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<title>DP Chemistry: Understanding hybridization</title>
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<meta name="description" content="The theory of hybridization is developed by first considering how atomic orbitals combine to form molecular orbitals which then leads on to how hybrid orbitals are formed. The relationships between shapes, bond angles and type of hybridization are discussed together with the type of bonds (σ or π) formed and examples of the different types of questions involving hybridization that are commonly asked in examination...">
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nuclear fission reactions</a></li><li><a href="../19429/solar-energy-1.html">Solar energy</a></li><li><a href="../19437/environmental-impact-global-warming-1.html">Environmental impact - global warming</a></li><li><a href="../19453/electrochemistry-rechargeable-batteries-fuel-cells-1.html">Electrochemistry, rechargeable batteries & fuel cells</a></li><li><a href="../19458/nuclear-fusion-fission-hl--1.html">Nuclear fusion & fission (HL) </a></li><li><a href="../19470/photovoltaic-cells-and-dsscs-1.html">Photovoltaic cells and DSSCs</a></li></ul></li><li><a href="../19078/option-d-1.html" class="father">Option D</a><ul class="level-2"><li><a href="../19079/pharmaceutical-products-drug-action--1.html">Pharmaceutical products & drug action </a></li><li><a href="../19158/aspirin-penicillin--1.html">Aspirin & penicillin </a></li><li><a href="../19174/opiates-1.html">Opiates</a></li><li><a href="../19184/ph-regulation-of-the-stomach-1.html">pH regulation of the stomach</a></li><li><a href="../19194/antiviral-medications--1.html">Antiviral medications </a></li><li><a href="../19211/environmental-impact-of-some-medications-1.html">Environmental impact of some medications</a></li><li><a href="../19254/taxol-a-chiral-auxiliary-case-study-1.html">Taxol - a chiral auxiliary case study</a></li><li><a href="../19258/nuclear-medicine--1.html">Nuclear medicine </a></li><li><a href="../19273/drug-detection-analysis--1.html">Drug detection & analysis </a></li></ul></li></ul></li><li><a href="../16592/practical-scheme-of-work-ia--1.html">Practical scheme of work & IA </a><ul class="level-1"><li><a href="../16682/internal-assessment-1.html" class="father">Internal Assessment</a><ul class="level-2"><li><a href="../18892/scaffolding-the-investigation-1.html">'Scaffolding' the investigation</a></li><li><a href="../18896/timing-organisation--1.html">Timing & organisation </a></li><li><a href="../18905/choosing-the-research-question-1.html">Choosing the research question</a></li><li><a href="../18946/personal-engagement-1.html">Personal engagement</a></li><li><a href="../18950/exploration-1.html">Exploration</a></li><li><a href="../18957/analysis-1.html">Analysis</a></li><li><a href="../18965/evaluation-1.html">Evaluation</a></li><li><a href="../18966/communication-1.html">Communication</a></li><li><a href="../19882/internal-standardization-of-the-ia-1.html">Internal standardization of the IA</a></li><li><a href="../19901/submitting-the-samples-for-moderation-2.html">Submitting the samples for moderation</a></li><li><a href="../33754/ten-suggestions-for-ias-using-secondary-data-1.html">Ten suggestions for IAs using secondary data</a></li><li><a href="../37544/gaining-full-marks-for-a-databased-ia--1.html">Gaining full marks for a databased IA </a></li><li><a href="../19506/ia-example-marking-exercise--1.html">IA example & marking exercise </a></li><li><a href="../23929/genuine-examples-of-moderated-ia-reports-1.html">Genuine examples of moderated IA reports</a></li><li><a href="../25234/examples-of-teacher-marked-ia-reports--1.html">Examples of teacher-marked IA reports </a></li><li><a href="../37542/history-of-internal-assessment-1.html">History of Internal Assessment</a></li></ul></li><li><a href="../16598/mandatory-laboratory-components-1.html" class="father">Mandatory laboratory components</a><ul class="level-2"><li><a href="../16613/formula-of-magnesium-oxide--1.html">Formula of magnesium oxide </a></li><li><a href="../16612/determining-the-mr-of-an-unknown-gas-1.html">Determining the <i>M</i><sub>r</sub> of an unknown gas</a></li><li><a href="../16615/acid-base-titrations--1.html">Acid-base titrations </a></li><li><a href="../16616/a-green-acid-base-practical-1.html">A green acid-base practical</a></li><li><a href="../16617/analysis-of-aspirin-tablets-1.html">Analysis of aspirin tablets</a></li><li><a href="../16618/caco3-in-egg-shells-1.html">CaCO<sub>3</sub> in egg shells</a></li><li><a href="../16644/enthalpy-changes-1.html">Enthalpy changes</a></li><li><a href="../16631/reaction-rates-1.html">Reaction rates</a></li><li><a href="../16635/rate-dependent-factors-1.html">Rate-dependent factors</a></li><li><a href="../16636/determining-ea-for-a-reaction-1.html">Determining <i>E</i><sub>a</sub> for a reaction</a></li><li><a href="../16637/iodination-of-propanone-1.html">Iodination of propanone</a></li><li><a href="../18144/titrations-with-a-ph-meter-1.html">Titrations with a pH meter</a></li><li><a href="../18355/redox-titration-with-kmno4--1.html">Redox titration with KMnO<sub>4</sub> </a></li><li><a href="../16640/voltaic-cells-1.html">Voltaic cells</a></li><li><a href="../16659/3-d-molecular-modelling--1.html">3-D molecular modelling </a></li></ul></li><li><a href="../17168/other-good-practicals-1.html" class="father">Other good practicals</a><ul class="level-2"><li><a href="../17196/common-chemical-reactions-1.html">Common chemical reactions</a></li><li><a href="../227/elements-oxides-of-the-third-period--1.html">Elements & oxides of the third period </a></li><li><a href="../17239/the-halogens-1.html">The halogens</a></li><li><a href="../17162/boiling-points-of-mixtures-1.html">Boiling points of mixtures</a></li><li><a href="../17170/polarity-of-molecules-1.html">Polarity of molecules</a></li><li><a href="../18083/le-chateliers-principle--1.html">Le Chatelier's principle </a></li><li><a href="../19582/determining-kc-for-an-esterification-reaction-1.html">Determining <i>K</i><sub>c</sub> for an esterification reaction</a></li><li><a href="../18164/redox-reactions-of-vanadium--1.html">Redox reactions of vanadium </a></li><li><a href="../18351/chlorine-in-swimming-pools--1.html">Chlorine in swimming pools </a></li><li><a href="../18178/analysis-of-cuii-ions-in-solution--1.html">Analysis of Cu(II) ions in solution </a></li><li><a href="../18179/percentage-of-copper-in-brass-1.html">Percentage of copper in brass</a></li><li><a href="../18356/electrolytic-cells--1.html">Electrolytic cells </a></li><li><a href="../18598/reactions-of-organic-compounds-1.html">Reactions of organic compounds</a></li><li><a href="../18752/hydrolysis-of-halogenoalkanes-1.html">Hydrolysis of halogenoalkanes</a></li><li><a href="../18784/preparation-of-13-dinitrobenzene--1.html">Preparation of 1,3-dinitrobenzene </a></li><li><a href="../19022/determination-of-an-organic-structure-1.html">Determination of an organic structure</a></li><li><a href="../19887/preparation-of-nylon-66-1.html">Preparation of nylon 6,6</a></li><li><a href="../19343/determination-of-vitamin-c-content--1.html">Determination of vitamin C content </a></li><li><a href="../19342/hydrolysis-of-starch--1.html">Hydrolysis of starch </a></li><li><a href="../19159/preparation-purification-of-aspirin--1.html">Preparation & purification of aspirin </a></li></ul></li><li><a href="../18851/ict-in-practical-work-1.html" class="father">ICT in practical work</a><ul class="level-2"><li><a href="../18852/data-logging--1.html">Data logging </a></li><li><a href="../18853/software-for-graph-plotting--1.html">Software for graph plotting </a></li><li><a href="../18854/spreadsheets-for-data-processing--1.html">Spreadsheets for data processing </a></li><li><a href="../18855/databases-1.html">Databases</a></li><li><a href="../18856/computer-modelling-simulations--1.html">Computer modelling & simulations </a></li></ul></li><li><a href="../16594/group-4-project-1.html" class="father">Group 4 Project</a><ul class="level-2"><li><a href="../16595/practicalities-1.html">Practicalities</a></li><li><a href="../16596/reflective-statement--2.html">Reflective statement </a></li></ul></li><li><a href="../16666/a-new-laboratory-1.html">A new laboratory?</a></li></ul></li><li class="selected"><a href="../16284/exams-1.html">Exams</a><ul class="level-1"><li><a href="../16286/essential-facts-1.html" class="father">Essential Facts</a><ul class="level-2"><li><a 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concepts</a></li><li><a href="../3507/why-tok-chemistry-1.html">Why TOK & Chemistry?</a></li><li><a href="../3505/a-modern-paradigm-1.html">A modern paradigm</a></li></ul></li></ul></li><li><a href="../17783/fast-track-to-tests-questions-1.html">Fast track to tests & questions</a><ul class="level-1"><li><a href="../17784/sl-multiple-choice-tests-on-individual-topics-1.html">SL Multiple choice tests on individual topics</a></li><li><a href="../24351/sl-multiple-choice-quizzes-on-sub-topics-1.html">SL Multiple choice 'quizzes' on sub-topics</a></li><li><a href="../31519/sl-practice-paper-1-exams-1.html">SL Practice Paper 1 exams</a></li><li><a href="../17786/sl-questions-on-each-sub-topic-1.html">SL Questions on each sub-topic</a></li><li><a href="../20431/sl-paper-3-section-a-questions-1.html">SL Paper 3 Section A questions</a></li><li><a href="../17792/sl-questions-on-the-options-1.html">SL Questions on the options</a></li><li><a href="../24897/sl-quizzes-on-option-sub-topics--1.html">SL Quizzes on option sub-topics </a></li><li><a href="../17785/hl-multiple-choice-tests-on-individual-topics-1.html">HL Multiple choice tests on individual topics</a></li><li><a href="../24352/hl-multiple-choice-quizzes-on-sub-topics-1.html">HL Multiple choice 'quizzes' on sub-topics</a></li><li><a href="../31520/hl-practice-paper-1-exams--1.html">HL Practice Paper 1 exams </a></li><li><a href="../17787/hl-questions-on-each-sub-topic--1.html">HL Questions on each sub-topic </a></li><li><a href="../20428/hl-paper-3-section-a-questions-1.html">HL Paper 3 Section A questions</a></li><li><a href="../17793/hl-questions-on-the-options-1.html">HL Questions on the options</a></li><li><a href="../24973/hl-quizzes-on-option-sub-topics-1.html">HL Quizzes on option sub-topics</a></li><li><a href="../41573/printable-versions-of-written-tasks--1.html">Printable versions of written tasks </a></li></ul></li><li><a 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</div><section id="main-content"><p><img alt="" class="noborder" src="../../../ib/chemistry/images/2014%20Exams/benzene-hybridization.png" style="width: 2px; height: 1px;">The theory of hybridization is developed by first considering how atomic orbitals combine to form molecular orbitals which then leads on to how hybrid orbitals are formed. The relationships between shapes, bond angles and type of hybridization are discussed together with the type of bonds (σ or π) formed and examples of the different types of questions involving hybridization that are commonly asked in examination questions are comprehensively covered.</p><div class="blueBg"><h1>The theory</h1><h4>Linear combination of atomic orbitals</h4><p class="MsoNormal">Understanding and applying the concept of hybridization is one of the topics that many students have difficulty with.<span style="mso-spacerun:yes"> </span>It is only a theory and builds upon the simpler theory of the linear combination of atomic orbitals from different atoms to form covalent bonds. Possibly the difficulty with hybridization may be due to the fact that students<span style="mso-spacerun:yes"> </span>do not really understand how molecular orbitals form from atomic orbitals as the topic is not clearly covered by the IB in sub-topic <a href="../17260/further-aspects-of-covalent-bonding--1.html" title="Core & AHL » Teaching each topic & sub-topic » Topics 4 & 14 » Further aspects of covalent bonding ">14.1 Further aspects of covalent bonding</a>. This is because the 'understandings' in the IB chemistry guide refers to "overlap" rather than the combination of atomic orbitals and does not include the existence of anti-bonding orbitals. To understand this consider the simplest case of the combination of two s orbitals (one from each atom) to form a sigma (<span style="mso-ascii-font-family:Cambria;mso-hansi-font-family:
Cambria">σ</span>) bond.<span style="mso-spacerun:yes"> </span>When two s orbitals combine together they form <b>two</b> molecular orbitals. One of these molecular orbitals is at a lower energy level than the atomic orbitals and is known as a sigma (<span style="mso-ascii-font-family:
Cambria;mso-hansi-font-family:Cambria">σ</span>) bonding orbital. It is formed when the two s atomic orbitals combine constructively. The other, formed when the two s orbitals combine destructively, is at a higher energy and is known as a sigma antibonding orbital denoted by <span style="mso-ascii-font-family:Cambria;mso-hansi-font-family:Cambria">σ*. Overall there is no energy change as the average energy of the bonding and antibonding molecular orbitals is the same as that of the atomic orbitals.</span></p><hr class="hidden"><p class="MsoNormal"><span style="mso-ascii-font-family:Cambria;mso-hansi-font-family:Cambria"></span></p><p class="MsoNormal" style="text-align: center;"><img alt="" class="noborder" src="../../../ib/chemistry/images/2014%20Exams/screenshot-2020-04-14-at-15.40.57.png" style="width: 227px; height: 240px;"></p><hr class="hidden"><p class="MsoNormal">This can be used to explain the bonding in hydrogen. Each hydrogen atom contains one electron in an s orbital. When two hydrogen atoms are brought into contact with each other the orbitals combine to give the two molecular orbitals, each of which can contain two electrons.</p><hr class="hidden"><p style="text-align: center;"><img alt="" class="noborder" src="../../../ib/chemistry/images/2014%20Exams/bonding-in-hydrogen-molecule.png" style="width: 244px; height: 238px;"></p><p class="MsoNormal"><span style="mso-ascii-font-family:Cambria;mso-hansi-font-family:
Cambria"></span></p><hr class="hidden"><p class="MsoNormal"><span style="mso-ascii-font-family:Cambria;mso-hansi-font-family:
Cambria">According to the aufbau principle both of the electrons from the two hydrogen atoms will go into the molecular orbital with the lowest energy, i.e. the bonding orbital, and a sigma bond is formed as it is more energetically favourable than if the two electrons remain in their separate atomic orbitals. Consider if two helium atoms are brought into close contact. Each contains two electrons (1s<sup>2</sup>) so two will go into the bonding orbital and two will go into the antibonding orbital so that there is no net gain in energy and so no bond is formed between the helium atoms. An analogous compound to hydrogen is the helium hydride ion HHe<sup>+</sup>,<span style="mso-spacerun:yes"> </span>which is the strongest acid known. It is formed when H (1s<sup>1</sup>) and He<sup>+</sup> (1s<sup>1</sup>) combine.. The compound He<sub>2</sub><sup>+ </sup>, formed by the combination of He (1s<sup>2</sup>) with He<sup>+</sup> (Is<sup>1</sup>), contains two electrons in the bonding molecular orbital and one in the antibonding molecular orbital so overall forms a weak ‘half’ covalent bond (described as having a bond order of ½) which is longer and weaker than the bond in H<sub>2</sub>.</span><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman""></span></p><hr class="hidden"><p class="MsoNormal"><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman"">When an s atomic orbital on one atom combines with a p orbital on another atom a sigma bonding and a sigma antibonding molecular orbital are formed. Similarly p<sub>x</sub> and p<sub>x</sub> atomic orbitals combine ‘head on’ to give sigma molecular bonding and antibonding orbitals but the combinations of p<sub>y</sub> and p<sub>y</sub> and p<sub>z</sub> and p<sub>z</sub> both involve ‘sideways on’ combinations and pi (π) bonding and antibonding molecular orbitals (π*) are formed.</span></p><hr class="hidden"><p class="MsoNormal"><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman""></span></p><h4 class="MsoNormal"><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman"">Hybridization</span></h4><p class="MsoNormal"><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman"">To understand hybridization it is best to start by considering the bonding in methane. Each of the four hydrogen atoms has the electron configuration 1s<sup>1</sup> and the electron configuration of carbon is 1s<sup>2</sup>2s<sup>2</sup>2p<sup>2</sup>. Carbon contains four outer electrons, two paired together in the 2s orbital and one each in two of the three 2p orbitals. It is not easy to see how these can form four sigma bonds without the unpairing of the two 2s electrons nor why the shape of methane is tetrahedral as the p orbitals are orthogonal (at right angles) to each other.<span style="mso-spacerun:yes"> </span>The mixing of atomic orbitals to form new hybrid orbitals with their own properties (e.g. energy and shape) is known as hybridization. When the carbon atom bonds in methane the 2s orbital and the three 2p orbitals hybridize to form four new hybrid orbitals. This is known as sp<sup>3</sup> hybridization and the four new hybrid orbitals, which each contain one unpaired electron, point towards the corners of a tetrahedron giving a bond angle of 109.5<sup>o</sup>. The electron in each of the sp<sup>3</sup> hybrid orbitals is able to combine with an electron in the s orbital of a hydrogen atom to fill the four bonding sigma molecular orbitals leaving the antibonding orbitals empty resulting in four equal C−H sigma bonds. This is shown in slide 1 the gallery below which can also be found on the page on the sub-topic on <a href="../27985/142-hybridization-1.html" title="Complete course for students » Topics 4 & 14 : Chemical bonding & structure » 14.2 Hybridization">14.2 Hybridization</a>. </span></p><hr class="hidden"><p class="MsoNormal"><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman""></span></p><div id="myCarousel-1" class="carousel slide" data-id="247"><!-- Carousel items --><div class="carousel-inner"><div class="active item"><a class="fancy" href="../../../tib-galleries/3-247/1.png" rel="gallery-247" title=""><img alt="" src="files/tib-galleries/3-247/1.png"></a><div class="carousel-caption"><p>Hybridization: </p></div></div><div class="item"><a class="fancy" href="../../../tib-galleries/3-247/2.png" rel="gallery-247" title=""><img alt="" src="files/tib-galleries/3-247/2.png"></a><div class="carousel-caption"><p>Hybridization: </p></div></div><div class="item"><a class="fancy" href="../../../tib-galleries/3-247/3.png" rel="gallery-247" title=""><img alt="" src="files/tib-galleries/3-247/3.png"></a><div class="carousel-caption"><p>Hybridization: </p></div></div><div class="item"><a class="fancy" href="../../../tib-galleries/3-247/4.png" rel="gallery-247" title=""><img alt="" src="files/tib-galleries/3-247/4.png"></a><div class="carousel-caption"><p>Hybridization: </p></div></div><div class="item"><a class="fancy" href="../../../tib-galleries/3-247/5.png" rel="gallery-247" title=""><img alt="" src="files/tib-galleries/3-247/5.png"></a><div class="carousel-caption"><p>Hybridization: </p></div></div><div class="item"><a class="fancy" href="../../../tib-galleries/3-247/6.png" rel="gallery-247" title=""><img alt="" src="files/tib-galleries/3-247/6.png"></a><div class="carousel-caption"><p>Hybridization: </p></div></div><div class="item"><a class="fancy" href="../../../tib-galleries/3-247/7.png" rel="gallery-247" title=""><img alt="" src="files/tib-galleries/3-247/7.png"></a><div class="carousel-caption"><p>Hybridization: </p></div></div></div><!-- Carousel nav --><a class="carousel-control left" href="#myCarousel-1" data-slide="prev">‹</a><a class="carousel-control right" href="#myCarousel-1" data-slide="next">›</a><div class="tib-indicators"><img class="" title="Click to view" style="margin: 10px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-247/1-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-247/2-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-247/3-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-247/4-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-247/5-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-247/6-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-247/7-thumb128.jpg"></div></div><p> </p><p class="MsoNormal"><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman""></span><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman"">Slide 2 in the gallery explains why organic compounds containing three electron domains have a bond angle of 120<sup>o</sup> as now the hybridization is sp<sup>2</sup>, i.e. three hybrid orbitals are formed from the s and two of the three p orbitals. The remaining p orbital is free to form a π bond with the p orbital of the bonding atom at right angles to the plane of the sigma bonds. This occurs in alkenes and carbonyl compounds such as aldehydes and ketones. In compounds where<span style="mso-spacerun:yes"> </span>the central carbon atom has two electron domains the bond angle will be 180<sup>o</sup> and the two hybrid orbitals are formed from one s and one p orbital to give sp hybridization. This leaves two p orbitals which can each form a π bond with the p orbitals on the bonding atom. This occurs in carbon dioxide, alkynes and nitriles (see Slide 3). It also occurs in carbon monoxide where one of the sp hybrid orbitals on both the carbon and oxygen atoms contains a non-bonding pair of electrons and the other forms a σ bond between the carbon and oxygen atoms along with two π bonds to form the triple bond.</span></p><hr class="hidden"><p class="MsoNormal"><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman""></span><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman""></span></p><p class="MsoNormal" style="text-align: center;"><img alt="" class="noborder" src="../../../ib/chemistry/images/Exams/carbon-monoxide-hybridization(1).png" style="width: 344px; height: 200px;"></p><p class="MsoNormal" style="text-align: center;"><strong>Hybridization and bonding in carbon monoxide</strong></p><p class="MsoNormal" style="text-align: center;">(both the C and O atom are sp hybridized with the triple bond consisting of one σ and two π bonds)</p><hr class="hidden"><p class="MsoNormal"><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman""></span><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman"">The gallery then goes on to explain the structure of benzene (Slide 5). Delocalization will occur whenever there are alternate C=C and C−C bonds as each of the carbon atoms will be sp<sup>2</sup> hybridized so the electrons in the resulting π bonds can be spread over all the bonds equally. This results in an increase in electrical conductivity. The electron transition between the bonding and non-bonding orbitals is of lower energy in compounds containing much delocalization (also known as conjugation) than those where the bonding is localized. Hence when they are excited highly conjugated compounds tend to absorb light at a lower wavelength than compounds containing just localized bonds resulting in coloured compounds. Examples of highly conjugated molecules include porphyrins and carotenes (see for example the structure of β-carotene given below and the structures of chlorophyll, heme and α-carotene given in Section 35 of the IB data booklet). </span></p><hr class="hidden"><p class="MsoNormal"><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman""></span></p><p class="MsoNormal" style="text-align: center;"><img alt="" class="noborder" src="../../../ib/chemistry/images/Exams/beta-carotene.png" style="width: 653px; height: 150px;"></p><hr class="hidden"><p class="MsoNormal"><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman"">The IB limits the types of hybridization to sp<sup>3</sup>, sp<sup>2</sup> and sp and most examples relate to organic compounds but the concept can also be applied to other simple compounds such as NH<sub>3</sub>, NH<sub>4</sub><sup>+</sup> and H<sub>2</sub>O for sp<sup>3</sup>, BF<sub>3</sub> and CO<sub>3</sub><sup>2−</sup> for sp<sup>2</sup> and BeCl<sub>2</sub> for sp. Other types of hybridization exist, e.g. d<sup>2</sup>sp<sup>3</sup> for octahedral complexes, but these are beyond the IB syllabus.</span></p><hr class="hidden"></div><hr class="hidden"><div class="greenBg"><h1>Types of hybridization questions</h1><h4 class="MsoNormal"><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman"">1. Bond angles and shape</span></h4><p class="MsoNormal"><strong><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman"">(a) Shape and bond angles from the type of hybridization</span></strong></p><p class="MsoNormal"><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman"">Once the type of hybridization is known the shape and hence the bond angle(s) can be predicted. For example the central carbon atom in compounds with four bonding pairs of electrons around the central atom will all be sp<sup>3</sup> hybridized so will all have a regular tetrahedral shape with a bond angle of 109.5<sup>o</sup>. Examples include CH<sub>4</sub>, CCl<sub>4</sub> and CHCl<sub>3</sub>. Where one of the four electron domains is a non-bonding pair of electrons the ‘parent’ shape will be tetrahedral but the actual shape will be trigonal pyramidal with bond angles slightly less than 109.5<sup>o</sup>. An example is NH<sub>3</sub> with a bond angle of 107<sup>o</sup>. The bond angle will be even less when two of the electron domains contain non-bonding pairs of electrons to give a bent molecule, e.g. H<sub>2</sub>O with a bond angle of 105<sup>o</sup>.</span></p><p class="MsoNormal"><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman""></span><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman"">sp<sup>2</sup> hybridization leads to a trigonal planar shape with a bond angle of 120<sup>o</sup> (e.g. alkenes, ketones, aldehydes CO<sub>3</sub><sup>2</sup><sup>−</sup>) and sp hybridization leads to a linear shape with a<span style="mso-spacerun:yes"> </span>bond angle of 180<sup>o</sup> (e.g. alkynes, HCN).</span></p><p class="MsoNormal"><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman""> </span></p><p class="MsoNormal"><strong><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman"">(b) Type of hybridization from the shape or bond angle(s) </span></strong></p><p class="MsoNormal"><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman"">If the shape of the molecule or simple ion is known or can be deduced using <a href="../16311/vsepr.html" title="Exams » Paper 2 » Areas of difficulty » VSEPR">VSEPR</a> theory then the hybridization can also be deduced. If the ‘parent’ shape is tetrahedral, i.e. the bond angle is 109.5<sup>o</sup> (or slightly less) the hybridization will be sp<sup>3</sup>, if it is trigonal planar (bond angle 120<sup>o</sup>) it will be sp<sup>2</sup> and if the shape is linear (bond angle 180<sup>o</sup>) it will be sp hybridized.</span></p><p class="MsoNormal"><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman""> </span></p><h4 class="MsoNormal"><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman"">2. Types of hybridization shown in a molecule</span></h4><p class="MsoNormal"><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman"">If all the bonds around a carbon atom are single the carbon atom will be sp<sup>3</sup> hybridized. If the carbon atom has one double bond it will be sp<sup>2</sup> hybridized and if it has two double bonds (as in carbon dioxide) or a triple bond it will be sp hybridized.</span><strong><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman""></span></strong></p><p><strong><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman""></span></strong><strong><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman"">For example:</span></strong><strong><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman""></span></strong></p><p><strong><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman"">(i) </span></strong><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman"">What type of hybridization is shown by each carbon atom in phenylalanine?</span></p><p class="MsoListParagraphCxSpFirst" style="text-indent:-18.0pt;mso-list:l0 level1 lfo1"><strong><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman""></span></strong></p><p class="MsoListParagraphCxSpFirst" style="text-indent: -18pt; text-align: center;"><img alt="" class="noborder" src="../../../ib/chemistry/images/2014%20Exams/phenylalanine-structure.png" style="width: 170px; height: 186px;"></p><p class="MsoListParagraphCxSpFirst" style="text-indent: -18pt;"></p><section class="tib-hiddenbox"><p style="text-align: center;"><img alt="" class="noborder" src="../../../ib/chemistry/images/2014%20Exams/phenylalanine---hybridzation.png" style="width: 170px; height: 198px;"></p></section><p class="MsoListParagraphCxSpLast" style="text-indent:-18.0pt;mso-list:l0 level1 lfo1"><span style="font-family:Helvetica;mso-fareast-font-family:Helvetica;mso-bidi-font-family:
Helvetica"><span style="mso-list:Ignore"><span style="font:7.0pt "Times New Roman""></span></span></span> <strong>(ii)</strong> What is the hybridization of the nitrogen atom in phenylalanine?</p><section class="tib-hiddenbox"><p>sp<sup>3</sup> (as there are four electron domains around the N atom - three bonding pairs and one non-bonding pair of electrons)</p></section><p class="MsoNormal"><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman""></span><strong><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman""></span></strong></p><hr class="hidden"><h4 class="MsoNormal"><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman"">3. Type of bonds (</span><span style="mso-ascii-font-family:
Cambria;mso-hansi-font-family:Cambria">σ or </span><span style="font-family:
Helvetica;mso-fareast-font-family:"Times New Roman"">π ) shown in a molecule</span></h4><p class="MsoNormal"><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman"">If the carbon atom is sp<sup>2</sup> hybridized the double bond will contain one sigma and one pi bond and if it is sp hybridized the triple bond will contain one sigma and two pi bonds. If it is sp<sup>3</sup> hybridized all the bonds will be sigma bonds.</span></p><p class="MsoNormal"><strong><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman"">For example</span></strong></p><p class="MsoNormal"><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman"">How many sigma and how many pi bonds are present in caffeine?</span></p><p class="MsoNormal" style="text-align: center;"><img alt="" class="noborder" src="../../../ib/chemistry/images/2014%20Exams/caffeine.png" style="width: 170px; height: 179px;"></p><section class="tib-hiddenbox"><p style="text-align: center;">24 sigma bonds and 4 pi bonds (although some delocalization occurs)</p><p style="text-align: center;"><img alt="" class="noborder" src="../../../ib/chemistry/images/2014%20Exams/caffeine-with-bonds.png" style="width: 200px; height: 177px;"></p></section><hr class="hidden"><h4 class="MsoNormal"><span style="font-family:Helvetica;mso-fareast-font-family:
"Times New Roman"">4. Change in hybridization during a reaction</span></h4><p>When the number or type of bonds around an atom changes then there will be a change in hybridization.<br>The classic example is addition reactions.</p><p>For example:</p><p style="text-align: center;"><span style="font-size:12.0pt;font-family:Helvetica;mso-fareast-font-family:
"Times New Roman";mso-bidi-font-family:"Times New Roman";mso-bidi-theme-font:
minor-bidi;mso-ansi-language:EN-GB;mso-fareast-language:EN-US;mso-bidi-language:
AR-SA"></span><img alt="" class="noborder" src="../../../ib/chemistry/images/2014%20Exams/addition-reaction-(2).png" style="width: 434px; height: 157px;"></p><hr class="hidden"><h4>5. Type of hybridization shown by allotropes of carbon</h4><p><strong>Diamond: </strong>sp<sup>3</sup></p><p>Regular giant tetrahedral structure with four equal C−C bonds.</p><p><strong>Graphite: </strong>sp<sup>2</sup></p><p>Planar hexagonal rings in layers with weak bonds between the layers.</p><p><strong>Graphene: </strong>sp<sup>2</sup></p><p>Single layer of carbon atoms in a two-dimensional hexagonal lattice</p><p>F<strong>ullerenes</strong><strong>: </strong>Intermediate between sp<sup>3</sup> and sp<sup>2</sup></p><p>Fusion of five and six membered carbon rings - see <a href="../../../doi/pdf/10.1098/rsta.1993.0040.pdf">R.Hadden, Phil. Trans. R. Soc. Lond. A (1993)</a></p><hr class="hidden"></div><div class="blueBg"><h4>Practice quiz</h4><p>You should now be in a position to answer all of the ten questions which can be found in the quiz on the <a href="../17258/hybridization-1.html" title="Core & AHL » Teaching each topic & sub-topic » Topics 4 & 14 » Hybridization">hybridization</a> page.</p><hr class="hidden"></div></section></article><section id="media-extras"><div class="page-actions no-print navbar inline hidden-desktop"><div class="navbar-inner"><ul class="nav"><li><a class="presentation" href="#" onclick="return false;"><i class="fa fa-desktop"></i></a></li><li><a class="print-section-blog" href="#" onclick="return false;"><i class="fa fa-print"></i></a></li><li><a class="page-bookmarker" data-ticket="IB Docs (2) Team" data-pid="33687" href="#" onclick="return false;"><i class="fa fa-star"></i></a></li><li><a class="personal-notes" href="#" onclick="return false;"><i class="fa fa-file-text"></i></a></li><li><a class="" data-toggle="modal" href="#modal-feedback" onclick="return false;"><i class="fa fa-envelope-o"></i></a></li><li class="dropdown"><a class="dropdown-toggle" data-toggle="dropdown" data-target="#" href="#"><i class="fa fa-share-alt"></i></a><ul class="dropdown-menu" role="menu"><li><a class="" target="_blank" title="Share on Twitter" href="https://twitter.com/share?text=%22Understanding+hybridization%22+-+via+%40InThinker+%23chemistry%0A&url=https%3A%2F%2Fwww.thinkib.net%2Fchemistry%2Fpage%2F33687%2Funderstanding-hybridization"><i class="fa fa-twitter-square"></i><span>Twitter</span></a></li><li><a class="" target="_blank" title="Share on Facebook" href="https://www.facebook.com/sharer.php?u=https%3A%2F%2Fwww.thinkib.net%2Fchemistry%2Fpage%2F33687%2Funderstanding-hybridization&t=Understanding+hybridization"><i class="fa fa-facebook-square"></i><span>Facebook</span></a></li><li><a class="" href="http://www.linkedin.com/shareArticle?mini=true&url=https%3A%2F%2Fwww.thinkib.net%2Fchemistry%2Fpage%2F33687%2Funderstanding-hybridization"><i class="fa fa-linkedin-square"></i><span>LinkedIn</span></a></li><li><a class="" href="https://plus.google.com/share?url=https%3A%2F%2Fwww.thinkib.net%2Fchemistry%2Fpage%2F33687%2Funderstanding-hybridization"><i class="fa fa-google-plus-square"></i><span>Google +</span></a></li><li><a class="" href="mailto:?subject=Understanding hybridization&body=The theory of hybridization is developed by first considering how atomic orbitals combine to form molecular orbitals which then leads on to how hybrid orbitals are formed. The relationships between shapes, bond angles and...%0Ahttps%3A%2F%2Fwww.thinkib.net%2Fchemistry%2Fpage%2F33687%2Funderstanding-hybridization"><i class="fa fa-envelope"></i><span>Email</span></a></li></ul></li><li><a class="" href="chemistry/teaching-materials"><i class="fa fa-puzzle-piece colored"></i></a></li></ul></div></div><div style="border-top: solid 1px #eee;border-bottom: solid 1px #eee;padding: 4px 0 4px 0;line-height: 1em;color: #666;font-size: .8em"><small><em>All materials on this website are for the exclusive use of teachers and students at subscribing schools for the period of their subscription. Any unauthorised copying or posting of materials on other websites is an infringement of our copyright and could result in your account being blocked and legal action being taken against you.</em></small></div></section><section id="comments"></section></div><!-- /#main-column -->
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