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.

Filter by
Sorted by
Tagged with
1
vote
1answer
45 views

is this compound meso? trans-1,4 dimethylcyclohexane [duplicate]

I had a question on a quiz that asked if the compound below was meso or not. I thought that it would be meso because there is a plane of symmetry going through the two methyls, but the answer was that ...
1
vote
0answers
39 views

Reactivity with rubbing alcohol and PVC

Rubbing alcohol seems to make polyvinyl plastic more sticky; i.e. if I clean a tube connector with rubbing alcohol first and then insert it into the plastic tube, it supposedly secures the seal ...
0
votes
0answers
68 views

Why is the NMR result for my p-toluic acid product so odd?

I just started learning about NMR and did a lab session where we conducted Grignard rxn with CO2 to form p-toluic acid and my NMR result is: 1H NMR (400 MHz, CDCl3) δ 9.63 (s, 4H), 8.07 – 8.00 (m, 5H),...
1
vote
0answers
38 views

Hazards of eating non-stick coating, particularly considering the coating primer [closed]

How unhealthy are teflon / non-stick coating chips that end up eaten? What role does the primer coating play? Existing similar threads that don't go into enough detail: 1, 2 I understand that there is ...
1
vote
0answers
85 views

TCP and KCP product [closed]

Q: According to me, the kinetic controlled product(KCP) should be While the Temperature controlled product(TCP) is: What should be the answer to this question because no temperature has been ...
2
votes
2answers
127 views

Efficacy of Intramolecular Friedel-Crafts reaction on =o, c=o bonds of ring structures?

Updated Q: Inquiring to understand the efficacy of intramolecular Friedel-Craft like reaction on stability on the ring structures with =o, c=o bonds. Keen to know if ring structures are challenged ...
0
votes
0answers
11 views

Organic solvent that won’t attack either PET or butyl rubber?

I am looking for a suitable organic solvent for dissolving dried-on polyurethane adhesive on a substrate of nylon/butyl/polyester. Acetone is ruled out because it attacks polyester (PET) and Toluene ...
3
votes
2answers
71 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 ...
5
votes
1answer
131 views

Photochemical cycloaddition of ethene

I've got a question regarding the (2pi+2pi)-photocycloaddition of ethene to form cyclobutane. If I understood correctly, the reaction doesn't take place under normal conditions, even if we increase ...
13
votes
1answer
1k views

What causes plastic to become brittle and can it be softened again?

I have some old computer case parts made of ABS plastic. Two decades of storage has embrittled the plastic to the point where they easily crack or shatter with the slightest bend. What is going on ...
-2
votes
1answer
53 views

Making pyridine with copper sulfate

I have a simple question. I am going to make some pyridine by thermal decarboxylation of niacin. Copper carbonate is out of the question, as is copper chromite. I was just wondering if copper sulfate ...
3
votes
1answer
106 views

Which of these protons are equivalent? Which NMR signals correspond to which protons?

Here are is the NMR spectrum and the compound (both images are the same spectrum, just close up). I know the deshielded signals are the aromatic protons and the ones ~6ppm are the alkene protons but ...
1
vote
1answer
66 views

Why is meta xylene formed when toluene undergoes alkylation in presence of excess AlCl3?

My book says that in presence of excess aluminium chloride, when toluene reacts with methyl iodide, meta-xylene is the major product. Why aren't ortho-para products favored here? Edit: The book is &...
2
votes
0answers
27 views

Solvent choice in imine formation from quercetin and poly(allylamine)

I am trying to react quercetin and poly(allylamine) to form imine on the repeating units. Poly(allylamine) is dissolved in water. The problem is the choice of solvent. Poly(allylamine) is soluble in ...
6
votes
1answer
131 views

Two different definitions for chemical shift (NMR)

Looking online I seem to have found 2 different definitions for chemical shift $\delta$ (in the context of NMR). The first definition uses the chemical shift of the reference in both the numerator and ...
-2
votes
1answer
51 views

Does Fischer esterification occur when mixing alcoholic drinks with lemon juice?

I would assume it does happen because the ethanol in the drink would be in an acidic environment because of the lemon juice and would react with the citric acid in it. But the thing is, how come we ...
0
votes
1answer
38 views

Finding the order of decreasing rate of solvolysis of the following molecules with aqueous ethanol [closed]

In this question, I need to find the order of decreasing rate of solvolysis of the above molecules with aqueous ethanol. I think this can be done by finding the species that can form the most stable ...
0
votes
1answer
48 views

Effect of substituents on aromatic character

Does the presence of substituents (electron withdrawing or electron donating) on an aromatic system have any effect on the aromatic character? In other words, would it be correct to say that benzene ...
1
vote
1answer
89 views

Should we consider reactant as the product of a no reaction?

If a reaction doesn't take place, should we call the reactant as the product? What is the convention? Let me illustrate the question with an example from JEE Advanced 2021, paper 1: The reaction of Q ...
0
votes
1answer
82 views

Are terminals alkyne reduced by Na/liq NH3? [closed]

By the mechanism, it appears that any alkyne should be reduced, but I couldn't find any source supporting or disapproving it. One possibility is that first acid-base rxn takes place but still the ...
1
vote
0answers
30 views

Reaction of aqueous KOH and alcoholic KOH with alkyl halide [duplicate]

CONTEXT: Here's reaction of alkyl halide with aqueous $\ce{KOH}$ and here's the reaction for dehydrohalogenation by alcoholic $\ce{KOH}$ Question Initially $\ce{KOH}$ is aqueous. On reacting with ...
0
votes
0answers
40 views

Calculation of Repeating units in polymer

Assume that I want to react A with repeating units of the polymer with ratio of 1:1. That is, I want to calculate that if I have $M_A$ mol of A, then what grams of polymer will I need to afford $M_A$ ...
1
vote
0answers
38 views

Prochirality and major/minor products

I got the following exercise question on configurations, which the textbook does not have an explanation that matches this question, so could someone please tell me whether my attempt is correct or ...
-1
votes
1answer
52 views

pKa of the alpha proton of an alpha amino ester [closed]

Is there a theoretical pKa value for the proton on the alpha carbon of a methylated amino acid, or just a general alpha amino methyl ester?
2
votes
1answer
64 views

Chain transfer in polystyrene synthesis

while I was studying the many side reactions of radical polymerization, I stumbled across this source which illustrates the chain transfer side reaction in polystyrene synthesis: Of course, there is ...
0
votes
2answers
93 views

Carbocation Stability question

Arrange, the following carbocation on increasing order of stability: What have I though is that in second it will be most unstable, as $\ce{-OH}$ group will create most inductive effect (negative), ...
0
votes
0answers
28 views

Why is the synthesis of graphene through alkyne trimerization not viable?

I have been looking for a rationale on this as massive polycyclic aromatic hydrocarbons have been synthesized this way, and with Graphene just being an indefinite expansion of aromatic rings, this has ...
-4
votes
1answer
59 views

CH3I + NaCl in acetone gives [closed]

How will methyl iodide react with $\ce{NaCl}$ in acetone? According to me $S_N2$ reaction will take place where iodine will be replaced by chlorine and we will get $\ce{CH3Cl}$. Can anyone suggest why ...
2
votes
0answers
48 views

Isolable activated esters: Other than N-Hydroxysuccinimidyl ester and Pentafluorophenyl ester?

Are there activated esters that undergo amide bond formation with an amino group in a mild and selective fashion, other than NHS ester and Pentafluorophenyl ester? I am aware that there are many ...
3
votes
0answers
42 views

Degradation of Pd catalyst in Buchwald-Hartwig amination

I am conducting Buchwald-Hartwig amination. I use $\ce{Pd_2(dba)3}$ and $\ce{P(o-tol)_3}$ as catalyst and toluene as solvent. Temperature is 100 ℃ and reaction time is 24 hours. During the reaction, ...
2
votes
0answers
38 views

What are the major products formed by reaction of methylidene cyclopropane with HBr in CCl4 solvent?

I am confused between two products: bromomethyl cyclopropane Allyl bromide Reason for my confusion: We know CPM cation will be formed which is stabilized by dancing resonating structures why can't ...
1
vote
1answer
63 views

Name of a beehive like organic structure, is it aromatic? [duplicate]

I was just studying organic chemistry and came across a weird, yet beautiful, structure, don't know its name but its structure is given below:                                                 I wanted ...
1
vote
0answers
50 views

Are these two molecules enantiomers or diastereomers?

I had a long discussion with my professor about these two molecules, and we both agreed to do some of our own research and reconvene. These two molecules appear to be non-superimposable mirror images ...
2
votes
0answers
49 views

When do the Wolff-Kishner Reduction and Clemmensen Reduction not take place for carbonyl compounds?

I came across some examples of organic compounds with acidic groups that didn't undergo the Clemmensen reduction. So, I was wondering which types of compounds the two reagents cannot reduce. Also, why?...
0
votes
1answer
68 views

Number of enol forms of acetylacetone

Here is what I tried: These are the two enolic forms that I could make. So according to me, the total number of distinct enol forms of acetylacetone is $2$. But the answer is 3, what am I missing?
5
votes
1answer
119 views

Does the Oxy or Alkoxy Claisen Rearrangement Exist?

@Waylander's cogent Comment to the query of @Random Guy inspired me to post a problem in synthesis to test a question I have pondered for some time. The activation energy (AE) for the Cope ...
0
votes
0answers
46 views

Converting Newman projection to dash and wedge structure

I want to convert the following Newman projection to a dash and wedge structure but the examples I've seen online are with simple molecules with methyl groups on the side. I wanted to show the long ...
2
votes
0answers
21 views

DEG monobutyl ether pH change

We are using DEG monobutyl ether (CAS 112-34-5) in our production. Normally it is pH neutral, however suddenly we noticed that it has shifted to being acidic (pH=3.4). What has changed in the material?...
3
votes
1answer
163 views

What are the major products when naphthalene reacts with ethyl chloride in the presence of AlCl₃?

From Arihant Test Drive, JEE Advanced 2020; Ramchaya builiding, Daryanganj, New Delhi, India; January 2019, p. 342: Napthalene gives 1-ethylnapthalene on reaction with ethyl choride in the presence ...
6
votes
0answers
53 views

Alcohol to Ketone by CrO3 in cyclohexane

I have encountered an exercise question on conformation of cyclohexane and there is a statement saying, 'converting alcohol to ketone by CrO3 is much faster when R-OH is in axial position'. I would ...
0
votes
0answers
35 views

Waste management of hazardous solvents

How should one safely dispose of chemicals like dichloromethane, toluene or acetone that were mixed with water? Is the water contaminated to a degree that it needs also treatment? For example ...
0
votes
0answers
55 views

Comparing stability of two carbocations [duplicate]

Which of the following ions(A and B respectively) is more stable? How can we explain this on the basis of resonance? Here's what the solution said: Structure (A) is a primary carbocation and has no ...
0
votes
0answers
52 views

Is the reaction stated below a SN1 or SN2 when ethanol is a solvent?

According to me, ethanol has an acidic H (attached to O) so it should support SN1 as a protic solvent. But in case of the following example, it is taken as an aprotic solvent, and thusly the reaction ...
0
votes
0answers
51 views

Can amide form Schiff base?

Can amide ($\ce{RCONH2}$) form Schiff base? When I searched for it, most papers deal with aliphatic amines. Some paper conducted synthesis with amide-containing compound, but iminization occured at β-...
0
votes
0answers
24 views

When does chain termination occur exactly?

In the reaction of substitution of alkane. There are chain initiation, chain propagation and chain termination. However, when does the chain termination reaction occur? Does it occur simultaneously ...
-2
votes
2answers
92 views

Why is the chirality center in (1R, 2S)-2-fluorocyclopentane-1-carboxylic acid 1R and not 1S?

I'm confused why the chirality center in (1R, 2S)-2-fluorocyclopentane-1-carboxylic acid, is 1R and not 1S. I'm personally think that the carboxyl carbon at C1 should have a higher priority than the ...
0
votes
1answer
53 views

Mesylation of cyanohydrins [closed]

Is it possible to add methane sulfonyl chloride to benzaldehyde cyanohydrin, or add toluene sulfonyl chloride to form the tosylate group on the alcohol and then perfom a grignard reaction on the ...
-1
votes
1answer
64 views

SN1 mechanism on 3,5-dimethylbenzyl bromide [closed]

I wanted to see how to make the product on the right so my thought was to have an SN1 reaction to remove water and have the bromine ion attack making the product on the right hand side. Is this ...
1
vote
1answer
157 views

Mechanism for alcohol synthesis via terminal acetylene reaction with sodium amide followed with epoxide and protonation

If anyone can give me some guidance here, it'd be much appreciated. I know the NaNH2 would dissociate and the NH2- base would deprotonate the terminal acetylene. I'm assuming the resultant product ...
2
votes
2answers
121 views

Elucidating an unknown compound using 1H- and 13C-NMR spectral data [closed]

I am currently struggling with the following NMR spectrum for this compound: I know for sure that we should multiply the integrals of the hydrogen atoms by four, and that the compound contains at ...