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Questions tagged [physical-organic-chemistry]

For questions about how organic molecules and reactions are investigated using physical experiments.

49 votes
6 answers
11k views

Why does wood burn but not sugar?

Fundamentally, they're both carbohydrates, although the cellulose in wood is essentially polymerized glucose, which combined with its isomer fructose forms sucrose. So why does wood readily burn ...
SwagMcMuffins's user avatar
16 votes
3 answers
90k views

Difference between intermediates and transition states

Can someone please explain what exactly the difference between an intermediate and a transition state is? I understand that they are formed as part of the process in converting the reactants to ...
tkhanna42's user avatar
  • 2,545
10 votes
1 answer
1k views

What can we say about the dipole moment of terephthalic acid?

The dipole moment of quinol is not zero because it can exist in two different energetically favourable conformations. The weighted average is calculated to arrive a dipole moment of 1.6 D. According ...
Apurvium's user avatar
  • 1,280
8 votes
1 answer
242 views

Out of tropolone and tropone, which is more soluble in water?

According to me tropolone has intramolecular H-bonding, so extent of H-bonding with water will decrease and thus, will be less soluble. Tropone (Cyclohepta-2,4,6-trien-1-one): Tropolone (2-...
ProBro's user avatar
  • 89
7 votes
1 answer
1k views

Fluorine detection in organic compounds

Many of you will know why I am asking this question. There is a lot of attention recently to the dangers of the so called Perfluoroalkyl and Polyfluoroalkyl Substances (PFAS). In essence organic ...
Boris Hamanov's user avatar
7 votes
2 answers
1k views

How can isotope labelling be used to determine the mechanism of ether cleavage with hydrogen iodide?

When methyl tert-butyl ether (MTBE) is treated with one equivalent of hydrogen iodide, the ether C–O bond is cleaved. I read that if the oxygen in MTBE is isotopically labelled, it is possible to ...
Kaustubh Shankar's user avatar
7 votes
1 answer
4k views

Aspirin Hydrolysis at pH 2

Conducting an experiment, I found that very little salicylic acid was evolved performing hydrolysis at $\mathrm{pH \ 2}$ and at $\pu{45 ^\circ C}$. In fact, far more salicylic acid was evolved at $\...
Mas's user avatar
  • 467
6 votes
0 answers
141 views

How do bonds rotate in pericyclic reactions?

In Pericyclic reactions, it is shown that the terminal bonds rotate (conrotation or disrotation) to allow for allignment of the FMO's, thereby forming the sigma bond However, a detail that most of my ...
Aniruddha Deb's user avatar
5 votes
0 answers
161 views

Does π values vary in Hansch-Fujita equations for a given substituent?

I was reading about Hansch-Fujita equations from Hansch-Fujita paramaters and observed that the $π$ values of substituents (analogous to Hammet $σ$ values) change according to the specific environment ...
Anton's user avatar
  • 766
4 votes
1 answer
958 views

How do we obtain the π molecular orbitals for allene via Hückel theory?

For a conjugated system, for instance 1,3-butadiene, we can try to obtain the π molecular orbital energies and wavefunctions via Hückel theory. In our given molecule, there are 4 interacting Pz ...
LamGyro's user avatar
  • 302
4 votes
1 answer
610 views

Overlap integrals in Hückel theory

In Hückel theory we are only interested in π systems, where $\mathrm p_z$ orbitals overlap. One of the approximations in Hückel theory is that the overlapping $\mathrm p_z$ orbitals are orthonormal: $...
LamGyro's user avatar
  • 302
4 votes
2 answers
230 views

Enzyme Kinetics

How come enzymes with a lower $K_\mathrm{m}$ are more easily saturated with substrate than an enzyme with higher $K_\mathrm{m}?$ Is it because enzymes with higher $K_\mathrm{m}$ are able to bind ...
Ahmer Imam's user avatar
4 votes
1 answer
91 views

Vapors of Aqueous solutions

I'm dealing with a common photoresist developer TMAH (tetramethylammonium hydroxide) and attempting to design a vapor sensor for a sealed chamber. Now I havent been able to confirm what exactly is ...
Greg M's user avatar
  • 51
4 votes
1 answer
184 views

What exchange timescales are needed to cause decoupling in NMR?

I'll try to explain the source of my confusion as clear as possible: (*) The methyl protons in toluene are decoupled because the C-C bond between the methyl group and benzene allows very fast ...
Stikke's user avatar
  • 497
4 votes
1 answer
172 views

What is the probability the bonds broken with sunlight reforming back?

The maximum wavelength $\lambda$ capable of breaking a chemical bond can be estimated as $\lambda = hc/E.$ UV-A $(\pu{380 nm})$ can break bonds with the energy up to $\pu{315 kJ mol^-1},$ UV-B $(\pu{...
Neal Conroy's user avatar

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