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Questions tagged [hybridization]

Hybridisation is the concept of mixing atomic orbitals to form new hybrid orbitals suitable for the qualitative description of atomic bonding properties.

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Hybridization of oxygen in phenol [duplicate]

What is the hybridization of oxygen in phenol molecule? I assume it is $sp^3$ hybridized because it forms 2 bonds - 1 with benzene, another with hydrogen, as in how oxygen is hybridized in a water ...
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Difference between oxygens in a carboxylic acid?

I've been reading about MO theory and am wondering if the traditional model of carboxylic acids is correct. Usually, how it's presented is that the carbonyl carbon is doubly bonded to one oxygen and ...
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How does an hybridised orbital become unhybridised after bond cleavage?

In $\ce{CH4}$, $1 s$ and $3 p$ orbitals are hybridised into four $sp^3$ orbitals. But on homolytic bond cleavage an unpaired electron remains in an unhybridised $p$ orbital? Similarly in heterolytic ...
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What Causes Atomic Orbitals to Hybridise?

I'm finding it difficult to visualise the process of hybridisation. Taking the example of formation of $\ce{CH4}$, can it viewed as the collapsing of the p orbitals of the Carbon atoms as they get "...
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How can hybrid orbitals be equivalent?

How can hybrid orbitals be equivalent? Take, for example, $\mathrm{sp^3}$ hybridization. The wave functions of each hybrid orbitals are given by: \begin{align} \psi_1 &= \psi_s + \psi_{p_x} + \...
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Is the hybridization only related to atomic orbitals but not to the molecular orbitals?

What is Hybridization? (Spelling: Hybridisation (British English) / Hybridization (American English)) The hybridization is a concept that describes atomic orbitals. In other words: Hybridization ...
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Through bond interaction in biradical dioxo compound and its correlation diagram

I'd like to investigate into the ring opening, the migratory reverse reaction of the electrocyclic ring-closure of Dimethyldioxirane: As a first question I'd like to ask if I have drawn the through ...
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Are the p orbitals of the biradical dioxo compound in the HOMO perpendicular to the plane?

I tried to draw the frontier molecular orbitals of the following biradical structure: (A) At the top I've drawn the HOMO and LUMO, because I know that the reaction coordinate belongs to the $\ce{C_{$...
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Why allene cannot be described with an allyl system?

Why is it impossible in allene to have two pi-bonds in the same orientation? => Why isn't allene planar? (4 $p$ electrons are in two 2x2 $p$-orbitals) From my chemical intuition I would guess that ...
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Hybridization of Ester Oxygen [duplicate]

I'm on the email list of an Organic Chemistry help website, and they sent out this problem: http://orgomadesimple.com/june-9-email-practice-problem/ This got me thinking: What if the nitrogen here ...
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Is ClH7 possible? [duplicate]

Chlorine can be $sp^3d^3$ hybridized. If so, it can form $\ce{ClH_7}$ and then chlorine, being more electronegative, will have (-7) as its oxidation number. But we know that the oxidation number of $\...
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Why can there not be more than one sigma bond in a set of bonds?

A question on an exam asked why there is exactly one sigma bond in double and triple covalent bonds. I looked in my text and online after the exam, but couldn't find an anawer to the question. Why ...
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Relative acidities of alkanes, alkenes, and alkynes

How does one explain the trend in bond lengths and acidity of the following hydrocarbons? $$\begin{array}{ccc} \hline \text{Species} & \ce{C-H}\text{ bond length / Å} & \mathrm{p}K_\mathrm{a} ...
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Why does hybridization produce a more stable configuration?

My text, and the other sources I've checked, include information on the effects, and kinds, of hybridized orbitals; however, they do not explain what properties of hybridized bonds conduce greater ...
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Are the bonding orbitals in methane equivalent - photoelectron spectrum

The low energy portion (the part dealing with the $\ce{2s}$ and $\ce{2p}$ electrons) of the photoelectron (PE) spectrum of methane is reproduced below. (image source) The reaction being examined is ...
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What does it mean when it is said that an sp³ orbital has 25% s character?

My textbook frequently mentions: $\mathrm{sp^3}$ hybrid orbital has 25% $\mathrm{s}$-character and 75% $\mathrm{p}$-character. What are these "characters"? And how do these characters influence ...
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Change of electron spin in Carbon after Hybridization?

During bond formation in Carbon, one of the electrons from the 2s orbital jumps to one the empty p orbitals creating a hybrid orbital as seen in the figure below. Now clearly one electron from the 2s ...
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Why an asymmetric geometry with sp3d and sp3d3 hybridization?

A molecule in which the central atom is $sp^3d^2$ hybridized ($\ce{SF_6}$), for example, acquires an octahedral shape, which can be explained by assuming that the hybrid orbitals arrange themselves to ...
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Hybridization of Na in [Na(H2O)6]+

In the complex ion $\ce{[Na(H2O)6]+}$, the sodium cation forms 6 coordinate bonds with water ligands. Typically this octahedral form is associated with $\mathrm{sp^3d^2}$ hybridization as far as I ...
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Is nitrogen of aniline sp² or sp³ hybridized? [duplicate]

I found a thread which discussed this which totally confused me. (refer to the part of the link which talks about $\ce{sp^2/sp^3}$) The question "How to rationalise the resonance structures and ...
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Length of C-H bonds in hybridized bonding orbitals

What is the effect of hybridization and double-bond formation on the rest of the atoms/molecules attached to the central atom? For example, in a benzene molecule, the Carbon-Carbon bonds are ...
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sp, sp2 and sp3 hybrid orbitals are actual solutions of Schrodinger's equation or only a heuristic?

According to Wikipedia's article about orbital hybridisation: [...] today it is considered an effective heuristic for rationalising the structures of organic compounds. [...] Hybrid orbitals are ...
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What is the hybridization of the carbonyl oxygen in a carboxylic acid?

My professor sent out a review guide. One of the questions on this guide is The carboxylic acid carbonyl oxygen is: 1. $\ce{sp^2}$ 2. $\ce{sp^3}$ 3. $\ce{H}$-bond donor 4. rapidly ...
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Why are the axial bonds of PF5 longer than those of the equatorial bonds? (Hybridization) [duplicate]

The axial bonds of $\ce{PF5}$ are longer than those of the equatorial positions. One explanation is that because the axial bonds are experiencing more repulsion than those of the equatorial and ...
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Understanding the hybridization of cyclohexane?

I'm having quite a fair bit of trouble comprehending the hybridization of cyclohexane. I understand that this is a ringed structure with single C-C bonds, therefore all the carbons should have sp3 ...
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Order of priority in hybridization of d-orbitals

During hybridization of d-orbitals why the $d_{z^2}$ and $d_{x^2-y^2}$ orbitals are used up before the $d_{xy}$, $d_{yz}$ and $d_{zx}$ ?
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What is the hybridization of oxygen in furan?

I fail to understand why the hybridization of oxygen in furan is $\ce{sp^2}$. I think that since there are 2 bond pairs and two lone pairs so it should be $\ce{sp^3}$ hybridized? Is it to do with the ...
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sp² hybridized orbital

I do not understand why and how an atom with $\ce{sp^2}$ hybridization has only one p orbital?? For example in pyridine why is the lone pair of nitrogen not counted as a pi electron.
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Is s-p mixing referring to hybridization or is it the mixing of one atoms s orbital with the other's p orbital?

According to molecular orbital theory s and p orbitals can mix if they are close enough in energy to each other. For period 2 diatomics, this occurs for $\ce{Li}$, $\ce{Be}$, $\ce{B}$, $\ce{C}$ and $\...
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How can the electronic structure of pentaaquanitrosyliron be explained?

The magnetic moment of $\ce{[Fe(H2O)5NO]^2+}$ is 3.87 Bohr magneton, which implies that there are 3 unpaired electrons. Since iron is in $+1$ oxidation state (due to charge transfer with nitrosyl ...
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Chemical bonding and hybridization of organic compounds

What happens to the lobe of the p-orbital during sp² hybridization? During the formation of $\ce{C2H4}$ molecule: We know that both the carbon atoms will have a total of 3 p-orbitals and they will ...
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Why are sp hybridized carbocations high energy?

You don’t see carbocations on double bonds very much, and here's a good reason: compared to sp3, there is more s character in the orbitals, so the empty orbital is held more closely to the nucleus. ...
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Electron Pair Geometry in Ibuprofen (Electron Pair Geometry in Organic Compounds)

I am trying to determine the electron pair geometry (and molecular geometry) of some atoms in ibuprofen. The first one I am trying to do is the double bonded oxygen. Ibuprofen is pictured below: I ...
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Hybridization - Mixing one atomic s orbital with 2p orbitals

Explain why three ${sp^2}$ hybrid orbitals result when one s atomic orbital is blended with two p atomic orbitals.
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Determine which orbitals will form hybrids with one another

I've been teaching myself chemistry, so any help is greatly appreciated. I've been reading an online tutorial that claims the two orbitals that merge in Aluminum trihydride are 1 orbital of 2s and 2 ...
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Determine the bond angle in a compound [closed]

How can we find the bond angle between 3 atoms in a compound? Please specify an equation which can be used for all compounds.
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What is the hybridization of the nitrogen in the azide ion?

In the azide ion, there is a symmetrical arrangement of three nitrogen atoms. If I've been told to figure out the hybridization of each nitrogen atom, what's the best way to go about doing this? My ...
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What is lowest energy state, how does an atom gain it and what does it have to do with hybridization?

I understand that hybridisation occurs due to the atom wanting to exist in the most stable state possible, and the most stable state has the lowest energy. What I don't understand, however, is say, in ...
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Why hybridization occurs in diatomic molecule

In diatomic nitrogen There are two electron configurations I'd like to compare: 1s2 2s2(lone pair) 2p3(the bonding electrons sigma,pi,pi) 1s2 2sp(lone pair) 2sp(sigma bonding) 2p2(pi,pi bonding) Why ...
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Doesn't the fact that the lone pair on the nitrogen in amides occupy a p orbital contradict Hund's rules?

Since the $\ce{sp^2}$ hybridized orbitals are lower in energy than the p orbital shouldn't the $\ce{sp^2}$ orbitals fill first? Why is this not the case - two electrons fill the p orbitals while all ...
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Why does F replace the axial bond in PCl5?

Why does $\ce{F}$ replace an axial bond in $\ce{PCl5}$? I realize that it would be more stable there than at equatorial bond, but what is the reason of its stability? Similarly in $\ce{AB4}$ type of ...
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Explanation of Bent's Rule [duplicate]

Why does the %s character increase on the orbital with electropositive atom? I do not seem to properly grasp this concept. Is this rule based on observation or is there any proof to it? If there is a ...
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Hybridised orbitals

What determines which type of hybridisation (sp3/sp2/sp) a molecule will take? Methane/ethylene/acetylene all have the same electron configuration but undergo different different types of ...
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Type of hybridisation

State the hybridisation of asterisked carbon in $\ce{CH3-CH=C^{✪}=CH2}$ I am not sure between $sp^2$ and $sp$ hybridization. Because of double bond I think it should be $sp^2$ but because of 2 $\pi$ ...
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Bent's rule for Sulfur trioxide and Sulfur dioxide

How is Bent's rule applied on $\ce{SO3}$ and $\ce{SO2}$? Bond length of $\ce{SO3}$ < $\ce{SO2}$. Is this a direct consequence of applying the Bent's rule?
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Carbon atoms at the edge of a diamond

It is well known (the simplest textbook example) that a diamond has a well-defined arrangement of sp3 carbon atoms, as each atom is connected to four others in a ...
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Why is one lobe of an sp3 hybridized orbital smaller than its other half?

A hybrid sp3 orbital is drawn with one lobe smaller than its other half, the latter which is of equal size when drawing the p orbital. Why is it so?
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What is Bent's rule?

I'm all bent out of shape trying to figure out what Bent's rule means. I have several formulations of it, and the most common formulation is also the hardest to understand. Atomic s character ...
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Why does bond angle decrease in the order H2O, H2S, H2Se?

I know that bond angle decreases in the order $\ce{H2O}$, $\ce{H2S}$ and $\ce{H2Se}$. I wish to know the reason for this. I think this is because of the lone pair repulsion but how?
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Hybridization in PH3

Does $\ce{PH3}$ exhibit $\ce{sp^3}$ hybridization? Arguments against hybridization: $\ce{PH3}$ is less basic than $\ce{NH3}$. This jibes with the supposition that $\ce{PH3}$ keeps its lone pair in ...