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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13 views

Does an electronegative atom which carries a negative formal charge withdraw electrons by induction?

Electronegative atoms withdraw electrons by their inductuve effect. Does this fact remain true even when they are heavily loaded with electrons through negative formal charge? Are these two ideas ...
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2answers
89 views

Number of sterioisomers of 2,3,5,6-tetrachloroheptane [closed]

The answer given by Himanshu Pandey in the book Advanced Problems in Organic Chemistry, Chapter Isomerism, Page 76 is 10. But by calculating using the fundamental principle of counting and by viewing ...
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2answers
53 views

Resonance and mesomeric effect [closed]

Can you please explain to me why are A and E not relevant resonance structures of the molecule F? And is B aromatic?
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23 views

Inductive effect on benzene ring [closed]

I have read that : "Any charge on benzene ring gets stabilized or destabilized by Inductive effect only " If it is true then what is the reason behind this? Why don't we use Mesmeric and other ...
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1answer
31 views

Negative hyperconjugation

Compare the acidity of the following compounds: $\ce{CF3OH}$ and $\ce{CCl3OH}$. My attempt: according to me $\ce{CCl3}$ group will show a stronger Negative hyperconjugation effect than $\ce{CF3}$, ...
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2answers
54 views

does table salt dissolve in glycerin [closed]

Tell me, does table salt dissolve in glycerin? And is it possible to increase its solubility? I have vegetable glycerin with nicotine that I use for vape. So that nicotine would not be bitter, on ...
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1answer
54 views

How to convert 1,4 pentadiene to 1,3 pentadiene? [closed]

Are there any 'conjugating agents' to accomplish the above transformation? If not, then how to proceed?
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1answer
36 views

Comparison of stability of aromatic compounds [closed]

What is the basis of comparison between two aromatic compounds having different ring structures Like in propyl and heptyl rings
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1answer
61 views

Lactone acylation

Can anyone propose/draw a mechanism for Method A, below, from this paper? Almost all other literature use method B and reagents such as SOCl2.
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1answer
40 views

Does 1,3-butadiene in bromine/water do addition twice?

Considering 1,3-butadiene (below) added to bromine water (considering it as $\ce{Br2(aq)}$): I've seen online that the products are 1,2-dibromobutene and 1,4 but what I don't understand is why ...
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1answer
42 views

Finding structural isomers of an alkene

I am doing problems on finding structural isomers. I am asked to find the structural isomers of $\ce{C5H10}$. The answer to problem states there are 10 structural isomers possible. I was able to find ...
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2answers
49 views

Energetic stability in relation to α-hydrogens

I am new to organic chemistry and was asked to rank the following materials according to energetic stability. I think I have understood that the way to do this is to count the amount of α-hydrogens: ...
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0answers
40 views

What does a simple or a complex substituent mean? [duplicate]

I am reading rules for IUPAC Nomenclature. The following statement is from my book. Prefixes di, tri, tetra, etc., are not considered in deciding alphabetical order for simple substituents but ...
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46 views

Parameters by which to distinguish SN1 from E1

I am new to organic chemistry and am struggling with the following very basic question: Given is the following reaction: $$\ce{(CH3)3CCl + NH3(aq) →}$$ I am supposed to analyse the end-product (the ...
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1answer
33 views

will charcoal briquettes (not activated) absorb water out of the air in the house in a sub tropical climat?

I live in Florida--incredibly wet environment-very difficult to get moisture out of house w/o using de-humidifier 24/7--which is too expensive. Would charcoal briquettes be of any use?
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1answer
68 views

Why methoxy group acts similar to trifluoromethyl in nucleophilic aromatic substitution

In an online test, the following question was asked: The answer to this question was: I totally agree with the answer, as $\ce{OCH_3}$ is an EDG, hence it will tend to form meta product in this ...
2
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1answer
59 views

Mechanism for Synthesis of Tetranitromethane from Acetic Anhydride and Fuming Nitric Acid

In my undergraduate Mechanisms-class the formation of tetranitromethane from acetic Anhydride with fuming $\ce{HNO3}$ was listed as optional knowledge in a chapter about the reactions of enols, ...
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0answers
57 views

Mechanism of decarboxylation of cyclohexane-1,2-dicarboxylic acid

According to AIITS exam answer key, it was given that the following compound decarboxylates on heating: Then, I read Why are beta-ketoacids better at decarboxylation than gamma or delta? which is ...
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32 views

Why can't carboxylic acid + NaH + tert-butyl bromide react to create an ester?

So, the picture I showed above asks for which reagents can form the ester product. I was wondering why D can't form it? I was thinking that first, the $\ce{NaH}$ would react with the carboxylic acid ...
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0answers
10 views

Why 2-hydroxytetrahydrofuran passes Tollen's test?

In FIITJEE's AIITS (an internal test series), I was asked to select the compound(s) which gives positive Tollen's test. And, 2-hydroxytetrahydofuran was an answer. So far, I know that Tollen's test ...
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1answer
57 views

Question on ring expansion

In the orange box, I think that the blue-carbon should be a carbocation instead. So, option A should be correct. But, the answer is B. Why is it so?
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1answer
85 views

Preparation of Effexor

I take venlafaxine (Effexor) as medication, and having wrapped up 2 semesters of Organic Chemistry I thought it might be fun to design a synthesis for it. A picture of venlafaxine: I came up with the ...
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0answers
98 views

Will N,N‐diethylbenzamide show geometrical isomerism?

I know for a compound to show geometrical isomerism it should have site of restricted rotation; be connected to two different groups on either side of site of restricted rotation; the distance ...
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1answer
35 views

Why is p-methoxyphenol less acidic than phenol?

They have slightly different $\mathrm{p}K_\mathrm{a}$ values of 9.9 (phenol) vs 10.2 (p-methoxyphenol). They both have the same number of resonance structures too. My guess is that the resonance ...
5
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1answer
55 views

Why does the tautomerism of purine favor 9H-purine? [duplicate]

I tried to explain the equilibrium by comparing the basicity of different nitrogen atoms in a purine anion, but I can’t see any obvious difference. Seems like that the 9-N will be the most basic ...
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0answers
20 views

Will a Lewis acid catalyze the reaction of HBr with primary alcohols?

It is well-established that a Lewis acid catalyst (popularly $\ce{ZnCl2})$ is necessary to form an alkyl chloride when reacting $\ce{HCl}$ with a primary alcohol. This actually changes the mechanism: ...
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28 views

Formylation of an Indole [closed]

What methods are available for the C-3 formylation of 2-phenylindole?
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35 views

What is Liebermann nitroso test?

From the articles in the internet , I found that there are two reactions which are being called Lieberman nitroso test . One is the test of 2 degree amine in which a 2 degree amine is converted to N -...
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1answer
59 views

Steric Inhibition of Resonance in ortho-substituted Benzoic Acids

It has been given that due to Steric Inhibition of Resonance (SIR), the acidity of ortho-substituted benzoic acid increases with respect to benzoic acid. If this is the case then the conjugate base of ...
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0answers
35 views

Number of aromatic rings in triphenylene

My question is how to find the number of aromatic rings in triphenylene: My professor said that there are 3 aromatic rings, after which he added that the carbons of the middle rings are only ...
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1answer
302 views

Which is more basic: 1,2‐dihydropyridine or 1,4‐dihydropyridine?

Which compound is more basic of the two? My thinking: In compound A, the lone pair of nitrogen are in resonance with two other double bonds. The resonance chain here seems to be longer as ...
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1answer
43 views

What is the maximum amount of medicine that could accumulate in the body if the compound has a half-life of 24 hours? [closed]

If a patient is prescribed 25mg per day of a compound that has a half-life of roughly 24 hours, what is the maximum accumulated amount of the medicine that would build in the patients body?
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1answer
41 views

Which of the Following is Optically Active?

Which of the Following is Optically Active? I understand that for a compound to be optically active, it needs to be chiral and not have any planes of symmetry. I know 1 is symmetric, but I am ...
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0answers
24 views

Why do carbonyl groups lower antibonding orbital energies of conjugated systems?

In the chapter on conjugation in Organic Chemistry by Clayden, Greeves, Warren and Wothers, there's a brief discussion of pigments with conjugated systems that includes the following paragraph (first ...
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0answers
50 views

Acidity of α-hydrogens in ketones

The compound having the most acidic hydrogen is A) hexan-3-one B) hexane-2,4-dione C) hexane-2,5-dione D) hexane-2,3-dione The book in which this question is listed has the solution as ...
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1answer
42 views

The synthesis of 1-phenylprop-1-ene from propiophenone [closed]

I would like to know how to make 1-phenylprop-1-ene ($\ce{C6H5-CH=CH-CH3}$) from propiophenone ($\ce{C6H5-CO-CH2-CH3}$)? I think carbonyl group ($\ce{C=O}$) of propiophenone is electron-withdrawing ...
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0answers
18 views

Oxime to amine mechanism [duplicate]

I'm basically searching a mechanism for turning oxime to amine.My book gives me the reagent, LiAlH4 , but no mechanism, I suppose the first attack will be on the oxime carbon, I don't know what to do ...
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0answers
46 views

Acidic character of hydroxy benzoic acid

Which is more acidic between salicylic acid and 2,6-dihydroxybenzoic acid? Please also explain the reason behind the same. According to me, salicylic acid should be more acidic. Reason for that is ...
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1answer
52 views

Why is Oxygen compulsory for free radical reactions? [closed]

Why is presence of oxygen compulsory for free radical mechanism? Can it take place in presence of any other element?
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1answer
39 views

Mono chloro substituted products of naphthalene

My chemistry teacher today told that only two mono chloro substituted products are possible for naphthalene. He explained this by saying since the naphthalene molecule is symmetrical about the axis ...
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1answer
44 views

Can anyone please help me how do you determine kinetically the fastest product of sulphonation of $\beta$ napthol?

I was asked a question in a paper where I was asked to identify the kinetically fastest product of sulphonation of $\beta$ naphthol. Can anyone please help me how do you determine kinetically the ...
7
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1answer
184 views

Is it possible to build or embed the SMILES representation of compounds in 3D?

I would like to know if there is a proper way to get the 3D information from a SMILES string. Is there a standard way to embed a SMILES string in 3D space? Are there other representations of ...
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3answers
83 views

Nucleophilicity in polar aprotic solvent (DMSO)

The strength of a nucleophile in polar aprotic solvent is proportional to its basicity. Lone pair on O- in the molecules will donate an e- pair to an atom. I'm not sure why the alkene ring in 2 makes ...
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0answers
21 views

Catenation of Carbon [duplicate]

I know that Carbon can form long chains of it's own because of its tetravalency and catenation property. But why is the catenation property of Silicon (which is also tetravalent) and other elements ...
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1answer
27 views

Does aminosugars give positive response in alkaloid tests?

Does aminosugars give positive response to test for alkaloids such as tests with Dragendorff's reagent, mayer's reagent, Hager's reagent, Wagner's reagent etc?
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0answers
18 views

Acidity of ethanal vs propyne

I want to compare the acidities of 1)terminal hydrogen of propyne 2)hydrogen bonded to the sp3 carbon in propyne 3)alpha hydrogen of ethanal. My idea is that the terminal hydrogen of propyne is ...
2
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1answer
40 views

Why is detergent better at cleaning than soap?

Soaps and detergent are both molecules that have a polar head and a long organic tail. In Soaps, the head is often a carboxylate ion $\ce{COO-}$ where as a detergent has a benzosulphonate $\ce{...
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1answer
77 views

Use IUPAC system to name the structural diagram below

Can someone break down the steps for naming $\ce{CH3-C(Cl)=C(Cl)-CH2-CH3}$?
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22 views

White Spot Turning Red on Egg when Wet

NOTE: Not sure this is the right forum, but hope it is. I have a chicken egg with some white spots. See below and the white spot at the top. When making this egg wet with normal tap water, this spot ...
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0answers
11 views

In which order should you prepare a microemulsion?

So I have isoooctane (oil phase) ,CTAB (surfactant) ,1-butanol (cosurfactant) , and an aqueous solution of metal nitrates as the water phase. In which order should i add these components? Or any ...