was presented in a set of lecture notes as an example of the use of the Tebbe reagent, however it's not immediately obvious (to me, at least) that the product should be the ...
2 votes
0 answers
41 views

Stability of carbenes

For predicting the order of formation of carbenes from the following compounds (CHI3, CHBr3, CHF3), we can take a look at the stability of the halide anion that is formed (I- vs. Br- vs. F-) and the ...
18 votes
1 answer
1k views

Alkylation of conjugated nitriles - regioselectivity

Why does the enolate of the nitrile attack the alkyl chloride from the bond shown in the picture and not from the far end pi bond?
-4 votes
0 answers
28 views

Breaking of halonium ion in unsymmetrical alkanes [closed]

So what i have learnt is that breaking of halonium ring follows partial sn1 sn2 reaction. in that the carbon where partial positive charge is more stable is attacked. my doubt is for checking the ...
1 vote
1 answer
216 views

Is there a quantitative definition of inductive effect?

Usually, Inductive effects are compared using the electronegativities and distances. However, this only works in compounds with similar structures. For example, we can predict the following orders of ...
1 vote
0 answers
46 views

Why DMSO has much higher freezing point than DMF (19 °C vs -61 °C)?

Recently, while solvent optimization of a reaction, I found DMSO froze in an ice-bath but DMF didn't. From Wikipedia, I found out that DMSO (dimethyl sulfoxide) has a freezing point of 19 °C (ref. 1) ...
4 votes
1 answer
537 views

What type of interaction in a π-complex?

From Beyer-Walter Lehrbuch der Organischen Chemie, 24. Ed., P.72: We have Ethene interacting with an electrophile $\ce{X+}$ with 2 different options: The short living formation of an π-complex, ...
2 votes
1 answer
97 views

Why can't ethyne form hydrogen bonds in water?

I was recently taught about hydrogen bonding and I learnt that a hydrogen atom attached to fluorine, nitrogen, oxygen or a sp-hybridized carbon (EN = 3.25) can get into a hydrogen bond with another ...
23 votes
1 answer
2k views

What does the newest IUPAC nomenclature have against unsaturation?

IUPAC nomenclature 2013 changed a couple of rules very commonly used in naming simple acyclic compounds. As a result, depending on which nomencalture we choose, the answer to this question varies ...
1 vote
2 answers
1k views

What is the pH of acetone in water?

Reaction of Acetone with Water Acetone in water can react in three ways: The different reactions change the concentrations of $\ce{H+}$ and, consequently the pH, differently. My question is what is ...
-2 votes
1 answer
159 views

Hydration of alkenes [closed]

In the image I've provided, I offer two alkenes. The first is in conjugation while the second isn't. Additionally, both of the C=C groups are symmetrical, in the sense that they both have one hydrogen ...
3 votes
0 answers
56 views

Major product of reaction between 1,1-dibromo-2-(pent-4-en-1-yl)cyclopropane and methyllithium

What is the major product of the reaction between 1,1-dibromo-2-(pent-4-en-1-yl)cyclopropane and methyllithium in diethyl ether? I suppose the nucleophilic double bond will react with the ...
3 votes
2 answers
724 views

Reaction of 1,3-butadiene with HBr in the presence of peroxides

I have learnt that the reaction of 1,3-butadiene with HBr depends on the temperature as the temperature determines whether the reaction is under kinetic or thermodynamic control. I believe that this ...
9 votes
3 answers
547 views

Synthesis of racemic nicotine

In my advanced organic chemistry course, we were asked to fill the following scheme for the synthesis of racemic nicotine, starting with ethyl nicotinate: Exercise 6: Complete the following scheme ...
-3 votes
0 answers
27 views

Organic Rest verification in Cheminformatics

So I am using SMARTS-Pattern to find molecules that have certain functional groups / properties. As a simple example lets take an Aldehyde. Structurally is R=O - i can match this with a pattern of &...
0 votes
2 answers
141 views

Reasonable mechanism for conversion of 2-methylbut-3-en-2-ol to 1-Bromo-3-methylbut-2-ene

In the book "Designing Organic Syntheses - A programmed approach to the Synthon Approach" pg 23, the author proposes that one route to 1-bromo-3-methylbut-2-ene would be by reacting 2-...
-3 votes
0 answers
26 views

Lewis structure and its real-life application [closed]

From textbooks (Advanced ochem by Carey, Ochem by McMurry,...) it seems to me that it is a miracle that Lewis structures (together with their permitted resonances and contributions) indeed represent ...
-2 votes
0 answers
42 views

Are all helicenes optically active? Aren't they having a plane of symmetry? [closed]

Are all helicenes optically active? Aren't they having a plane of symmetry or centre of symmetry? Please give a detailed explanation
-1 votes
0 answers
23 views

Does -NO₂ group goes out of plane due to steric interactions during ortho effect?

From the two compounds (a) and (b) , (a) (b) It is already known fact that (a) is more basic than (b) , because of : -NH₂ group in (b) goes out of the plane due to steric effects of 2 ethyl group (...
3 votes
2 answers
14k views

Salicylic acid - polarity and solubility

I'm really confused about the polarity and solubility of salicylic acid. Since there is carbon and two other types of atoms, it should be polar, right? However, some people online say it is non-polar. ...
0 votes
1 answer
175 views

Why is an Octet Complete Cation more stable than a Resonance Stabilized Cation?

Our instructor taught us about different types of cations: classical, non-classical, resonance stabilized (R.S.C.) and octet complete cation (O.C.C.), and how O.C.C is more stable than a R.S.C. I did ...
2 votes
1 answer
96 views

Stability of hemiaminals

How stable are hemiaminals compounds with NH2 and OH groups attached to the same carbon atom? Does the removal of ammonia take place just like water is removed in case when 2 -OH are attached to the ...
-1 votes
0 answers
21 views

Which is more acidic between ethene and propene? [duplicate]

When we form the conjugate bases of both pairs we will see the the propene ion gets destabilized due to +I effect of methyl group so acidicity of propene will be less than that of ethene but answer ...
6 votes
2 answers
629 views

Acidic strength comparison of squaric acid and rhodizonic acid

These two are dibasic acids with the following structures (squaric acid and rhodizonic acid in order). Empirical evidence proves that squaric acid is more acidic than rhodizonic acid. It is a ...
1 vote
0 answers
27 views

How to avoid side reactions when making boronic esters (Homocoupling, Hydrogen specie)?

I have been working with suzuki couplings using substituted naphtalenes (typically 2-bromo-7-R-naphtalene) for a while now, and making the boronic specie is always a pain. I can't make the boronic ...
-1 votes
2 answers
48 views

Does ABS contain natural rubber

Does ABS otherwise known as acrylonitrile butadiene styrene contain natural rubber also known as natural latex or is it synthetic latex?
4 votes
1 answer
336 views

What are the best conditions for coupling small molecules with EDC?

I want to couple a DNA oligo containing an amino group with another small molecule possessing a carboxyl group. I found protocols for EDC (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide) coupling of ...
-1 votes
1 answer
54 views

Will methyl group donates its electron density to only carbon atoms and not to other heteroatoms ?? Why this is so?

I initially thought in every possible case methyl group always donates its electron density to the atom to which it is bonded. But today I came across a problem, in which it asks us to point out the ...
2 votes
1 answer
426 views

Elimination reactions of vicinal dibromide

When a vicinal dibromide undergoes elimination reactions in vigorous basic conditions, say in ammonia with $\ce {NaNH2}$, is the product an alkyne or is it a conjugated diene? I would think that the ...
0 votes
1 answer
35 views

How are major products defined- Thermodynamically or Kinetically?

In many organic chemistry questions, we use mechanisms that favours thermodynamically stable product (like aromatic rings), compromising the rate by some factor. For example, if there were two ...
3 votes
1 answer
179 views

Will a nitro aryl resist an halogen exchange using nBuLi?

I would like to boronate 2-bromo-6-nitro-naphtalene using nBuLi and quenching with 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. Since there is no alpha proton to the nitro, and that the nitro ...
0 votes
1 answer
168 views

Why does a hydroxyl group decrease the acidity of an Aromatic ring?

We are currently learning about resonance and induction, but I am confused why the addition of the hydroxyl group increases the pKa. As oxygen is more electronegative, should it not increase the ...

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