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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Direct addition (1,2) or conjugate addition (1,4)?

Problem: Reaction of alpha - beta unsaturated carboxylic acid derivatives with alcohol. I came to know that acid chloride gives direct addition Whereas amides,esters give conjugate addition However I ...
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Applying The Mechanism of Electrophilic Aromatic substitution for different products

I am studying Organic Chemistry especially about Aromatic compounds and their reactions. I knew and Understand Mechanism for basic things but I can't able to figure out the products for give complex ...
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Mechanism of Hofmann Elimination [closed]

what is the mechanism for hofmann elimination? is it E1CB? why hofmann product is formed as major?can you please explain it.
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Why Benzene does not react with alkaline KMnO4?

Why Benzene don't react with alkaline KMnO4 but other substituted benzene does ? (and also why when there is no Benzylic hydrogen in substituted benzene) Thanks
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what are the possible products of cannizaro reaction of phthalaldehyde?

I know the main product that is ortho-hydroxymethyl benzoate ion but I think that phthalic acid and catechol must be formed also in very small amounts but I am unable to get any confirmation from the ...
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Conversion of but-1-yne to but-2-yne with alcoholic KOH

It is a known reaction that an internal alkyne is converted into a terminal alkyne with soda amide.However, my instructor told me that(no sources) the terminal alkyne can be converted back into an ...
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41 views

Conversion of a wedge-dash model into Fischer Projection

The question I am trying to solve involves this structure. It asks to convert this model into its Fischer projection and then find the enantiomer for it. This is what I got as the Fischer projection ...
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How to chose alphabetical order in IUPAC nomenclature?

Which one is correct, 3-ethyl-5-(1-ethyl-2-methylpropyl)nonane or 5-(1-ethyl-2-methylpropyl)-3-ethylnonane?
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I can't find the two minor products

I am unsure of what the two missing minor products would look like. I believe it's an elimination reaction, but I didn't even know there could be two minor products.
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Confusion over number of chair conformations

There's obviously something simple that I'm not understanding about chair conformations that keeps popping up any time I do a related problem. For example, when I'm asked to draw trans-1,2-...
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30 views

Boiling point of meta and para dibromobenzene

The boiling point of p-Dibromobenzene is 220.4°C and the boiling point of m-dibromobenzene is 218°C.meta isomer is polar and para is not. So why the boiling point of meta isomer is lower than para ...
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HSAB theory details

I have read a bit about HSAB theory and its applications, but I couldn't find sources for details about the theory and especially the direct explanation for the reason of that phenomena.So, what books ...
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1answer
25 views

Ring expansion in cyclo compounds

In the following reaction, why does ring expansion not take place? Mechanism that was the correct one: In the second step when there is a protonated carbon the ring should expand to become 6 ...
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26 views

Primary kinetic isotope effect

Why does the transition state in both protonated and deuterated molecules have the same energy? My textbook assumes that during transitional state the isotopic bond is half-broken or on its way to ...
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34 views

Maximum distance for intramolecular proton transfer

In this reaction (formation of ester from ketone / aldehyde), intramolecular proton transfer happens, since it can stabilize the formal positive charge by resonance after that. This transfer happens ...
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“Greater the stability of free radicals , higher is it's reactivity.”? Explain the statement? [closed]

actually stability and reactivity are inversely proportional.Then how the given statement will be correct?
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1answer
49 views

Why is methyl parathion less toxic than ethyl parathion?

According to the pubchem pages on ethyl parathion and methyl parathion (pages 11 and 12 of the toxicity section, respectively), methyl parathion is significantly less toxic than ethyl parathion. The ...
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Hydrolysis of phosphoryl-oximes

When acetylcholinesterase that has been inhibited by an organophosphorus compound is reactivated by an oxime, a phosphoryl-oxime is formed, which is then somehow hydrolyzed in the blood. One study ...
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What is the order of inductive effect among amines and N-alkyl amines?

What will be the order of inductive effect among -NH2 -NR2 and -NHR? (I read somewhere that it would be -NR2> -NH2. Is this correct and if so why? Where will -NHR fit in?)
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What is the order of inductive effect among the following groups?

What will be the order of inductive effect among carboxylic acid and acid derivatives? (My guess is that it is acid anhydride> carboxylic acid> ester> acid chloride> amide based on ...
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1answer
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Can aged acetylcholinesterase be reactivated?

it is a well-known fact that certain phosphorus compounds can inhibit the enzyme acetylcholinesterase, and that the treatment of poisoning with such compounds is administration of atropine and some ...
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1answer
29 views

Difference in mechanisms between formation of acetal and enamine

When forming acetal from a C=O group with alcohol, the alcohol will act as a nucleophile and attack twice as the carbon is made very electrophilic twice. I wonder in the last intermediate before ...
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16 views

Do non-ionic surfactants have more or less cleansing (oil removal) power than amphoteric surfactants? [closed]

Regarding surfactants and their cleansing power (oil removal capabilities), are non-ionic surfactants more or less effective than amphoteric surfactants? Non-Ionic surfactants examples: Decyl ...
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23 views

Acid catalyst choice on reaction of carbonyl group and O/N nucleophiles

For oxygen nucleophiles, e.g. $\ce{ROH}$, when reacting with a carbonyl group to form acetal, the acid catalyst used is protonated alcohol. for nitrogen nucleophiles, e.g. $\ce{RNH2/RR'NH}$, when ...
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Why does C6H5OH + CH3O- —> C6H5O- + CH3OH and not C6H5OCH3 + OH-? [closed]

I got this question wrong on a test and I don’t understand why. Can someone please explain to me why me answer was wrong?
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1answer
56 views

NGP in Finkelstein reaction

The question is to find the product in the following reaction- In the answer given, they have replaced Cl with I and inverted the configuration at that carbon(Finkelstein reaction). But $\text{I}^-$ ...
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1answer
40 views

Rate of solvolysis of allyl and alkyl halides

Suppose I have 2 compounds, 3-chloropropene and 1-bromo-1-methylcyclohexane. Without knowing the values, how can we compare the rate of solvolysis? My attempt: Resonance is quite dominant character ...
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Why doesn't HIO4 cleave acetals?

Recently, I started reading about the cleavage reactions done by $\ce{HIO4}$.I came across a statement which read $\ce{HIO4}$ can't cleave acetals but it can cleave hemiacetals. But when I tried to ...
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Why paraldehyde is the major product when acetaldehyde is treated with concentrated acid? [duplicate]

I came across the following problem. The answer given is d,that is paraldehyde(note the misprint in option d, it is carbon there in place of oxygen), and I have verified that it is the correct ...
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What are the properties of esters made from aldehyde? [closed]

Any information on properties of esters formed from aldehydes would be extremely helpful.
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1answer
62 views

Why is H in OH group is more shielded than in H in CH2 group (ethanol NMR spectroscopy)?

I am confused with this $\mathrm{^1H}$-$\mathrm{NMR}$ spectroscopy result: Shouldn't $\ce{H}$ in $\ce{OH}$ group the singlet be more towards the left of the $\mathrm{NMR}$ spectrum? It is near the ...
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19 views

Was is formed when ethanol reacts with acrylic? Is it dangerous to ingest? [closed]

I was flavoring a batch of spirits, 4 gallons of 80% ethanol (vodka). This was my first experience with flavoring distilled spirits, after adding spices and sweetener I stirred the batch with an ...
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How does ammonia react with half sulfur mustard? [closed]

How does ammonia $(\ce{NH3})$ react with 2-chloroethyl ethyl sulfide $(\ce{Cl-CH2-CH2-S-CH2-CH3})?$ Is it a nucleophilic substitution, i.e. $\ce{Cl}$ replaced by $\ce{NH2}?$
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How to remove Acetic Anhydride?

I am trying to form 2,2-diacetoxy acid using acetic anhydride and glyoxylic acid monohydrate (Scheme below) I could not find a suitable synthetic protocol for this, so I just added 10 equivalents of ...
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1answer
34 views

What is the derivation of the formula for finding number of pure and hybrid orbital?

I am studying Organic Chemistry. Recently I came up with the formula for finding number of Pure and Hybrid orbital that can be present in a organic compound , That is Number of Hybrid Orbital = ...
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1answer
33 views

Reaction of cinnamic acid with Br2/Na2CO3

The first reaction produces benzaldehyde, and the next one (perkin's condensation)produces Cinnamic acid.(X) Now the treatment of X with $\ce{Br2/Na2CO3}$ is whats troubling me. $\ce{Na2CO3}$ being a ...
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27 views

“e and a” as combinations of pi bonds

I am trying to get a better intuition on solid-state physics but I am a chemist by degree. I came across this article that attempts to bridge the gap between solid-state physics and molecular ...
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51 views

Order of nucleophilicity of ammonia, hydrazine and hydroxylamine

I was reading about nucleophilicity and basic strength orders. I came across this interesting set of three compounds $\ce{NH3},$ $\ce{N2H4}$ and $\ce{NH2OH}$ where I am not able to apply the rules I ...
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1answer
67 views

Would any alkene possibly aromatize with proper conditions?

I was reading about 2 specific reactions: polymerisation of alkene and aromatization of alkane (of a sufficient size). I thought why can't, having a condition that favored both these reactions be ...
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1answer
45 views

Absolute Configuration in Stereochemistry

I got all the rules of writing RS nomenclature for Perspective formula of chirality center only problem being, I m confused that given compound can have any configuration depending on how I write the ...
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1answer
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Temperature required for E1 elimination reaction

I wanted to ask what's the temperature required for carrying out elimination reactions? Wherever I read about elimination reactions, they just mention that elimination reactions occur at high ...
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1answer
53 views

Reaction of 2,4,6-triaminobenzoic acid in a protic medium and heat

The given answer is (A). At first I thought that it was a simple decarboxylation (due to high heat). But that does not seem feasible at all as the ring has no electron withdrawing groups which ...
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1answer
46 views

how to calculate the dihedral angle [closed]

I need to calculate the dihedral angle between C20 and C19, as well as between C19-C18. Can someone help me choosing the right combination? I have used the following one: C18C19C20C23 for the first ...
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Washing a lab coat [closed]

my lab coat ended up with a load of laundry (don't ask how). I've used it for organic chem labs >2 years ago (if age of the stains matters) and it had some stains on it. Should the whole load of ...
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1answer
54 views

Phenoquinone vs benzoquinone [closed]

Are phenoquinone and benzoquinone the same thing? When I searched for the colour of benzoquinone I found that it's yellow. But when I searched oxidation of phenol in air. It states that it turns pink/...
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45 views

Nomenclature of halogenoalkanes

Why is the following compound called "1,1,1-trifluoro-2-chloro-2-bromoethane"? Why is this not called "1-bromo-1-chloro-2,2,2,trifluoroethane" alphabetically? (the name, 1,1,1-...
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2answers
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In the question given below [closed]

in the question if we go in accordance with+M effect instead of+I effect we will get the required answer but why are we going in accordance with +M effect and when do and how do we choose which ...
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100 views

Differences in Novichok agent mass spectra

As we have all heard, in 2018, a series of poisonings with a nerve agent alleged to be of the Novichok series was carried out on British soil. It is claimed that the agent used was A-234. However, a ...
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1answer
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When can you use the direct flame of a Bunsen burner, and when must you boil a beaker of water first?

I'd like to ask when you would do the following: use the direct Bunsen flame to heat a substance; place the substance in a test tube, which is placed in a beaker of water, then boil the water with the ...
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30 views

Prevention of inversion due to transannular interaction [closed]

I am reading about DABCO(1,4-Diazabicyclo[2.2.2]octane), catalyst of Baylis Hilmann reaction. In a research paper it is written that Cyclic structure of DABCO and the transannular interactions of the ...

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