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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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H-NMR: Why are coupling and integration values not matching?

I am trying to synthesize Ethyl 2-(triphenylphosphoranylidene)propionate. I recently ran an NMR which is attached below. I am ignoring impurities for now. Considering the ethyl group, the number of ...
jona173's user avatar
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1 answer
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Why is chlorine atom in chlorobenzene deactivating the benzene ring when it has M+ effect, which is stronger than I- in other cases?

McMurry says that halogens are deactivating the benzene aromatic ring, but in contrast, -OH group in phenol is (strongly) activating the ring. So I- in halogens is much stronger than I- in -OH group? ...
AcetoneSniffer's user avatar
0 votes
0 answers
35 views

Naming alkanes with two branches in symmetrical positions [duplicate]

When naming an alkane with two substituents (e.g. methyl and ethyl branches), the carbon atoms in the main chain need to be assigned to lowest numbers possible. In the example in this link, why is the ...
1123581321's user avatar
2 votes
0 answers
30 views

Relation between formation of carbocation and availability of nucleophile

Many sources suggest that in SN1 reactions the leaving group first exits the molecule, and the resulting carbocation is subsequently attacked by the nucleophile, suggesting that there is no relation ...
Eisenstein's user avatar
0 votes
0 answers
42 views

Dehalogenation of geminal dihalide

I found a reaction of a geminal dihalide with zinc in the book Organic chemistry by Clayden. The reaction in question is : I cannot find any reference online to the second reaction of Zn which seems ...
Priyesha Jha's user avatar
4 votes
0 answers
64 views

Does catechol give Tollens’ test?

Do hydroquinones like catechol or p-hydroxyphenol give Tollens’ test? I know that β-diketones can reduce Tollens’ reagent to give a “silver mirror”, so I would guess that due to tautomerization ...
KMT's user avatar
  • 49
3 votes
0 answers
42 views

TsOH and 5% NaHCO3 Interaction: Unexpected Dark Green Color

Here's the brief: I synthesized alkyl gallates (ethyl gallate, butyl gallate, and amyl gallate) using Fischer esterification. I used TsOH instead of concentrated H2SO4 as the catalyst. After ...
Jonathan's user avatar
  • 155
2 votes
1 answer
77 views

3,3'-methylimino-di-propionic acid diethyl ester, to 1-Methyl-4-piperidone, via an Intermediate

They ask us to give the structure of the intermediate "A" and the mechanisms of both steps My attempt: I found the name of the started and end molecules on reaxys.com NaOEt could ...
wengen's user avatar
  • 423
3 votes
2 answers
76 views

Why is this amine called this way?

I used a molecule drawing app to name the compound in the image, an amine. The name of the compound is 3-(aminomethyl)hexane according to the app. Shouldn't the name be 2-ethylpentan-1-amine? The ...
URIZEN's user avatar
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-1 votes
1 answer
49 views

Salt & hand sanitizer

When you mix salt and hand-sanitizer; the hand-sanitizer becomes more of a liquid. Can you explain chemically why? Thoughts: I’m assuming some reaction between the salt and in the hand sanitizer. I ...
Mac's user avatar
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1 vote
1 answer
33 views

Mesomeric effect comparison

How do I compare the -M effect due aldehyde and a carboxylic acid? Which will have stronger mesomeric effect?
Aarush Saharan's user avatar
-1 votes
0 answers
42 views

Confused with CIP Rules

I really tried very hard to understand what the highlighted text means, but I didn't find anything. I also tried very hard myself, but I cannot understand what the author is trying to say. And one ...
Peter swift's user avatar
0 votes
2 answers
82 views

What exactly does 'isomerism' mean?

Today, I was confronted with this question - Is 2-methylpenten-3-one an isomer of 5-hexen-1-ol? Some people say yes; while some say otherwise. I'll put forward the logic on both sides. The side of ...
ChemGeek007's user avatar
5 votes
3 answers
190 views

How is it known that proteins are polymers of amino acids?

I read the following here. In 1902, Emil Fischer and Frank Hofmeister independently proposed that proteins are formed from many amino acids, whereby bonds are formed between the amino group of one ...
powerful_bob's user avatar
-1 votes
0 answers
56 views

Why doesn't alcoholic silver(I) nitrite undergo elimination reaction?

When bromoethane reacts with aqueous $\ce{KOH}$, ethanol forms through an SN2 mechanism. However, in the presence of $\ce{EtOH}$, $\ce{KOH}$ reacts to form $\ce{EtOK}$, a stronger base than $\ce{KOH}$,...
RandomGuy's user avatar
0 votes
0 answers
25 views

Most acidic hydrogen atom in an alphahydroxy ketone

My question is Which Hydrogen atom is the most acidic in an alphahydroxy ketone? I have learnt that acidic character arises from the formation of a stable conjugate base after deprotonation. A ...
Suhail Sahib's user avatar
-2 votes
0 answers
18 views

Which substituted alkene reacts faster with HCl? 1- methylcyclopropene or 2-methylpropene?

1-methylcyclopropene is a more substituted alkene and so it is supposed to react faster. But also, it has angle strain. So, I guess 2-methylpropene reacts faster then. Does hydride or methyl shift, or ...
Jebrjrkco's user avatar
5 votes
1 answer
255 views

Identify the more acidic hydrogen in 1-(methylsulfanyl)propane-2-thione

This was a question that was asked in one of my exams, in which we had to confirm if the given order was correct or incorrect. The key says the given order is correct and the professor at my high ...
Meme's user avatar
  • 61
0 votes
0 answers
34 views

Explaination of order of leaving groups

In Solomons' Organic Chemistry, in a section discussing leaving groups, it is stated that$-$ Among the halogens, an iodide ion is the best leaving group and a fluoride ion is the poorest: $$I− > ...
Eisenstein's user avatar
0 votes
0 answers
18 views

I generate a waste machine coolant that contains a chelated Cd after use. Is there anything I can add to the coolant to prevent chelation of the Cd?

I have a machining process that uses a coolant. The coolant, which contains 8-12% triethanolamine, comes in contact with a low melting point alloy during use that contains Cd and Pb. When the coolant ...
James Williamson's user avatar
0 votes
0 answers
21 views

How to extract Copper from softgel?

I have an assignment. I need to determine the concentration of copper in a pharmaceutical product using UV-Vis spectroscopy. The product is Chophyll of Healthy America, a softgel that contains: copper ...
Juan Cobos's user avatar
1 vote
0 answers
49 views

Nucleophilicity order in polar protic solvent

The relative nucleophilicity in polar protic solvents of the following is $\pu{1)}$ $\ce{CH3CH2S-}$ $\pu{2)}$ $\ce{CH3CH2O-}$ $\pu{3)}$ $\ce{CH3COO-}$ This is a question from my problem book. As per ...
Punisher's user avatar
-1 votes
0 answers
26 views

Is 5-ethyl-3,3-dimethylheptane or 3-ethyl-5,5-dimethylheptane correct? [duplicate]

Is 5-ethyl-3,3-dimethylheptane or 3-ethyl-5,5-dimethylheptane correct? They are supposed to be in ascending order but 5, 3, 3 is lower than 3, 5, 5...
photon's user avatar
  • 57
0 votes
0 answers
53 views

what role does mesomeric effect and inductive effect play in stability of carbocations in presence of halogens

what should be the ideal explanation behind the order of stability of these three compounds? Case-1 In these three examples the first two structures have a positive mesomeric effect and it is greater ...
Lakshya Dubey's user avatar
-3 votes
0 answers
15 views

Which are the reactions of diphenyl ether and p-phenylphenol as byproducts from phenol manufacture dow's process? [duplicate]

How are these compounds side produced?
Luis Alberto Lozada's user avatar
2 votes
0 answers
48 views

Why aren't aldehydes more acidic than saturated alcohols?

Aldehydes (pKa ~17-20) and ketones (pKa >20) are worse acids than alcohols (pKa ~15-16). I have seen that the equilibrium of aldehydes (and ketones) with their hydrates greatly decreases pKa values ...
mechanist's user avatar
  • 107
3 votes
0 answers
27 views

What is the purpose of chloromercuration of HgOAc group?

In some reactions using $\ce{Hg(OAc)_2}$, I saw some cases that convert $\ce{-HgOAc}$ group into $\ce{-HgCl}$ group by adding $\ce{NaCl}$. Below is one example, the synthesis of (+)-preussin. Mercury(...
Krang Lee's user avatar
  • 1,111
3 votes
1 answer
43 views

Iminium formation rate between formaldehyde and secondary amine

Given the significantly more favored hydrate of formaldehyde in the presence of water under neutral conditions, can we say that this is the slow step in iminium formation? Would removing water/working ...
moreQthanA's user avatar
0 votes
0 answers
29 views

Why do carbenes react differently with different alkenes in Reimer-Tiemann reaction?

Carbenes in the usual form of reimer-tiemann reaction react by forming one bond and getting negatively charged like this but in abnormal reactions of cyclopentadiene(and I suspect all 5 member rings) ...
mechanist's user avatar
  • 107
0 votes
0 answers
21 views

Is sequential diazotization of benzene possible?

I am trying to diazotize one of the nitro groups in 1,3-dinitro-5-bromobenzene while leaving the other as NO2. I'm trying to sequentially diazotize them and perform a Sandmeyer to add two different ...
Stanley's user avatar
  • 11
1 vote
0 answers
52 views

Aldol reaction with KOH and methanol doesn't work as intended, rather works with NaOH and ethanol

I was carrying out an aldol reaction of 2'-hydroxyacetophenone and 4-methylthiobenzaldehyde with KOH and methanol; however, there was no reaction after being left overnight. I repeated the process ...
garjj's user avatar
  • 19
0 votes
0 answers
34 views

An investigation on the rate of degradation (in %) of Chrysoidine-Y dye, as measured by UV-Vis spectrophotometry

Planning to do an investigation on the rate of degradation (in %) of Chrysoidine-Y dye, using UV-Vis spectrophotometry. I am planning to take an approach of increasing the concentration of Hydrogen ...
Ronith's user avatar
  • 1,339
0 votes
0 answers
34 views

Why nitration of aniline carried out after acetylation give ortho and para major products?

I was reading about the meta directing nature of anilinium cations and the answer mentioned that these reactions are usually carried out with 90-98% sulphuric acid. At these concentrations I would ...
mechanist's user avatar
  • 107
0 votes
0 answers
18 views

Reconciling bonding and antibonding MOs with how reactions proceed

Take the reaction between MeI and some nucleophile (Nu:) to give Me-Nu. Does the approach of the Nu, provide the energy input necessary to promote the Me-I electrons to the antibonding MO? Do the Me-I ...
moreQthanA's user avatar
6 votes
1 answer
349 views

What is the difference between 2,6-di-tert-butyl-4-methylphenol and 3,5-di-tert-butyl-4-methylphenol 1H NMR spectra?

So there was this exercise in my book (picture below) a compound I got to the conclusion that the compound might be either 2,6-di-tert-butyl-4-methylphenol or 3,5-di-tert-butyl-4-methylphenol. I was ...
Roxtron's user avatar
  • 105
-4 votes
1 answer
41 views

Why do the reactions of organic matter tend to be endothermic?

I am studying a level chemistry. I have come across this fact that organic matter generally undergo endothermic reactions. I can't find an explanation for this anywhere online.
user57928's user avatar
5 votes
3 answers
212 views

Why is the Markovnikov product favoured in electrophilic addition of alkenes in non-polar solvents?

I understand the reason for why Markovnikov product is favoured in the addition of acidic reagents (HX) where the electrophilic addition reaction is brought out by the attack of a proton on the double ...
Nothing's user avatar
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1 vote
0 answers
33 views

What do the pi antibonding orbitals of 1,5-hexadiene look like?

Hi so right now I'm learning about the Cope and Claisen rearrangements, and often something is shown where the antibonding pi orbitals of the two alkenes have to overlap in a certain way, like in the ...
Bozo San's user avatar
-2 votes
1 answer
48 views

Organic compound nomenclature

As I learn nomenclature, I was told that -OH has higher priority than alkene. However, the last compound says otherwise. What is the key here?
Shira's user avatar
  • 568
11 votes
1 answer
261 views

How to apply the Cahn–Ingold–Prelog priority rules to an isotopically-labeled molecule?

Is the following the correct designation (S) for the chiral carbon in a skeletal representation of 1-chloro(3-13C)butan-2-amine? The CIP rules say to go one at a time by each rule until you find an ...
Parker Willett's user avatar
1 vote
1 answer
62 views

How does potassium hydroxide break down organic peroxides?

It is always recommended to store diethyl ether over potassium hydroxide. However, given that organic peroxides form via radical reactions, which mechanism involving hydroxide ions will result in the ...
jona173's user avatar
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5 votes
0 answers
47 views

Mechanism of Cu Catalyzed reaction between Benzoic acid with DMF

I'm looking for the mechanism of this reaction that I have stumbled upon. It is believed to be a radical reaction and I can kinda see that but I'm not convinced that I can understand all of the steps, ...
GabrielAlx's user avatar
0 votes
1 answer
72 views

Minimum volume of benzene with percentage yield

The overall yield for the synthesis of N-phenylethanamide from benzene was found to be $35.2\%$. Calculate the minimum volume of benzene, in $\mathrm{cm}^3$, required to make $10.0\, \mathrm{g}$ of N-...
Jane902's user avatar
  • 117
0 votes
1 answer
108 views

In what cases can LiAlH4 reduce alkene, or alkyne?

Lithium aluminium hydride $(\ce{LiAlH4})$ is known for its vast usability as reducing agent since it can reduce almost any organic functional group to alcohols, amines etc. Despite being so versatile, ...
Ansh's user avatar
  • 86
-2 votes
2 answers
57 views

Stability of phenylic carbocations [closed]

Problem: Structure (1) is more stable than structure (2). My teacher stated that Structure (1) is more stable than Structure (2). I find this confusing. How can Structure (1) be more stable when ...
Haider's user avatar
  • 93
8 votes
1 answer
1k views

What is 'spray foam' or 'expanding foam'?

At the wikipedia are: Spray foam (expanding foam in the UK) is a chemical product created by two materials, isocyanate and polyol resin, which react when mixed with each other and expand up to 30-60 ...
Imyaf's user avatar
  • 191
2 votes
0 answers
47 views

Palladium coupling reactions and purification

I tried to synthesize 2-(6-fluoropyridin-3-yl) acetic acid from 5-(Chloromethyl)-2-fluoropyridine using Pd(OAc)2/PPh3 catalyst,Na2CO3 and DCC. I eluted my product on TLC with Ethyl acetate/hexane/...
Ella's user avatar
  • 39
-3 votes
1 answer
34 views

ease of dehydration [closed]

ease of dehydration for the following alcohols is? I understand the most easiest would be for III, but shouldn't it be easier for I than for II? because II forms an anti aromatic compound? But the ...
user145228's user avatar
1 vote
2 answers
80 views

Use of Equivalent in organic chemistry

The question is taken from an engineering entrance exam in India(JEE 2024) If 3 mole of aniline is reacted with one equivalent of benzene diazonium chloride the maximum amount of aniline yellow formed ...
Rishikesh's user avatar
  • 127
0 votes
0 answers
73 views

Reaction SMARTS for Secondary Amine and Carboxylic Acid

I'm working on replicating methods from Klarich et al. [1] and the authors do not provide the reaction SMARTS used for synthesizing secondary amine + carboxylic acid building blocks. Does anyone have ...
Karl's user avatar
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