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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Is nitrogen with 3 different substituents and lone pair a chiral center? Does it make the whole compound chiral too? [duplicate]

Is nitrogen considered a chiral centre or stereocenter when it has three different substituents attached to it along with a lone pair. By definition LG Wade says An asymmetric carbon atom is the ...
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Definition of throughput

I wonder what's the exact meaning of throughput in chemistry synthesis, eg. in organic synthesis or production of pharmaceutical products. For instance, what are their units? How are they measured? I'...
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What specific toxins are formed during deep frying? And how (chemically) do they attack the body cells? [closed]

From what I understand, deep frying causes the oxidation of lipids into advanced lipid oxidation products. When these are consumed and metabolized by the body, they release ROS or free radicals which ...
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Gas chemistry preasure [closed]

5.00 g of CO2 gas occupy a volume of 5.4 L at a pressure of 350 mm Hg. What will the volume of the gas sample be if the pressure is changed to 70.0 kPa?
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Reason for inability of hexoses to form seven membered rings [closed]

I know that hexoses can form pyranoses and furanoses but they always have a side-chain with a $\ce{-CH2-OH}$ bond. Why doesn't this $\ce{-OH}$ group form a seven membered ring with the aldehyde?
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Reaction of 2,3-dichlorobutanoate with a decarboxylating agent followed by hydrochloric acid and then aq. potassium hydroxide

Question $$\ce{CH3-CH(Cl)-CH(Cl)-COO- ->[-CO2]A->[HCl]B->[aq KOH]C}$$ Product C is: a) $\ce{CH3-CH2-CHO}$ b) $\ce{CH3-CH(OH)-CH2-CH2-OH}$ c) $\ce{CH3-CHO}$ d)$\ce{CH3-C(=O)-CH3}$ Answer My ...
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Consequences of String Theory on Chemistry [closed]

I've read about String Theory and how many people are sceptical of it due to lack of evidence even after many decades of extragavant claims. Still if String Theory is proven it would be the greatest ...
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reactions for alcohols into alkyl halides with 100% retention

I learnt that alcohols can be converted into alkyl halides in the following ways with 1/2 steps: adding H-X (X=Cl/Br/I): primary alcohol: inversion (SN2), secondary / tertiary alcohol: racemization (...
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Why is the reaction of 2-Bromo-5-methylhex-3-ene + KOH --> 5-Methylhex-1,3-diene and not 5-Methylhex-2,3-diene? [closed]

I got this question wrong on a test and I don't understand why. On option B, the double bond that forms is disubstituted. On option D, the double bond that forms is monosubstituted. When the product ...
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167 views

Mechansim of reaction between 1‐bromo‐2‐fluorobenzene and furan in the presence of Li/Hg

Problem From FITJEE AITS test series: What is the mechanism of the following reaction? Solution My approach It looks like Birch reduction with $\ce{Li}$ converting to $\ce{Li+}.$ But I can't make ...
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Most favorable position of attack of an electrophile on 4-trifluoromethyl-1,2-diphenylbenzene

Problem This problem is from a FIITJEE AITS paper Which position is most favorable for the attack of an electrophile? Answer My attempt The more favorable position for attack should be the on the ...
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Do alkanes have a functional group carbon carbon or carbon hydrogen single bond? [closed]

I was studing about classes of organic compounds . We know that in organic chemistry classes of organic compounds are formed on the basis of functional groups like alkane,alkene,alkyne,alcohols and so ...
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Factors affecting rate of β-elimination reaction with alcoholic KOH

The question asks for the rate of reaction in $\beta$-elimination using alcoholic $\ce{KOH}$. Arrange the following alkyl halides in decreasing order of rate of $\beta$-elimination reaction with ...
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Reagent to reduce aliphatic aldehyde to alcohol while protecting double bond

I have a straight chain, aliphatic aldehyde (liquid) with a double bond in it. I want to reduce the terminal carbonyl group to an alcohol but without touching the C=C double bond. The double bond is ...
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27 views

Behavior of xylitol in water [closed]

I know xylitol in water is an endothermic reaction. The temperature of water drops when xylitol is added. When xylitol is added in high concentration, the temperature of the water drops fast (for ...
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Product of the reaction of ethyl acetoacetate with alkaline benzoyl chloride followed by addition of ammonium chloride

What does this β-keto ester give when reacted with $\ce{PhCOCl/NaOH}$ followed by $\ce{NH4Cl(aq)}?$ According to me, the $\ce{PhCOCl}$ should react with $\ce{NaOH}$ forming benzoic acid which should ...
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Out of pyrrole and pyrrolidine,which is more soluble in benzene [closed]

Question:- Out of pyrrole and pyrrolidine,which is more soluble in benzene. Dipole moment values suggests that pyrrole has more polarity than pyrrolidine.So pyrrolidine should be more soluble in ...
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1answer
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Reaction of acyl chlorides with diazomethane and silver(I) oxide

$$\ce{R-COOH ->[SOCl2,CH2N2][Ag2O/CH3OH] X}$$ While solving Carboxylic derivatives recently, I came across this. so following the reagents one by one- $\ce{SOCl2}$ will form acid chloride. $\ce{...
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In IUPAC naming, is the name of the compound “(4S)-pentane-1,1,4-triol” or just “pentane-1,1,4-triol”? [closed]

I was trying to name $\ce{CH(OH)2-CH2-CH2-CH(OH)-CH3}$ according to IUPAC rules. However, when I search it up online, PubChem says there should be $(4S)$. Is that supposed to be there, and what does ...
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1answer
96 views

Why do Grignard reagents act as sources of nucleophilic R− and not Br−?

In reactions with Grignard reagents, I've always seen the alkyl group being the nucleophilic component, with the R–MgBr bond being broken. This is always rationalised by the fact that the alkyl carbon ...
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X - membered rings in formation of epoxide

https://youtu.be/d4RczD122QI?t=2025 In this lecture, I am learning to form epoxides from the intramolecular version of Williamson Ether synthesis. During that, the professor says the ring formation is ...
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42 views

Diazotisation of 2-aminophenol-N-methyl-4-sulphonamide with 1-acetylamino-7-naphthol

I have been trying to make diazonium salt of 2-aminophenol-N-methyl-4-sulphonamide (Compound 1) in $\ce{HCl}$ with $\ce{NaNO2}$ solution. Then I want to make coupling with 1-acetylamino-7-naphthol. ...
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2answers
185 views

Recognising a rate-determining step in E1

If there is a hydride/methyl shift possible in E1, then is the carbocation formation the rate-determining step (RDS), or the shift, or is it considered a cumulative step and happens all at once?
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181 views

Comparing equilibrium constants between acetone and benzaldehyde in nucleophilic addition reaction

My teacher told me that the $K_\mathrm{eq}$ of acetone is greater than that of benzaldehyde in nucleophilic addition reaction. But I am not able to understand how is this possible. Acetone has a +I ...
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1answer
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How can I synthesize phenylpiracetam from styrene or benzaldehyde?

I am trying to design a proper synthesis route for phenylpiracetam. I am thinking a good starting material would be styrene or benzaldehyde. Here is my proposed route. Is there a better method? ...
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How much copper is necessary to sanitize water [closed]

I apologize if this is wrong board but will copper piping left inside an outdoor summertime cold water hot tub be enough to prevent algae formation and other microbe formation? I have such a tub that ...
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1answer
92 views

Mechanism of three-membered lactone hydrolysis in base

I was reading up on the participation of neighboring functional groups and in the reaction below, I was wondering why hydroxide attacks the C–O bond instead of the carbonyl group of the lactone. ...
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Stability of free radicals [closed]

If given a question to compare stability of free radicals, can we always check it by same parameters that we use for stability of cations (since both are electron deficient) or is there any exception ...
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Equilibrium between hydroxides and ketones/aldehydes

In the reaction between hydroxides and ketones/aldehydes, an equilibrium will be established between the tetrahedral intermediate and the reactants. For aldehydes, significant amounts of the ...
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2answers
107 views

Rate of dehydration of alcohols having keto group

The following question was asked in IITJEE 2000, Which of the following will be most readily dehydrated in acidic conditions? I thought that the answer would simply be (c), as its intermediate would ...
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Any open-source to animate 2D materials in 3D. (e.g. van der Waals heterostructures, 2D crystal layers etc.)

I want to model different 2D nano-structures, layered materials in 3D (animated version). Is there any open source where I can build these structures. Like this:
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Stability of carbocations with -M groups in beta position

First part The original question was to arrange the following compounds in the order of their rate of dehydration with conc. $\ce{H2SO4}$:- (A) $\ce{CH3-CH(OH)-CH2-CH=O}$ (B) $\ce{CH3-CH(OH)-CH2-C(=O)...
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Choosing polar aprotic solvents for substitution reaction

It is known that common polar aprotic solvents include acetone and DMSO. Since they do not have hydrogen bonded to highly electronegative atom, they cannot only form dipole-dipole interaction with ...
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303 views

Solubility of ortho- and para-nitrophenol in benzene

Which one between o-nitrophenol and p-nitrophenol is more soluble in benzene? And what is the reason? If the solvent had been polar, hydrogen bonding would have provided a lot of explanation, but what ...
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Grignard with nitrile: why is the imine protonated twice?

Steps 2 and 3 in the picture show the imine being protonated twice to form the iminium ion in step 4. I'm a little confused as to why the second protonation occurs; does the imine after step 2 still ...
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How to choose between an SN1 and SN2 reaction?

If a compound and a solvent is given, how do we decide whether the reaction proceeds via SN1 or SN2? I am asking this question specifically for a case where the substrate has the leaving group ...
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How are solutions prepared from hydrated compounds? [duplicate]

Preparation of solutions from hydrated compounds
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Stubborn CuAAC reaction as derivatization for ESI-MS

Problem description I have a substance that is extremely non-polar and therefore does not ionize in the ESI source, which makes it impossible to quantify small amounts. The substance contains only two ...
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1answer
332 views

Is benzocyclobutadiene aromatic or anti-aromatic?

My teacher told that benzocyclobutadiene is both aromatic and anti-aromatic. I do not understand why. Can anyone explain?
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1answer
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Plasticisers and other impurities from polyethylene laboratory bottles?

Does polyethylene (PE), widely used for wash/squirt bottles in labs, contain soluble compounds such as plasticizers that can accumulate in organic solvents (e.g. alcohols, acetone) after prolonged ...
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Is methylchloride reaction with water SN1 or SN2

I wanted to know if methylchloride reacting with $\ce{H2O}$ would be SN1 or SN2. Methyl halide would not react using SN1 because methyl carbocation is very unstable but it would also not react using ...
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1answer
107 views

Acidity of phenol and carboxylic acid [duplicate]

Carboxylic acid is much more acidic than phenol ($\mathrm{pK}_\mathrm{a}$ difference of ~6). I wonder why? In terms of resonance, there are 5 resonance structures for phenol, and only 2 in carboxyl ...
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478 views

Why is 4-hydroxypyridine more acidic than benzoic acid?

4-hydroxypyridine (or 4-pyridone) has a $\mathrm{p}K_\mathrm{a}$ in the ballpark of $3$ to $3.33\:^1$ (in the pdf linked below, the $\mathrm{p}K_\mathrm{a}$ of 1-methyl-4-pyridone has been given to be ...
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1answer
125 views

Biodegrability of straight chain and branched chain detergents

From NCERT Chemistry: Textbook for class XII, Part II [1, p. 461]: Main problem that appears in the use of detergents is that if their hydrocarbon chain is highly branched, then bacteria cannot ...
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1answer
110 views

Role of alcoholic potassium hydroxide in an E2 reaction

Which of the following compound will give least substituted alkene as major product with alcoholic $\ce{KOH}$. The options are: 1. 2. 3. 4. I am confused between options 1 and 3. Both seem to give ...
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1answer
109 views

Rate of dehydration for butan-2-ol and butane-2,3-diol

A question taken from a test series (Vibrant, India): Amongst butan-2-ol and butane-2,3-diol, which has higher rate of dehydration? The carbocation formed in butane-2,3-diol is more stable as it ...
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33 views

Solvent shell collapse

In "advanced organic chemistry part A" book page:306&307 , the author uses the term 'solvent shell collapse' when talking about the reason for retention of conformation in tertiary ...
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1answer
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What is the mechanism of AChE inhibition by Onchidal?

A naturally-occuring neurotoxin, called Onchidal, produced by a species of sea slug acts as an irreversible inhibitor of acetylcholinesterase. The structure of Onchidal is presented below: How and ...
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Role of intermediate in determining the exothermic or endothermic nature of reaction

I was given a question to answer: Which of the following reactions is “not” exothermic? $\ce{CH3-Cl + CH3-CH3 -> CH4 + CH3-CH2-Cl}$ $\ce{CH3-Cl + (CH3)3-CH -> CH4 + (CH3)3C-Cl}$ $\ce{CH3-Cl + ...
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1answer
90 views

Steric effect of t-butyl group on SN1 on a cyclohexane ring [closed]

This is a question from GRB Kota Question Bank Organic Chemistry , Chapter 3, Reasoning type, Q. 4 Assertion: trans-1-t-butyl-4-chlorocyclohexane is less reactive than cis-1-t-butyl-4-...